diff --git a/src/lib/adapters/openshell/resolve.test.ts b/src/lib/adapters/openshell/resolve.test.ts
index a62e4c72ca..1f187c59bd 100644
--- a/src/lib/adapters/openshell/resolve.test.ts
+++ b/src/lib/adapters/openshell/resolve.test.ts
@@ -64,6 +64,25 @@ describe("lib/resolve-openshell", () => {
     ).toBe("/usr/local/bin/openshell");
   });
 
+  it("falls back to /opt/homebrew/bin (Apple Silicon Homebrew prefix, #5334)", () => {
+    expect(
+      resolveOpenshell({
+        commandVResult: null,
+        checkExecutable: (p) => p === "/opt/homebrew/bin/openshell",
+      }),
+    ).toBe("/opt/homebrew/bin/openshell");
+  });
+
+  it("prefers /opt/homebrew/bin over /usr/local/bin (#5334)", () => {
+    expect(
+      resolveOpenshell({
+        commandVResult: null,
+        checkExecutable: (p) =>
+          p === "/opt/homebrew/bin/openshell" || p === "/usr/local/bin/openshell",
+      }),
+    ).toBe("/opt/homebrew/bin/openshell");
+  });
+
   it("falls back to /usr/bin", () => {
     expect(
       resolveOpenshell({
diff --git a/src/lib/adapters/openshell/resolve.ts b/src/lib/adapters/openshell/resolve.ts
index 4e71900d9f..fdb3833571 100644
--- a/src/lib/adapters/openshell/resolve.ts
+++ b/src/lib/adapters/openshell/resolve.ts
@@ -50,8 +50,17 @@ export function resolveOpenshell(opts: ResolveOpenshellOptions = {}): string | n
   }
 
   // Step 2: fallback candidates
+  //
+  // `/opt/homebrew/bin` is the Apple Silicon Homebrew prefix. It is frequently
+  // absent from the non-interactive/login shell that drives onboarding (Homebrew
+  // only adds it via `brew shellenv`, which many profiles source after the
+  // non-interactive guard), so `command -v openshell` above can miss a perfectly
+  // good Homebrew install. Probing the prefix directly keeps NemoClaw coherent
+  // with a Homebrew-installed OpenShell instead of reporting "openshell not
+  // found" while the binary sits in `/opt/homebrew/bin` (#5334).
   const candidates = [
     ...(home?.startsWith("/") ? [`${home}/.local/bin/openshell`] : []),
+    "/opt/homebrew/bin/openshell",
     "/usr/local/bin/openshell",
     "/usr/bin/openshell",
   ];
diff --git a/src/lib/onboard/docker-driver-gateway-failure.test.ts b/src/lib/onboard/docker-driver-gateway-failure.test.ts
index b8fc814514..30cb5d2805 100644
--- a/src/lib/onboard/docker-driver-gateway-failure.test.ts
+++ b/src/lib/onboard/docker-driver-gateway-failure.test.ts
@@ -75,6 +75,30 @@ describe("reportDockerDriverGatewayStartFailure (#3111)", () => {
     expect(joined).not.toContain("before becoming ready");
   });
 
+  it("reports an unhealthy-within-timeout gateway without asserting liveness, and points at status commands (#5334)", () => {
+    reportDockerDriverGatewayStartFailure("/tmp/nonexistent-gateway.log", makeExitState(), {
+      exitOnFailure: false,
+    });
+    const joined = errSpy.mock.calls.map((c: string[]) => c.join(" ")).join("\n");
+    expect(joined).toContain("did not become healthy within the timeout");
+    // Must not claim the process is still running: the caller can reach here
+    // after liveness dropped before the 'exit' event fired (#5334 review).
+    expect(joined).not.toContain("still running");
+    expect(joined).toContain("openshell status");
+    expect(joined).toContain("openshell gateway info");
+  });
+
+  it("prefers the specific exit description over the generic line when the gateway exited (#5334)", () => {
+    reportDockerDriverGatewayStartFailure(
+      "/tmp/nonexistent-gateway.log",
+      makeExitState({ exited: true, code: 1, describeExit: () => "exited with code 1" }),
+      { exitOnFailure: false },
+    );
+    const joined = errSpy.mock.calls.map((c: string[]) => c.join(" ")).join("\n");
+    expect(joined).toContain("exited with code 1");
+    expect(joined).not.toContain("did not become healthy within the timeout");
+  });
+
   it("includes a tail of the gateway log when the file exists", () => {
     const dir = fs.mkdtempSync(path.join(os.tmpdir(), "gw-fail-"));
     const log = path.join(dir, "openshell-gateway.log");
diff --git a/src/lib/onboard/docker-driver-gateway-failure.ts b/src/lib/onboard/docker-driver-gateway-failure.ts
index 4dd097283c..4326733b99 100644
--- a/src/lib/onboard/docker-driver-gateway-failure.ts
+++ b/src/lib/onboard/docker-driver-gateway-failure.ts
@@ -61,6 +61,14 @@ export function reportDockerDriverGatewayStartFailure(
   console.error("  Docker-driver gateway failed to start.");
   if (childExit.exited) {
     console.error(`  Gateway process ${childExit.describeExit()} before becoming ready.`);
+  } else {
+    // #5334: the start loop also reaches this reporter when the poll budget is
+    // exhausted, or when the process's liveness dropped before its 'exit' event
+    // was observed. We therefore do NOT assert the process is "still running"
+    // (that would misreport a gateway that already died) and instead state only
+    // the observable fact: it never became healthy in time. The status commands
+    // in the Troubleshooting footer below are what reveal why.
+    console.error("  The gateway process did not become healthy within the timeout.");
   }
   if (tail) {
     console.error("  Gateway log tail:");
@@ -71,6 +79,8 @@ export function reportDockerDriverGatewayStartFailure(
   }
   console.error("  Troubleshooting:");
   console.error(`    tail -100 ${logPath}`);
+  console.error("    openshell status");
+  console.error("    openshell gateway info");
   console.error("    docker info --format '{{json .CDISpecDirs}}'");
 
