diff --git a/CHANGES.md b/CHANGES.md
index 872ac440b..f1a9d58e4 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -1,3 +1,13 @@
+Synapse 0.99.1.1 (2019-02-14)
+=============================
+
+Bugfixes
+--------
+
+- Fix "TypeError: '>' not supported" when starting without an existing certificate.
+  Fix a bug where an existing certificate would be reprovisoned every day. ([\#4648](https://github.com/matrix-org/synapse/issues/4648))
+
+
 Synapse 0.99.1 (2019-02-14)
 ===========================
 
diff --git a/debian/changelog b/debian/changelog
index bc1ba153e..124128920 100644
--- a/debian/changelog
+++ b/debian/changelog
@@ -1,3 +1,9 @@
+matrix-synapse-py3 (0.99.1.1) stable; urgency=medium
+
+  * New synapse release 0.99.1.1
+
+ -- Synapse Packaging team <packages@matrix.org>  Thu, 14 Feb 2019 17:19:44 +0000
+
 matrix-synapse-py3 (0.99.1) stable; urgency=medium
 
   [ Damjan Georgievski ]
diff --git a/docker/Dockerfile-dhvirtualenv b/docker/Dockerfile-dhvirtualenv
index ab28e4929..224c92352 100644
--- a/docker/Dockerfile-dhvirtualenv
+++ b/docker/Dockerfile-dhvirtualenv
@@ -58,7 +58,11 @@ RUN apt-get update -qq -o Acquire::Languages=none \
         sqlite3
 
 COPY --from=builder /dh-virtualenv_1.1-1_all.deb /
-RUN apt-get install -yq /dh-virtualenv_1.1-1_all.deb
+
+# install dhvirtualenv. Update the apt cache again first, in case we got a
+# cached cache from docker the first time.
+RUN apt-get update -qq -o Acquire::Languages=none \
+    && apt-get install -yq /dh-virtualenv_1.1-1_all.deb
 
 WORKDIR /synapse/source
 ENTRYPOINT ["bash","/synapse/source/docker/build_debian.sh"]
diff --git a/synapse/__init__.py b/synapse/__init__.py
index f7bac0ea4..2004375f9 100644
--- a/synapse/__init__.py
+++ b/synapse/__init__.py
@@ -27,4 +27,4 @@ try:
 except ImportError:
     pass
 
-__version__ = "0.99.1"
+__version__ = "0.99.1.1"
diff --git a/synapse/app/homeserver.py b/synapse/app/homeserver.py
index dbd9a8387..05a97979e 100755
--- a/synapse/app/homeserver.py
+++ b/synapse/app/homeserver.py
@@ -1,6 +1,7 @@
 #!/usr/bin/env python
 # -*- coding: utf-8 -*-
 # Copyright 2014-2016 OpenMarket Ltd
+# Copyright 2019 New Vector Ltd
 #
 # Licensed under the Apache License, Version 2.0 (the "License");
 # you may not use this file except in compliance with the License.
@@ -14,11 +15,12 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
+from __future__ import print_function
+
 import gc
 import logging
 import os
 import sys
-import traceback
 
 from six import iteritems
 
@@ -27,6 +29,7 @@ from prometheus_client import Gauge
 
 from twisted.application import service
 from twisted.internet import defer, reactor
+from twisted.python.failure import Failure
 from twisted.web.resource import EncodingResourceWrapper, NoResource
 from twisted.web.server import GzipEncoderFactory
 from twisted.web.static import File
@@ -394,10 +397,10 @@ def setup(config_options):
         # is less than our re-registration threshold.
         provision = False
 
-        if (cert_days_remaining is None):
-            provision = True
-
-        if cert_days_remaining > hs.config.acme_reprovision_threshold:
+        if (
+            cert_days_remaining is None or
+            cert_days_remaining < hs.config.acme_reprovision_threshold
+        ):
             provision = True
 
         if provision:
@@ -438,7 +441,11 @@ def setup(config_options):
             hs.get_datastore().start_doing_background_updates()
         except Exception:
             # Print the exception and bail out.
-            traceback.print_exc(file=sys.stderr)
+            print("Error during startup:", file=sys.stderr)
+
+            # this gives better tracebacks than traceback.print_exc()
+            Failure().printTraceback(file=sys.stderr)
+
             if reactor.running:
                 reactor.stop()
             sys.exit(1)
diff --git a/synapse/config/logger.py b/synapse/config/logger.py
index 4b938053f..9b5994d55 100644
--- a/synapse/config/logger.py
+++ b/synapse/config/logger.py
@@ -242,3 +242,5 @@ def setup_logging(config, use_worker_options=False):
         [_log],
         redirectStandardIO=not config.no_redirect_stdio,
     )
+    if not config.no_redirect_stdio:
+        print("Redirected stdout/stderr to logs")