diff --git a/lemur/common/celery.py b/lemur/common/celery.py
index 10747d31..ce386ffd 100644
--- a/lemur/common/celery.py
+++ b/lemur/common/celery.py
@@ -12,9 +12,11 @@ import sys
 from datetime import datetime, timezone, timedelta
 
 from celery import Celery
+from celery.exceptions import SoftTimeLimitExceeded
 from flask import current_app
 
 from lemur.authorities.service import get as get_authority
+from lemur.extensions import metrics, sentry
 from lemur.factory import create_app
 from lemur.notifications.messaging import send_pending_failure_notification
 from lemur.pending_certificates import service as pending_certificate_service
@@ -62,7 +64,7 @@ def is_task_active(fun, task_id, args):
     return False
 
 
-@celery.task()
+@celery.task(soft_time_limit=600)
 def fetch_acme_cert(id):
     """
     Attempt to get the full certificate for the pending certificate listed.
@@ -70,11 +72,24 @@ def fetch_acme_cert(id):
     Args:
         id: an id of a PendingCertificate
     """
+    task_id = None
+    if celery.current_task:
+        task_id = celery.current_task.request.id
+
     log_data = {
         "function": "{}.{}".format(__name__, sys._getframe().f_code.co_name),
-        "message": "Resolving pending certificate {}".format(id)
+        "message": "Resolving pending certificate {}".format(id),
+        "task_id": task_id,
+        "id": id,
     }
+
     current_app.logger.debug(log_data)
+
+    if task_id and is_task_active(log_data["function"], task_id, (id,)):
+        log_data["message"] = "Skipping task: Task is already active"
+        current_app.logger.debug(log_data)
+        return
+
     pending_certs = pending_certificate_service.get_pending_certs([id])
     new = 0
     failed = 0
@@ -192,7 +207,7 @@ def remove_old_acme_certs():
             log_data['pending_cert_name'] = cert.name
             log_data['message'] = "Deleting pending certificate"
             current_app.logger.debug(log_data)
-            pending_certificate_service.delete(cert.id)
+            pending_certificate_service.delete(cert)
 
 
 @celery.task()
@@ -231,7 +246,7 @@ def sync_all_sources():
         sync_source.delay(source.label)
 
 
-@celery.task()
+@celery.task(soft_time_limit=3600)
 def sync_source(source):
     """
     This celery task will sync the specified source.
@@ -241,7 +256,9 @@ def sync_source(source):
     """
 
     function = "{}.{}".format(__name__, sys._getframe().f_code.co_name)
-    task_id = celery.current_task.request.id
+    task_id = None
+    if celery.current_task:
+        task_id = celery.current_task.request.id
     log_data = {
         "function": function,
         "message": "Syncing source",
@@ -250,11 +267,19 @@ def sync_source(source):
     }
     current_app.logger.debug(log_data)
 
-    if is_task_active(function, task_id, (source,)):
+    if task_id and is_task_active(function, task_id, (source,)):
         log_data["message"] = "Skipping task: Task is already active"
         current_app.logger.debug(log_data)
         return
-    sync([source])
+    try:
+        sync([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})
+        return
+
     log_data["message"] = "Done syncing source"
     current_app.logger.debug(log_data)
 
diff --git a/lemur/plugins/lemur_acme/plugin.py b/lemur/plugins/lemur_acme/plugin.py
index 06dec882..d9c41968 100644
--- a/lemur/plugins/lemur_acme/plugin.py
+++ b/lemur/plugins/lemur_acme/plugin.py
@@ -17,7 +17,7 @@ import time
 
 import OpenSSL.crypto
 import josepy as jose
-from acme import challenges, messages
+from acme import challenges, errors, messages
 from acme.client import BackwardsCompatibleClientV2, ClientNetwork
 from acme.errors import PollError, TimeoutError, WildcardUnsupportedError
 from acme.messages import Error as AcmeError
@@ -155,6 +155,11 @@ class AcmeHandler(object):
             metrics.send('request_certificate_error', 'counter', 1)
             current_app.logger.error(f"Unable to resolve Acme order: {order.uri}", exc_info=True)
             raise
+        except errors.ValidationError:
+            if order.fullchain_pem:
+                orderr = order
+            else:
+                raise
 
