diff --git a/docs/administration.rst b/docs/administration.rst
index 8f055147..157af478 100644
--- a/docs/administration.rst
+++ b/docs/administration.rst
@@ -735,6 +735,12 @@ The following configuration properties are required to use the Digicert issuer p
             This is the default validity (in years), if no end date is specified. (Default: 1)
 
 
+.. data:: DIGICERT_MAX_VALIDITY
+    :noindex:
+
+            This is the maximum validity (in years). (Default: value of DIGICERT_DEFAULT_VALIDITY)
+
+
 .. data:: DIGICERT_PRIVATE
     :noindex:
 
@@ -1008,6 +1014,18 @@ The following configuration properties are required to use the PowerDNS ACME Plu
 
             This is the number of times DNS Verification should be attempted (i.e. 20)
 
+
+.. data:: ACME_POWERDNS_VERIFY
+    :noindex:
+
+            This configures how TLS certificates on the PowerDNS API target are validated.  The PowerDNS Plugin depends on the PyPi requests library, which supports the following options for the verify parameter:
+
+            True: Verifies the TLS certificate was issued by a known publicly-trusted CA. (Default)
+
+            False: Disables certificate validation (Not Recommended)
+
+            File/Dir path to CA Bundle: Verifies the TLS certificate was issued by a Certificate Authority in the provided CA bundle.
+
 .. _CommandLineInterface:
 
 Command Line Interface
diff --git a/lemur/auth/views.py b/lemur/auth/views.py
index e7f87356..eaed419d 100644
--- a/lemur/auth/views.py
+++ b/lemur/auth/views.py
@@ -127,6 +127,10 @@ def retrieve_user(user_api_url, access_token):
 
     # retrieve information about the current user.
     r = requests.get(user_api_url, params=user_params, headers=headers)
+    # Some IDPs, like "Keycloak", require a POST instead of a GET
+    if r.status_code == 400:
+        r = requests.post(user_api_url, data=user_params, headers=headers)
+
     profile = r.json()
 
     user = user_service.get_by_email(profile["email"])
@@ -434,7 +438,7 @@ class OAuth2(Resource):
             verify_cert=verify_cert,
         )
 
-        jwks_url = current_app.config.get("PING_JWKS_URL")
+        jwks_url = current_app.config.get("OAUTH2_JWKS_URL")
         error_code = validate_id_token(id_token, args["clientId"], jwks_url)
         if error_code:
             return error_code
diff --git a/lemur/certificates/models.py b/lemur/certificates/models.py
index 0a76cd6b..58630ee6 100644
--- a/lemur/certificates/models.py
+++ b/lemur/certificates/models.py
@@ -321,7 +321,8 @@ class Certificate(db.Model):
 
     @hybrid_property
     def expired(self):
-        if self.not_after <= arrow.utcnow():
+        # can't compare offset-naive and offset-aware datetimes
+        if arrow.Arrow.fromdatetime(self.not_after) <= arrow.utcnow():
             return True
 
     @expired.expression
@@ -445,6 +446,9 @@ def update_destinations(target, value, initiator):
     """
     destination_plugin = plugins.get(value.plugin_name)
     status = FAILURE_METRIC_STATUS
+
+    if target.expired:
+        return
     try:
         if target.private_key or not destination_plugin.requires_key:
             destination_plugin.upload(
diff --git a/lemur/certificates/service.py b/lemur/certificates/service.py
index 0e91b563..a6bbba30 100644
--- a/lemur/certificates/service.py
+++ b/lemur/certificates/service.py
@@ -102,12 +102,13 @@ def get_all_certs():
     return Certificate.query.all()
 
 
-def get_all_pending_cleaning(source):
+def get_all_pending_cleaning_expired(source):
     """
-    Retrieves all certificates that are available for cleaning.
+    Retrieves all certificates that are available for cleaning. These are certificates which are expired and are not
+    attached to any endpoints.
 
-    :param source:
-    :return:
+    :param source: the source to search for certificates
+    :return: list of pending certificates
     """
     return (
         Certificate.query.filter(Certificate.sources.any(id=source.id))
@@ -117,6 +118,41 @@ def get_all_pending_cleaning(source):
     )
 
 
+def get_all_pending_cleaning_expiring_in_days(source, days_to_expire):
+    """
+    Retrieves all certificates that are available for cleaning, not attached to endpoint,
+    and within X days from expiration.
+
+    :param days_to_expire: defines how many days till the certificate is expired
+    :param source: the source to search for certificates
+    :return: list of pending certificates
+    """
+    expiration_window = arrow.now().shift(days=+days_to_expire).format("YYYY-MM-DD")
+    return (
+        Certificate.query.filter(Certificate.sources.any(id=source.id))
+        .filter(not_(Certificate.endpoints.any()))
+        .filter(Certificate.not_after < expiration_window)
+        .all()
+    )
+
+
+def get_all_pending_cleaning_issued_since_days(source, days_since_issuance):
+    """
+    Retrieves all certificates that are available for cleaning: not attached to endpoint, and X days since issuance.
+
+    :param days_since_issuance: defines how many days since the certificate is issued
+    :param source: the source to search for certificates
+    :return: list of pending certificates
+    """
+    not_in_use_window = arrow.now().shift(days=-days_since_issuance).format("YYYY-MM-DD")
+    return (
+        Certificate.query.filter(Certificate.sources.any(id=source.id))
+        .filter(not_(Certificate.endpoints.any()))
+        .filter(Certificate.date_created > not_in_use_window)
+        .all()
+    )
+
+
 def get_all_pending_reissue():
     """
     Retrieves all certificates that need to be rotated.
diff --git a/lemur/common/celery.py b/lemur/common/celery.py
index 4af33d86..7c183dc9 100644
--- a/lemur/common/celery.py
+++ b/lemur/common/celery.py
@@ -10,27 +10,27 @@ command: celery -A lemur.common.celery worker --loglevel=info -l DEBUG -B
 import copy
 import sys
 import time
-from datetime import datetime, timezone, timedelta
-
 from celery import Celery
+from celery.app.task import Context
 from celery.exceptions import SoftTimeLimitExceeded
+from celery.signals import task_failure, task_received, task_revoked, task_success
+from datetime import datetime, timezone, timedelta
 from flask import current_app
 
 from lemur.authorities.service import get as get_authority
+from lemur.certificates import cli as cli_certificate
 from lemur.common.redis import RedisHandler
 from lemur.destinations import service as destinations_service
+from lemur.dns_providers import cli as cli_dns_providers
+from lemur.endpoints import cli as cli_endpoints
 from lemur.extensions import metrics, sentry
 from lemur.factory import create_app
+from lemur.notifications import cli as cli_notification
 from lemur.notifications.messaging import send_pending_failure_notification
 from lemur.pending_certificates import service as pending_certificate_service
 from lemur.plugins.base import plugins
 from lemur.sources.cli import clean, sync, validate_sources
 from lemur.sources.service import add_aws_destination_to_sources
-from lemur.certificates import cli as cli_certificate
-from lemur.dns_providers import cli as cli_dns_providers
-from lemur.notifications import cli as cli_notification
-from lemur.endpoints import cli as cli_endpoints
-
 
 if current_app:
     flask_app = current_app
@@ -67,7 +67,7 @@ def is_task_active(fun, task_id, args):
     from celery.task.control import inspect
 
     if not args:
-        args = '()'  # empty args
+        args = "()"  # empty args
 
     i = inspect()
     active_tasks = i.active()
@@ -80,6 +80,37 @@ def is_task_active(fun, task_id, args):
     return False
 
 
+def get_celery_request_tags(**kwargs):
+    request = kwargs.get("request")
+    sender_hostname = "unknown"
+    sender = kwargs.get("sender")
+    if sender:
+        try:
+            sender_hostname = sender.hostname
+        except AttributeError:
+            sender_hostname = vars(sender.request).get("origin", "unknown")
+    if request and not isinstance(
+        request, Context
+    ):  # unlike others, task_revoked sends a Context for `request`
+        task_name = request.name
+        task_id = request.id
+        receiver_hostname = request.hostname
+    else:
+        task_name = sender.name
+        task_id = sender.request.id
+        receiver_hostname = sender.request.hostname
+
+    tags = {
+        "task_name": task_name,
+        "task_id": task_id,
+        "sender_hostname": sender_hostname,
+        "receiver_hostname": receiver_hostname,
+    }
+    if kwargs.get("exception"):
+        tags["error"] = repr(kwargs["exception"])
+    return tags
+
+
 @celery.task()
 def report_celery_last_success_metrics():
     """
@@ -89,7 +120,6 @@ def report_celery_last_success_metrics():
     report_celery_last_success_metrics should be ran periodically to emit metrics on when a task was last successful.
     Admins can then alert when tasks are not ran when intended. Admins should also alert when no metrics are emitted
     from this function.
-
     """
     function = f"{__name__}.{sys._getframe().f_code.co_name}"
     task_id = None
@@ -108,15 +138,91 @@ def report_celery_last_success_metrics():
         return
 
     current_time = int(time.time())
-    schedule = current_app.config.get('CELERYBEAT_SCHEDULE')
+    schedule = current_app.config.get("CELERYBEAT_SCHEDULE")
     for _, t in schedule.items():
         task = t.get("task")
         last_success = int(red.get(f"{task}.last_success") or 0)
-        metrics.send(f"{task}.time_since_last_success", 'gauge', current_time - last_success)
+        metrics.send(
+            f"{task}.time_since_last_success", "gauge", current_time - last_success
+        )
     red.set(
         f"{function}.last_success", int(time.time())
     )  # Alert if this metric is not seen
-    metrics.send(f"{function}.success", 'counter', 1)
+    metrics.send(f"{function}.success", "counter", 1)
+
+
+@task_received.connect
+def report_number_pending_tasks(**kwargs):
+    """
+    Report the number of pending tasks to our metrics broker every time a task is published. This metric can be used
+    for autoscaling workers.
+    https://docs.celeryproject.org/en/latest/userguide/signals.html#task-received
+    """
+    with flask_app.app_context():
+        metrics.send(
+            "celery.new_pending_task",
+            "TIMER",
+            1,
+            metric_tags=get_celery_request_tags(**kwargs),
+        )
+
+
+@task_success.connect
+def report_successful_task(**kwargs):
+    """
+    Report a generic success metric as tasks to our metrics broker every time a task finished correctly.
+    This metric can be used for autoscaling workers.
+    https://docs.celeryproject.org/en/latest/userguide/signals.html#task-success
+    """
+    with flask_app.app_context():
+        tags = get_celery_request_tags(**kwargs)
+        red.set(f"{tags['task_name']}.last_success", int(time.time()))
+        metrics.send("celery.successful_task", "TIMER", 1, metric_tags=tags)
+
+
+@task_failure.connect
+def report_failed_task(**kwargs):
+    """
+    Report a generic failure metric as tasks to our metrics broker every time a task fails.
+    This metric can be used for alerting.
+    https://docs.celeryproject.org/en/latest/userguide/signals.html#task-failure
+    """
+    with flask_app.app_context():
+        log_data = {
+            "function": f"{__name__}.{sys._getframe().f_code.co_name}",
+            "Message": "Celery Task Failure",
+        }
+
+        # Add traceback if exception info is in the kwargs
+        einfo = kwargs.get("einfo")
+        if einfo:
+            log_data["traceback"] = einfo.traceback
+
+        error_tags = get_celery_request_tags(**kwargs)
+
+        log_data.update(error_tags)
+        current_app.logger.error(log_data)
+        metrics.send("celery.failed_task", "TIMER", 1, metric_tags=error_tags)
+
+
+@task_revoked.connect
+def report_revoked_task(**kwargs):
+    """
+    Report a generic failure metric as tasks to our metrics broker every time a task is revoked.
+    This metric can be used for alerting.
+    https://docs.celeryproject.org/en/latest/userguide/signals.html#task-revoked
+    """
+    with flask_app.app_context():
+        log_data = {
+            "function": f"{__name__}.{sys._getframe().f_code.co_name}",
+            "Message": "Celery Task Revoked",
+        }
+
+        error_tags = get_celery_request_tags(**kwargs)
+
+        log_data.update(error_tags)
+        current_app.logger.error(log_data)
+        metrics.send("celery.revoked_task", "TIMER", 1, metric_tags=error_tags)
 
 
 @celery.task(soft_time_limit=600)
@@ -217,15 +323,15 @@ def fetch_acme_cert(id):
     log_data["failed"] = failed
     log_data["wrong_issuer"] = wrong_issuer
     current_app.logger.debug(log_data)
-    metrics.send(f"{function}.resolved", 'gauge', new)
-    metrics.send(f"{function}.failed", 'gauge', failed)
-    metrics.send(f"{function}.wrong_issuer", 'gauge', wrong_issuer)
+    metrics.send(f"{function}.resolved", "gauge", new)
+    metrics.send(f"{function}.failed", "gauge", failed)
+    metrics.send(f"{function}.wrong_issuer", "gauge", wrong_issuer)
     print(
         "[+] Certificates: New: {new} Failed: {failed} Not using ACME: {wrong_issuer}".format(
             new=new, failed=failed, wrong_issuer=wrong_issuer
         )
     )
-    red.set(f'{function}.last_success', int(time.time()))
+    return log_data
 
 
 @celery.task()
@@ -262,8 +368,8 @@ def fetch_all_pending_acme_certs():
                 current_app.logger.debug(log_data)
                 fetch_acme_cert.delay(cert.id)
 
-    red.set(f'{function}.last_success', int(time.time()))
-    metrics.send(f"{function}.success", 'counter', 1)
+    metrics.send(f"{function}.success", "counter", 1)
+    return log_data
 
 
 @celery.task()
@@ -296,8 +402,8 @@ def remove_old_acme_certs():
             current_app.logger.debug(log_data)
             pending_certificate_service.delete(cert)
 
-    red.set(f'{function}.last_success', int(time.time()))
-    metrics.send(f"{function}.success", 'counter', 1)
+    metrics.send(f"{function}.success", "counter", 1)
+    return log_data
 
 
 @celery.task()
@@ -328,11 +434,11 @@ def clean_all_sources():
         current_app.logger.debug(log_data)
         clean_source.delay(source.label)
 
