diff --git a/scripts/deploy/restart-toolkit-socket.sh b/scripts/deploy/restart-toolkit-socket.sh
index 32de296..5c424ad 100755
--- a/scripts/deploy/restart-toolkit-socket.sh
+++ b/scripts/deploy/restart-toolkit-socket.sh
@@ -91,7 +91,22 @@ if ! kill -0 "$socket_pid" 2>/dev/null; then
 fi
 
 if command -v curl >/dev/null 2>&1; then
-  curl -fsS "http://127.0.0.1:$socket_port/health" >/dev/null
+  socket_ready="false"
+
+  for _ in 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15; do
+    if curl -fsS "http://127.0.0.1:$socket_port/health" >/dev/null; then
+      socket_ready="true"
+      break
+    fi
+
+    sleep 1
+  done
+
+  if [ "$socket_ready" != "true" ]; then
+    echo "[deploy:toolkit] socket did not become healthy; recent log output follows."
+    tail -n 80 "$log_file" || true
+    exit 1
+  fi
 fi
 
 echo "[deploy:toolkit] socket running as $socket_pid"
diff --git a/src/data/toolkit/changelog.json b/src/data/toolkit/changelog.json
index 089f7b9..50a3438 100644
--- a/src/data/toolkit/changelog.json
+++ b/src/data/toolkit/changelog.json
@@ -19,6 +19,7 @@
     "summary": "Fixed deployed Toolkit socket restarts when SSH sessions do not load the user's Node path.",
     "changes": [
       "Updated the Toolkit socket restart script to find Node and npm from standard macOS, Homebrew, and NVM locations.",
+      "Added a bounded health retry so deploys wait for the socket to bind before failing.",
       "Kept the restart command safe for non-interactive SSH deploy sessions.",
       "Preserved the shared workspace socket behavior for deployed Toolkit editing."
     ]