diff --git a/.circleci/config.yml b/.circleci/config.yml
index 74ae3d3..4491d98 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -51,6 +51,21 @@ jobs:
             gem build pronto-commentator
             gem push pronto-commentator-*.gem
 
+  update_jira:
+    docker:
+      - image: alpine:3.8
+        auth:
+          username: $DOCKERHUB_USERNAME
+          password: $DOCKERHUB_TOKEN
+    steps:
+      - run:
+          name: Install dependencies
+          command: apk add --no-cache bash curl git openssh
+      - checkout
+      - run:
+          name: Update JIRA
+          command: .circleci/update-jira.sh
+
 workflows:
   version: 2
   test_and_deploy:
@@ -74,3 +89,10 @@ workflows:
                 - /^v.*/
           context:
             - DockerHub
+            - RubyGems
+      - update_jira:
+          context:
+            - DockerHub
+            - update-jira-webhook
+          requires:
+            - push_to_rubygems
diff --git a/.circleci/update-jira.sh b/.circleci/update-jira.sh
new file mode 100755
index 0000000..4eadf3f
--- /dev/null
+++ b/.circleci/update-jira.sh
@@ -0,0 +1,10 @@
+#!/usr/bin/env bash
+
+set -euo pipefail
+
+# Use JIRA automation webhooks to move issues to SHIPPED:
+# https://support.atlassian.com/jira-software-cloud/docs/automation-triggers/#Automationtriggers-Incomingwebhook
+
+git log --max-count=50 --pretty=format:'%s' | grep -Eo '^\w+-[0-9]+' | sort -u | while read i; do
+  curl -X POST "$UPDATE_JIRA_WEBHOOK_URL?issue=$i"
+done