-    red.set(f'{function}.last_success', int(time.time()))
-    metrics.send(f"{function}.success", 'counter', 1)
+    metrics.send(f"{function}.success", "counter", 1)
+    return log_data
 
 
-@celery.task(soft_time_limit=600)
+@celery.task(soft_time_limit=3600)
 def clean_source(source):
     """
     This celery task will clean the specified source. This is a destructive operation that will delete unused
@@ -366,6 +472,7 @@ def clean_source(source):
         current_app.logger.error(log_data)
         sentry.captureException()
         metrics.send("celery.timeout", "counter", 1, metric_tags={"function": function})
+    return log_data
 
 
 @celery.task()
@@ -395,8 +502,8 @@ def sync_all_sources():
         current_app.logger.debug(log_data)
         sync_source.delay(source.label)
 
-    red.set(f'{function}.last_success', int(time.time()))
-    metrics.send(f"{function}.success", 'counter', 1)
+    metrics.send(f"{function}.success", "counter", 1)
+    return log_data
 
 
 @celery.task(soft_time_limit=7200)
@@ -428,19 +535,23 @@ def sync_source(source):
     current_app.logger.debug(log_data)
     try:
         sync([source])
-        metrics.send(f"{function}.success", 'counter', 1, metric_tags={"source": source})
+        metrics.send(
+            f"{function}.success", "counter", 1, metric_tags={"source": source}
+        )
     except SoftTimeLimitExceeded:
         log_data["message"] = "Error syncing source: Time limit exceeded."
         current_app.logger.error(log_data)
         sentry.captureException()
-        metrics.send("sync_source_timeout", "counter", 1, metric_tags={"source": source})
+        metrics.send(
+            "sync_source_timeout", "counter", 1, metric_tags={"source": source}
+        )
         metrics.send("celery.timeout", "counter", 1, metric_tags={"function": function})
         return
 
     log_data["message"] = "Done syncing source"
     current_app.logger.debug(log_data)
-    metrics.send(f"{function}.success", 'counter', 1, metric_tags={"source": source})
-    red.set(f'{function}.last_success', int(time.time()))
+    metrics.send(f"{function}.success", "counter", 1, metric_tags={"source": source})
+    return log_data
 
 
 @celery.task()
@@ -477,8 +588,8 @@ def sync_source_destination():
 
     log_data["message"] = "completed Syncing AWS destinations and sources"
     current_app.logger.debug(log_data)
-    red.set(f'{function}.last_success', int(time.time()))
-    metrics.send(f"{function}.success", 'counter', 1)
+    metrics.send(f"{function}.success", "counter", 1)
+    return log_data
 
 
 @celery.task(soft_time_limit=3600)
@@ -515,8 +626,8 @@ def certificate_reissue():
 
     log_data["message"] = "reissuance completed"
     current_app.logger.debug(log_data)
-    red.set(f'{function}.last_success', int(time.time()))
-    metrics.send(f"{function}.success", 'counter', 1)
+    metrics.send(f"{function}.success", "counter", 1)
+    return log_data
 
 
 @celery.task(soft_time_limit=3600)
@@ -534,7 +645,6 @@ def certificate_rotate():
         "function": function,
         "message": "rotating certificates",
         "task_id": task_id,
-
     }
 
     if task_id and is_task_active(function, task_id, None):
@@ -554,8 +664,8 @@ def certificate_rotate():
 
     log_data["message"] = "rotation completed"
     current_app.logger.debug(log_data)
-    red.set(f'{function}.last_success', int(time.time()))
-    metrics.send(f"{function}.success", 'counter', 1)
+    metrics.send(f"{function}.success", "counter", 1)
+    return log_data
 
 
 @celery.task(soft_time_limit=3600)
@@ -590,8 +700,8 @@ def endpoints_expire():
         metrics.send("celery.timeout", "counter", 1, metric_tags={"function": function})
         return
 
-    red.set(f'{function}.last_success', int(time.time()))
-    metrics.send(f"{function}.success", 'counter', 1)
+    metrics.send(f"{function}.success", "counter", 1)
+    return log_data
 
 
 @celery.task(soft_time_limit=600)
@@ -626,8 +736,8 @@ def get_all_zones():
         metrics.send("celery.timeout", "counter", 1, metric_tags={"function": function})
         return
 
-    red.set(f'{function}.last_success', int(time.time()))
-    metrics.send(f"{function}.success", 'counter', 1)
+    metrics.send(f"{function}.success", "counter", 1)
+    return log_data
 
 
 @celery.task(soft_time_limit=3600)
@@ -662,8 +772,8 @@ def check_revoked():
         metrics.send("celery.timeout", "counter", 1, metric_tags={"function": function})
         return
 
-    red.set(f'{function}.last_success', int(time.time()))
-    metrics.send(f"{function}.success", 'counter', 1)
+    metrics.send(f"{function}.success", "counter", 1)
+    return log_data
 
 
 @celery.task(soft_time_limit=3600)
@@ -690,7 +800,9 @@ def notify_expirations():
 
     current_app.logger.debug(log_data)
     try:
-        cli_notification.expirations(current_app.config.get("EXCLUDE_CN_FROM_NOTIFICATION", []))
+        cli_notification.expirations(
+            current_app.config.get("EXCLUDE_CN_FROM_NOTIFICATION", [])
+        )
     except SoftTimeLimitExceeded:
         log_data["message"] = "Notify expiring Time limit exceeded."
         current_app.logger.error(log_data)
@@ -698,5 +810,5 @@ def notify_expirations():
         metrics.send("celery.timeout", "counter", 1, metric_tags={"function": function})
         return
 
-    red.set(f'{function}.last_success', int(time.time()))
-    metrics.send(f"{function}.success", 'counter', 1)
+    metrics.send(f"{function}.success", "counter", 1)
+    return log_data
diff --git a/lemur/common/defaults.py b/lemur/common/defaults.py
index d563dbd0..b9c88e49 100644
--- a/lemur/common/defaults.py
+++ b/lemur/common/defaults.py
@@ -2,6 +2,7 @@ import re
 import unicodedata
 
 from cryptography import x509
+from cryptography.hazmat.primitives.serialization import Encoding
 from flask import current_app
 
 from lemur.common.utils import is_selfsigned
@@ -71,12 +72,20 @@ def common_name(cert):
     :return: Common name or None
     """
     try:
-        return cert.subject.get_attributes_for_oid(x509.OID_COMMON_NAME)[
-            0
-        ].value.strip()
+        subject_oid = cert.subject.get_attributes_for_oid(x509.OID_COMMON_NAME)
+        if len(subject_oid) > 0:
+            return subject_oid[0].value.strip()
+        return None
     except Exception as e:
         sentry.captureException()
-        current_app.logger.error("Unable to get common name! {0}".format(e))
+        current_app.logger.error(
+            {
+                "message": "Unable to get common name",
+                "error": e,
+                "public_key": cert.public_bytes(Encoding.PEM).decode("utf-8")
+            },
+            exc_info=True
+        )
 
 
 def organization(cert):
diff --git a/lemur/plugins/lemur_acme/plugin.py b/lemur/plugins/lemur_acme/plugin.py
index 91781966..3fc1df61 100644
--- a/lemur/plugins/lemur_acme/plugin.py
+++ b/lemur/plugins/lemur_acme/plugin.py
@@ -54,18 +54,30 @@ class AcmeHandler(object):
             current_app.logger.error(f"Unable to fetch DNS Providers: {e}")
             self.all_dns_providers = []
 
-    def find_dns_challenge(self, host, authorizations):
+    def get_dns_challenges(self, host, authorizations):
+        """Get dns challenges for provided domain"""
+
+        domain_to_validate, is_wildcard = self.strip_wildcard(host)
         dns_challenges = []
         for authz in authorizations:
-            if not authz.body.identifier.value.lower() == host.lower():
+            if not authz.body.identifier.value.lower() == domain_to_validate.lower():
+                continue
+            if is_wildcard and not authz.body.wildcard:
+                continue
+            if not is_wildcard and authz.body.wildcard:
                 continue
             for combo in authz.body.challenges:
                 if isinstance(combo.chall, challenges.DNS01):
                     dns_challenges.append(combo)
+
         return dns_challenges
 
-    def maybe_remove_wildcard(self, host):
-        return host.replace("*.", "")
+    def strip_wildcard(self, host):
+        """Removes the leading *. and returns Host and whether it was removed or not (True/False)"""
+        prefix = "*."
+        if host.startswith(prefix):
+            return host[len(prefix):], True
+        return host, False
 
     def maybe_add_extension(self, host, dns_provider_options):
         if dns_provider_options and dns_provider_options.get(
@@ -86,9 +98,8 @@ class AcmeHandler(object):
         current_app.logger.debug("Starting DNS challenge for {0}".format(host))
 
         change_ids = []
-
-        host_to_validate = self.maybe_remove_wildcard(host)
-        dns_challenges = self.find_dns_challenge(host_to_validate, order.authorizations)
+        dns_challenges = self.get_dns_challenges(host, order.authorizations)
+        host_to_validate, _ = self.strip_wildcard(host)
         host_to_validate = self.maybe_add_extension(
             host_to_validate, dns_provider_options
         )
@@ -325,7 +336,7 @@ class AcmeHandler(object):
                     )
                     dns_provider_options = json.loads(dns_provider.credentials)
                     account_number = dns_provider_options.get("account_id")
-                    host_to_validate = self.maybe_remove_wildcard(authz_record.host)
+                    host_to_validate, _ = self.strip_wildcard(authz_record.host)
                     host_to_validate = self.maybe_add_extension(
                         host_to_validate, dns_provider_options
                     )
@@ -357,7 +368,7 @@ class AcmeHandler(object):
                 dns_provider_options = json.loads(dns_provider.credentials)
                 account_number = dns_provider_options.get("account_id")
                 dns_challenges = authz_record.dns_challenge
-                host_to_validate = self.maybe_remove_wildcard(authz_record.host)
+                host_to_validate, _ = self.strip_wildcard(authz_record.host)
                 host_to_validate = self.maybe_add_extension(
                     host_to_validate, dns_provider_options
                 )
diff --git a/lemur/plugins/lemur_acme/powerdns.py b/lemur/plugins/lemur_acme/powerdns.py
index f3ad9965..a5d02353 100644
--- a/lemur/plugins/lemur_acme/powerdns.py
+++ b/lemur/plugins/lemur_acme/powerdns.py
@@ -1,11 +1,10 @@
-import time
-import requests
 import json
 import sys
+import time
 
 import lemur.common.utils as utils
 import lemur.dns_providers.util as dnsutil
-
+import requests
 from flask import current_app
 from lemur.extensions import metrics, sentry
 
@@ -17,7 +16,9 @@ REQUIRED_VARIABLES = [
 
 
 class Zone:
-    """ This class implements a PowerDNS zone in JSON. """
+    """
+    This class implements a PowerDNS zone in JSON.
+    """
 
     def __init__(self, _data):
         self._data = _data
@@ -39,7 +40,9 @@ class Zone:
 
 
 class Record:
-    """ This class implements a PowerDNS record. """
+    """
+    This class implements a PowerDNS record.
+    """
 
     def __init__(self, _data):
         self._data = _data
@@ -49,20 +52,30 @@ class Record:
         return self._data["name"]
 
     @property
-    def disabled(self):
-        return self._data["disabled"]
+    def type(self):
+        return self._data["type"]
+
+    @property
+    def ttl(self):
+        return self._data["ttl"]
 
     @property
     def content(self):
         return self._data["content"]
 
     @property
-    def ttl(self):
-        return self._data["ttl"]
+    def disabled(self):
+        return self._data["disabled"]
 
 
 def get_zones(account_number):
-    """Retrieve authoritative zones from the PowerDNS API and return a list"""
+    """
+    Retrieve authoritative zones from the PowerDNS API and return a list of zones
+
+    :param account_number:
+    :raise: Exception
+    :return: list of Zone Objects
+    """
     _check_conf()
     server_id = current_app.config.get("ACME_POWERDNS_SERVERID", "localhost")
     path = f"/api/v1/servers/{server_id}/zones"
@@ -90,44 +103,41 @@ def get_zones(account_number):
 
 
 def create_txt_record(domain, token, account_number):
-    """ Create a TXT record for the given domain and token and return a change_id tuple """
+    """
+    Create a TXT record for the given domain and token and return a change_id tuple
+
+    :param domain: FQDN
+    :param token: challenge value
+    :param account_number:
+    :return: tuple of domain/token
+    """
     _check_conf()
-    zone_name = _get_zone_name(domain, account_number)
-    server_id = current_app.config.get("ACME_POWERDNS_SERVERID", "localhost")
-    zone_id = zone_name + "."
-    domain_id = domain + "."
-    path = f"/api/v1/servers/{server_id}/zones/{zone_id}"
-    payload = {
-        "rrsets": [
-            {
-                "name": domain_id,
-                "type": "TXT",
-                "ttl": 300,
-                "changetype": "REPLACE",
-                "records": [
-                    {
-                        "content": f"\"{token}\"",
-                        "disabled": False
-                    }
-                ],
-                "comments": []
-            }
-        ]
-    }
+
     function = sys._getframe().f_code.co_name
     log_data = {
         "function": function,
         "fqdn": domain,
         "token": token,
     }
+
+    # Create new record
+    domain_id = domain + "."
+    records = [Record({'name': domain_id, 'content': f"\"{token}\"", 'disabled': False})]
+
+    # Get current records
+    cur_records = _get_txt_records(domain)
+    for record in cur_records:
+        if record.content != token:
+            records.append(record)
+
     try:
-        _patch(path, payload)
-        log_data["message"] = "TXT record successfully created"
+        _patch_txt_records(domain, account_number, records)
+        log_data["message"] = "TXT record(s) successfully created"
         current_app.logger.debug(log_data)
     except Exception as e:
         sentry.captureException()
         log_data["Exception"] = e
-        log_data["message"] = "Unable to create TXT record"
+        log_data["message"] = "Unable to create TXT record(s)"
         current_app.logger.debug(log_data)
 
     change_id = (domain, token)
@@ -136,8 +146,11 @@ def create_txt_record(domain, token, account_number):
 
