diff --git a/bower.json b/bower.json
index f7d5500d..44cce994 100644
--- a/bower.json
+++ b/bower.json
@@ -11,12 +11,12 @@
     "angular": "1.4.9",
     "json3": "~3.3",
     "es5-shim": "~4.5.0",
-    "bootstrap": "~3.3.6",
     "angular-bootstrap": "~1.1.1",
     "angular-animate": "~1.4.9",
     "restangular": "~1.5.1",
     "ng-table": "~0.8.3",
     "moment": "~2.11.1",
+    "bootstrap": "~3.4.1",
     "angular-loading-bar": "~0.8.0",
     "angular-moment": "~0.10.3",
     "moment-range": "~2.1.0",
@@ -24,7 +24,7 @@
     "angularjs-toaster": "~1.0.0",
     "angular-chart.js": "~0.8.8",
     "ngletteravatar": "~4.0.0",
-    "bootswatch": "~3.3.6",
+    "bootswatch": "~3.4.1",
     "fontawesome": "~4.5.0",
     "satellizer": "~0.13.4",
     "angular-ui-router": "~0.2.15",
diff --git a/docs/production/index.rst b/docs/production/index.rst
index cd044ca4..b91ed6bd 100644
--- a/docs/production/index.rst
+++ b/docs/production/index.rst
@@ -390,6 +390,10 @@ Here are the Celery configuration variables that should be set::
     CELERY_IMPORTS = ('lemur.common.celery')
     CELERY_TIMEZONE = 'UTC'
 
+Do not forget to import crontab module in your configuration file::
+
+    from celery.task.schedules import crontab
+
 You must start a single Celery scheduler instance and one or more worker instances in order to handle incoming tasks.
 The scheduler can be started with::
 
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/cli.py b/lemur/certificates/cli.py
index b57ff175..d007e458 100644
--- a/lemur/certificates/cli.py
+++ b/lemur/certificates/cli.py
@@ -5,29 +5,19 @@
     :license: Apache, see LICENSE for more details.
 .. moduleauthor:: Kevin Glisson <kglisson@netflix.com>
 """
-import sys
 import multiprocessing
-from tabulate import tabulate
-from sqlalchemy import or_
-
+import sys
 from flask import current_app
-
-from flask_script import Manager
 from flask_principal import Identity, identity_changed
-
+from flask_script import Manager
+from sqlalchemy import or_
+from tabulate import tabulate
 
 from lemur import database
-from lemur.extensions import sentry
-from lemur.extensions import metrics
-from lemur.plugins.base import plugins
-from lemur.constants import SUCCESS_METRIC_STATUS, FAILURE_METRIC_STATUS
-from lemur.deployment import service as deployment_service
-from lemur.endpoints import service as endpoint_service
-from lemur.notifications.messaging import send_rotation_notification
-from lemur.domains.models import Domain
 from lemur.authorities.models import Authority
-from lemur.certificates.schemas import CertificateOutputSchema
+from lemur.authorities.service import get as authorities_get_by_id
 from lemur.certificates.models import Certificate
+from lemur.certificates.schemas import CertificateOutputSchema
 from lemur.certificates.service import (
     reissue_certificate,
     get_certificate_primitives,
@@ -35,9 +25,16 @@ from lemur.certificates.service import (
     get_by_name,
     get_all_certs,
     get,
+    get_all_certs_attached_to_endpoint_without_autorotate,
 )
-
 from lemur.certificates.verify import verify_string
+from lemur.constants import SUCCESS_METRIC_STATUS, FAILURE_METRIC_STATUS
+from lemur.deployment import service as deployment_service
+from lemur.domains.models import Domain
+from lemur.endpoints import service as endpoint_service
+from lemur.extensions import sentry, metrics
+from lemur.notifications.messaging import send_rotation_notification
+from lemur.plugins.base import plugins
 
 manager = Manager(usage="Handles all certificate related tasks.")
 
