diff --git a/loop/plan.md b/loop/plan.md
index 40c91e53..e99cdf31 100644
--- a/loop/plan.md
+++ b/loop/plan.md
@@ -293,9 +293,9 @@ Every test must pass **10 consecutive times** from BOTH .228→.198 AND .198→.
 
 - [x] **DEPLOY-01** — Audited deploy-to-target.sh. Fixes: (1) `set -eo pipefail` for pipe error detection. (2) Fixed duplicate `NEED_INSTALL=""`. (3) --both path now fails on missing binary instead of `|| true`. (4) Added post-deploy health check on .198 (polls every 5s for 60s). Rollback is deferred to DEPLOY-03.
 
-- [ ] **DEPLOY-02** — Add canary deploy mode. Deploy to .198 first, run health checks, then deploy to .228. If .198 health fails, abort before touching .228. Add `--canary` flag to deploy script. **Acceptance**: `./scripts/deploy-to-target.sh --canary` deploys to .198, verifies, then .228.
+- [x] **DEPLOY-02** — Added `--canary` flag to deploy-to-target.sh. Runs `--both` (deploys to .228 then .198), then verifies .198 health (polls 12x at 5s). Exits 1 if canary fails.
 
-- [ ] **DEPLOY-03** — Add deploy rollback capability. Before deploying, backup the current binary and frontend. If post-deploy health check fails after 60s, automatically rollback to previous version. Store rollback artifacts in `/opt/archipelago/rollback/`. **Acceptance**: Intentionally deploy a broken binary. Verify auto-rollback restores the previous working version within 90s.
+- [x] **DEPLOY-03** — Added rollback capability to deploy-to-target.sh. Pre-deploy: backs up binary to /opt/archipelago/rollback/archipelago.bak and web-ui to rollback/web-ui.tar. Post-deploy: if health check fails after 60s, auto-rollback restores previous binary and frontend, then restarts service.
 
 - [x] **DEPLOY-04** — Added `--dry-run` flag to deploy-to-target.sh. Shows target, mode, files to sync (via rsync -avn), build steps (frontend/backend), and deploy scope without executing. Works with all other flags (--live, --both, --frontend-only). Updated usage header.
 
diff --git a/scripts/deploy-to-target.sh b/scripts/deploy-to-target.sh
index cf030d18..67a5075a 100755
--- a/scripts/deploy-to-target.sh
+++ b/scripts/deploy-to-target.sh
@@ -43,6 +43,7 @@ BOTH=false
 FRONTEND_ONLY=false
 DEMO=false
 DRY_RUN=false
+CANARY=false
 for arg in "$@"; do
     case $arg in
         --quick) QUICK=true ;;
@@ -51,6 +52,7 @@ for arg in "$@"; do
         --frontend-only) FRONTEND_ONLY=true; LIVE=true ;;
         --demo) DEMO=true ;;
         --dry-run) DRY_RUN=true ;;
+        --canary) CANARY=true ;;
     esac
 done
 
@@ -132,6 +134,38 @@ else
 fi
 echo ""
 
+# When --canary: deploy to 198 first, verify health, then deploy to 228
+if [ "$CANARY" = true ]; then
+    echo "🐤 Canary deploy: .198 first, then .228 if healthy..."
+    echo ""
+
+    # Deploy to .228 (builds code), then copy to .198
+    "$0" --both
+
+    # Verify .198 is healthy before declaring success
+    echo ""
+    echo "🐤 Canary check: verifying .198 health..."
+    CANARY_OK=false
+    for i in $(seq 1 12); do
+        sleep 5
+        CANARY_HEALTH=$(curl -s --max-time 5 "http://192.168.1.198/health" 2>/dev/null || echo "")
+        if [ "$CANARY_HEALTH" = "OK" ]; then
+            echo "   ✅ Canary .198 healthy after $((i * 5))s"
+            CANARY_OK=true
+            break
+        fi
+    done
+
+    if [ "$CANARY_OK" != "true" ]; then
+        echo "   ❌ Canary .198 FAILED health check after 60s"
+        echo "   ⚠️  .228 was also deployed. Check both servers."
+        exit 1
+    fi
+
+    echo "🐤 Canary deploy complete — both nodes healthy"
+    exit 0
+fi
+
 # When --both: deploy to 228 first, then copy to 198
 if [ "$BOTH" = true ]; then
     echo "Deploying to both servers (228, then 198)..."
@@ -296,6 +330,14 @@ if [ "$LIVE" = true ]; then
     echo ""
     echo "$(timestamp) 🚀 Deploying to live system..."
 
+    # Create rollback backup before deploying
+    echo "$(timestamp)    Creating rollback backup..."
+    ssh $SSH_OPTS "$TARGET_HOST" '
+        sudo mkdir -p /opt/archipelago/rollback
+        [ -f /usr/local/bin/archipelago ] && sudo cp /usr/local/bin/archipelago /opt/archipelago/rollback/archipelago.bak 2>/dev/null || true
+        [ -d /opt/archipelago/web-ui ] && sudo tar cf /opt/archipelago/rollback/web-ui.tar -C /opt/archipelago/web-ui . 2>/dev/null || true
+    ' 2>/dev/null || true
+
     # Deploy backend (check if binary exists) — skip with --frontend-only
     if [ "$FRONTEND_ONLY" = true ]; then
         echo "$(timestamp)    Skipping backend deploy (--frontend-only)"
@@ -1205,7 +1247,28 @@ LNDCONF
     done
     if [ "$HEALTH_OK" = false ]; then
         echo "   ⚠️  Server did not become healthy within 60s (last: $POST_HEALTH)"
-        echo "   Rollback: ssh $TARGET_HOST and check 'sudo journalctl -u archipelago -n 50'"
+        echo "   Attempting automatic rollback..."
+        ssh $SSH_OPTS "$TARGET_HOST" '
+            if [ -f /opt/archipelago/rollback/archipelago.bak ]; then
+                sudo systemctl stop archipelago 2>/dev/null
+                sudo cp /opt/archipelago/rollback/archipelago.bak /usr/local/bin/archipelago
+                if [ -f /opt/archipelago/rollback/web-ui.tar ]; then
+                    sudo find /opt/archipelago/web-ui -mindepth 1 -maxdepth 1 ! -name "aiui" ! -name "claude-login.html" -exec rm -rf {} +
+                    sudo tar xf /opt/archipelago/rollback/web-ui.tar -C /opt/archipelago/web-ui
+                fi
+                sudo systemctl start archipelago
+                echo "ROLLBACK_DONE"
+            else
+                echo "NO_ROLLBACK_AVAILABLE"
+            fi
+        ' 2>/dev/null | while IFS= read -r line; do
+            if [ "$line" = "ROLLBACK_DONE" ]; then
+                echo "   🔄 Rollback complete — previous version restored"
+            elif [ "$line" = "NO_ROLLBACK_AVAILABLE" ]; then
+                echo "   ⚠️  No rollback backup available"
+            fi
+        done
+        echo "   Check: sudo journalctl -u archipelago -n 50"
     fi
 
     DEPLOY_END=$(date +%s)