 def wait_for_dns_change(change_id, account_number=None):
     """
-    Checks the authoritative DNS Server to see if changes have propagated to DNS
-    Retries and waits until successful.
+    Checks the authoritative DNS Server to see if changes have propagated.
+
+    :param change_id: tuple of domain/token
+    :param account_number:
+    :return:
     """
     _check_conf()
     domain, token = change_id
@@ -171,53 +184,115 @@ def wait_for_dns_change(change_id, account_number=None):
 
 
 def delete_txt_record(change_id, account_number, domain, token):
-    """ Delete the TXT record for the given domain and token """
+    """
+    Delete the TXT record for the given domain and token
+
+    :param change_id: tuple of domain/token
+    :param account_number:
+    :param domain: FQDN
+    :param token: challenge to delete
+    :return:
+    """
     _check_conf()
-    zone_name = _get_zone_name(domain, account_number)
-    server_id = current_app.config.get("ACME_POWERDNS_SERVERID", "localhost")
-    zone_id = zone_name + "."
-    domain_id = domain + "."
-    path = f"/api/v1/servers/{server_id}/zones/{zone_id}"
-    payload = {
-        "rrsets": [
-            {
-                "name": domain_id,
-                "type": "TXT",
-                "ttl": 300,
-                "changetype": "DELETE",
-                "records": [
-                    {
-                        "content": f"\"{token}\"",
-                        "disabled": False
-                    }
-                ],
-                "comments": []
-            }
-        ]
-    }
+
     function = sys._getframe().f_code.co_name
     log_data = {
         "function": function,
         "fqdn": domain,
-        "token": token
+        "token": token,
     }
-    try:
-        _patch(path, payload)
-        log_data["message"] = "TXT record successfully deleted"
-        current_app.logger.debug(log_data)
-    except Exception as e:
-        sentry.captureException()
-        log_data["Exception"] = e
-        log_data["message"] = "Unable to delete TXT record"
+
+    """
+    Get existing TXT records matching the domain from DNS
+    The token to be deleted should already exist
+    There may be other records with different tokens as well
+    """
+    cur_records = _get_txt_records(domain)
+    found = False
+    new_records = []
+    for record in cur_records:
+        if record.content == f"\"{token}\"":
+            found = True
+        else:
+            new_records.append(record)
+
+    # Since the matching token is not in DNS, there is nothing to delete
+    if not found:
+        log_data["message"] = "Unable to delete TXT record: Token not found in existing TXT records"
         current_app.logger.debug(log_data)
+        return
+
+    # The record to delete has been found AND there are other tokens set on the same domain
+    # Since we only want to delete one token value from the RRSet, we need to use the Patch command to
+    # overwrite the current RRSet with the existing records.
+    elif new_records:
+        try:
+            _patch_txt_records(domain, account_number, new_records)
+            log_data["message"] = "TXT record successfully deleted"
+            current_app.logger.debug(log_data)
+        except Exception as e:
+            sentry.captureException()
+            log_data["Exception"] = e
+            log_data["message"] = "Unable to delete TXT record: patching exception"
+            current_app.logger.debug(log_data)
+
+    # The record to delete has been found AND there are no other token values set on the same domain
+    # Use the Delete command to delete the whole RRSet.
+    else:
+        zone_name = _get_zone_name(domain, account_number)
+        server_id = current_app.config.get("ACME_POWERDNS_SERVERID", "localhost")
+        zone_id = zone_name + "."
+        domain_id = domain + "."
+        path = f"/api/v1/servers/{server_id}/zones/{zone_id}"
+        payload = {
+            "rrsets": [
+                {
+                    "name": domain_id,
+                    "type": "TXT",
+                    "ttl": 300,
+                    "changetype": "DELETE",
+                    "records": [
+                        {
+                            "content": f"\"{token}\"",
+                            "disabled": False
+                        }
+                    ],
+                    "comments": []
+                }
+            ]
+        }
+        function = sys._getframe().f_code.co_name
+        log_data = {
+            "function": function,
+            "fqdn": domain,
+            "token": token
+        }
+        try:
+            _patch(path, payload)
+            log_data["message"] = "TXT record successfully deleted"
+            current_app.logger.debug(log_data)
+        except Exception as e:
+            sentry.captureException()
+            log_data["Exception"] = e
+            log_data["message"] = "Unable to delete TXT record"
+            current_app.logger.debug(log_data)
 
 
 def _check_conf():
+    """
+    Verifies required configuration variables are set
+
+    :return:
+    """
     utils.validate_conf(current_app, REQUIRED_VARIABLES)
 
 
 def _generate_header():
-    """Generate a PowerDNS API header and return it as a dictionary"""
+    """
+    Generate a PowerDNS API header and return it as a dictionary
+
+    :return: Dict of header parameters
+    """
     api_key_name = current_app.config.get("ACME_POWERDNS_APIKEYNAME")
     api_key = current_app.config.get("ACME_POWERDNS_APIKEY")
     headers = {api_key_name: api_key}
@@ -225,7 +300,13 @@ def _generate_header():
 
 
 def _get_zone_name(domain, account_number):
-    """Get most specific matching zone for the given domain and return as a String"""
+    """
+    Get most specific matching zone for the given domain and return as a String
+
+    :param domain: FQDN
+    :param account_number:
+    :return: FQDN of domain
+    """
     zones = get_zones(account_number)
     zone_name = ""
     for z in zones:
@@ -243,25 +324,113 @@ def _get_zone_name(domain, account_number):
     return zone_name
 
 
+def _get_txt_records(domain):
+    """
+    Retrieve TXT records for a given domain and return list of Record Objects
+
+    :param domain: FQDN
+    :return: list of Record objects
+    """
+    server_id = current_app.config.get("ACME_POWERDNS_SERVERID", "localhost")
+
+    path = f"/api/v1/servers/{server_id}/search-data?q={domain}&max=100&object_type=record"
+    function = sys._getframe().f_code.co_name
+    log_data = {
+        "function": function
+    }
+    try:
+        records = _get(path)
+        log_data["message"] = "Retrieved TXT Records Successfully"
+        current_app.logger.debug(log_data)
+
+    except Exception as e:
+        sentry.captureException()
+        log_data["Exception"] = e
+        log_data["message"] = "Failed to Retrieve TXT Records"
+        current_app.logger.debug(log_data)
+        return []
+
+    txt_records = []
+    for record in records:
+        cur_record = Record(record)
+        txt_records.append(cur_record)
+    return txt_records
+
+
 def _get(path, params=None):
-    """ Execute a GET request on the given URL (base_uri + path) and return response as JSON object """
+    """
+    Execute a GET request on the given URL (base_uri + path) and return response as JSON object
+
+    :param path: Relative URL path
+    :param params: additional parameters
+    :return: json response
+    """
     base_uri = current_app.config.get("ACME_POWERDNS_DOMAIN")
+    verify_value = current_app.config.get("ACME_POWERDNS_VERIFY", True)
     resp = requests.get(
         f"{base_uri}{path}",
         headers=_generate_header(),
         params=params,
-        verify=True,
+        verify=verify_value
     )
     resp.raise_for_status()
     return resp.json()
 
 
+def _patch_txt_records(domain, account_number, records):
+    """
+    Send Patch request to PowerDNS Server
+
+    :param domain: FQDN
+    :param account_number:
+    :param records: List of Record objects
+    :return:
+    """
+    domain_id = domain + "."
+
+    # Create records
+    txt_records = []
+    for record in records:
+        txt_records.append(
+            {'content': record.content, 'disabled': record.disabled}
+        )
+
+    # Create RRSet
+    payload = {
+        "rrsets": [
+            {
+                "name": domain_id,
+                "type": "TXT",
+                "ttl": 300,
+                "changetype": "REPLACE",
+                "records": txt_records,
+                "comments": []
+            }
+        ]
+    }
+
+    # Create Txt Records
+    server_id = current_app.config.get("ACME_POWERDNS_SERVERID", "localhost")
+    zone_name = _get_zone_name(domain, account_number)
+    zone_id = zone_name + "."
+    path = f"/api/v1/servers/{server_id}/zones/{zone_id}"
+    _patch(path, payload)
+
+
 def _patch(path, payload):
-    """ Execute a Patch request on the given URL (base_uri + path) with given payload """
+    """
+    Execute a Patch request on the given URL (base_uri + path) with given payload
+
+    :param path:
+    :param payload:
+    :return:
+    """
     base_uri = current_app.config.get("ACME_POWERDNS_DOMAIN")
+    verify_value = current_app.config.get("ACME_POWERDNS_VERIFY", True)
     resp = requests.patch(
         f"{base_uri}{path}",
         data=json.dumps(payload),
-        headers=_generate_header()
+        headers=_generate_header(),
+        verify=verify_value
     )
     resp.raise_for_status()
diff --git a/lemur/plugins/lemur_acme/tests/test_acme.py b/lemur/plugins/lemur_acme/tests/test_acme.py
index 990a556e..bec7be2b 100644
--- a/lemur/plugins/lemur_acme/tests/test_acme.py
+++ b/lemur/plugins/lemur_acme/tests/test_acme.py
@@ -1,11 +1,10 @@
 import unittest
+from unittest.mock import patch, Mock
 
 from cryptography.x509 import DNSName
-from requests.models import Response
-
-from mock import MagicMock, Mock, patch
-
 from lemur.plugins.lemur_acme import plugin, ultradns
+from mock import MagicMock
+from requests.models import Response
 
 
 class TestAcme(unittest.TestCase):
@@ -23,11 +22,12 @@ class TestAcme(unittest.TestCase):
         }
 
     @patch("lemur.plugins.lemur_acme.plugin.len", return_value=1)
-    def test_find_dns_challenge(self, mock_len):
+    def test_get_dns_challenges(self, mock_len):
         assert mock_len
 
         from acme import challenges
 
+        host = "example.com"
         c = challenges.DNS01()
 
         mock_authz = Mock()
@@ -35,9 +35,18 @@ class TestAcme(unittest.TestCase):
         mock_entry = Mock()
         mock_entry.chall = c
         mock_authz.body.resolved_combinations.append(mock_entry)
-        result = yield self.acme.find_dns_challenge(mock_authz)
+        result = yield self.acme.get_dns_challenges(host, mock_authz)
         self.assertEqual(result, mock_entry)
 
+    def test_strip_wildcard(self):
+        expected = ("example.com", False)
+        result = self.acme.strip_wildcard("example.com")
+        self.assertEqual(expected, result)
+
+        expected = ("example.com", True)
+        result = self.acme.strip_wildcard("*.example.com")
+        self.assertEqual(expected, result)
+
     def test_authz_record(self):
         a = plugin.AuthorizationRecord("host", "authz", "challenge", "id")
         self.assertEqual(type(a), plugin.AuthorizationRecord)
@@ -45,9 +54,9 @@ class TestAcme(unittest.TestCase):
     @patch("acme.client.Client")
     @patch("lemur.plugins.lemur_acme.plugin.current_app")
     @patch("lemur.plugins.lemur_acme.plugin.len", return_value=1)
-    @patch("lemur.plugins.lemur_acme.plugin.AcmeHandler.find_dns_challenge")
+    @patch("lemur.plugins.lemur_acme.plugin.AcmeHandler.get_dns_challenges")
     def test_start_dns_challenge(
-        self, mock_find_dns_challenge, mock_len, mock_app, mock_acme
+            self, mock_get_dns_challenges, mock_len, mock_app, mock_acme
     ):
         assert mock_len
         mock_order = Mock()
@@ -65,7 +74,7 @@ class TestAcme(unittest.TestCase):
         mock_dns_provider.create_txt_record = Mock(return_value=1)
 
         values = [mock_entry]
-        iterable = mock_find_dns_challenge.return_value
+        iterable = mock_get_dns_challenges.return_value
         iterator = iter(values)
         iterable.__iter__.return_value = iterator
         result = self.acme.start_dns_challenge(
@@ -78,7 +87,7 @@ class TestAcme(unittest.TestCase):
     @patch("lemur.plugins.lemur_acme.cloudflare.wait_for_dns_change")
     @patch("time.sleep")
     def test_complete_dns_challenge_success(
-        self, mock_sleep, mock_wait_for_dns_change, mock_current_app, mock_acme
+            self, mock_sleep, mock_wait_for_dns_change, mock_current_app, mock_acme
     ):
         mock_dns_provider = Mock()
         mock_dns_provider.wait_for_dns_change = Mock(return_value=True)
@@ -102,7 +111,7 @@ class TestAcme(unittest.TestCase):
     @patch("lemur.plugins.lemur_acme.plugin.current_app")
     @patch("lemur.plugins.lemur_acme.cloudflare.wait_for_dns_change")
     def test_complete_dns_challenge_fail(
-        self, mock_wait_for_dns_change, mock_current_app, mock_acme
+            self, mock_wait_for_dns_change, mock_current_app, mock_acme
     ):
         mock_dns_provider = Mock()
         mock_dns_provider.wait_for_dns_change = Mock(return_value=True)
@@ -127,15 +136,15 @@ class TestAcme(unittest.TestCase):
     @patch("acme.client.Client")
     @patch("OpenSSL.crypto", return_value="mock_cert")
     @patch("josepy.util.ComparableX509")
-    @patch("lemur.plugins.lemur_acme.plugin.AcmeHandler.find_dns_challenge")
+    @patch("lemur.plugins.lemur_acme.plugin.AcmeHandler.get_dns_challenges")
     @patch("lemur.plugins.lemur_acme.plugin.current_app")
     def test_request_certificate(
-        self,
-        mock_current_app,
-        mock_find_dns_challenge,
-        mock_jose,
-        mock_crypto,
-        mock_acme,
+            self,
+            mock_current_app,
+            mock_get_dns_challenges,
+            mock_jose,
+            mock_crypto,
+            mock_acme,
     ):
         mock_cert_response = Mock()
         mock_cert_response.body = "123"
@@ -172,7 +181,7 @@ class TestAcme(unittest.TestCase):
         assert result_client
         assert result_registration
 
