diff --git a/.github/workflows/release-cli.yml b/.github/workflows/release-cli.yml
new file mode 100644
index 000000000..1796f5d03
--- /dev/null
+++ b/.github/workflows/release-cli.yml
@@ -0,0 +1,39 @@
+name: Release CLI
+
+on:
+  push:
+    tags:
+      - "cli/v*"
+
+permissions:
+  contents: write
+
+jobs:
+  release:
+    runs-on: ubuntu-latest
+    defaults:
+      run:
+        working-directory: packages/browseros-agent/apps/cli
+
+    steps:
+      - uses: actions/checkout@v6
+        with:
+          fetch-depth: 0
+
+      - uses: actions/setup-go@v5
+        with:
+          go-version-file: packages/browseros-agent/apps/cli/go.mod
+
+      - name: Run tests
+        run: go test ./... -v
+
+      - name: Run vet
+        run: go vet ./...
+
+      - uses: goreleaser/goreleaser-action@v6
+        with:
+          version: "~> v2"
+          args: release --clean
+          workdir: packages/browseros-agent/apps/cli
+        env:
+          GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
diff --git a/packages/browseros-agent/apps/cli/.gitignore b/packages/browseros-agent/apps/cli/.gitignore
index d0c8d32a7..1e02ee36c 100644
--- a/packages/browseros-agent/apps/cli/.gitignore
+++ b/packages/browseros-agent/apps/cli/.gitignore
@@ -1 +1,2 @@
 browseros-cli
+dist
diff --git a/packages/browseros-agent/apps/cli/.goreleaser.yml b/packages/browseros-agent/apps/cli/.goreleaser.yml
new file mode 100644
index 000000000..94d6c37ca
--- /dev/null
+++ b/packages/browseros-agent/apps/cli/.goreleaser.yml
@@ -0,0 +1,47 @@
+version: 2
+
+project_name: browseros-cli
+
+builds:
+  - main: .
+    binary: browseros-cli
+    env:
+      - CGO_ENABLED=0
+    flags:
+      - -trimpath
+    ldflags:
+      - -s -w -X main.version={{ .Version }}
+    targets:
+      - darwin_amd64
+      - darwin_arm64
+      - linux_amd64
+      - linux_arm64
+      - windows_amd64
+      - windows_arm64
+
+archives:
+  - format: tar.gz
+    format_overrides:
+      - goos: windows
+        format: zip
+    name_template: "{{ .ProjectName }}_{{ .Version }}_{{ .Os }}_{{ .Arch }}"
+    files:
+      - "none*"
+
+checksum:
+  name_template: checksums.txt
+
+changelog:
+  sort: asc
+  filters:
+    exclude:
+      - "^docs:"
+      - "^test:"
+      - "^ci:"
+
+release:
+  github:
+    owner: browseros-ai
+    name: BrowserOS
+  prerelease: auto
+  name_template: "browseros-cli v{{ .Version }}"
diff --git a/packages/browseros-agent/apps/cli/Makefile b/packages/browseros-agent/apps/cli/Makefile
index 520c660cf..c27b510ac 100644
--- a/packages/browseros-agent/apps/cli/Makefile
+++ b/packages/browseros-agent/apps/cli/Makefile
@@ -18,3 +18,9 @@ vet:
 
 test:
 	go test -tags integration -v -timeout 120s ./...
+
+release-dry:
+	goreleaser release --snapshot --clean
+
+release:
+	goreleaser release --clean
diff --git a/packages/browseros-agent/apps/cli/cmd/init.go b/packages/browseros-agent/apps/cli/cmd/init.go
index df0fd8139..c38793c08 100644
--- a/packages/browseros-agent/apps/cli/cmd/init.go
+++ b/packages/browseros-agent/apps/cli/cmd/init.go
@@ -17,8 +17,10 @@ import (
 )
 
 func init() {
+	var autoDiscover bool
+
 	cmd := &cobra.Command{
-		Use:   "init",
+		Use:   "init [url]",
 		Short: "Configure the BrowserOS server connection",
 		Long: `Set up the CLI by providing the MCP server URL from BrowserOS.
 
