diff --git a/.github/workflows/update-dependencies.yml b/.github/workflows/update-dependencies.yml
new file mode 100644
index 0000000..0dd69a7
--- /dev/null
+++ b/.github/workflows/update-dependencies.yml
@@ -0,0 +1,58 @@
+name: Update dependencies
+on:
+  schedule:
+    # Run automatically at 7AM PST Tuesday
+    - cron: '0 14 * * 2'
+  workflow_dispatch:
+
+jobs:
+  update-dependencies-and-test:
+    name: Update Dependencies & Test
+    runs-on: ubuntu-latest
+    timeout-minutes: 20
+    strategy:
+      max-parallel: 1
+      matrix:
+        java: [ 8, 11, 17 ]
+
+    steps:
+      - name: Checkout java-http-client
+        uses: actions/checkout@v2
+
+      - name: Set up Java
+        uses: actions/setup-java@v2
+        with:
+          distribution: 'temurin'
+          java-version: ${{ matrix.java }}
+          cache: 'maven'
+
+      - name: Updating semver dependencies
+        run: make update-deps
+
+      - run: mvn install -Dgpg.skip -Dmaven.javadoc.skip=true -B -V
+
+      - name: Add & Commit
+        if: matrix.java == '17'
+        uses: EndBug/add-and-commit@v8.0.2
+        with:
+          add: 'pom.xml'
+          default_author: 'github_actions'
+          message: 'chore: update java-http-client dependencies'
+
+  notify-on-failure:
+    name: Slack notify on failure
+    if: failure()
+    needs: [ update-dependencies-and-test ]
+    runs-on: ubuntu-latest
+    steps:
+      - uses: rtCamp/action-slack-notify@v2
+        env:
+          SLACK_COLOR: failure
+          SLACK_ICON_EMOJI: ':github:'
+          SLACK_MESSAGE: ${{ format('Update dependencies *{0}*, {1}/{2}/actions/runs/{3}', needs.update-dependencies-and-test.result, github.server_url, github.repository, github.run_id) }}
+          SLACK_TITLE: Action Failure - ${{ github.repository }}
+          SLACK_USERNAME: GitHub Actions
+          SLACK_MSG_AUTHOR: twilio-dx
+          SLACK_FOOTER: Posted automatically using GitHub Actions
+          SLACK_WEBHOOK: ${{ secrets.SLACK_WEBHOOK }}
+          MSG_MINIMAL: true
diff --git a/Makefile b/Makefile
index 3d76197..851986a 100644
--- a/Makefile
+++ b/Makefile
@@ -1,4 +1,4 @@
-.PHONY: install package test test-integration clean
+.PHONY: install package test update-deps test-integration clean
 
 VERSION := $(shell mvn help:evaluate -Dexpression=project.version --batch-mode | grep -e '^[^\[]')
 install:
@@ -13,5 +13,8 @@ package:
 test:
 	mvn test
 
+update-deps:
+	mvn versions:use-latest-releases versions:commit -DallowMajorUpdates=false
+
 clean:
 	mvn clean