@@ -482,3 +479,45 @@ def check_revoked():
             cert.status = "unknown"
 
         database.update(cert)
+
+
+@manager.command
+def automatically_enable_autorotate():
+    """
+    This function automatically enables auto-rotation for unexpired certificates that are
+    attached to an endpoint but do not have autorotate enabled.
+
+    WARNING: This will overwrite the Auto-rotate toggle!
+    """
+    log_data = {
+        "function": f"{__name__}.{sys._getframe().f_code.co_name}",
+        "message": "Enabling auto-rotate for certificate"
+    }
+
+    permitted_authorities = current_app.config.get("ENABLE_AUTO_ROTATE_AUTHORITY", [])
+
+    eligible_certs = get_all_certs_attached_to_endpoint_without_autorotate()
+    for cert in eligible_certs:
+
+        if cert.authority_id not in permitted_authorities:
+            continue
+
+        log_data["certificate"] = cert.name
+        log_data["certificate_id"] = cert.id
+        log_data["authority_id"] = cert.authority_id
+        log_data["authority_name"] = authorities_get_by_id(cert.authority_id).name
+        if cert.destinations:
+            log_data["destination_names"] = ', '.join([d.label for d in cert.destinations])
+        else:
+            log_data["destination_names"] = "NONE"
+        current_app.logger.info(log_data)
+        metrics.send("automatically_enable_autorotate",
+                     "counter", 1,
+                     metric_tags={"certificate": log_data["certificate"],
+                                  "certificate_id": log_data["certificate_id"],
+                                  "authority_id": log_data["authority_id"],
+                                  "authority_name": log_data["authority_name"],
+                                  "destination_names": log_data["destination_names"]
+                                  })
+        cert.rotation = True
+        database.update(cert)
diff --git a/lemur/certificates/models.py b/lemur/certificates/models.py
index 2ca88b00..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
diff --git a/lemur/certificates/service.py b/lemur/certificates/service.py
index a6bbba30..5d1e6e63 100644
--- a/lemur/certificates/service.py
+++ b/lemur/certificates/service.py
@@ -118,6 +118,21 @@ def get_all_pending_cleaning_expired(source):
     )
 
 
+def get_all_certs_attached_to_endpoint_without_autorotate():
+    """
+        Retrieves all certificates that are attached to an endpoint, but that do not have autorotate enabled.
+
+        :return: list of certificates attached to an endpoint without autorotate
+        """
+    return (
+        Certificate.query.filter(Certificate.endpoints.any())
+        .filter(Certificate.rotation == False)
+        .filter(Certificate.not_after >= arrow.now())
+        .filter(not_(Certificate.replaced.any()))
+        .all()  # noqa
+    )
+
+
 def get_all_pending_cleaning_expiring_in_days(source, days_to_expire):
     """
     Retrieves all certificates that are available for cleaning, not attached to endpoint,
@@ -144,7 +159,9 @@ def get_all_pending_cleaning_issued_since_days(source, days_since_issuance):
     :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")
+    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()))
@@ -367,9 +384,11 @@ def render(args):
 
     show_expired = args.pop("showExpired")
     if show_expired != 1:
-        one_month_old = arrow.now()\
-            .shift(months=current_app.config.get("HIDE_EXPIRED_CERTS_AFTER_MONTHS", -1))\
+        one_month_old = (
+            arrow.now()
+            .shift(months=current_app.config.get("HIDE_EXPIRED_CERTS_AFTER_MONTHS", -1))
             .format("YYYY-MM-DD")
+        )
         query = query.filter(Certificate.not_after > one_month_old)
 
     time_range = args.pop("time_range")
diff --git a/lemur/common/celery.py b/lemur/common/celery.py
index 4af33d86..5df470ab 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 +810,29 @@ 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
+
+
+@celery.task(soft_time_limit=3600)
+def enable_autorotate_for_certs_attached_to_endpoint():
+    """
+    This celery task automatically enables autorotation for unexpired certificates that are
+    attached to an endpoint but do not have autorotate enabled.
+    :return:
+    """
+    function = f"{__name__}.{sys._getframe().f_code.co_name}"
+    task_id = None
+    if celery.current_task:
+        task_id = celery.current_task.request.id
+
+    log_data = {
+        "function": function,
+        "task_id": task_id,
+        "message": "Enabling autorotate to eligible certificates",
+    }
+    current_app.logger.debug(log_data)
+
+    cli_certificate.automatically_enable_autorotate()
+    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/powerdns.py b/lemur/plugins/lemur_acme/powerdns.py
index a26faaac..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:
@@ -243,8 +324,47 @@ 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(
@@ -257,8 +377,54 @@ def _get(path, params=None):
     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(
diff --git a/lemur/plugins/lemur_acme/route53.py b/lemur/plugins/lemur_acme/route53.py
index 55da5161..aaccb57e 100644
--- a/lemur/plugins/lemur_acme/route53.py
+++ b/lemur/plugins/lemur_acme/route53.py
@@ -35,9 +35,10 @@ def get_zones(client=None):
     zones = []
     for page in paginator.paginate():
         for zone in page["HostedZones"]:
-            zones.append(
-                zone["Name"][:-1]
-            )  # We need [:-1] to strip out the trailing dot.
+            if not zone["Config"]["PrivateZone"]:
+                zones.append(
+                    zone["Name"][:-1]
+                )  # We need [:-1] to strip out the trailing dot.
     return zones
 
