diff --git a/apps/macos/Sources/Clawdis/WebChatServer.swift b/apps/macos/Sources/Clawdis/WebChatServer.swift
index f70378eae..9fce94744 100644
--- a/apps/macos/Sources/Clawdis/WebChatServer.swift
+++ b/apps/macos/Sources/Clawdis/WebChatServer.swift
@@ -61,6 +61,7 @@ final class WebChatServer: @unchecked Sendable {
         connection.stateUpdateHandler = { state in
             switch state {
             case .ready:
+                webChatServerLogger.debug("WebChatServer connection ready")
                 self.receive(on: connection)
             case let .failed(error):
                 webChatServerLogger
@@ -79,6 +80,9 @@ final class WebChatServer: @unchecked Sendable {
                 self.respond(to: connection, requestData: data)
             }
             if isComplete || error != nil {
+                if let error {
+                    webChatServerLogger.error("WebChatServer receive error: \(error.localizedDescription, privacy: .public)")
+                }
                 connection.cancel()
             } else {
                 self.receive(on: connection)
@@ -104,6 +108,7 @@ final class WebChatServer: @unchecked Sendable {
         if path.hasPrefix("webchat/") {
             path = String(path.dropFirst("webchat/".count))
         }
+        webChatServerLogger.debug("WebChatServer request path=\(path, privacy: .public)")
         if path.isEmpty { path = "index.html" }
 
         guard let root else {
diff --git a/apps/macos/Sources/Clawdis/WebChatWindow.swift b/apps/macos/Sources/Clawdis/WebChatWindow.swift
index 0a7f5c3f1..68aa64bce 100644
--- a/apps/macos/Sources/Clawdis/WebChatWindow.swift
+++ b/apps/macos/Sources/Clawdis/WebChatWindow.swift
@@ -105,7 +105,7 @@ final class WebChatWindowController: NSWindowController, WKScriptMessageHandler,
         self.webView.configuration.userContentController.addUserScript(userScript)
 
         WebChatServer.shared.start(root: webChatURL)
-        guard let baseURL = WebChatServer.shared.baseURL() else {
+        guard let baseURL = self.waitForWebChatServer() else {
             webChatLogger.error("WebChatServer not ready; cannot load web chat")
             return
         }
@@ -114,6 +114,22 @@ final class WebChatWindowController: NSWindowController, WKScriptMessageHandler,
         webChatLogger.debug("loadPage queued HTML into WKWebView url=\(url.absoluteString, privacy: .public)")
     }
 
+    private func waitForWebChatServer(timeout: TimeInterval = 2.0) -> URL? {
+        let deadline = Date().addingTimeInterval(timeout)
+        var base: URL?
+        while Date() < deadline {
+            if let url = WebChatServer.shared.baseURL() {
+                base = url
+                break
+            }
+            RunLoop.current.run(mode: .default, before: Date().addingTimeInterval(0.05))
+        }
+        if base == nil {
+            webChatLogger.error("WebChatServer failed to become ready within \(timeout, privacy: .public)s")
+        }
+        return base
+    }
+
     func webView(_ webView: WKWebView, didFinish navigation: WKNavigation!) {
         webChatLogger.debug("didFinish navigation url=\(webView.url?.absoluteString ?? "nil", privacy: .public)")
         webView.evaluateJavaScript("document.body.innerText") { result, error in