diff --git a/packages/web/bin/lib/cli-control.js b/packages/web/bin/lib/cli-control.js
index 6cbbc864..2a6df6eb 100644
--- a/packages/web/bin/lib/cli-control.js
+++ b/packages/web/bin/lib/cli-control.js
@@ -10,14 +10,27 @@ const asNonEmptyString = (value) => {
 const DEFAULT_WAIT_TIMEOUT_SECONDS = 600;
 const WAIT_HTTP_TIMEOUT_BUFFER_MS = 30_000;
 
+// Provisioning a worktree is not one of the instant control calls the short
+// default is sized for: it runs git against the repository and prepares a new
+// directory, which on a cold path takes longer than the default allows. The
+// server finishes the work regardless of the client giving up, so a client-side
+// timeout here reported a failure for a worktree that was in fact created.
+const WORKTREE_PROVISION_TIMEOUT_MS = 120_000;
+
 // The control service blocks server-side while wait is set, so the client
 // HTTP timeout must outlive the requested wait window instead of the short
 // default used for instant control calls.
 export const resolveControlTimeoutMs = (input, options) => {
   if (Number.isFinite(options?.timeoutMs) && options.timeoutMs > 0) return options.timeoutMs;
-  if (input?.wait !== true) return undefined;
+  const provisionsWorktree = asNonEmptyString(input?.worktree) !== null;
+  if (input?.wait !== true) {
+    return provisionsWorktree ? WORKTREE_PROVISION_TIMEOUT_MS : undefined;
+  }
   const waitSeconds = Number(input?.timeout) > 0 ? Number(input.timeout) : DEFAULT_WAIT_TIMEOUT_SECONDS;
-  return (waitSeconds * 1000) + WAIT_HTTP_TIMEOUT_BUFFER_MS;
+  const waitTimeoutMs = (waitSeconds * 1000) + WAIT_HTTP_TIMEOUT_BUFFER_MS;
+  // Waiting for the session and provisioning its worktree are additive, so the
+  // window must cover whichever is longer rather than only the wait.
+  return provisionsWorktree ? Math.max(waitTimeoutMs, WORKTREE_PROVISION_TIMEOUT_MS) : waitTimeoutMs;
 };
 
 export const requestControlAction = async (port, action, input, options = {}) => {
diff --git a/packages/web/bin/lib/cli-control.test.js b/packages/web/bin/lib/cli-control.test.js
index 0e259e58..1ae93015 100644
--- a/packages/web/bin/lib/cli-control.test.js
+++ b/packages/web/bin/lib/cli-control.test.js
@@ -19,4 +19,20 @@ describe('resolveControlTimeoutMs', () => {
   it('never shrinks an explicitly requested HTTP timeout', () => {
     expect(resolveControlTimeoutMs({ wait: true, timeout: 30 }, { timeoutMs: 5000 })).toBe(5000);
   });
+
+  it('allows a worktree to be provisioned without waiting for the session', () => {
+    expect(resolveControlTimeoutMs({ worktree: 'feature' }, {})).toBe(120_000);
+  });
+
+  it('ignores a blank worktree name', () => {
+    expect(resolveControlTimeoutMs({ worktree: '   ' }, {})).toBeUndefined();
+  });
+
+  it('covers worktree provisioning even when the wait window is shorter', () => {
+    expect(resolveControlTimeoutMs({ wait: true, timeout: 30, worktree: 'feature' }, {})).toBe(120_000);
+  });
+
+  it('keeps a longer wait window when it outlasts worktree provisioning', () => {
+    expect(resolveControlTimeoutMs({ wait: true, worktree: 'feature' }, {})).toBe(630_000);
+  });
 });