-    @patch("lemur.plugins.lemur_acme.plugin.current_app")
+    @patch('lemur.plugins.lemur_acme.plugin.current_app')
     def test_get_domains_single(self, mock_current_app):
         options = {"common_name": "test.netflix.net"}
         result = self.acme.get_domains(options)
@@ -256,11 +265,11 @@ class TestAcme(unittest.TestCase):
     @patch("lemur.plugins.lemur_acme.cloudflare.current_app")
     @patch("lemur.plugins.lemur_acme.plugin.dns_provider_service")
     def test_get_dns_provider(
-        self,
-        mock_dns_provider_service,
-        mock_current_app_cloudflare,
-        mock_current_app_dyn,
-        mock_current_app,
+            self,
+            mock_dns_provider_service,
+            mock_current_app_cloudflare,
+            mock_current_app_dyn,
+            mock_current_app,
     ):
         provider = plugin.ACMEIssuerPlugin()
         route53 = provider.get_dns_provider("route53")
@@ -278,14 +287,14 @@ class TestAcme(unittest.TestCase):
     @patch("lemur.plugins.lemur_acme.plugin.AcmeHandler.finalize_authorizations")
     @patch("lemur.plugins.lemur_acme.plugin.AcmeHandler.request_certificate")
     def test_get_ordered_certificate(
-        self,
-        mock_request_certificate,
-        mock_finalize_authorizations,
-        mock_get_authorizations,
-        mock_dns_provider_service,
-        mock_authorization_service,
-        mock_current_app,
-        mock_acme,
+            self,
+            mock_request_certificate,
+            mock_finalize_authorizations,
+            mock_get_authorizations,
+            mock_dns_provider_service,
+            mock_authorization_service,
+            mock_current_app,
+            mock_acme,
     ):
         mock_client = Mock()
         mock_acme.return_value = (mock_client, "")
@@ -309,14 +318,14 @@ class TestAcme(unittest.TestCase):
     @patch("lemur.plugins.lemur_acme.plugin.AcmeHandler.finalize_authorizations")
     @patch("lemur.plugins.lemur_acme.plugin.AcmeHandler.request_certificate")
     def test_get_ordered_certificates(
-        self,
-        mock_request_certificate,
-        mock_finalize_authorizations,
-        mock_get_authorizations,
-        mock_dns_provider_service,
-        mock_authorization_service,
-        mock_current_app,
-        mock_acme,
+            self,
+            mock_request_certificate,
+            mock_finalize_authorizations,
+            mock_get_authorizations,
+            mock_dns_provider_service,
+            mock_authorization_service,
+            mock_current_app,
+            mock_acme,
     ):
         mock_client = Mock()
         mock_acme.return_value = (mock_client, "")
@@ -349,14 +358,14 @@ class TestAcme(unittest.TestCase):
     @patch("lemur.plugins.lemur_acme.plugin.AcmeHandler.request_certificate")
     @patch("lemur.plugins.lemur_acme.plugin.authorization_service")
     def test_create_certificate(
-        self,
-        mock_authorization_service,
-        mock_request_certificate,
-        mock_finalize_authorizations,
-        mock_get_authorizations,
-        mock_current_app,
-        mock_dns_provider_service,
-        mock_acme,
+            self,
+            mock_authorization_service,
+            mock_request_certificate,
+            mock_finalize_authorizations,
+            mock_get_authorizations,
+            mock_current_app,
+            mock_dns_provider_service,
+            mock_acme,
     ):
         provider = plugin.ACMEIssuerPlugin()
         mock_authority = Mock()
@@ -423,10 +432,10 @@ class TestAcme(unittest.TestCase):
         ultradns._post = Mock()
         ultradns._get = Mock()
         ultradns._get.return_value = {'zoneName': 'test.example.com.com',
-                'rrSets': [{'ownerName': '_acme-challenge.test.example.com.',
-                            'rrtype': 'TXT (16)', 'ttl': 5, 'rdata': ['ABCDEFGHIJ']}],
-                'queryInfo': {'sort': 'OWNER', 'reverse': False, 'limit': 100},
-                'resultInfo': {'totalCount': 1, 'offset': 0, 'returnedCount': 1}}
+                                      'rrSets': [{'ownerName': '_acme-challenge.test.example.com.',
+                                                  'rrtype': 'TXT (16)', 'ttl': 5, 'rdata': ['ABCDEFGHIJ']}],
+                                      'queryInfo': {'sort': 'OWNER', 'reverse': False, 'limit': 100},
+                                      'resultInfo': {'totalCount': 1, 'offset': 0, 'returnedCount': 1}}
         ultradns._delete = Mock()
         mock_metrics.send = Mock()
         ultradns.delete_txt_record(change_id, account_number, domain, token)
diff --git a/lemur/plugins/lemur_acme/tests/test_powerdns.py b/lemur/plugins/lemur_acme/tests/test_powerdns.py
index c8b0a11e..714cc938 100644
--- a/lemur/plugins/lemur_acme/tests/test_powerdns.py
+++ b/lemur/plugins/lemur_acme/tests/test_powerdns.py
@@ -1,5 +1,5 @@
 import unittest
-from mock import Mock, patch
+from unittest.mock import patch, Mock
 from lemur.plugins.lemur_acme import plugin, powerdns
 
 
@@ -48,13 +48,14 @@ class TestPowerdns(unittest.TestCase):
         self.assertEqual(result, zone)
 
     @patch("lemur.plugins.lemur_acme.powerdns.current_app")
-    def test_create_txt_record(self, mock_current_app):
+    def test_create_txt_record_write_only(self, mock_current_app):
         domain = "_acme_challenge.test.example.com"
         zone = "test.example.com"
         token = "ABCDEFGHIJ"
         account_number = "1234567890"
         change_id = (domain, token)
         powerdns._check_conf = Mock()
+        powerdns._get_txt_records = Mock(return_value=[])
         powerdns._get_zone_name = Mock(return_value=zone)
         mock_current_app.logger.debug = Mock()
         mock_current_app.config.get = Mock(return_value="localhost")
@@ -63,24 +64,74 @@ class TestPowerdns(unittest.TestCase):
             "function": "create_txt_record",
             "fqdn": domain,
             "token": token,
-            "message": "TXT record successfully created"
+            "message": "TXT record(s) successfully created"
         }
         result = powerdns.create_txt_record(domain, token, account_number)
         mock_current_app.logger.debug.assert_called_with(log_data)
         self.assertEqual(result, change_id)
 
+    @patch("lemur.plugins.lemur_acme.powerdns.current_app")
+    def test_create_txt_record_append(self, mock_current_app):
+        domain = "_acme_challenge.test.example.com"
+        zone = "test.example.com"
+        token = "ABCDEFGHIJ"
+        account_number = "1234567890"
+        change_id = (domain, token)
+        powerdns._check_conf = Mock()
+        cur_token = "123456"
+        cur_records = [powerdns.Record({'name': domain, 'content': f"\"{cur_token}\"", 'disabled': False})]
+        powerdns._get_txt_records = Mock(return_value=cur_records)
+        powerdns._get_zone_name = Mock(return_value=zone)
+        mock_current_app.logger.debug = Mock()
+        mock_current_app.config.get = Mock(return_value="localhost")
+        powerdns._patch = Mock()
+        log_data = {
+            "function": "create_txt_record",
+            "fqdn": domain,
+            "token": token,
+            "message": "TXT record(s) successfully created"
+        }
+        expected_path = f"/api/v1/servers/localhost/zones/test.example.com."
+        expected_payload = {
+            "rrsets": [
+                {
+                    "name": domain + ".",
+                    "type": "TXT",
+                    "ttl": 300,
+                    "changetype": "REPLACE",
+                    "records": [
+                        {
+                            "content": f"\"{token}\"",
+                            "disabled": False
+                        },
+                        {
+                            "content": f"\"{cur_token}\"",
+                            "disabled": False
+                        }
+                    ],
+                    "comments": []
+                }
+            ]
+        }
+
+        result = powerdns.create_txt_record(domain, token, account_number)
+        mock_current_app.logger.debug.assert_called_with(log_data)
+        powerdns._patch.assert_called_with(expected_path, expected_payload)
+        self.assertEqual(result, change_id)
+
     @patch("lemur.plugins.lemur_acme.powerdns.dnsutil")
     @patch("lemur.plugins.lemur_acme.powerdns.current_app")
     @patch("lemur.extensions.metrics")
     @patch("time.sleep")
     def test_wait_for_dns_change(self, mock_sleep, mock_metrics, mock_current_app, mock_dnsutil):
         domain = "_acme-challenge.test.example.com"
-        token = "ABCDEFG"
+        token1 = "ABCDEFG"
+        token2 = "HIJKLMN"
         zone_name = "test.example.com"
         nameserver = "1.1.1.1"
-        change_id = (domain, token)
+        change_id = (domain, token1)
         powerdns._check_conf = Mock()
-        mock_records = (token,)
+        mock_records = (token2, token1)
         mock_current_app.config.get = Mock(return_value=1)
         powerdns._get_zone_name = Mock(return_value=zone_name)
         mock_dnsutil.get_authoritative_nameserver = Mock(return_value=nameserver)
@@ -114,7 +165,7 @@ class TestPowerdns(unittest.TestCase):
             "function": "delete_txt_record",
             "fqdn": domain,
             "token": token,
-            "message": "TXT record successfully deleted"
+            "message": "Unable to delete TXT record: Token not found in existing TXT records"
         }
         powerdns.delete_txt_record(change_id, account_number, domain, token)
         mock_current_app.logger.debug.assert_called_with(log_data)
diff --git a/lemur/plugins/lemur_aws/iam.py b/lemur/plugins/lemur_aws/iam.py
index 13590ddd..8d80e020 100644
--- a/lemur/plugins/lemur_aws/iam.py
+++ b/lemur/plugins/lemur_aws/iam.py
@@ -24,6 +24,12 @@ def retry_throttled(exception):
         if exception.response["Error"]["Code"] == "NoSuchEntity":
             return False
 
+        # No need to retry deletion requests if there is a DeleteConflict error.
+        # This error indicates that the certificate is still attached to an entity
+        # and cannot be deleted.
+        if exception.response["Error"]["Code"] == "DeleteConflict":
+            return False
+
     metrics.send("iam_retry", "counter", 1, metric_tags={"exception": str(exception)})
     return True
 
diff --git a/lemur/plugins/lemur_aws/plugin.py b/lemur/plugins/lemur_aws/plugin.py
index 6669f641..8692348a 100644
--- a/lemur/plugins/lemur_aws/plugin.py
+++ b/lemur/plugins/lemur_aws/plugin.py
@@ -216,22 +216,24 @@ class AWSSourcePlugin(SourcePlugin):
 
         for region in regions:
             elbs = elb.get_all_elbs(account_number=account_number, region=region)
-            current_app.logger.info(
-                "Describing classic load balancers in {0}-{1}".format(
-                    account_number, region
-                )
-            )
+            current_app.logger.info({
+                "message": "Describing classic load balancers",
+                "account_number": account_number,
+                "region": region,
+                "number_of_load_balancers": len(elbs)
+            })
 
             for e in elbs:
                 endpoints.extend(get_elb_endpoints(account_number, region, e))
 
             # fetch advanced ELBs
             elbs_v2 = elb.get_all_elbs_v2(account_number=account_number, region=region)
-            current_app.logger.info(
-                "Describing advanced load balancers in {0}-{1}".format(
-                    account_number, region
-                )
-            )
+            current_app.logger.info({
+                "message": "Describing advanced load balancers",
+                "account_number": account_number,
+                "region": region,
+                "number_of_load_balancers": len(elbs_v2)
+            })
 
             for e in elbs_v2:
                 endpoints.extend(get_elb_endpoints_v2(account_number, region, e))
@@ -325,14 +327,17 @@ class AWSDestinationPlugin(DestinationPlugin):
     ]
 
     def upload(self, name, body, private_key, cert_chain, options, **kwargs):
-        iam.upload_cert(
-            name,
-            body,
-            private_key,
-            self.get_option("path", options),
-            cert_chain=cert_chain,
-            account_number=self.get_option("accountNumber", options),
-        )
+        try:
+            iam.upload_cert(
+                name,
+                body,
+                private_key,
+                self.get_option("path", options),
+                cert_chain=cert_chain,
+                account_number=self.get_option("accountNumber", options),
+            )
+        except ClientError:
+            sentry.captureException()
 
     def deploy(self, elb_name, account, region, certificate):
         pass
diff --git a/lemur/plugins/lemur_digicert/plugin.py b/lemur/plugins/lemur_digicert/plugin.py
index 88ea5b6b..e5c4b2ce 100644
--- a/lemur/plugins/lemur_digicert/plugin.py
+++ b/lemur/plugins/lemur_digicert/plugin.py
@@ -14,21 +14,17 @@
 .. moduleauthor:: Kevin Glisson <kglisson@netflix.com>
 """
 import json
+
 import arrow
-import requests
-
 import pem
-from retrying import retry
-
-from flask import current_app
-
+import requests
 from cryptography import x509
-
-from lemur.extensions import metrics
+from flask import current_app
 from lemur.common.utils import validate_conf
-from lemur.plugins.bases import IssuerPlugin, SourcePlugin
-
+from lemur.extensions import metrics
 from lemur.plugins import lemur_digicert as digicert
+from lemur.plugins.bases import IssuerPlugin, SourcePlugin
+from retrying import retry
 
 
 def log_status_code(r, *args, **kwargs):
@@ -64,24 +60,37 @@ def signature_hash(signing_algorithm):
     raise Exception("Unsupported signing algorithm.")
 
