diff --git a/apps/desktop/src/shell/DesktopShellEnvironment.test.ts b/apps/desktop/src/shell/DesktopShellEnvironment.test.ts
index 0c7869194323c..c00e2ea7c65a2 100644
--- a/apps/desktop/src/shell/DesktopShellEnvironment.test.ts
+++ b/apps/desktop/src/shell/DesktopShellEnvironment.test.ts
@@ -637,6 +637,52 @@ describe("DesktopShellEnvironment", () => {
     }),
   );
 
+  it.effect("recovers the login-shell PATH when the first probe outlasts the timeout", () =>
+    Effect.gen(function* () {
+      const env: NodeJS.ProcessEnv = { SHELL: "/bin/zsh", PATH: "/usr/bin:/bin:/usr/sbin:/sbin" };
+      const output = envOutput({ PATH: "/opt/homebrew/bin:/usr/bin" });
+      let shellProbes = 0;
+      yield* runShellEnvironment({
+        env,
+        platform: "darwin",
+        handler: () => "",
+        processSpawner: ChildProcessSpawner.make((command) => {
+          if (command._tag !== "StandardCommand" || command.command !== "/bin/zsh") {
+            return Effect.succeed(makeProcess(""));
+          }
+          shellProbes += 1;
+          if (shellProbes > 1) return Effect.succeed(makeProcess(output));
+          // A cold start: the first login shell answers, but only after 7s.
+          const slow = Effect.sleep("7 seconds");
+          const stdout = Stream.fromEffect(slow.pipe(Effect.as(textEncoder.encode(output))));
+          return Effect.succeed(
+            ChildProcessSpawner.makeHandle({
+              pid: ChildProcessSpawner.ProcessId(125),
+              stdout,
+              stderr: Stream.empty,
+              all: stdout,
+              exitCode: slow.pipe(Effect.as(ChildProcessSpawner.ExitCode(0))),
+              isRunning: Effect.succeed(true),
+              kill: () => Effect.void,
+              stdin: Sink.drain,
+              getInputFd: () => Sink.drain,
+              getOutputFd: () => Stream.empty,
+              unref: Effect.succeed(Effect.void),
+            }),
+          );
+        }),
+        use: (service) =>
+          Effect.gen(function* () {
+            yield* service.installIntoProcess;
+            yield* TestClock.adjust("10 minutes");
+            return true;
+          }),
+      }).pipe(Effect.provide(Logger.layer([])));
+
+      assert.equal(env.PATH, "/opt/homebrew/bin:/usr/bin:/bin:/usr/sbin:/sbin");
+    }),
+  );
+
   it.effect("loads PowerShell profile environment on Windows", () =>
     Effect.gen(function* () {
       const env: NodeJS.ProcessEnv = {
diff --git a/apps/desktop/src/shell/DesktopShellEnvironment.ts b/apps/desktop/src/shell/DesktopShellEnvironment.ts
index 9d9e390c95496..f0983ca622490 100644
--- a/apps/desktop/src/shell/DesktopShellEnvironment.ts
+++ b/apps/desktop/src/shell/DesktopShellEnvironment.ts
@@ -117,6 +117,8 @@ const LOCALE_ENV_NAMES = ["LANG", "LC_ALL", "LC_CTYPE"] as const;
 const FALLBACK_LC_CTYPE = "en_US.UTF-8";
 const WINDOWS_SHELL_CANDIDATES = ["pwsh.exe", "powershell.exe"] as const;
 const LOGIN_SHELL_TIMEOUT = Duration.seconds(5);
+// A profile can be slow only while the machine boots; one longer wait covers it.
+const SLOW_LOGIN_SHELL_TIMEOUT = Duration.seconds(20);
 const LAUNCHCTL_TIMEOUT = Duration.seconds(2);
 const PROCESS_TERMINATE_GRACE = Duration.seconds(1);
 
@@ -261,7 +263,11 @@ const runCommandOutput = Effect.fn("desktop.shellEnvironment.runCommandOutput")(
   readonly env: NodeJS.ProcessEnv;
   readonly timeout: Duration.Duration;
   readonly shell?: boolean;
-}): Effect.fn.Return<string, never, ChildProcessSpawner.ChildProcessSpawner> {
+}): Effect.fn.Return<
+  string,
+  DesktopShellEnvironmentCommandTimeoutError,
+  ChildProcessSpawner.ChildProcessSpawner
+> {
   const spawner = yield* ChildProcessSpawner.ChildProcessSpawner;
   const fiber = yield* Effect.scoped(
     Effect.gen(function* () {
@@ -317,21 +323,34 @@ const runCommandOutput = Effect.fn("desktop.shellEnvironment.runCommandOutput")(
     return output.value;
   }
 
