diff --git a/.github/dependabot.yml b/.github/dependabot.yml
new file mode 100644
index 0000000..6dbd2dd
--- /dev/null
+++ b/.github/dependabot.yml
@@ -0,0 +1,47 @@
+# Dependabot configuration.
+#
+# This repo had NO dependency watching until 2026-09-09, which is the
+# same gap that produced the Sentinel AI agent's three production
+# breakages in two days: mcp 2.x renaming a symbol, Starlette removing
+# on_startup, and a ceiling added to stop the second one silently
+# pinning the service to a Starlette line with 7 advisories. All three
+# surfaced on a rebuild of a repo nobody had rebuilt since June.
+#
+# `pip-audit --strict` in the Test workflow catches a *known advisory*
+# in what is already pinned. It does nothing about a lockfile quietly
+# ageing out of support. That is what this is for.
+#
+# NO AUTO-MERGE WORKFLOW HERE, DELIBERATELY.
+#
+# This repo now deploys to Fly on push to master. GitHub does not
+# trigger `on: push` workflows for commits pushed with GITHUB_TOKEN, so
+# an auto-merge action would land a bump on master WITHOUT deploying it
+# — master and production drift apart, and nothing reports an error.
+# That is a real, observed bug in Sentinel-Command (four frontend bumps
+# merged and never shipped on 2026-09-09). A human merge triggers the
+# deploy normally, so these PRs are reviewed and merged by hand until
+# that repo's PAT fix is proven.
+version: 2
+updates:
+  # Python (uv) — pyproject.toml + uv.lock live at the repo root.
+  - package-ecosystem: "uv"
+    directory: "/"
+    schedule:
+      interval: "weekly"
+      day: "monday"
+    open-pull-requests-limit: 5
+    commit-message:
+      prefix: "build(deps)"
+    labels:
+      - "dependencies"
+
+  # GitHub Actions — pinned action versions age out the same way.
+  - package-ecosystem: "github-actions"
+    directory: "/"
+    schedule:
+      interval: "weekly"
+      day: "monday"
+    open-pull-requests-limit: 5
+    labels:
+      - "dependencies"
+      - "ci"
diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index 5e1247a..5d25613 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -1,10 +1,15 @@
-name: Test
+name: Test & Deploy
 
-# Deploy automation is deferred deliberately (see the Sentinel Command
-# plan doc, Phase 1: "fine to start with a manual `fly deploy` for the
-# very first cut given a human should be watching the first-ever deploy
-# of new infrastructure anyway; automate once phase 1 is stable"). This
-# workflow only covers lint + dependency audit + tests.
+# Tests on every push and PR; deploys to Fly on pushes to master.
+#
+# Deploy automation was deferred so a human could watch the first-ever
+# deploy of new infrastructure, with a note to "automate once phase 1 is
+# stable". Phase 1 is stable, and leaving it deferred created a worse
+# problem than it avoided: fly.toml became a file that did nothing. A
+# scale-to-zero change merged with CI green on 2026-09-09 and never
+# reached Fly — the app kept running always-on until someone noticed and
+# deployed by hand. Config that silently doesn't apply is more dangerous
+# than no config.
 
 on:
   push:
@@ -68,3 +73,36 @@ jobs:
         env:
           TEST_DATABASE_URL: ${{ matrix.test_database_url }}
         run: uv run pytest -v
+
+  deploy:
+    name: Deploy to Fly.io
+    runs-on: ubuntu-latest
+    # Waits on BOTH matrix legs (sqlite and postgres) — this service runs
+    # the same code against either dialect, so a green sqlite run alone
+    # is not evidence the deploy is safe.
+    needs: test
+    # Push-only: a PR runs the tests above but never ships.
+    if: github.event_name == 'push'
+    # Serialize so two quick pushes don't race on the machine update.
+    concurrency:
+      group: deploy-sentinel-license
+      cancel-in-progress: true
+    steps:
+      - uses: actions/checkout@v7
+
+      - uses: superfly/flyctl-actions/setup-flyctl@master
+
+      # --strategy immediate because this app mounts a volume
+      # (sentinel_license_data). The default rolling strategy tries to
+      # stand up a parallel machine first and errors on the volume's
+      # single attachment slot. Sentinel-Sync has no volume and so needs
+      # no override; Command Center has the same constraint and the same
+      # flag.
+      #
+      # --ha=false because Fly otherwise provisions TWO machines, which
+      # this service does not need and which the volume cannot serve
+      # anyway.
+      - name: flyctl deploy
+        run: flyctl deploy --remote-only --strategy immediate --ha=false --yes
+        env:
+          FLY_API_TOKEN: ${{ secrets.FLY_API_TOKEN }}