 
-def determine_validity_years(end_date):
+def determine_validity_years(years):
     """Given an end date determine how many years into the future that date is.
+    :param years:
+    :return: validity in years
+    """
+    default_years = current_app.config.get("DIGICERT_DEFAULT_VALIDITY", 1)
+    max_years = current_app.config.get("DIGICERT_MAX_VALIDITY", default_years)
+
+    if years > max_years:
+        return max_years
+    if years not in [1, 2, 3]:
+        return default_years
+    return years
+
+
+def determine_end_date(end_date):
+    """
+    Determine appropriate end date
 
     :param end_date:
-    :return: str validity in years
+    :return: validity_end
     """
-    now = arrow.utcnow()
+    default_years = current_app.config.get("DIGICERT_DEFAULT_VALIDITY", 1)
+    max_validity_end = arrow.utcnow().shift(years=current_app.config.get("DIGICERT_MAX_VALIDITY", default_years))
 
-    if end_date < now.shift(years=+1):
-        return 1
-    elif end_date < now.shift(years=+2):
-        return 2
-    elif end_date < now.shift(years=+3):
-        return 3
+    if not end_date:
+        end_date = arrow.utcnow().shift(years=default_years)
 
-    raise Exception(
-        "DigiCert issued certificates cannot exceed three" " years in validity"
-    )
+    if end_date > max_validity_end:
+        end_date = max_validity_end
+    return end_date
 
 
 def get_additional_names(options):
@@ -107,12 +116,6 @@ def map_fields(options, csr):
     :param csr:
     :return: dict or valid DigiCert options
     """
-    if not options.get("validity_years"):
-        if not options.get("validity_end"):
-            options["validity_years"] = current_app.config.get(
-                "DIGICERT_DEFAULT_VALIDITY", 1
-            )
-
     data = dict(
         certificate={
             "common_name": options["common_name"],
@@ -125,9 +128,11 @@ def map_fields(options, csr):
     data["certificate"]["dns_names"] = get_additional_names(options)
 
     if options.get("validity_years"):
-        data["validity_years"] = options["validity_years"]
+        data["validity_years"] = determine_validity_years(options.get("validity_years"))
+    elif options.get("validity_end"):
+        data["custom_expiration_date"] = determine_end_date(options.get("validity_end")).format("YYYY-MM-DD")
     else:
-        data["custom_expiration_date"] = options["validity_end"].format("YYYY-MM-DD")
+        data["validity_years"] = determine_validity_years(0)
 
     if current_app.config.get("DIGICERT_PRIVATE", False):
         if "product" in data:
@@ -144,18 +149,15 @@ def map_cis_fields(options, csr):
 
     :param options:
     :param csr:
-    :return:
+    :return: data
     """
-    if not options.get("validity_years"):
-        if not options.get("validity_end"):
-            options["validity_end"] = arrow.utcnow().shift(
-                years=current_app.config.get("DIGICERT_DEFAULT_VALIDITY", 1)
-            )
-        options["validity_years"] = determine_validity_years(options["validity_end"])
+
+    if options.get("validity_years"):
+        validity_end = determine_end_date(arrow.utcnow().shift(years=options["validity_years"]))
+    elif options.get("validity_end"):
+        validity_end = determine_end_date(options.get("validity_end"))
     else:
-        options["validity_end"] = arrow.utcnow().shift(
-            years=options["validity_years"]
-        )
+        validity_end = determine_end_date(False)
 
     data = {
         "profile_name": current_app.config.get("DIGICERT_CIS_PROFILE_NAMES", {}).get(options['authority'].name),
@@ -164,7 +166,7 @@ def map_cis_fields(options, csr):
         "csr": csr,
         "signature_hash": signature_hash(options.get("signing_algorithm")),
         "validity": {
-            "valid_to": options["validity_end"].format("YYYY-MM-DDTHH:MM") + "Z"
+            "valid_to": validity_end.format("YYYY-MM-DDTHH:MM") + "Z"
         },
         "organization": {
             "name": options["organization"],
@@ -173,7 +175,8 @@ def map_cis_fields(options, csr):
     }
     #  possibility to default to a SIGNING_ALGORITHM for a given profile
     if current_app.config.get("DIGICERT_CIS_SIGNING_ALGORITHMS", {}).get(options['authority'].name):
-        data["signature_hash"] = current_app.config.get("DIGICERT_CIS_SIGNING_ALGORITHMS", {}).get(options['authority'].name)
+        data["signature_hash"] = current_app.config.get("DIGICERT_CIS_SIGNING_ALGORITHMS", {}).get(
+            options['authority'].name)
 
     return data
 
diff --git a/lemur/plugins/lemur_digicert/tests/test_digicert.py b/lemur/plugins/lemur_digicert/tests/test_digicert.py
index 77b0a1fa..8bfd1dcf 100644
--- a/lemur/plugins/lemur_digicert/tests/test_digicert.py
+++ b/lemur/plugins/lemur_digicert/tests/test_digicert.py
@@ -1,117 +1,125 @@
-import pytest
-import arrow
 import json
-from unittest.mock import patch
+from unittest.mock import patch, Mock
 
+import arrow
+import pytest
+from cryptography import x509
 from freezegun import freeze_time
-
+from lemur.plugins.lemur_digicert import plugin
 from lemur.tests.vectors import CSR_STR
 
-from cryptography import x509
 
-
-def test_map_fields_with_validity_end_and_start(app):
-    from lemur.plugins.lemur_digicert.plugin import map_fields
-
-    names = [u"one.example.com", u"two.example.com", u"three.example.com"]
-
-    options = {
-        "common_name": "example.com",
-        "owner": "bob@example.com",
-        "description": "test certificate",
-        "extensions": {"sub_alt_names": {"names": [x509.DNSName(x) for x in names]}},
-        "validity_end": arrow.get(2017, 5, 7),
-        "validity_start": arrow.get(2016, 10, 30),
-    }
-
-    data = map_fields(options, CSR_STR)
-
-    assert data == {
-        "certificate": {
-            "csr": CSR_STR,
-            "common_name": "example.com",
-            "dns_names": names,
-            "signature_hash": "sha256",
-        },
-        "organization": {"id": 111111},
-        "custom_expiration_date": arrow.get(2017, 5, 7).format("YYYY-MM-DD"),
+def config_mock(*args):
+    values = {
+        "DIGICERT_ORG_ID": 111111,
+        "DIGICERT_PRIVATE": False,
+        "DIGICERT_DEFAULT_SIGNING_ALGORITHM": "sha256",
+        "DIGICERT_DEFAULT_VALIDITY": 1,
+        "DIGICERT_MAX_VALIDITY": 2,
+        "DIGICERT_CIS_PROFILE_NAMES": {"digicert": 'digicert'},
+        "DIGICERT_CIS_SIGNING_ALGORITHMS": {"digicert": 'digicert'},
     }
+    return values[args[0]]
 
 
-def test_map_fields_with_validity_years(app):
-    from lemur.plugins.lemur_digicert.plugin import map_fields
-
-    names = [u"one.example.com", u"two.example.com", u"three.example.com"]
-
-    options = {
-        "common_name": "example.com",
-        "owner": "bob@example.com",
-        "description": "test certificate",
-        "extensions": {"sub_alt_names": {"names": [x509.DNSName(x) for x in names]}},
-        "validity_years": 2,
-        "validity_end": arrow.get(2017, 10, 30),
-    }
-
-    data = map_fields(options, CSR_STR)
-
-    assert data == {
-        "certificate": {
-            "csr": CSR_STR,
-            "common_name": "example.com",
-            "dns_names": names,
-            "signature_hash": "sha256",
-        },
-        "organization": {"id": 111111},
-        "validity_years": 2,
-    }
+@patch("lemur.plugins.lemur_digicert.plugin.current_app")
+def test_determine_validity_years(mock_current_app):
+    mock_current_app.config.get = Mock(return_value=2)
+    assert plugin.determine_validity_years(1) == 1
+    assert plugin.determine_validity_years(0) == 2
+    assert plugin.determine_validity_years(3) == 2
 
 
-def test_map_cis_fields(app, authority):
-    from lemur.plugins.lemur_digicert.plugin import map_cis_fields
-
-    names = [u"one.example.com", u"two.example.com", u"three.example.com"]
-
-    options = {
-        "common_name": "example.com",
-        "owner": "bob@example.com",
-        "description": "test certificate",
-        "extensions": {"sub_alt_names": {"names": [x509.DNSName(x) for x in names]}},
-        "organization": "Example, Inc.",
-        "organizational_unit": "Example Org",
-        "validity_end": arrow.get(2017, 5, 7),
-        "validity_start": arrow.get(2016, 10, 30),
-        "authority": authority,
-    }
-
-    data = map_cis_fields(options, CSR_STR)
-
-    assert data == {
-        "common_name": "example.com",
-        "csr": CSR_STR,
-        "additional_dns_names": names,
-        "signature_hash": "sha256",
-        "organization": {"name": "Example, Inc.", "units": ["Example Org"]},
-        "validity": {
-            "valid_to": arrow.get(2017, 5, 7).format("YYYY-MM-DDTHH:MM") + "Z"
-        },
-        "profile_name": None,
-    }
-
-    options = {
-        "common_name": "example.com",
-        "owner": "bob@example.com",
-        "description": "test certificate",
-        "extensions": {"sub_alt_names": {"names": [x509.DNSName(x) for x in names]}},
-        "organization": "Example, Inc.",
-        "organizational_unit": "Example Org",
-        "validity_years": 2,
-        "authority": authority,
-    }
-
+@patch("lemur.plugins.lemur_digicert.plugin.current_app")
+def test_determine_end_date(mock_current_app):
+    mock_current_app.config.get = Mock(return_value=2)
     with freeze_time(time_to_freeze=arrow.get(2016, 11, 3).datetime):
-        data = map_cis_fields(options, CSR_STR)
+        assert arrow.get(2018, 11, 3) == plugin.determine_end_date(0)
+        assert arrow.get(2018, 5, 7) == plugin.determine_end_date(arrow.get(2018, 5, 7))
+        assert arrow.get(2018, 11, 3) == plugin.determine_end_date(arrow.get(2020, 5, 7))
 
-        assert data == {
+
+@patch("lemur.plugins.lemur_digicert.plugin.current_app")
+def test_map_fields_with_validity_years(mock_current_app):
+    mock_current_app.config.get = Mock(side_effect=config_mock)
+
+    with patch('lemur.plugins.lemur_digicert.plugin.signature_hash') as mock_signature_hash:
+        mock_signature_hash.return_value = "sha256"
+
+        names = [u"one.example.com", u"two.example.com", u"three.example.com"]
+        options = {
+            "common_name": "example.com",
+            "owner": "bob@example.com",
+            "description": "test certificate",
+            "extensions": {"sub_alt_names": {"names": [x509.DNSName(x) for x in names]}},
+            "validity_years": 2
+        }
+        expected = {
+            "certificate": {
+                "csr": CSR_STR,
+                "common_name": "example.com",
+                "dns_names": names,
+                "signature_hash": "sha256",
+            },
+            "organization": {"id": 111111},
+            "validity_years": 2,
+        }
+        assert expected == plugin.map_fields(options, CSR_STR)
+
+
+@patch("lemur.plugins.lemur_digicert.plugin.current_app")
+def test_map_fields_with_validity_end_and_start(mock_current_app):
+    mock_current_app.config.get = Mock(side_effect=config_mock)
+    plugin.determine_end_date = Mock(return_value=arrow.get(2017, 5, 7))
+
+    with patch('lemur.plugins.lemur_digicert.plugin.signature_hash') as mock_signature_hash:
+        mock_signature_hash.return_value = "sha256"
+
+        names = [u"one.example.com", u"two.example.com", u"three.example.com"]
+        options = {
+            "common_name": "example.com",
+            "owner": "bob@example.com",
+            "description": "test certificate",
+            "extensions": {"sub_alt_names": {"names": [x509.DNSName(x) for x in names]}},
+            "validity_end": arrow.get(2017, 5, 7),
+            "validity_start": arrow.get(2016, 10, 30),
+        }
+
+        expected = {
+            "certificate": {
+                "csr": CSR_STR,
+                "common_name": "example.com",
+                "dns_names": names,
+                "signature_hash": "sha256",
+            },
+            "organization": {"id": 111111},
+            "custom_expiration_date": arrow.get(2017, 5, 7).format("YYYY-MM-DD"),
+        }
+
+        assert expected == plugin.map_fields(options, CSR_STR)
+
+
+@patch("lemur.plugins.lemur_digicert.plugin.current_app")
+def test_map_cis_fields_with_validity_years(mock_current_app, authority):
+    mock_current_app.config.get = Mock(side_effect=config_mock)
+    plugin.determine_end_date = Mock(return_value=arrow.get(2018, 11, 3))
+
+    with patch('lemur.plugins.lemur_digicert.plugin.signature_hash') as mock_signature_hash:
+        mock_signature_hash.return_value = "sha256"
+
+        names = [u"one.example.com", u"two.example.com", u"three.example.com"]
+        options = {
+            "common_name": "example.com",
+            "owner": "bob@example.com",
+            "description": "test certificate",
+            "extensions": {"sub_alt_names": {"names": [x509.DNSName(x) for x in names]}},
+            "organization": "Example, Inc.",
+            "organizational_unit": "Example Org",
+            "validity_years": 2,
+            "authority": authority,
+        }
+
+        expected = {
             "common_name": "example.com",
             "csr": CSR_STR,
             "additional_dns_names": names,
@@ -123,21 +131,59 @@ def test_map_cis_fields(app, authority):
             "profile_name": None,
         }
 
+        assert expected == plugin.map_cis_fields(options, CSR_STR)
 
-def test_signature_hash(app):
-    from lemur.plugins.lemur_digicert.plugin import signature_hash
 