-  const error = new DesktopShellEnvironmentCommandTimeoutError({
+  return yield* new DesktopShellEnvironmentCommandTimeoutError({
     probe: input.probe,
     executable: executableName(input.command),
     argumentCount: input.args.length,
     timeoutMs: Duration.toMillis(input.timeout),
   });
-  yield* logShellEnvironmentCommandError(error);
-  return "";
 });
 
+const orEmptyOnTimeout = <R>(
+  effect: Effect.Effect<string, DesktopShellEnvironmentCommandTimeoutError, R>,
+): Effect.Effect<string, never, R> =>
+  effect.pipe(
+    Effect.catchTags({
+      DesktopShellEnvironmentCommandTimeoutError: (error) =>
+        logShellEnvironmentCommandError(error).pipe(Effect.as("")),
+    }),
+  );
+
 const readLoginShellEnvironment = (
   shell: string,
   names: ReadonlyArray<string>,
   env: NodeJS.ProcessEnv,
-): Effect.Effect<EnvironmentPatch, never, ChildProcessSpawner.ChildProcessSpawner> =>
+  timeout: Duration.Duration,
+): Effect.Effect<
+  EnvironmentPatch,
+  DesktopShellEnvironmentCommandTimeoutError,
+  ChildProcessSpawner.ChildProcessSpawner
+> =>
   names.length === 0
     ? Effect.succeed({})
     : runCommandOutput({
@@ -339,7 +358,7 @@ const readLoginShellEnvironment = (
         command: shell,
         args: ["-ilc", buildEnvironmentCaptureCommand(shell, names)],
         env,
-        timeout: LOGIN_SHELL_TIMEOUT,
+        timeout,
       }).pipe(Effect.map((output) => extractEnvironment(output, names)));
 
 const readLaunchctlPath = (env: NodeJS.ProcessEnv) =>
@@ -349,7 +368,7 @@ const readLaunchctlPath = (env: NodeJS.ProcessEnv) =>
     command: "/bin/launchctl",
     args: ["getenv", "PATH"],
     timeout: LAUNCHCTL_TIMEOUT,
-  }).pipe(Effect.map(trimNonEmpty));
+  }).pipe(orEmptyOnTimeout, Effect.map(trimNonEmpty));
 
 const readWindowsEnvironment = Effect.fn("desktop.shellEnvironment.readWindowsEnvironment")(
   function* (
@@ -374,7 +393,7 @@ const readWindowsEnvironment = Effect.fn("desktop.shellEnvironment.readWindowsEn
         args,
         env,
         timeout: LOGIN_SHELL_TIMEOUT,
-      });
+      }).pipe(orEmptyOnTimeout);
       const environment = extractEnvironment(output, names);
       if (Object.keys(environment).length > 0) {
         return environment;
@@ -429,10 +448,27 @@ const installPosixEnvironment = Effect.fn("desktop.shellEnvironment.installPosix
     const userShells = [config.env.SHELL?.trim(), readUserLoginShell()];
 
     let answeredBy: string | undefined;
+    let waitedForSlowShell = false;
     for (const shell of listLoginShellCandidates(config.platform, config.env.SHELL)) {
+      const read = (timeout: Duration.Duration) =>
+        readLoginShellEnvironment(shell, LOGIN_SHELL_ENV_NAMES, config.env, timeout);
       Object.assign(
         shellEnvironment,
-        yield* readLoginShellEnvironment(shell, LOGIN_SHELL_ENV_NAMES, config.env),
+        yield* read(LOGIN_SHELL_TIMEOUT).pipe(
+          Effect.catchTags({
+            DesktopShellEnvironmentCommandTimeoutError: (error) => {
+              const retry = !waitedForSlowShell;
+              waitedForSlowShell = true;
+              return logShellEnvironmentCommandError(error).pipe(
+                Effect.andThen(retry ? read(SLOW_LOGIN_SHELL_TIMEOUT) : Effect.succeed({})),
+              );
+            },
+          }),
+          Effect.catchTags({
+            DesktopShellEnvironmentCommandTimeoutError: (error) =>
+              logShellEnvironmentCommandError(error).pipe(Effect.as({})),
+          }),
+        ),
       );
       if (shellEnvironment.PATH) {
         answeredBy = shell;