diff --git a/.github/workflows/annotate.yml b/.github/workflows/annotate.yml
new file mode 100644
index 000000000000..c81542c693dc
--- /dev/null
+++ b/.github/workflows/annotate.yml
@@ -0,0 +1,54 @@
+name: Make sure annotate is up to date
+on:
+  push:
+    branches:
+      - 'main'
+  pull_request:
+    types: [opened, synchronize, reopened]
+jobs:
+  test-annotations:
+    name: test annotations
+    runs-on: ubuntu-latest
+    services:
+      postgres:
+        image: postgres:14-alpine
+        ports:
+          - '5432:5432'
+        env:
+          POSTGRES_DB: lago
+          POSTGRES_USER: lago
+          POSTGRES_PASSWORD: lago
+    env:
+      RAILS_ENV: test
+      DATABASE_URL: 'postgres://lago:lago@localhost:5432/lago'
+      LAGO_REDIS_CACHE_URL: 'redis://localhost:6379'
+      RAILS_MASTER_KEY: ${{ secrets.RAILS_TEST_KEY }}
+      SECRET_KEY_BASE: ${{ secrets.SECRET_KEY_BASE }}
+      LAGO_API_URL: https://api.lago.dev
+      LAGO_PDF_URL: https://pdf.lago.dev
+      SEGMENT_WRITE_KEY: ${{ secrets.SEGMENT_WRITE_KEY }}
+      LAGO_FROM_EMAIL: noreply@getlago.com
+      LAGO_CLICKHOUSE_ENABLED: true
+      LAGO_CLICKHOUSE_MIGRATIONS_ENABLED: true
+      LAGO_CLICKHOUSE_HOST: localhost
+      LAGO_CLICKHOUSE_DATABASE: default
+      LAGO_CLICKHOUSE_USERNAME: ''
+      LAGO_CLICKHOUSE_PASSWORD: ''
+    steps:
+      - name: Checkout code
+        uses: actions/checkout@v4
+      - name: Install Ruby and gems
+        uses: ruby/setup-ruby@v1
+        with:
+          ruby-version: '3.3.4'
+          bundler-cache: true
+      - name: Start Clickhouse database
+        run: |
+          docker run -d --rm -p 8123:8123 -p 9000:9000 --ulimit nofile=262144:262144 -v ./clickhouse-s3:/var/lib/clickhouse-s3 -v ./ci/clickhouse/config.xml:/etc/clickhouse-server/config.d/config.xml clickhouse/clickhouse-server
+        shell: bash
+      - name: Generate RSA keys
+        run: ./scripts/generate.rsa.sh
+      - name: Set up Postgres database schema
+        run: bin/rails db:schema:load:primary
+      - name: run annotate --frozen
+        run: bundle exec annotate --frozen
diff --git a/.github/workflows/migrations-test.yml b/.github/workflows/migrations-test.yml
index 1c547f4cfd47..ddc17d52b9dd 100644
--- a/.github/workflows/migrations-test.yml
+++ b/.github/workflows/migrations-test.yml
@@ -2,7 +2,7 @@ name: Run rails migrations
 on:
   push:
     branches:
-      - "main"
+      - 'main'
   pull_request:
     types: [opened, synchronize, reopened]
 jobs:
@@ -13,14 +13,14 @@ jobs:
       postgres:
         image: postgres:14-alpine
         ports:
-          - "5432:5432"
+          - '5432:5432'
         env:
           POSTGRES_DB: lago
           POSTGRES_USER: lago
           POSTGRES_PASSWORD: lago
     env:
       RAILS_ENV: test
-      DATABASE_URL: "postgres://lago:lago@localhost:5432/lago"
+      DATABASE_URL: 'postgres://lago:lago@localhost:5432/lago'
       RAILS_MASTER_KEY: ${{ secrets.RAILS_TEST_KEY }}
       SECRET_KEY_BASE: ${{ secrets.SECRET_KEY_BASE }}
       ENCRYPTION_PRIMARY_KEY: 5I9mjfzry2P787x4S5ZuDdJwXNgYEwqo
@@ -34,8 +34,8 @@ jobs:
       LAGO_CLICKHOUSE_MIGRATIONS_ENABLED: true
       LAGO_CLICKHOUSE_HOST: localhost
       LAGO_CLICKHOUSE_DATABASE: default
-      LAGO_CLICKHOUSE_USERNAME: ""
-      LAGO_CLICKHOUSE_PASSWORD: ""
+      LAGO_CLICKHOUSE_USERNAME: ''
+      LAGO_CLICKHOUSE_PASSWORD: ''
       LAGO_DISABLE_SCHEMA_DUMP: true
     steps:
       - name: Checkout code
@@ -43,7 +43,7 @@ jobs:
       - name: Install Ruby and gems
         uses: ruby/setup-ruby@v1
         with:
-          ruby-version: "3.3.4"
+          ruby-version: '3.3.4'
           bundler-cache: true
       - name: Start Clickhouse database
         run: |