-    assert signature_hash(None) == "sha256"
-    assert signature_hash("sha256WithRSA") == "sha256"
-    assert signature_hash("sha384WithRSA") == "sha384"
-    assert signature_hash("sha512WithRSA") == "sha512"
+@patch("lemur.plugins.lemur_digicert.plugin.current_app")
+def test_map_cis_fields_with_validity_end_and_start(mock_current_app, app, authority):
+    mock_current_app.config.get = Mock(side_effect=config_mock)
+    plugin.determine_end_date = Mock(return_value=arrow.get(2017, 5, 7))
+
+    with patch('lemur.plugins.lemur_digicert.plugin.signature_hash') as mock_signature_hash:
+        mock_signature_hash.return_value = "sha256"
+
+        names = [u"one.example.com", u"two.example.com", u"three.example.com"]
+        options = {
+            "common_name": "example.com",
+            "owner": "bob@example.com",
+            "description": "test certificate",
+            "extensions": {"sub_alt_names": {"names": [x509.DNSName(x) for x in names]}},
+            "organization": "Example, Inc.",
+            "organizational_unit": "Example Org",
+            "validity_end": arrow.get(2017, 5, 7),
+            "validity_start": arrow.get(2016, 10, 30),
+            "authority": authority
+        }
+
+        expected = {
+            "common_name": "example.com",
+            "csr": CSR_STR,
+            "additional_dns_names": names,
+            "signature_hash": "sha256",
+            "organization": {"name": "Example, Inc.", "units": ["Example Org"]},
+            "validity": {
+                "valid_to": arrow.get(2017, 5, 7).format("YYYY-MM-DDTHH:MM") + "Z"
+            },
+            "profile_name": None,
+        }
+
+        assert expected == plugin.map_cis_fields(options, CSR_STR)
+
+
+@patch("lemur.plugins.lemur_digicert.plugin.current_app")
+def test_signature_hash(mock_current_app, app):
+    mock_current_app.config.get = Mock(side_effect=config_mock)
+    assert plugin.signature_hash(None) == "sha256"
+    assert plugin.signature_hash("sha256WithRSA") == "sha256"
+    assert plugin.signature_hash("sha384WithRSA") == "sha384"
+    assert plugin.signature_hash("sha512WithRSA") == "sha512"
 
     with pytest.raises(Exception):
-        signature_hash("sdfdsf")
+        plugin.signature_hash("sdfdsf")
 
 
 def test_issuer_plugin_create_certificate(
-    certificate_="""\
+        certificate_="""\
 -----BEGIN CERTIFICATE-----
 abc
 -----END CERTIFICATE-----
diff --git a/lemur/sources/cli.py b/lemur/sources/cli.py
index c41a1cf7..c415b567 100644
--- a/lemur/sources/cli.py
+++ b/lemur/sources/cli.py
@@ -54,6 +54,24 @@ def validate_sources(source_strings):
     return sources
 
 
+def execute_clean(plugin, certificate, source):
+    try:
+        plugin.clean(certificate, source.options)
+        certificate.sources.remove(source)
+
+        # If we want to remove the source from the certificate, we also need to clear any equivalent destinations to
+        # prevent Lemur from re-uploading the certificate.
+        for destination in certificate.destinations:
+            if destination.label == source.label:
+                certificate.destinations.remove(destination)
+
+        certificate_service.database.update(certificate)
+        return SUCCESS_METRIC_STATUS
+    except Exception as e:
+        current_app.logger.exception(e)
+        sentry.captureException()
+
+
 @manager.option(
     "-s",
     "--sources",
@@ -132,11 +150,9 @@ def clean(source_strings, commit):
         s = plugins.get(source.plugin_name)
 
         if not hasattr(s, "clean"):
-            print(
-                "Cannot clean source: {0}, source plugin does not implement 'clean()'".format(
-                    source.label
-                )
-            )
+            info_text = f"Cannot clean source: {source.label}, source plugin does not implement 'clean()'"
+            current_app.logger.warning(info_text)
+            print(info_text)
             continue
 
         start_time = time.time()
@@ -144,35 +160,147 @@ def clean(source_strings, commit):
         print("[+] Staring to clean source: {label}!\n".format(label=source.label))
 
         cleaned = 0
-        for certificate in certificate_service.get_all_pending_cleaning(source):
+        certificates = certificate_service.get_all_pending_cleaning_expired(source)
+        for certificate in certificates:
             status = FAILURE_METRIC_STATUS
             if commit:
-                try:
-                    s.clean(certificate, source.options)
-                    certificate.sources.remove(source)
-                    certificate_service.database.update(certificate)
-                    status = SUCCESS_METRIC_STATUS
-                except Exception as e:
-                    current_app.logger.exception(e)
-                    sentry.captureException()
+                status = execute_clean(s, certificate, source)
 
             metrics.send(
-                "clean",
+                "certificate_clean",
                 "counter",
                 1,
-                metric_tags={"source": source.label, "status": status},
+                metric_tags={"status": status, "source": source.label, "certificate": certificate.name},
             )
-
-            current_app.logger.warning(
-                "Removed {0} from source {1} during cleaning".format(
-                    certificate.name, source.label
-                )
-            )
-
+            current_app.logger.warning(f"Removed {certificate.name} from source {source.label} during cleaning")
             cleaned += 1
 
-        print(
-            "[+] Finished cleaning source: {label}. Removed {cleaned} certificates from source. Run Time: {time}\n".format(
-                label=source.label, time=(time.time() - start_time), cleaned=cleaned
+        info_text = f"[+] Finished cleaning source: {source.label}. " \
+                    f"Removed {cleaned} certificates from source. " \
+                    f"Run Time: {(time.time() - start_time)}\n"
+        print(info_text)
+        current_app.logger.warning(info_text)
+
+
+@manager.option(
+    "-s",
+    "--sources",
+    dest="source_strings",
+    action="append",
+    help="Sources to operate on.",
+)
+@manager.option(
+    "-d",
+    "--days",
+    dest="days_to_expire",
+    type=int,
+    action="store",
+    required=True,
+    help="The expiry range within days.",
+)
+@manager.option(
+    "-c",
+    "--commit",
+    dest="commit",
+    action="store_true",
+    default=False,
+    help="Persist changes.",
+)
+def clean_unused_and_expiring_within_days(source_strings, days_to_expire, commit):
+    sources = validate_sources(source_strings)
+    for source in sources:
+        s = plugins.get(source.plugin_name)
+
+        if not hasattr(s, "clean"):
+            info_text = f"Cannot clean source: {source.label}, source plugin does not implement 'clean()'"
+            current_app.logger.warning(info_text)
+            print(info_text)
+            continue
+
+        start_time = time.time()
+
+        print("[+] Staring to clean source: {label}!\n".format(label=source.label))
+
+        cleaned = 0
+        certificates = certificate_service.get_all_pending_cleaning_expiring_in_days(source, days_to_expire)
+        for certificate in certificates:
+            status = FAILURE_METRIC_STATUS
+            if commit:
+                status = execute_clean(s, certificate, source)
+
+            metrics.send(
+                "certificate_clean",
+                "counter",
+                1,
+                metric_tags={"status": status, "source": source.label, "certificate": certificate.name},
             )
-        )
+            current_app.logger.warning(f"Removed {certificate.name} from source {source.label} during cleaning")
+            cleaned += 1
+
+        info_text = f"[+] Finished cleaning source: {source.label}. " \
+                    f"Removed {cleaned} certificates from source. " \
+                    f"Run Time: {(time.time() - start_time)}\n"
+        print(info_text)
+        current_app.logger.warning(info_text)
+
+
+@manager.option(
+    "-s",
+    "--sources",
+    dest="source_strings",
+    action="append",
+    help="Sources to operate on.",
+)
+@manager.option(
+    "-d",
+    "--days",
+    dest="days_since_issuance",
+    type=int,
+    action="store",
+    required=True,
+    help="Days since issuance.",
+)
+@manager.option(
+    "-c",
+    "--commit",
+    dest="commit",
+    action="store_true",
+    default=False,
+    help="Persist changes.",
+)
+def clean_unused_and_issued_since_days(source_strings, days_since_issuance, commit):
+    sources = validate_sources(source_strings)
+    for source in sources:
+        s = plugins.get(source.plugin_name)
+
+        if not hasattr(s, "clean"):
+            info_text = f"Cannot clean source: {source.label}, source plugin does not implement 'clean()'"
+            current_app.logger.warning(info_text)
+            print(info_text)
+            continue
+
+        start_time = time.time()
+
+        print("[+] Staring to clean source: {label}!\n".format(label=source.label))
+
+        cleaned = 0
+        certificates = certificate_service.get_all_pending_cleaning_issued_since_days(source, days_since_issuance)
+        for certificate in certificates:
+            status = FAILURE_METRIC_STATUS
+            if commit:
+                status = execute_clean(s, certificate, source)
+
+            metrics.send(
+                "certificate_clean",
+                "counter",
+                1,
+                metric_tags={"status": status, "source": source.label, "certificate": certificate.name},
+            )
+            current_app.logger.warning(f"Removed {certificate.name} from source {source.label} during cleaning")
+            cleaned += 1
+
+        info_text = f"[+] Finished cleaning source: {source.label}. " \
+                    f"Removed {cleaned} certificates from source. " \
+                    f"Run Time: {(time.time() - start_time)}\n"
+        print(info_text)
+        current_app.logger.warning(info_text)
diff --git a/lemur/sources/service.py b/lemur/sources/service.py
index f4783313..fafa6f5a 100644
--- a/lemur/sources/service.py
+++ b/lemur/sources/service.py
@@ -123,15 +123,19 @@ def sync_endpoints(source):
                                               "acct": s.get_option("accountNumber", source.options)})
 
         if not endpoint["certificate"]:
-            current_app.logger.error(
-                "Certificate Not Found. Name: {0} Endpoint: {1}".format(
-                    certificate_name, endpoint["name"]
-                )
-            )
+            current_app.logger.error({
+                "message": "Certificate Not Found",
+                "certificate_name": certificate_name,
+                "endpoint_name": endpoint["name"],
+                "dns_name": endpoint.get("dnsname"),
+                "account": s.get_option("accountNumber", source.options),
+            })
+
             metrics.send("endpoint.certificate.not.found",
                          "counter", 1,
                          metric_tags={"cert": certificate_name, "endpoint": endpoint["name"],
-                                      "acct": s.get_option("accountNumber", source.options)})
+                                      "acct": s.get_option("accountNumber", source.options),
+                                      "dnsname": endpoint.get("dnsname")})
             continue
 
         policy = endpoint.pop("policy")
@@ -193,6 +197,11 @@ def sync_certificates(source, user):
     s = plugins.get(source.plugin_name)
     certificates = s.get_certificates(source.options)
 
+    # emitting the count of certificates on the source
+    metrics.send("sync_certificates_count",
+                 "gauge", len(certificates),
+                 metric_tags={"source": source.label})
+
     for certificate in certificates:
         exists, updated_by_hash = find_cert(certificate)
 
diff --git a/lemur/static/app/angular/certificates/certificate/tracking.tpl.html b/lemur/static/app/angular/certificates/certificate/tracking.tpl.html
index 7ac2107f..027add0f 100644
--- a/lemur/static/app/angular/certificates/certificate/tracking.tpl.html
+++ b/lemur/static/app/angular/certificates/certificate/tracking.tpl.html
@@ -140,7 +140,6 @@
         <select ng-model="certificate.validityYears" class="form-control">
           <option value="">-</option>
           <option value="1">1 year</option>
-          <option value="2">2 years</option>
         </select>
       </div>
       <span style="padding-top: 15px" class="text-center col-sm-1">
diff --git a/lemur/tests/test_certificates.py b/lemur/tests/test_certificates.py
index adafa605..41584cb3 100644
--- a/lemur/tests/test_certificates.py
+++ b/lemur/tests/test_certificates.py
@@ -9,7 +9,8 @@ from cryptography import x509
 from cryptography.hazmat.backends import default_backend
 from marshmallow import ValidationError
 from freezegun import freeze_time
-from mock import patch
+# from mock import patch
+from unittest.mock import patch
 
 from lemur.certificates.service import create_csr
 from lemur.certificates.views import *  # noqa
@@ -906,12 +907,12 @@ def test_certificate_get_body(client):
     assert response_body["serial"] == "211983098819107449768450703123665283596"
     assert response_body["serialHex"] == "9F7A75B39DAE4C3F9524C68B06DA6A0C"
     assert response_body["distinguishedName"] == (
-        "CN=LemurTrust Unittests Class 1 CA 2018,"
-        "O=LemurTrust Enterprises Ltd,"
-        "OU=Unittesting Operations Center,"
-        "C=EE,"
+        "L=Earth,"
         "ST=N/A,"
-        "L=Earth"
+        "C=EE,"
+        "OU=Unittesting Operations Center,"
+        "O=LemurTrust Enterprises Ltd,"
+        "CN=LemurTrust Unittests Class 1 CA 2018"
     )
 
 
diff --git a/package.json b/package.json
index a34fc745..771a4386 100644
--- a/package.json
+++ b/package.json
@@ -60,7 +60,7 @@
   },
   "devDependencies": {
     "gulp": "^3.9.1",
-    "jshint": "^2.8.0",
+    "jshint": "^2.11.0",
     "karma-chrome-launcher": "^2.0.0"
   }
 }
diff --git a/requirements-dev.txt b/requirements-dev.txt
index d1423888..cb2edc22 100644
--- a/requirements-dev.txt
+++ b/requirements-dev.txt
@@ -4,38 +4,44 @@
 #
 #    pip-compile --no-index --output-file=requirements-dev.txt requirements-dev.in
 #
-aspy.yaml==1.3.0          # via pre-commit
-bleach==3.1.0             # via readme-renderer
-certifi==2019.11.28       # via requests
-cfgv==2.0.1               # via pre-commit
+appdirs==1.4.3            # via virtualenv
+bleach==3.1.4             # via readme-renderer
+certifi==2020.4.5.1       # via requests
+cffi==1.14.0              # via cryptography
+cfgv==3.1.0               # via pre-commit
 chardet==3.0.4            # via requests
-docutils==0.15.2          # via readme-renderer
-flake8==3.5.0
-identify==1.4.9           # via pre-commit
-idna==2.8                 # via requests
-importlib-metadata==1.3.0  # via keyring, pre-commit, twine
-invoke==1.3.0
-keyring==21.0.0           # via twine
+cryptography==2.9         # via secretstorage
+distlib==0.3.0            # via virtualenv
+docutils==0.16            # via readme-renderer
+filelock==3.0.12          # via virtualenv
+flake8==3.5.0             # via -r requirements-dev.in
+identify==1.4.14          # via pre-commit
+idna==2.9                 # via requests
+importlib-metadata==1.6.0  # via keyring, pre-commit, twine, virtualenv
+invoke==1.4.1             # via -r requirements-dev.in
+jeepney==0.4.3            # via keyring, secretstorage
+keyring==21.2.0           # via twine
 mccabe==0.6.1             # via flake8
-more-itertools==8.0.2     # via zipp
-nodeenv==1.3.3
+nodeenv==1.3.5            # via -r requirements-dev.in, pre-commit
 pkginfo==1.5.0.1          # via twine
-pre-commit==1.21.0
+pre-commit==2.2.0         # via -r requirements-dev.in
 pycodestyle==2.3.1        # via flake8
+pycparser==2.20           # via cffi
 pyflakes==1.6.0           # via flake8
-pygments==2.5.2           # via readme-renderer
-pyyaml==5.2
-readme-renderer==24.0     # via twine
+pygments==2.6.1           # via readme-renderer
+pyyaml==5.3.1             # via -r requirements-dev.in, pre-commit
+readme-renderer==25.0     # via twine
 requests-toolbelt==0.9.1  # via twine
-requests==2.22.0          # via requests-toolbelt, twine
-six==1.13.0               # via bleach, cfgv, pre-commit, readme-renderer
+requests==2.23.0          # via requests-toolbelt, twine
+secretstorage==3.1.2      # via keyring
+six==1.14.0               # via bleach, cryptography, readme-renderer, virtualenv
 toml==0.10.0              # via pre-commit
-tqdm==4.41.1              # via twine
-twine==3.1.1
-urllib3==1.25.7           # via requests
-virtualenv==16.7.9        # via pre-commit
+tqdm==4.45.0              # via twine
+twine==3.1.1              # via -r requirements-dev.in
+urllib3==1.25.8           # via requests
+virtualenv==20.0.17       # via pre-commit
 webencodings==0.5.1       # via bleach
-zipp==0.6.0               # via importlib-metadata
+zipp==3.1.0               # via importlib-metadata
 
