diff --git a/packages/cli/bin/binary-entry.ts b/packages/cli/bin/binary-entry.ts
index eee5717f..773c596b 100644
--- a/packages/cli/bin/binary-entry.ts
+++ b/packages/cli/bin/binary-entry.ts
@@ -37,4 +37,4 @@ if (!process.stdin.isTTY || !process.stdout.isTTY) {
   process.env.CI = "true";
 }
 
-await runCLI();
+await runCLI({ distribution: "binary" });
diff --git a/packages/cli/src/cli/index.ts b/packages/cli/src/cli/index.ts
index 8821542a..65fa89b2 100644
--- a/packages/cli/src/cli/index.ts
+++ b/packages/cli/src/cli/index.ts
@@ -6,11 +6,15 @@ import { readAuth } from "@/core/auth/index.js";
 import { CLIExitError } from "./errors.js";
 import { ErrorReporter } from "./telemetry/error-reporter.js";
 import { addCommandInfoToErrorReporter } from "./telemetry/index.js";
-import type { CLIContext } from "./types.js";
+import type { CLIContext, Distribution } from "./types.js";
 
 const __dirname = dirname(fileURLToPath(import.meta.url));
 
-async function runCLI(): Promise<void> {
+interface RunCLIOptions {
+  distribution?: Distribution;
+}
+
+async function runCLI(options?: RunCLIOptions): Promise<void> {
   ensureNpmAssets(join(__dirname, "../assets"));
 
   // Create error reporter - single instance for the CLI session
@@ -24,6 +28,7 @@ async function runCLI(): Promise<void> {
   const context: CLIContext = {
     errorReporter,
     isNonInteractive,
+    distribution: options?.distribution ?? "npm",
   };
 
   // Create program with injected context
diff --git a/packages/cli/src/cli/types.ts b/packages/cli/src/cli/types.ts
index 124ac9de..b72d30f6 100644
--- a/packages/cli/src/cli/types.ts
+++ b/packages/cli/src/cli/types.ts
@@ -1,6 +1,9 @@
 import type { ErrorReporter } from "./telemetry/error-reporter.js";
 
+export type Distribution = "npm" | "binary";
+
 export interface CLIContext {
   errorReporter: ErrorReporter;
   isNonInteractive: boolean;
+  distribution: Distribution;
 }
diff --git a/packages/cli/src/cli/utils/runCommand.ts b/packages/cli/src/cli/utils/runCommand.ts
index fa6be349..99f4dc1f 100644
--- a/packages/cli/src/cli/utils/runCommand.ts
+++ b/packages/cli/src/cli/utils/runCommand.ts
@@ -3,7 +3,10 @@ import { login } from "@/cli/commands/auth/login-flow.js";
 import type { CLIContext } from "@/cli/types.js";
 import { printBanner } from "@/cli/utils/banner.js";
 import { theme } from "@/cli/utils/theme.js";
-import { printUpgradeNotificationIfAvailable } from "@/cli/utils/upgradeNotification.js";
+import {
+  printUpgradeNotification,
+  startUpgradeCheck,
+} from "@/cli/utils/upgradeNotification.js";
 import { isLoggedIn, readAuth } from "@/core/auth/index.js";
 import { isCLIError } from "@/core/errors.js";
 import { initAppConfig } from "@/core/project/index.js";
@@ -76,7 +79,7 @@ export async function runCommand(
   } else {
     intro(theme.colors.base44OrangeBackground(" Base 44 "));
   }
-  await printUpgradeNotificationIfAvailable();
+  const upgradeCheckPromise = startUpgradeCheck();
 
   try {
     // Check authentication if required
@@ -105,6 +108,8 @@ export async function runCommand(
     }
 
     const result = await commandFn();
+    await printUpgradeNotification(upgradeCheckPromise, context.distribution);
+
     outro(result.outroMessage || "");
 
     if (result.stdout) {
diff --git a/packages/cli/src/cli/utils/upgradeNotification.ts b/packages/cli/src/cli/utils/upgradeNotification.ts
index eaf3f173..912a31ab 100644
--- a/packages/cli/src/cli/utils/upgradeNotification.ts
+++ b/packages/cli/src/cli/utils/upgradeNotification.ts
@@ -1,22 +1,61 @@
-import { log } from "@clack/prompts";
+import { note } from "@clack/prompts";
+import type { Distribution } from "@/cli/types.js";
 import { theme } from "@/cli/utils/theme.js";
 import type { UpgradeInfo } from "@/cli/utils/version-check.js";
 import { checkForUpgrade } from "@/cli/utils/version-check.js";
 
-function formatUpgradeMessage(info: UpgradeInfo): string {
+type InstallMethod = "npm" | "brew" | "binary";
+
+function detectInstallMethod(distribution: Distribution): InstallMethod {
+  if (distribution !== "binary") {
+    return "npm";
+  }
+  const execPath = process.execPath.toLowerCase();
+  if (execPath.includes("/homebrew/") || execPath.includes("/cellar/")) {
+    return "brew";
+  }
+  return "binary";
+}
+
+function getUpgradeInstruction(method: InstallMethod): string {
+  switch (method) {
+    case "npm":
+      return "Run: npm install -g base44@latest";
+    case "brew":
+      return "Run: brew upgrade base44";
+    case "binary":
+      return "Download Base44 CLI from: https://github.com/base44/cli/releases/latest";
+  }
+}
+
+export function startUpgradeCheck(): Promise<UpgradeInfo | null> {
+  return checkForUpgrade().catch(() => null);
+}
+
+function formatUpgradeMessage(
+  info: UpgradeInfo,
+  distribution: Distribution,
+): string {
   const { shinyOrange } = theme.colors;
   const { bold } = theme.styles;
+  const instruction = getUpgradeInstruction(detectInstallMethod(distribution));
 
-  return `${shinyOrange("Update available!")} ${shinyOrange(`${info.currentVersion} → ${info.latestVersion}`)}  ${shinyOrange("Run:")} ${bold(shinyOrange("npm install -g base44@latest"))}`;
+  return [
+    shinyOrange(
+      `Update available! ${info.currentVersion} → ${bold(info.latestVersion)}`,
+    ),
+    shinyOrange(instruction),
+  ].join("\n");
 }
 
-export async function printUpgradeNotificationIfAvailable(): Promise<void> {
+export async function printUpgradeNotification(
+  upgradeCheckPromise: Promise<UpgradeInfo | null>,
+  distribution: Distribution,
+): Promise<void> {
   try {
-    const upgradeInfo = await checkForUpgrade();
+    const upgradeInfo = await upgradeCheckPromise;
     if (upgradeInfo) {
-      log.message(formatUpgradeMessage(upgradeInfo));
+      note(formatUpgradeMessage(upgradeInfo, distribution));
     }
-  } catch {
-    // Silently ignore errors
-  }
+  } catch {}
 }
diff --git a/packages/cli/tests/cli/version-check.spec.ts b/packages/cli/tests/cli/version-check.spec.ts
index 66cb8708..e9f826f5 100644
--- a/packages/cli/tests/cli/version-check.spec.ts
+++ b/packages/cli/tests/cli/version-check.spec.ts
@@ -13,7 +13,6 @@ describe("upgrade notification", () => {
     t.expectResult(result).toSucceed();
     t.expectResult(result).toContain("Update available!");
     t.expectResult(result).toContain("1.0.0");
-    t.expectResult(result).toContain("npm install -g base44@latest");
   });
 
   it("does not display notification when version is current", async () => {