diff --git a/src/hooks/gmail-ops.ts b/src/hooks/gmail-ops.ts
index 4aae31ae3..0749abbf7 100644
--- a/src/hooks/gmail-ops.ts
+++ b/src/hooks/gmail-ops.ts
@@ -132,7 +132,7 @@ export async function runGmailSetup(opts: GmailSetupOptions) {
 
   const serveBind = opts.bind ?? DEFAULT_GMAIL_SERVE_BIND;
   const servePort = opts.port ?? DEFAULT_GMAIL_SERVE_PORT;
-  const servePath = normalizeServePath(opts.path ?? DEFAULT_GMAIL_SERVE_PATH);
+  const configuredServePath = opts.path ?? baseConfig.hooks?.gmail?.serve?.path;
 
   const includeBody = opts.includeBody ?? true;
   const maxBytes = opts.maxBytes ?? DEFAULT_GMAIL_MAX_BYTES;
@@ -140,7 +140,20 @@ export async function runGmailSetup(opts: GmailSetupOptions) {
     opts.renewEveryMinutes ?? DEFAULT_GMAIL_RENEW_MINUTES;
 
   const tailscaleMode = opts.tailscale ?? "funnel";
-  const tailscalePath = normalizeServePath(opts.tailscalePath ?? servePath);
+  // Tailscale strips the path before proxying; keep a public path while gog
+  // listens on "/" unless the user explicitly configured a serve path.
+  const servePath = normalizeServePath(
+    tailscaleMode !== "off" && !configuredServePath
+      ? "/"
+      : configuredServePath ?? DEFAULT_GMAIL_SERVE_PATH,
+  );
+  const tailscalePath = normalizeServePath(
+    opts.tailscalePath ??
+      baseConfig.hooks?.gmail?.tailscale?.path ??
+      (tailscaleMode !== "off"
+        ? configuredServePath ?? DEFAULT_GMAIL_SERVE_PATH
+        : servePath),
+  );
 
   await runGcloud(["config", "set", "project", projectId, "--quiet"]);
   await runGcloud([
diff --git a/src/hooks/gmail.test.ts b/src/hooks/gmail.test.ts
index f76052af7..e496d81b4 100644
--- a/src/hooks/gmail.test.ts
+++ b/src/hooks/gmail.test.ts
@@ -60,4 +60,49 @@ describe("gmail hook config", () => {
     );
     expect(result.ok).toBe(false);
   });
+
+  it("defaults serve path to / when tailscale is enabled", () => {
+    const result = resolveGmailHookRuntimeConfig(
+      {
+        hooks: {
+          token: "hook-token",
+          gmail: {
+            account: "clawdbot@gmail.com",
+            topic: "projects/demo/topics/gog-gmail-watch",
+            pushToken: "push-token",
+            tailscale: { mode: "funnel" },
+          },
+        },
+      },
+      {},
+    );
+    expect(result.ok).toBe(true);
+    if (result.ok) {
+      expect(result.value.serve.path).toBe("/");
+      expect(result.value.tailscale.path).toBe("/gmail-pubsub");
+    }
+  });
+
+  it("keeps explicit serve path for tailscale when set", () => {
+    const result = resolveGmailHookRuntimeConfig(
+      {
+        hooks: {
+          token: "hook-token",
+          gmail: {
+            account: "clawdbot@gmail.com",
+            topic: "projects/demo/topics/gog-gmail-watch",
+            pushToken: "push-token",
+            serve: { path: "/custom" },
+            tailscale: { mode: "funnel" },
+          },
+        },
+      },
+      {},
+    );
+    expect(result.ok).toBe(true);
+    if (result.ok) {
+      expect(result.value.serve.path).toBe("/custom");
+      expect(result.value.tailscale.path).toBe("/custom");
+    }
+  });
 });
diff --git a/src/hooks/gmail.ts b/src/hooks/gmail.ts
index 46ab27e53..d11d53ad8 100644
--- a/src/hooks/gmail.ts
+++ b/src/hooks/gmail.ts
@@ -152,14 +152,25 @@ export function resolveGmailHookRuntimeConfig(
     servePortRaw > 0
       ? Math.floor(servePortRaw)
       : DEFAULT_GMAIL_SERVE_PORT;
-  const servePath = normalizeServePath(
-    overrides.servePath ?? gmail?.serve?.path,
-  );
+  const servePathRaw = overrides.servePath ?? gmail?.serve?.path;
+  const hasExplicitServePath =
+    typeof servePathRaw === "string" && servePathRaw.trim().length > 0;
 
   const tailscaleMode =
     overrides.tailscaleMode ?? gmail?.tailscale?.mode ?? "off";
+  // When exposing the push endpoint via Tailscale, the public path is stripped
+  // before proxying; use "/" internally unless the user set a path explicitly.
+  const servePath = normalizeServePath(
+    tailscaleMode !== "off" && !hasExplicitServePath ? "/" : servePathRaw,
+  );
+
+  const tailscalePathRaw = overrides.tailscalePath ?? gmail?.tailscale?.path;
   const tailscalePath = normalizeServePath(
-    overrides.tailscalePath ?? gmail?.tailscale?.path ?? servePath,
+    tailscaleMode !== "off" && !tailscalePathRaw
+      ? hasExplicitServePath
+        ? servePathRaw
+        : DEFAULT_GMAIL_SERVE_PATH
+      : tailscalePathRaw ?? servePath,
   );
 
   return {