 # The following packages are considered to be unsafe in a requirements file:
 # setuptools
diff --git a/requirements-docs.txt b/requirements-docs.txt
index 893965ca..54bde14e 100644
--- a/requirements-docs.txt
+++ b/requirements-docs.txt
@@ -4,111 +4,108 @@
 #
 #    pip-compile --no-index --output-file=requirements-docs.txt requirements-docs.in
 #
-acme==1.0.0
+acme==1.3.0               # via -r requirements.txt
 alabaster==0.7.12         # via sphinx
-alembic-autogenerate-enums==0.0.2
-alembic==1.3.2
-amqp==2.5.2
-aniso8601==8.0.0
-arrow==0.15.5
-asyncpool==1.0
+alembic-autogenerate-enums==0.0.2  # via -r requirements.txt
+alembic==1.4.2            # via -r requirements.txt, flask-migrate
+amqp==2.5.2               # via -r requirements.txt, kombu
+aniso8601==8.0.0          # via -r requirements.txt, flask-restful
+arrow==0.15.5             # via -r requirements.txt
+asyncpool==1.0            # via -r requirements.txt
 babel==2.8.0              # via sphinx
-bcrypt==3.1.7
-billiard==3.6.1.0
-blinker==1.4
-boto3==1.10.46
-botocore==1.13.46
-celery[redis]==4.4.0
-certifi==2019.11.28
-certsrv==2.1.1
-cffi==1.13.2
-chardet==3.0.4
-click==7.0
-cloudflare==2.3.1
-cryptography==2.8
-dnspython3==1.15.0
-dnspython==1.15.0
-docutils==0.15.2
-dyn==1.8.1
-flask-bcrypt==0.7.1
-flask-cors==3.0.8
-flask-mail==0.9.1
-flask-migrate==2.5.2
-flask-principal==0.4.0
-flask-replicated==1.3
-flask-restful==0.3.7
-flask-script==2.0.6
-flask-sqlalchemy==2.4.1
-flask==1.1.1
-future==0.18.2
-gunicorn==20.0.4
-hvac==0.9.6
-idna==2.8
+bcrypt==3.1.7             # via -r requirements.txt, flask-bcrypt, paramiko
+billiard==3.6.3.0         # via -r requirements.txt, celery
+blinker==1.4              # via -r requirements.txt, flask-mail, flask-principal, raven
+boto3==1.12.39            # via -r requirements.txt
+botocore==1.15.39         # via -r requirements.txt, boto3, s3transfer
+celery[redis]==4.4.2      # via -r requirements.txt
+certifi==2020.4.5.1       # via -r requirements.txt, requests
+certsrv==2.1.1            # via -r requirements.txt
+cffi==1.14.0              # via -r requirements.txt, bcrypt, cryptography, pynacl
+chardet==3.0.4            # via -r requirements.txt, requests
+click==7.1.1              # via -r requirements.txt, flask
+cloudflare==2.6.5         # via -r requirements.txt
+cryptography==2.9         # via -r requirements.txt, acme, josepy, paramiko, pyopenssl, requests
+dnspython3==1.15.0        # via -r requirements.txt
+dnspython==1.15.0         # via -r requirements.txt, dnspython3
+docutils==0.15.2          # via -r requirements.txt, botocore, sphinx
+dyn==1.8.1                # via -r requirements.txt
+flask-bcrypt==0.7.1       # via -r requirements.txt
+flask-cors==3.0.8         # via -r requirements.txt
+flask-mail==0.9.1         # via -r requirements.txt
+flask-migrate==2.5.3      # via -r requirements.txt
+flask-principal==0.4.0    # via -r requirements.txt
+flask-replicated==1.3     # via -r requirements.txt
+flask-restful==0.3.8      # via -r requirements.txt
+flask-script==2.0.6       # via -r requirements.txt
+flask-sqlalchemy==2.4.1   # via -r requirements.txt, flask-migrate
+flask==1.1.2              # via -r requirements.txt, flask-bcrypt, flask-cors, flask-mail, flask-migrate, flask-principal, flask-restful, flask-script, flask-sqlalchemy, raven
+future==0.18.2            # via -r requirements.txt, cloudflare
+gunicorn==20.0.4          # via -r requirements.txt
+hvac==0.10.1              # via -r requirements.txt
+idna==2.9                 # via -r requirements.txt, requests
 imagesize==1.2.0          # via sphinx
-importlib-metadata==1.3.0
-inflection==0.3.1
-itsdangerous==1.1.0
-javaobj-py3==0.4.0.1
-jinja2==2.10.3
-jmespath==0.9.4
-josepy==1.2.0
-jsonlines==1.2.0
-kombu==4.6.7
-lockfile==0.12.2
-logmatic-python==0.1.7
-mako==1.1.0
-markupsafe==1.1.1
-marshmallow-sqlalchemy==0.21.0
-marshmallow==2.20.4
-mock==3.0.5
-more-itertools==8.0.2
-ndg-httpsclient==0.5.1
-packaging==19.2           # via sphinx
-paramiko==2.7.1
-pem==19.3.0
-psycopg2==2.8.4
-pyasn1-modules==0.2.7
-pyasn1==0.4.8
-pycparser==2.19
-pycryptodomex==3.9.4
-pygments==2.5.2           # via sphinx
-pyjks==19.0.0
-pyjwt==1.7.1
-pynacl==1.3.0
-pyopenssl==19.1.0
-pyparsing==2.4.6          # via packaging
-pyrfc3339==1.1
-python-dateutil==2.8.1
-python-editor==1.0.4
-python-json-logger==0.1.11
-pytz==2019.3
-pyyaml==5.2
-raven[flask]==6.10.0
-redis==3.3.11
-requests-toolbelt==0.9.1
-requests[security]==2.22.0
-retrying==1.3.3
-s3transfer==0.2.1
-six==1.13.0
+importlib-metadata==1.6.0  # via -r requirements.txt, kombu
+inflection==0.4.0         # via -r requirements.txt
+itsdangerous==1.1.0       # via -r requirements.txt, flask
+javaobj-py3==0.4.0.1      # via -r requirements.txt, pyjks
+jinja2==2.11.2            # via -r requirements.txt, flask, sphinx
+jmespath==0.9.5           # via -r requirements.txt, boto3, botocore
+josepy==1.3.0             # via -r requirements.txt, acme
+jsonlines==1.2.0          # via -r requirements.txt, cloudflare
+kombu==4.6.8              # via -r requirements.txt, celery
+lockfile==0.12.2          # via -r requirements.txt
+logmatic-python==0.1.7    # via -r requirements.txt
+mako==1.1.2               # via -r requirements.txt, alembic
+markupsafe==1.1.1         # via -r requirements.txt, jinja2, mako
+marshmallow-sqlalchemy==0.22.3  # via -r requirements.txt
+marshmallow==2.20.4       # via -r requirements.txt, marshmallow-sqlalchemy
+mock==4.0.2               # via -r requirements.txt, acme
+ndg-httpsclient==0.5.1    # via -r requirements.txt
+packaging==20.3           # via sphinx
+paramiko==2.7.1           # via -r requirements.txt
+pem==20.1.0               # via -r requirements.txt
+psycopg2==2.8.5           # via -r requirements.txt
+pycparser==2.20           # via -r requirements.txt, cffi
+pycryptodomex==3.9.7      # via -r requirements.txt, pyjks
+pygments==2.6.1           # via sphinx
+pyjks==19.0.0             # via -r requirements.txt
+pyjwt==1.7.1              # via -r requirements.txt
+pynacl==1.3.0             # via -r requirements.txt, paramiko
+pyopenssl==19.1.0         # via -r requirements.txt, acme, josepy, ndg-httpsclient, requests
+pyparsing==2.4.7          # via packaging
+pyrfc3339==1.1            # via -r requirements.txt, acme
+python-dateutil==2.8.1    # via -r requirements.txt, alembic, arrow, botocore
+python-editor==1.0.4      # via -r requirements.txt, alembic
+python-json-logger==0.1.11  # via -r requirements.txt, logmatic-python
+pytz==2019.3              # via -r requirements.txt, acme, babel, celery, flask-restful, pyrfc3339
+pyyaml==5.3.1             # via -r requirements.txt, cloudflare
+raven[flask]==6.10.0      # via -r requirements.txt
+redis==3.4.1              # via -r requirements.txt, celery
+requests-toolbelt==0.9.1  # via -r requirements.txt, acme
+requests[security]==2.23.0  # via -r requirements.txt, acme, certsrv, cloudflare, hvac, requests-toolbelt, sphinx
+retrying==1.3.3           # via -r requirements.txt
+s3transfer==0.3.3         # via -r requirements.txt, boto3
+six==1.14.0               # via -r requirements.txt, acme, bcrypt, cryptography, flask-cors, flask-restful, hvac, josepy, jsonlines, packaging, pynacl, pyopenssl, python-dateutil, retrying, sphinxcontrib-httpdomain, sqlalchemy-utils
 snowballstemmer==2.0.0    # via sphinx
-sphinx-rtd-theme==0.4.3
-sphinx==2.3.1
-sphinxcontrib-applehelp==1.0.1  # via sphinx
-sphinxcontrib-devhelp==1.0.1  # via sphinx
-sphinxcontrib-htmlhelp==1.0.2  # via sphinx
-sphinxcontrib-httpdomain==1.7.0
+sphinx-rtd-theme==0.4.3   # via -r requirements-docs.in
+sphinx==3.0.1             # via -r requirements-docs.in, sphinx-rtd-theme, sphinxcontrib-httpdomain
+sphinxcontrib-applehelp==1.0.2  # via sphinx
+sphinxcontrib-devhelp==1.0.2  # via sphinx
+sphinxcontrib-htmlhelp==1.0.3  # via sphinx
+sphinxcontrib-httpdomain==1.7.0  # via -r requirements-docs.in
 sphinxcontrib-jsmath==1.0.1  # via sphinx
-sphinxcontrib-qthelp==1.0.2  # via sphinx
-sphinxcontrib-serializinghtml==1.1.3  # via sphinx
-sqlalchemy-utils==0.36.1
-sqlalchemy==1.3.12
-tabulate==0.8.6
-twofish==0.3.0
-urllib3==1.25.7
-vine==1.3.0
-werkzeug==0.16.0
-xmltodict==0.12.0
-zipp==0.6.0
+sphinxcontrib-qthelp==1.0.3  # via sphinx
+sphinxcontrib-serializinghtml==1.1.4  # via sphinx
+sqlalchemy-utils==0.36.3  # via -r requirements.txt
+sqlalchemy==1.3.16        # via -r requirements.txt, alembic, flask-sqlalchemy, marshmallow-sqlalchemy, sqlalchemy-utils
+tabulate==0.8.7           # via -r requirements.txt
+twofish==0.3.0            # via -r requirements.txt, pyjks
+urllib3==1.25.8           # via -r requirements.txt, botocore, requests
+vine==1.3.0               # via -r requirements.txt, amqp, celery
+werkzeug==1.0.1           # via -r requirements.txt, flask
+xmltodict==0.12.0         # via -r requirements.txt
+zipp==3.1.0               # via -r requirements.txt, importlib-metadata
 
