diff --git a/base/Dockerfile b/base/Dockerfile
index 5f5e2fc6..ebd6800e 100644
--- a/base/Dockerfile
+++ b/base/Dockerfile
@@ -1,4 +1,4 @@
-FROM ubuntu:xenial
+FROM ubuntu:bionic
 
 ARG DEBIAN_FRONTEND=noninteractive
 
@@ -23,6 +23,8 @@ RUN apt-get -qq update \
   && apt-get install -y \
     curl \
     locales \
+    gpg \
+    lsb-release \
   && rm -rf /var/lib/apt/lists/* \
   && locale-gen en_US.UTF-8 \
   && update-locale LANG=en_US.UTF-8 LANGUAGE=en_US:en LC_ALL=en_US.UTF-8
diff --git a/base/files/.welcome.sh b/base/files/.welcome.sh
index 144f1d16..a2390b08 100644
--- a/base/files/.welcome.sh
+++ b/base/files/.welcome.sh
@@ -1,8 +1,9 @@
 #!/bin/bash
 
 # Get st2 version based on hardcoded string in st2common
-ST2_VERSION=$(/opt/stackstorm/st2/bin/python -c 'execfile("/opt/stackstorm/st2/lib/python2.7/site-packages/st2common/__init__.py"); print __version__')
-printf "Welcome to \033[1;38;5;208mStackStorm HA\033[0m \033[1m%s\033[0m (Ubuntu 16.04 LTS %s %s)\n" "v${ST2_VERSION}" "$(uname -o)" "$(uname -m)"
+ST2_VERSION=$(/opt/stackstorm/st2/bin/python -c 'exec(open("/opt/stackstorm/st2/lib/python3.6/site-packages/st2common/__init__.py").read()); print(__version__)')
+UBUNTU_VERSION=$(lsb_release -s -d)
+printf "Welcome to \033[1;38;5;208mStackStorm HA\033[0m \033[1m%s\033[0m (${UBUNTU_VERSION} %s %s)\n" "v${ST2_VERSION}" "$(uname -o)" "$(uname -m)"
 printf " * Documentation: https://docs.stackstorm.com/\n"
 printf " * Community: https://stackstorm.com/community-signup\n"
 printf " * Forum: https://forum.stackstorm.com/\n"
diff --git a/st2chatops/Dockerfile b/st2chatops/Dockerfile
index 99b61641..f5c11b5a 100644
--- a/st2chatops/Dockerfile
+++ b/st2chatops/Dockerfile
@@ -1,4 +1,4 @@
-FROM ubuntu:xenial
+FROM ubuntu:bionic
 
 ARG DEBIAN_FRONTEND=noninteractive
 
@@ -31,6 +31,7 @@ RUN apt-get -qq update \
   && apt-get install -y \
     curl \
     locales \
+    gpg \
   && rm -rf /var/lib/apt/lists/* \
   && locale-gen en_US.UTF-8 \
   && update-locale LANG=en_US.UTF-8 LANGUAGE=en_US:en LC_ALL=en_US.UTF-8
diff --git a/st2web/Dockerfile b/st2web/Dockerfile
index d0866302..4631ebf3 100644
--- a/st2web/Dockerfile
+++ b/st2web/Dockerfile
@@ -1,4 +1,4 @@
-FROM ubuntu:xenial
+FROM ubuntu:bionic
 
 ARG DEBIAN_FRONTEND=noninteractive
 
@@ -29,6 +29,7 @@ RUN apt-get -qq update \
   && apt-get install -y \
     curl \
     locales \
+    gpg \
   && rm -rf /var/lib/apt/lists/* \
   && locale-gen en_US.UTF-8 \
   && update-locale LANG=en_US.UTF-8 LANGUAGE=en_US:en LC_ALL=en_US.UTF-8
@@ -37,7 +38,7 @@ ENV LANG='en_US.UTF-8' LANGUAGE='en_US:en' LC_ALL='en_US.UTF-8'
 
 # Install nginx
 RUN apt-key adv --keyserver hkp://keyserver.ubuntu.com:80 --recv-keys ABF5BD827BD9BF62 \
-  && echo "deb http://nginx.org/packages/ubuntu/ xenial nginx" > /etc/apt/sources.list.d/nginx.list \
+  && echo "deb http://nginx.org/packages/ubuntu/ bionic nginx" > /etc/apt/sources.list.d/nginx.list \
   && apt-get update \
   && apt-get install -y nginx \
   && rm -f /etc/apt/sources.list.d/nginx.list