diff --git a/.github/workflows/update-milestone-badge.yml b/.github/workflows/update-milestone-badge.yml
new file mode 100644
index 000000000..38c51dad1
--- /dev/null
+++ b/.github/workflows/update-milestone-badge.yml
@@ -0,0 +1,52 @@
+name: Update Milestone Badge
+
+on:
+  milestone:
+    types: [created, edited, closed, deleted]
+  schedule:
+    - cron: '0 6 * * *'
+  workflow_dispatch:
+
+permissions:
+  contents: write
+
+jobs:
+  update-badge:
+    runs-on: ubuntu-latest
+    steps:
+      - name: Checkout docs branch
+        uses: actions/checkout@v4
+        with:
+          ref: docs
+          fetch-depth: 1
+
+      - name: Fetch nearest milestone and generate badge
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+        run: |
+          set -euo pipefail
+
+          # Fetch open milestones with due dates, pick the nearest one
+          TITLE=$(gh api repos/${{ github.repository }}/milestones \
+            --jq '[.[] | select(.state == "open" and .due_on != null)] | sort_by(.due_on) | .[0].title // empty')
+
+          if [ -z "$TITLE" ]; then
+            URL="https://img.shields.io/badge/Next%20Milestone-No%20milestone-lightgrey"
+          else
+            # URL-encode the title using jq, then escape dashes for shields.io
+            ENCODED=$(echo -n "$TITLE" | jq -sRr @uri | sed 's/-/--/g')
+            URL="https://img.shields.io/badge/Next%20Milestone-${ENCODED}-blue"
+          fi
+
+          mkdir -p milestone
+          curl -sfL "$URL" -o milestone/badge.svg
+          echo "Badge generated for: ${TITLE:-No milestone}"
+
+      - name: Commit and push
+        run: |
+          git config user.name "github-actions[bot]"
+          git config user.email "github-actions[bot]@users.noreply.github.com"
+          git add milestone/badge.svg
+          git diff --cached --quiet && echo "No changes" && exit 0
+          git commit -m "chore: update milestone badge"
+          git push
diff --git a/README.md b/README.md
index 6091df5f8..cfb5c556a 100644
--- a/README.md
+++ b/README.md
@@ -9,6 +9,7 @@
 [![E2E Tests](https://github.com/aws/aws-durable-execution-sdk-java/actions/workflows/e2e-tests.yml/badge.svg)](https://github.com/aws/aws-durable-execution-sdk-java/actions/workflows/e2e-tests.yml)
 [![CodeQL](https://github.com/aws/aws-durable-execution-sdk-java/actions/workflows/github-code-scanning/codeql/badge.svg)](https://github.com/aws/aws-durable-execution-sdk-java/actions/workflows/github-code-scanning/codeql)
 [![Spotless](https://github.com/aws/aws-durable-execution-sdk-java/actions/workflows/check-spotless.yml/badge.svg)](https://github.com/aws/aws-durable-execution-sdk-java/actions/workflows/check-spotless.yml)
+[![Roadmap](https://raw.githubusercontent.com/aws/aws-durable-execution-sdk-java/refs/heads/docs/milestone/badge.svg)](https://github.com/orgs/aws/projects/346/views/6)
 
 Build resilient, long-running AWS Lambda functions that automatically checkpoint progress and resume after failures. Durable functions can run for up to one year while you pay only for active compute time.