 # The following packages are considered to be unsafe in a requirements file:
 # setuptools
diff --git a/requirements-tests.txt b/requirements-tests.txt
index 293bd350..5f9cafcc 100644
--- a/requirements-tests.txt
+++ b/requirements-tests.txt
@@ -6,85 +6,87 @@
 #
 appdirs==1.4.3            # via black
 attrs==19.3.0             # via black, jsonschema, pytest
-aws-sam-translator==1.19.1  # via cfn-lint
-aws-xray-sdk==2.4.3       # via moto
-bandit==1.6.2
-black==19.10b0
-boto3==1.10.46            # via aws-sam-translator, moto
+aws-sam-translator==1.22.0  # via cfn-lint
+aws-xray-sdk==2.5.0       # via moto
+bandit==1.6.2             # via -r requirements-tests.in
+black==19.10b0            # via -r requirements-tests.in
+boto3==1.12.39            # via aws-sam-translator, moto
 boto==2.49.0              # via moto
-botocore==1.13.46         # via aws-xray-sdk, boto3, moto, s3transfer
-certifi==2019.11.28       # via requests
-cffi==1.13.2              # via cryptography
-cfn-lint==0.26.2          # via moto
+botocore==1.15.39         # via aws-xray-sdk, boto3, moto, s3transfer
+certifi==2020.4.5.1       # via requests
+cffi==1.14.0              # via cryptography
+cfn-lint==0.29.5          # via moto
 chardet==3.0.4            # via requests
-click==7.0                # via black, flask
-coverage==5.0.1
-cryptography==2.8         # via moto, sshpubkeys
-docker==4.1.0             # via moto
+click==7.1.1              # via black, flask
+coverage==5.1             # via -r requirements-tests.in
+cryptography==2.9         # via moto, sshpubkeys
+decorator==4.4.2          # via networkx
+docker==4.2.0             # via moto
 docutils==0.15.2          # via botocore
 ecdsa==0.15               # via python-jose, sshpubkeys
-factory-boy==2.12.0
-faker==3.0.0
-fakeredis==1.1.0
-flask==1.1.1              # via pytest-flask
-freezegun==0.3.12
+factory-boy==2.12.0       # via -r requirements-tests.in
+faker==4.0.3              # via -r requirements-tests.in, factory-boy
+fakeredis==1.4.0          # via -r requirements-tests.in
+flask==1.1.2              # via pytest-flask
+freezegun==0.3.15         # via -r requirements-tests.in
 future==0.18.2            # via aws-xray-sdk
-gitdb2==2.0.6             # via gitpython
-gitpython==3.0.5          # via bandit
+gitdb==4.0.4              # via gitpython
+gitpython==3.1.1          # via bandit
 idna==2.8                 # via moto, requests
-importlib-metadata==1.3.0  # via jsonschema, pluggy, pytest
+importlib-metadata==1.6.0  # via jsonpickle, jsonschema, pluggy, pytest
 itsdangerous==1.1.0       # via flask
-jinja2==2.10.3            # via flask, moto
-jmespath==0.9.4           # via boto3, botocore
+jinja2==2.11.2            # via flask, moto
+jmespath==0.9.5           # via boto3, botocore
 jsondiff==1.1.2           # via moto
-jsonpatch==1.24           # via cfn-lint
-jsonpickle==1.2           # via aws-xray-sdk
+jsonpatch==1.25           # via cfn-lint
+jsonpickle==1.4           # via aws-xray-sdk
 jsonpointer==2.0          # via jsonpatch
 jsonschema==3.2.0         # via aws-sam-translator, cfn-lint
 markupsafe==1.1.1         # via jinja2
-mock==3.0.5               # via moto
-more-itertools==8.0.2     # via pytest, zipp
-moto==1.3.14
-nose==1.3.7
-packaging==19.2           # via pytest
-pathspec==0.7.0           # via black
-pbr==5.4.4                # via stevedore
+mock==4.0.2               # via moto
+more-itertools==8.2.0     # via pytest
+moto==1.3.14              # via -r requirements-tests.in
+networkx==2.4             # via cfn-lint
+nose==1.3.7               # via -r requirements-tests.in
+packaging==20.3           # via pytest
+pathspec==0.8.0           # via black
+pbr==5.4.5                # via stevedore
 pluggy==0.13.1            # via pytest
 py==1.8.1                 # via pytest
 pyasn1==0.4.8             # via python-jose, rsa
-pycparser==2.19           # via cffi
-pyflakes==2.1.1
-pyparsing==2.4.6          # via packaging
-pyrsistent==0.15.6        # via jsonschema
-pytest-flask==0.15.0
-pytest-mock==1.13.0
-pytest==5.3.2
+pycparser==2.20           # via cffi
+pyflakes==2.2.0           # via -r requirements-tests.in
+pyparsing==2.4.7          # via packaging
+pyrsistent==0.16.0        # via jsonschema
+pytest-flask==1.0.0       # via -r requirements-tests.in
+pytest-mock==3.0.0        # via -r requirements-tests.in
+pytest==5.4.1             # via -r requirements-tests.in, pytest-flask, pytest-mock
 python-dateutil==2.8.1    # via botocore, faker, freezegun, moto
 python-jose==3.1.0        # via moto
 pytz==2019.3              # via moto
-pyyaml==5.2
-redis==3.3.11             # via fakeredis
-regex==2019.12.20         # via black
-requests-mock==1.7.0
-requests==2.22.0          # via docker, moto, requests-mock, responses
-responses==0.10.9         # via moto
+pyyaml==5.3.1             # via -r requirements-tests.in, bandit, cfn-lint, moto
+redis==3.4.1              # via fakeredis
+regex==2020.4.4           # via black
+requests-mock==1.7.0      # via -r requirements-tests.in
+requests==2.23.0          # via docker, moto, requests-mock, responses
+responses==0.10.12        # via moto
 rsa==4.0                  # via python-jose
-s3transfer==0.2.1         # via boto3
-six==1.13.0               # via aws-sam-translator, bandit, cfn-lint, cryptography, docker, ecdsa, faker, fakeredis, freezegun, jsonschema, mock, moto, packaging, pyrsistent, python-dateutil, python-jose, requests-mock, responses, stevedore, websocket-client
-smmap2==2.0.5             # via gitdb2
+s3transfer==0.3.3         # via boto3
+six==1.14.0               # via aws-sam-translator, bandit, cfn-lint, cryptography, docker, ecdsa, fakeredis, freezegun, jsonschema, moto, packaging, python-dateutil, python-jose, requests-mock, responses, stevedore, websocket-client
+smmap==3.0.2              # via gitdb
 sortedcontainers==2.1.0   # via fakeredis
 sshpubkeys==3.1.0         # via moto
-stevedore==1.31.0         # via bandit
+stevedore==1.32.0         # via bandit
 text-unidecode==1.3       # via faker
 toml==0.10.0              # via black
-typed-ast==1.4.0          # via black
-urllib3==1.25.7           # via botocore, requests
-wcwidth==0.1.8            # via pytest
+typed-ast==1.4.1          # via black
+urllib3==1.25.8           # via botocore, requests
+wcwidth==0.1.9            # via pytest
 websocket-client==0.57.0  # via docker
-werkzeug==0.16.0          # via flask, moto, pytest-flask
-wrapt==1.11.2             # via aws-xray-sdk
+werkzeug==1.0.1           # via flask, moto, pytest-flask
+wrapt==1.12.1             # via aws-xray-sdk
 xmltodict==0.12.0         # via moto
-zipp==0.6.0               # via importlib-metadata
+zipp==3.1.0               # via importlib-metadata
 
 # The following packages are considered to be unsafe in a requirements file:
 # setuptools
diff --git a/requirements.txt b/requirements.txt
index 639c9377..bdad75b0 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -4,96 +4,95 @@
 #
 #    pip-compile --no-index --output-file=requirements.txt requirements.in
 #
-acme==1.0.0
-alembic-autogenerate-enums==0.0.2
-alembic==1.3.2            # via flask-migrate
+acme==1.3.0               # via -r requirements.in
+alembic-autogenerate-enums==0.0.2  # via -r requirements.in
+alembic==1.4.2            # via flask-migrate
 amqp==2.5.2               # via kombu
 aniso8601==8.0.0          # via flask-restful
-arrow==0.15.5
-asyncpool==1.0
+arrow==0.15.5             # via -r requirements.in
+asyncpool==1.0            # via -r requirements.in
 bcrypt==3.1.7             # via flask-bcrypt, paramiko
-billiard==3.6.1.0         # via celery
+billiard==3.6.3.0         # via celery
 blinker==1.4              # via flask-mail, flask-principal, raven
-boto3==1.10.46
-botocore==1.13.46
-celery[redis]==4.4.0
-certifi==2019.11.28
-certsrv==2.1.1
-cffi==1.13.2              # via bcrypt, cryptography, pynacl
+boto3==1.12.39            # via -r requirements.in
+botocore==1.15.39         # via -r requirements.in, boto3, s3transfer
+celery[redis]==4.4.2      # via -r requirements.in
+certifi==2020.4.5.1       # via -r requirements.in, requests
+certsrv==2.1.1            # via -r requirements.in
+cffi==1.14.0              # via bcrypt, cryptography, pynacl
 chardet==3.0.4            # via requests
-click==7.0                # via flask
-cloudflare==2.3.1
-cryptography==2.8
-dnspython3==1.15.0
+click==7.1.1              # via flask
+cloudflare==2.6.5         # via -r requirements.in
+cryptography==2.9         # via -r requirements.in, acme, josepy, paramiko, pyopenssl, requests
+dnspython3==1.15.0        # via -r requirements.in
 dnspython==1.15.0         # via dnspython3
 docutils==0.15.2          # via botocore
-dyn==1.8.1
-flask-bcrypt==0.7.1
-flask-cors==3.0.8
-flask-mail==0.9.1
-flask-migrate==2.5.2
-flask-principal==0.4.0
-flask-replicated==1.3
-flask-restful==0.3.7
-flask-script==2.0.6
-flask-sqlalchemy==2.4.1
-flask==1.1.1
-future==0.18.2
-gunicorn==20.0.4
-hvac==0.9.6
-idna==2.8                 # via requests
-importlib-metadata==1.3.0  # via kombu
-inflection==0.3.1
+dyn==1.8.1                # via -r requirements.in
+flask-bcrypt==0.7.1       # via -r requirements.in
+flask-cors==3.0.8         # via -r requirements.in
+flask-mail==0.9.1         # via -r requirements.in
+flask-migrate==2.5.3      # via -r requirements.in
+flask-principal==0.4.0    # via -r requirements.in
+flask-replicated==1.3     # via -r requirements.in
+flask-restful==0.3.8      # via -r requirements.in
+flask-script==2.0.6       # via -r requirements.in
+flask-sqlalchemy==2.4.1   # via -r requirements.in, flask-migrate
+flask==1.1.2              # via -r requirements.in, flask-bcrypt, flask-cors, flask-mail, flask-migrate, flask-principal, flask-restful, flask-script, flask-sqlalchemy, raven
+future==0.18.2            # via -r requirements.in, cloudflare
+gunicorn==20.0.4          # via -r requirements.in
+hvac==0.10.1              # via -r requirements.in
+idna==2.9                 # via requests
+importlib-metadata==1.6.0  # via kombu
+inflection==0.4.0         # via -r requirements.in
 itsdangerous==1.1.0       # via flask
 javaobj-py3==0.4.0.1      # via pyjks
-jinja2==2.10.3
-jmespath==0.9.4           # via boto3, botocore
-josepy==1.2.0             # via acme
+jinja2==2.11.2            # via -r requirements.in, flask
+jmespath==0.9.5           # via boto3, botocore
+josepy==1.3.0             # via acme
 jsonlines==1.2.0          # via cloudflare
-kombu==4.6.7              # via celery
-lockfile==0.12.2
-logmatic-python==0.1.7
-mako==1.1.0               # via alembic
+kombu==4.6.8              # via celery
+lockfile==0.12.2          # via -r requirements.in
+logmatic-python==0.1.7    # via -r requirements.in
+mako==1.1.2               # via alembic
 markupsafe==1.1.1         # via jinja2, mako
-marshmallow-sqlalchemy==0.21.0
-marshmallow==2.20.4
-mock==3.0.5               # via acme
-more-itertools==8.0.2     # via zipp
-ndg-httpsclient==0.5.1
-paramiko==2.7.1
-pem==19.3.0
-psycopg2==2.8.4
-pyasn1-modules==0.2.7     # via pyjks, python-ldap
+marshmallow-sqlalchemy==0.22.3  # via -r requirements.in
+marshmallow==2.20.4       # via -r requirements.in, marshmallow-sqlalchemy
+mock==4.0.2               # via acme
+ndg-httpsclient==0.5.1    # via -r requirements.in
+paramiko==2.7.1           # via -r requirements.in
+pem==20.1.0               # via -r requirements.in
+psycopg2==2.8.5           # via -r requirements.in
+pyasn1-modules==0.2.8     # via pyjks, python-ldap
 pyasn1==0.4.8             # via ndg-httpsclient, pyasn1-modules, pyjks, python-ldap
-pycparser==2.19           # via cffi
-pycryptodomex==3.9.4      # via pyjks
-pyjks==19.0.0
-pyjwt==1.7.1
+pycparser==2.20           # via cffi
+pycryptodomex==3.9.7      # via pyjks
+pyjks==19.0.0             # via -r requirements.in
+pyjwt==1.7.1              # via -r requirements.in
 pynacl==1.3.0             # via paramiko
-pyopenssl==19.1.0
+pyopenssl==19.1.0         # via -r requirements.in, acme, josepy, ndg-httpsclient, requests
 pyrfc3339==1.1            # via acme
 python-dateutil==2.8.1    # via alembic, arrow, botocore
 python-editor==1.0.4      # via alembic
 python-json-logger==0.1.11  # via logmatic-python
-python-ldap==3.2.0
+python-ldap==3.2.0        # via -r requirements.in
 pytz==2019.3              # via acme, celery, flask-restful, pyrfc3339
-pyyaml==5.2
-raven[flask]==6.10.0
-redis==3.3.11
+pyyaml==5.3.1             # via -r requirements.in, cloudflare
+raven[flask]==6.10.0      # via -r requirements.in
+redis==3.4.1              # via -r requirements.in, celery
 requests-toolbelt==0.9.1  # via acme
-requests[security]==2.22.0
-retrying==1.3.3
-s3transfer==0.2.1         # via boto3
-six==1.13.0
-sqlalchemy-utils==0.36.1
-sqlalchemy==1.3.12        # via alembic, flask-sqlalchemy, marshmallow-sqlalchemy, sqlalchemy-utils
-tabulate==0.8.6
+requests[security]==2.23.0  # via -r requirements.in, acme, certsrv, cloudflare, hvac, requests-toolbelt
+retrying==1.3.3           # via -r requirements.in
+s3transfer==0.3.3         # via boto3
+six==1.14.0               # via -r requirements.in, acme, bcrypt, cryptography, flask-cors, flask-restful, hvac, josepy, jsonlines, pynacl, pyopenssl, python-dateutil, retrying, sqlalchemy-utils
+sqlalchemy-utils==0.36.3  # via -r requirements.in
+sqlalchemy==1.3.16        # via alembic, flask-sqlalchemy, marshmallow-sqlalchemy, sqlalchemy-utils
+tabulate==0.8.7           # via -r requirements.in
 twofish==0.3.0            # via pyjks
-urllib3==1.25.7           # via botocore, requests
+urllib3==1.25.8           # via botocore, requests
 vine==1.3.0               # via amqp, celery
-werkzeug==0.16.0          # via flask
-xmltodict==0.12.0
-zipp==0.6.0               # via importlib-metadata
+werkzeug==1.0.1           # via flask
+xmltodict==0.12.0         # via -r requirements.in
+zipp==3.1.0               # via importlib-metadata
 
 # The following packages are considered to be unsafe in a requirements file:
 # setuptools