 
diff --git a/lemur/plugins/lemur_acme/tests/test_acme.py b/lemur/plugins/lemur_acme/tests/test_acme.py
index b2c32eec..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):
@@ -57,7 +56,7 @@ class TestAcme(unittest.TestCase):
     @patch("lemur.plugins.lemur_acme.plugin.len", return_value=1)
     @patch("lemur.plugins.lemur_acme.plugin.AcmeHandler.get_dns_challenges")
     def test_start_dns_challenge(
-        self, mock_get_dns_challenges, mock_len, mock_app, mock_acme
+            self, mock_get_dns_challenges, mock_len, mock_app, mock_acme
     ):
         assert mock_len
         mock_order = Mock()
@@ -88,7 +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)
@@ -112,7 +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)
@@ -140,12 +139,12 @@ class TestAcme(unittest.TestCase):
     @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_get_dns_challenges,
-        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"
@@ -182,7 +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)
@@ -288,14 +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, "")
@@ -319,14 +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, "")
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 7bb7a3a2..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))
diff --git a/lemur/plugins/lemur_digicert/tests/test_digicert.py b/lemur/plugins/lemur_digicert/tests/test_digicert.py
index 1e9ebca4..8bfd1dcf 100644
--- a/lemur/plugins/lemur_digicert/tests/test_digicert.py
+++ b/lemur/plugins/lemur_digicert/tests/test_digicert.py
@@ -1,4 +1,5 @@
 import json
+from unittest.mock import patch, Mock
 
 import arrow
 import pytest
@@ -6,7 +7,6 @@ from cryptography import x509
 from freezegun import freeze_time
 from lemur.plugins.lemur_digicert import plugin
 from lemur.tests.vectors import CSR_STR
-from mock import Mock, patch
 
 
 def config_mock(*args):
diff --git a/lemur/sources/cli.py b/lemur/sources/cli.py
index 0d537500..c415b567 100644
--- a/lemur/sources/cli.py
+++ b/lemur/sources/cli.py
@@ -58,6 +58,13 @@ 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:
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/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 9b899176..1a54eccc 100644
--- a/package.json
+++ b/package.json
@@ -6,7 +6,7 @@
     "url": "git://github.com/netflix/lemur.git"
   },
   "dependencies": {
-    "bower": "^1.8.2",
+    "bower": "^1.8.8",
     "browser-sync": "^2.26.7",
     "del": "^2.2.2",
     "gulp-autoprefixer": "^3.1.1",
@@ -17,10 +17,10 @@
     "gulp-flatten": "^0.3.1",
     "gulp-foreach": "0.1.0",
     "gulp-if": "^2.0.2",
-    "gulp-imagemin": "^3.1.1",
+    "gulp-imagemin": "^7.1.0",
     "gulp-inject": "~4.1.0",
     "gulp-jshint": "^2.0.4",
-    "gulp-less": "^3.0.3",
+    "gulp-less": "^4.0.1",
     "gulp-load-plugins": "^1.4.0",
     "gulp-minify-css": "^1.2.4",
     "gulp-minify-html": "~1.0.6",
@@ -29,7 +29,7 @@
     "gulp-notify": "^2.2.0",
     "gulp-plumber": "^1.1.0",
     "gulp-print": "^2.0.1",
-    "gulp-protractor": "3.0.0",
+    "gulp-protractor": "^4.1.1",
     "gulp-replace": "~0.5.3",
     "gulp-replace-task": "~0.11.0",
     "gulp-rev": "^7.1.2",
@@ -41,7 +41,7 @@
     "gulp-util": "^3.0.1",
     "http-proxy": "~1.16.2",
     "jshint-stylish": "^2.2.1",
-    "karma": "~1.3.0",
+    "karma": "^4.4.1",
     "karma-jasmine": "^1.1.0",
     "main-bower-files": "^2.13.1",
     "merge-stream": "^1.0.1",
@@ -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 224789f6..785d3f29 100644
--- a/requirements-dev.txt
+++ b/requirements-dev.txt
@@ -4,39 +4,41 @@
 #
 #    pip-compile --no-index --output-file=requirements-dev.txt requirements-dev.in
 #
-aspy.yaml==1.3.0          # via pre-commit
-bleach==3.1.1             # via readme-renderer
-certifi==2019.11.28       # via requests
+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==2.0.1               # via pre-commit
+cfgv==3.1.0               # via pre-commit
 chardet==3.0.4            # via requests
-cryptography==2.8         # via secretstorage
-docutils==0.15.2          # via readme-renderer
-flake8==3.5.0
-identify==1.4.9           # via pre-commit
-idna==2.8                 # via requests
-invoke==1.3.0
-jeepney==0.4.2            # via secretstorage
-keyring==21.0.0           # via twine
+cryptography==2.9.2       # 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
+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
-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==2.4.0         # via -r requirements-dev.in
 pycodestyle==2.3.1        # via flake8
-pycparser==2.19           # via cffi
+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
+requests==2.23.0          # via requests-toolbelt, twine
 secretstorage==3.1.2      # via keyring
-six==1.13.0               # via bleach, cfgv, cryptography, pre-commit, readme-renderer
+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
 
