diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index c62cd2f2d1e..25d8348d8c4 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -92,7 +92,7 @@ jobs:
             ecr_repo_secret: ECR_PII
     steps:
       - name: Checkout code
-        uses: actions/checkout@34e114876b0b11c390a56381ad16ebd13914f8d5 # v4
+        uses: actions/checkout@df4cb1c069e1874edd31b4311f1884172cec0e10 # v6
 
       - name: Configure AWS credentials
         uses: aws-actions/configure-aws-credentials@e7f100cf4c008499ea8adda475de1042d6975c7b # v6
@@ -130,6 +130,49 @@ jobs:
           provenance: false
           sbom: false
 
+  # Dev: deploy Trigger.dev background tasks to the preview "dev-sim" branch.
+  # Gated after migrate-dev for the same reason as build-dev — the new task
+  # code runs against the dev DB, so the schema must be pushed first.
+  deploy-trigger-dev:
+    name: Deploy Trigger.dev (Dev)
+    needs: [migrate-dev]
+    if: github.event_name == 'push' && github.ref == 'refs/heads/dev'
+    runs-on: blacksmith-4vcpu-ubuntu-2404
+    steps:
+      - name: Checkout code
+        uses: actions/checkout@df4cb1c069e1874edd31b4311f1884172cec0e10 # v6
+
+      - name: Setup Bun
+        uses: oven-sh/setup-bun@0c5077e51419868618aeaa5fe8019c62421857d6 # v2
+        with:
+          bun-version: 1.3.13
+
+      - name: Cache Bun dependencies
+        uses: actions/cache@27d5ce7f107fe9357f9df03efb73ab90386fccae # v5
+        with:
+          path: |
+            ~/.bun/install/cache
+            node_modules
+            **/node_modules
+          key: ${{ runner.os }}-bun-${{ hashFiles('**/bun.lock') }}
+          restore-keys: |
+            ${{ runner.os }}-bun-
+
+      - name: Install dependencies
+        run: bun install --frozen-lockfile
+
+      - name: Deploy to Trigger.dev
+        working-directory: ./apps/sim
+        env:
+          TRIGGER_ACCESS_TOKEN: ${{ secrets.DEV_TRIGGER_ACCESS_TOKEN }}
+          TRIGGER_PROJECT_ID: ${{ secrets.TRIGGER_PROJECT_ID }}
+        run: |
+          if [ -z "$TRIGGER_ACCESS_TOKEN" ] || [ -z "$TRIGGER_PROJECT_ID" ]; then
+            echo "ERROR: DEV_TRIGGER_ACCESS_TOKEN and TRIGGER_PROJECT_ID repo secrets must both be set" >&2
+            exit 1
+          fi
+          bunx trigger.dev@4.4.3 deploy --env preview --branch dev-sim
+
   # Main/staging: build AMD64 images and push to ECR + GHCR
   build-amd64:
     name: Build AMD64
@@ -359,7 +402,7 @@ jobs:
     steps:
       - uses: actions/checkout@df4cb1c069e1874edd31b4311f1884172cec0e10 # v6
         with:
-          fetch-depth: 2  # Need at least 2 commits to detect changes
+          fetch-depth: 2 # Need at least 2 commits to detect changes
       - uses: dorny/paths-filter@fbd0ab8f3e69293af611ebaee6363fc25e6d187d # v4
         id: filter
         with:
diff --git a/.github/workflows/migrations.yml b/.github/workflows/migrations.yml
index f789ec32627..7965eaf5e6d 100644
--- a/.github/workflows/migrations.yml
+++ b/.github/workflows/migrations.yml
@@ -69,7 +69,16 @@ jobs:
 
           if [ "${ENVIRONMENT}" = "dev" ]; then
             echo "Dev environment — pushing schema directly (db:push)"
-            bun run db:push --force
+            # drizzle-kit push needs a TTY to resolve ambiguous renames (--force only
+            # covers data-loss). In CI it throws "Interactive prompts require a TTY
+            # terminal" but still exits 0, so the job goes green without applying the
+            # change. tee keeps the output live in the log; we then fail on drizzle's
+            # own TTY error. A genuine non-zero exit already fails via `set -e`.
+            bun run db:push --force < /dev/null 2>&1 | tee /tmp/db-push.log
+            if grep -q "Interactive prompts require a TTY terminal" /tmp/db-push.log; then
+              echo "ERROR: db:push needs an interactive rename decision; land it as a versioned migration instead of relying on push." >&2
+              exit 1
+            fi
           else
             echo "Applying versioned migrations (db:migrate)"
             bun run ./scripts/migrate.ts