   if (exitOnFailure) {
diff --git a/src/lib/onboard/docker-driver-gateway-runtime.test.ts b/src/lib/onboard/docker-driver-gateway-runtime.test.ts
index 665840b215..e108ef0575 100644
--- a/src/lib/onboard/docker-driver-gateway-runtime.test.ts
+++ b/src/lib/onboard/docker-driver-gateway-runtime.test.ts
@@ -286,6 +286,36 @@ describe("docker-driver gateway runtime helpers", () => {
     });
   });
 
+  it("falls back to /opt/homebrew/bin for the standalone gateway binary (#5334)", () => {
+    withEnv({ NEMOCLAW_OPENSHELL_GATEWAY_BIN: undefined }, () => {
+      const { helpers } = makeHelpers({
+        // A cached CLI binary in a directory with no sibling gateway forces the
+        // resolver past sibling resolution into the prefix fallback list.
+        getCachedOpenshellBinary: () => "/nonexistent/dir/openshell",
+      });
+      vi.spyOn(fs, "existsSync").mockImplementation(
+        ((candidate) =>
+          String(candidate) === "/opt/homebrew/bin/openshell-gateway") as typeof fs.existsSync,
+      );
+
+      expect(helpers.resolveOpenShellGatewayBinary()).toBe("/opt/homebrew/bin/openshell-gateway");
+    });
+  });
+
+  it("falls back to /opt/homebrew/bin for the standalone sandbox binary (#5334)", () => {
+    withEnv({ NEMOCLAW_OPENSHELL_SANDBOX_BIN: undefined }, () => {
+      const { helpers } = makeHelpers({
+        getCachedOpenshellBinary: () => "/nonexistent/dir/openshell",
+      });
+      vi.spyOn(fs, "existsSync").mockImplementation(
+        ((candidate) =>
+          String(candidate) === "/opt/homebrew/bin/openshell-sandbox") as typeof fs.existsSync,
+      );
+
+      expect(helpers.resolveOpenShellSandboxBinary()).toBe("/opt/homebrew/bin/openshell-sandbox");
+    });
+  });
+
   it("matches the docker compatibility gateway parent process", () => {
     const pid = 12_348;
     const { helpers, runCapture } = makeHelpers({
diff --git a/src/lib/onboard/docker-driver-gateway-runtime.ts b/src/lib/onboard/docker-driver-gateway-runtime.ts
index 299c366df6..5f68498236 100644
--- a/src/lib/onboard/docker-driver-gateway-runtime.ts
+++ b/src/lib/onboard/docker-driver-gateway-runtime.ts
@@ -120,8 +120,12 @@ export function createDockerDriverGatewayRuntimeHelpers(deps: DockerDriverGatewa
     if (configured && configured.trim()) return path.resolve(configured.trim());
     const sibling = resolveSiblingBinary("openshell-gateway");
     if (sibling) return sibling;
+    // Keep the standalone gateway fallbacks coherent with the CLI resolver
+    // (resolveOpenshell): `/opt/homebrew/bin` is the Apple Silicon Homebrew
+    // prefix and is often missing from the onboarding shell's PATH (#5334).
     for (const candidate of [
       path.join(os.homedir(), ".local", "bin", "openshell-gateway"),
+      "/opt/homebrew/bin/openshell-gateway",
       "/usr/local/bin/openshell-gateway",
       "/usr/bin/openshell-gateway",
     ]) {
@@ -135,8 +139,10 @@ export function createDockerDriverGatewayRuntimeHelpers(deps: DockerDriverGatewa
     if (configured && configured.trim()) return path.resolve(configured.trim());
     const sibling = resolveSiblingBinary("openshell-sandbox");
     if (sibling) return sibling;
+    // Apple Silicon Homebrew prefix kept in sync with the other resolvers (#5334).
     for (const candidate of [
       path.join(os.homedir(), ".local", "bin", "openshell-sandbox"),
+      "/opt/homebrew/bin/openshell-sandbox",
       "/usr/local/bin/openshell-sandbox",
       "/usr/bin/openshell-sandbox",
     ]) {