 # The following packages are considered to be unsafe in a requirements file:
diff --git a/requirements-docs.txt b/requirements-docs.txt
index 893965ca..16d97413 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==1.4.0               # 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==0.15.6             # 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==1.13.11            # via -r requirements.txt
+botocore==1.16.11         # 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==2.7.1         # via -r requirements.txt
+cryptography==2.9.2       # 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
+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==0.23.0  # via -r requirements.txt
+marshmallow==2.20.4       # via -r requirements.txt, marshmallow-sqlalchemy
+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
+pyasn1-modules==0.2.8     # via -r requirements.txt, pyjks, python-ldap
+pyasn1==0.4.8             # via -r requirements.txt, ndg-httpsclient, pyasn1-modules, pyjks, python-ldap
+pycparser==2.20           # via -r requirements.txt, cffi
+pycryptodomex==3.9.7      # via -r requirements.txt, pyjks
+pygments==2.6.1           # via sphinx
+pyjks==20.0.0             # 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
+python-ldap==3.2.0        # via -r requirements.txt
+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==3.5.2              # 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==3.0.3             # 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==0.36.5  # 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
 
 # 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..79340e51 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==1.13.11            # 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==1.16.11         # 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==2.9.2       # 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==4.1.0              # via -r requirements-tests.in, factory-boy
+fakeredis==1.4.1          # 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
 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==3.1.0        # via -r requirements-tests.in
+pytest==5.4.2             # 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==3.5.2              # via fakeredis
+regex==2020.4.4           # via black
+requests-mock==1.8.0      # 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, pyrsistent, 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..315f39b8 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -4,96 +4,92 @@
 #
 #    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==1.4.0               # 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==0.15.6             # 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==1.13.11            # via -r requirements.in
+botocore==1.16.11         # 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==2.7.1         # via -r requirements.in
+cryptography==2.9.2       # 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
+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==0.23.0  # via -r requirements.in
+marshmallow==2.20.4       # via -r requirements.in, marshmallow-sqlalchemy
+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==20.0.0             # 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==3.5.2              # 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==0.36.5  # 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
 
 # The following packages are considered to be unsafe in a requirements file:
 # setuptools
diff --git a/setup.py b/setup.py
index fa5a23bc..4ce03d70 100644
--- a/setup.py
+++ b/setup.py
@@ -45,16 +45,20 @@ with open(os.path.join(ROOT, 'lemur', '__about__.py')) as f:
     exec(f.read(), about)  # nosec: about file is benign
 
 install_requires_g = parse_requirements("requirements.txt", session=PipSession())
-install_requires = [str(ir.req) for ir in install_requires_g]
-
 tests_require_g = parse_requirements("requirements-tests.txt", session=PipSession())
-tests_require = [str(ir.req) for ir in tests_require_g]
-
 docs_require_g = parse_requirements("requirements-docs.txt", session=PipSession())
-docs_require = [str(ir.req) for ir in docs_require_g]
-
 dev_requires_g = parse_requirements("requirements-dev.txt", session=PipSession())
-dev_requires = [str(ir.req) for ir in dev_requires_g]
+
+if tuple(map(int, pip.__version__.split('.'))) >= (20, 1):
+    install_requires = [str(ir.requirement) for ir in install_requires_g]
+    tests_require = [str(ir.requirement) for ir in tests_require_g]
+    docs_require = [str(ir.requirement) for ir in docs_require_g]
+    dev_requires = [str(ir.requirement) for ir in dev_requires_g]
+else:
+    install_requires = [str(ir.req) for ir in install_requires_g]
+    tests_require = [str(ir.req) for ir in tests_require_g]
+    docs_require = [str(ir.req) for ir in docs_require_g]
+    dev_requires = [str(ir.req) for ir in dev_requires_g]
 
 
 class SmartInstall(install):