diff --git a/.circleci/config.yml b/.circleci/config.yml
index b5eb6fe85221..7373aa3a258e 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -14,13 +14,6 @@ workflows:
       - prep-build:
           requires:
             - prep-deps
-      - create_github_release:
-          requires:
-            - prep-build
-          filters:
-            branches:
-              only:
-                - develop
       # - prep-docs:
       #    requires:
       #      - prep-deps
@@ -243,6 +236,13 @@ jobs:
       - run:
           name: sentry sourcemaps upload
           command: yarn sentry:publish
+      - run:
+          name: Create GitHub release
+          command: |
+            .circleci/scripts/release-create-gh-release
+      - run:
+          name: Create GitHub Pull Request to sync master with develop
+          command: .circleci/scripts/release-create-master-pr
       # - run:
       #    name: github gh-pages docs publish
       #    command: >
@@ -321,15 +321,3 @@ jobs:
       - run:
           name: Coveralls upload
           command: yarn test:coveralls-upload
-
-  create_github_release:
-    docker:
-      - image: circleci/node:8.15.1-browsers
-    steps:
-      - checkout
-      - attach_workspace:
-          at: .
-      - run:
-          name: Create GitHub release
-          command: |
-            .circleci/scripts/release-create-gh-release
diff --git a/.circleci/scripts/release-create-gh-release b/.circleci/scripts/release-create-gh-release
index f40df49983fd..93303f576ebe 100755
--- a/.circleci/scripts/release-create-gh-release
+++ b/.circleci/scripts/release-create-gh-release
@@ -28,24 +28,24 @@ function install_github_cli ()
 
 current_commit_msg=$(git show -s --format='%s' HEAD)
 
-if grep --quiet '^Version v' <<< "$current_commit_msg"
+if [[ $current_commit_msg =~ Version[-[:space:]](v[[:digit:]]+.[[:digit:]]+.[[:digit:]]+) ]]
 then
+    tag="${BASH_REMATCH[1]}"
+
     install_github_cli
 
     printf '%s\n' 'Creating GitHub Release'
-    read -ra commit_words <<< "$current_commit_msg"
-    tag="${commit_words[1]}"
     release_body="$(awk -v version="${tag##v}" -f .circleci/scripts/show-changelog.awk CHANGELOG.md)"
     pushd builds
         hub release create \
             --attach metamask-chrome-*.zip \
             --attach metamask-firefox-*.zip \
-            --message "${commit_words[0]} ${commit_words[1]#v}" \
+            --message "Version ${tag##v}" \
             --message "$release_body" \
             --commitish "$CIRCLE_SHA1" \
             "$tag"
     popd
 else
-    printf '%s\n' 'Skipping GitHub Release'
+    printf '%s\n' 'Version not found in commit message; skipping GitHub Release'
     exit 0
 fi
diff --git a/.circleci/scripts/release-create-master-pr b/.circleci/scripts/release-create-master-pr
new file mode 100755
index 000000000000..74eeed86c84b
--- /dev/null
+++ b/.circleci/scripts/release-create-master-pr
@@ -0,0 +1,53 @@
+#!/usr/bin/env bash
+
+set -e
+set -u
+set -o pipefail
+
+if [[ "${CI:-}" != 'true' ]]
+then
+    printf '%s\n' 'CI environment variable must be set to true'
+    exit 1
+fi
+
+if [[ "${CIRCLECI:-}" != 'true' ]]
+then
+    printf '%s\n' 'CIRCLECI environment variable must be set to true'
+    exit 1
+fi
+
+if [[ -z "${GITHUB_TOKEN:-}" ]]
+then
+    printf '%s\n' 'GITHUB_TOKEN environment variable must be set'
+    exit 1
+fi
+
+function install_github_cli ()
+{
+    printf '%s\n' 'Installing hub CLI'
+    pushd "$(mktemp -d)"
+        curl -sSL 'https://github.com/github/hub/releases/download/v2.11.2/hub-linux-amd64-2.11.2.tgz' | tar xz
+        PATH="$PATH:$PWD/hub-linux-amd64-2.11.2/bin"
+    popd
+}
+
+base_branch='develop'
+
+if [[ -n "${CI_PULL_REQUEST:-}" ]]
+then
+    printf '%s\n' 'CI_PULL_REQUEST is set, pull request already exists for this build'
+    exit 0
+fi
+
+install_github_cli
+
+printf '%s\n' "Creating a Pull Request to sync 'master' with 'develop'"
+
+if ! hub pull-request \
+    --reviewer '@MetaMask/extension-release-team' \
+    --message "Master => develop" --message 'Merge latest release back into develop' \
+    --base "$CIRCLE_PROJECT_USERNAME:$base_branch" \
+    --head "$CIRCLE_PROJECT_USERNAME:$CIRCLE_BRANCH";
+then
+    printf '%s\n' 'Pull Request already exists'
+fi
diff --git a/.circleci/scripts/release-create-release-pr b/.circleci/scripts/release-create-release-pr
index 8a2238ec4467..76f30ece4c19 100755
--- a/.circleci/scripts/release-create-release-pr
+++ b/.circleci/scripts/release-create-release-pr
@@ -32,7 +32,7 @@ function install_github_cli ()
 }
 
 version="${CIRCLE_BRANCH/Version-v/}"
-base_branch='develop'
+base_branch='master'
 
 if [[ -n "${CI_PULL_REQUEST:-}" ]]
 then