         pem_certificate = OpenSSL.crypto.dump_certificate(OpenSSL.crypto.FILETYPE_PEM,
                                                           OpenSSL.crypto.load_certificate(OpenSSL.crypto.FILETYPE_PEM,
diff --git a/requirements-dev.txt b/requirements-dev.txt
index 29509d99..1a5b5f9d 100644
--- a/requirements-dev.txt
+++ b/requirements-dev.txt
@@ -2,7 +2,7 @@
 # This file is autogenerated by pip-compile
 # To update, run:
 #
-#    pip-compile --output-file requirements-dev.txt requirements-dev.in -U --no-index
+#    pip-compile --no-index --output-file=requirements-dev.txt requirements-dev.in
 #
 aspy.yaml==1.2.0          # via pre-commit
 bleach==3.1.0             # via readme-renderer
@@ -11,26 +11,26 @@ cfgv==1.6.0               # via pre-commit
 chardet==3.0.4            # via requests
 docutils==0.14            # via readme-renderer
 flake8==3.5.0
-identify==1.4.2           # via pre-commit
+identify==1.4.3           # via pre-commit
 idna==2.8                 # via requests
-importlib-metadata==0.9   # via pre-commit
+importlib-metadata==0.12  # via pre-commit
 invoke==1.2.0
 mccabe==0.6.1             # via flake8
 nodeenv==1.3.3
 pkginfo==1.5.0.1          # via twine
-pre-commit==1.16.0
+pre-commit==1.16.1
 pycodestyle==2.3.1        # via flake8
 pyflakes==1.6.0           # via flake8
-pygments==2.3.1           # via readme-renderer
+pygments==2.4.0           # via readme-renderer
 pyyaml==5.1
 readme-renderer==24.0     # via twine
 requests-toolbelt==0.9.1  # via twine
 requests==2.21.0          # via requests-toolbelt, twine
 six==1.12.0               # via bleach, cfgv, pre-commit, readme-renderer
 toml==0.10.0              # via pre-commit
-tqdm==4.31.1              # via twine
+tqdm==4.32.1              # via twine
 twine==1.13.0
 urllib3==1.24.3           # via requests
 virtualenv==16.5.0        # via pre-commit
 webencodings==0.5.1       # via bleach
-zipp==0.4.0               # via importlib-metadata
+zipp==0.5.0               # via importlib-metadata
diff --git a/requirements-docs.txt b/requirements-docs.txt
index fef37c08..f23de8f4 100644
--- a/requirements-docs.txt
+++ b/requirements-docs.txt
@@ -2,9 +2,9 @@
 # This file is autogenerated by pip-compile
 # To update, run:
 #
-#    pip-compile --output-file requirements-docs.txt requirements-docs.in -U --no-index
+#    pip-compile --no-index --output-file=requirements-docs.txt requirements-docs.in
 #
-acme==0.34.1
+acme==0.34.2
 alabaster==0.7.12         # via sphinx
 alembic-autogenerate-enums==0.0.2
 alembic==1.0.10
@@ -17,8 +17,8 @@ babel==2.6.0              # via sphinx
 bcrypt==3.1.6
 billiard==3.6.0.0
 blinker==1.4
-boto3==1.9.143
-botocore==1.12.143
+boto3==1.9.147
+botocore==1.12.147
 celery[redis]==4.3.0
 certifi==2019.3.9
 certsrv==2.1.1
@@ -54,11 +54,11 @@ josepy==1.1.0
 jsonlines==1.2.0
 kombu==4.5.0
 lockfile==0.12.2
-mako==1.0.9
+mako==1.0.10
 markupsafe==1.1.1
 marshmallow-sqlalchemy==0.16.3
 marshmallow==2.19.2
-mock==3.0.4
+mock==3.0.5
 ndg-httpsclient==0.5.1
 packaging==19.0           # via sphinx
 paramiko==2.4.2
@@ -68,7 +68,7 @@ pyasn1-modules==0.2.5
 pyasn1==0.4.5
 pycparser==2.19
 pycryptodomex==3.8.1
-pygments==2.3.1           # via sphinx
+pygments==2.4.0           # via sphinx
 pyjks==19.0.0
 pyjwt==1.7.1
 pynacl==1.3.0
diff --git a/requirements-tests.txt b/requirements-tests.txt
index 5d28412c..27837359 100644
--- a/requirements-tests.txt
+++ b/requirements-tests.txt
@@ -2,19 +2,19 @@
 # This file is autogenerated by pip-compile
 # To update, run:
 #
-#    pip-compile --output-file requirements-tests.txt requirements-tests.in -U --no-index
+#    pip-compile --no-index --output-file=requirements-tests.txt requirements-tests.in
 #
 asn1crypto==0.24.0        # via cryptography
 atomicwrites==1.3.0       # via pytest
 attrs==19.1.0             # via pytest
 aws-sam-translator==1.11.0  # via cfn-lint
 aws-xray-sdk==2.4.2       # via moto
-boto3==1.9.143            # via aws-sam-translator, moto
+boto3==1.9.147            # via aws-sam-translator, moto
 boto==2.49.0              # via moto
-botocore==1.12.143        # via aws-xray-sdk, boto3, moto, s3transfer
+botocore==1.12.147        # via aws-xray-sdk, boto3, moto, s3transfer
 certifi==2019.3.9         # via requests
 cffi==1.12.3              # via cryptography
-cfn-lint==0.19.1          # via moto
+cfn-lint==0.20.1          # via moto
 chardet==3.0.4            # via requests
 click==7.0                # via flask
 coverage==4.5.3
@@ -23,8 +23,8 @@ docker-pycreds==0.4.0     # via docker
 docker==3.7.2             # via moto
 docutils==0.14            # via botocore
 ecdsa==0.13.2             # via python-jose
-factory-boy==2.11.1
-faker==1.0.5
+factory-boy==2.12.0
+faker==1.0.7
 flask==1.0.2              # via pytest-flask
 freezegun==0.3.11
 future==0.17.1            # via aws-xray-sdk, python-jose
@@ -38,18 +38,18 @@ jsonpickle==1.1           # via aws-xray-sdk
 jsonpointer==2.0          # via jsonpatch
 jsonschema==2.6.0         # via aws-sam-translator, cfn-lint
 markupsafe==1.1.1         # via jinja2
-mock==3.0.4               # via moto
+mock==3.0.5               # via moto
 more-itertools==7.0.0     # via pytest
 moto==1.3.8
 nose==1.3.7
-pluggy==0.9.0             # via pytest
+pluggy==0.11.0            # via pytest
 py==1.8.0                 # via pytest
 pyasn1==0.4.5             # via rsa
 pycparser==2.19           # via cffi
 pyflakes==2.1.1
-pytest-flask==0.14.0
+pytest-flask==0.15.0
 pytest-mock==1.10.4
-pytest==4.4.1
+pytest==4.5.0
 python-dateutil==2.8.0    # via botocore, faker, freezegun, moto
 python-jose==3.0.1        # via moto
 pytz==2019.1              # via moto
@@ -62,6 +62,7 @@ s3transfer==0.2.0         # via boto3
 six==1.12.0               # via aws-sam-translator, cfn-lint, cryptography, docker, docker-pycreds, faker, freezegun, mock, moto, pytest, python-dateutil, python-jose, requests-mock, responses, websocket-client
 text-unidecode==1.2       # via faker
 urllib3==1.24.3           # via botocore, requests
+wcwidth==0.1.7            # via pytest
 websocket-client==0.56.0  # via docker
 werkzeug==0.15.2          # via flask, moto, pytest-flask
 wrapt==1.11.1             # via aws-xray-sdk
diff --git a/requirements.txt b/requirements.txt
index fe27838b..935e85ca 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -2,9 +2,9 @@
 # This file is autogenerated by pip-compile
 # To update, run:
 #
-#    pip-compile --output-file requirements.txt requirements.in -U --no-index
+#    pip-compile --no-index --output-file=requirements.txt requirements.in
 #
-acme==0.34.1
+acme==0.34.2
 alembic-autogenerate-enums==0.0.2
 alembic==1.0.10           # via flask-migrate
 amqp==2.4.2               # via kombu
@@ -15,8 +15,8 @@ asyncpool==1.0
 bcrypt==3.1.6             # via flask-bcrypt, paramiko
 billiard==3.6.0.0         # via celery
 blinker==1.4              # via flask-mail, flask-principal, raven
-boto3==1.9.143
-botocore==1.12.143
+boto3==1.9.147
+botocore==1.12.147
 celery[redis]==4.3.0
 certifi==2019.3.9
 certsrv==2.1.1
@@ -51,11 +51,11 @@ josepy==1.1.0             # via acme
 jsonlines==1.2.0          # via cloudflare
 kombu==4.5.0
 lockfile==0.12.2
-mako==1.0.9               # via alembic
+mako==1.0.10              # via alembic
 markupsafe==1.1.1         # via jinja2, mako
 marshmallow-sqlalchemy==0.16.3
 marshmallow==2.19.2
-mock==3.0.4               # via acme
+mock==3.0.5               # via acme
 ndg-httpsclient==0.5.1
 paramiko==2.4.2
 pem==19.1.0