@@ -26,33 +28,59 @@ Open BrowserOS → Settings → BrowserOS MCP to find your Server URL.
 The URL looks like: http://127.0.0.1:9004/mcp
 
 The port varies per installation, so this step is required on first use.
-Run again if your port changes.`,
+Run again if your port changes.
+
+Three modes:
+  browseros-cli init <url>    Non-interactive, use the provided URL
+  browseros-cli init --auto   Auto-discover from ~/.browseros/server.json
+  browseros-cli init          Interactive prompt`,
 		Annotations: map[string]string{"group": "Setup:"},
-		Args:        cobra.NoArgs,
+		Args:        cobra.MaximumNArgs(1),
 		Run: func(cmd *cobra.Command, args []string) {
 			bold := color.New(color.Bold)
 			green := color.New(color.FgGreen)
 			dim := color.New(color.Faint)
 
-			fmt.Println()
-			bold.Println("BrowserOS CLI Setup")
-			fmt.Println()
-			fmt.Println("Open BrowserOS → Settings → BrowserOS MCP")
-			fmt.Println("Copy the Server URL shown there.")
-			fmt.Println()
-			dim.Println("It looks like: http://127.0.0.1:9004/mcp")
-			fmt.Println()
+			var input string
 
-			reader := bufio.NewReader(os.Stdin)
-			fmt.Print("Server URL: ")
-			input, err := reader.ReadString('\n')
-			if err != nil {
-				output.Error("failed to read input", 1)
-			}
-			input = strings.TrimSpace(input)
+			switch {
+			case len(args) == 1:
+				// Non-interactive: URL provided as argument
+				input = args[0]
 
-			if input == "" {
-				output.Error("no URL provided", 1)
+			case autoDiscover:
+				// Auto-discover: server.json → config → probe common ports
+				discovered := probeRunningServer()
+				if discovered == "" {
+					output.Error("auto-discovery failed: no running BrowserOS found.\n\n"+
+						"  If not running:    browseros-cli launch\n"+
+						"  If not installed:  browseros-cli install", 1)
+				}
+				input = discovered
+				fmt.Printf("Auto-discovered server at %s\n", input)
+
+			default:
+				// Interactive prompt (original behavior)
+				fmt.Println()
+				bold.Println("BrowserOS CLI Setup")
+				fmt.Println()
+				fmt.Println("Open BrowserOS → Settings → BrowserOS MCP")
+				fmt.Println("Copy the Server URL shown there.")
+				fmt.Println()
+				dim.Println("It looks like: http://127.0.0.1:9004/mcp")
+				fmt.Println()
+
+				reader := bufio.NewReader(os.Stdin)
+				fmt.Print("Server URL: ")
+				line, err := reader.ReadString('\n')
+				if err != nil {
+					output.Error("failed to read input", 1)
+				}
+				input = strings.TrimSpace(line)
+
+				if input == "" {
+					output.Error("no URL provided", 1)
+				}
 			}
 
 			baseURL := normalizeServerURL(input)
@@ -88,5 +116,6 @@ Run again if your port changes.`,
 		},
 	}
 
+	cmd.Flags().BoolVar(&autoDiscover, "auto", false, "Auto-discover server URL from ~/.browseros/server.json")
 	rootCmd.AddCommand(cmd)
 }
diff --git a/packages/browseros-agent/apps/cli/cmd/install.go b/packages/browseros-agent/apps/cli/cmd/install.go
new file mode 100644
index 000000000..2f4815087
--- /dev/null
+++ b/packages/browseros-agent/apps/cli/cmd/install.go
@@ -0,0 +1,247 @@
+package cmd
+
+import (
+	"fmt"
+	"io"
+	"net/http"
+	"os"
+	"os/exec"
+	"path/filepath"
+	"runtime"
+	"time"
+
+	"browseros-cli/output"
+
+	"github.com/fatih/color"
+	"github.com/spf13/cobra"
+)
+
+func init() {
+	cmd := &cobra.Command{
+		Use:   "install",
+		Short: "Download and install BrowserOS for the current platform",
+		Long: `Download BrowserOS for your platform and start the installation.
+
+macOS:   Downloads .dmg, mounts it, and copies BrowserOS to /Applications
+Windows: Downloads installer .exe and launches it
+Linux:   Downloads AppImage (or .deb with --deb flag)
+
+After installation:
+  browseros-cli launch        # start BrowserOS
+  browseros-cli init --auto   # configure the CLI`,
+		Annotations: map[string]string{"group": "Setup:"},
+		Args:        cobra.NoArgs,
+		Run: func(cmd *cobra.Command, args []string) {
+			dir, _ := cmd.Flags().GetString("dir")
+			deb, _ := cmd.Flags().GetBool("deb")
+
+			if deb && runtime.GOOS != "linux" {
+				output.Error("--deb is only available on Linux", 1)
+			}
+
+			downloadURL, filename := resolveDownload(deb)
+			destPath := filepath.Join(dir, filename)
+
+			bold := color.New(color.Bold)
+			green := color.New(color.FgGreen)
+			dim := color.New(color.Faint)
+
+			bold.Printf("Downloading BrowserOS for %s...\n", platformDisplayName())
+			dim.Printf("  %s\n", downloadURL)
+			fmt.Println()
+
+			client := &http.Client{Timeout: 10 * time.Minute}
+			resp, err := client.Get(downloadURL)
+			if err != nil {
+				output.Errorf(1, "download failed: %v", err)
+			}
+			defer resp.Body.Close()
+
+			if resp.StatusCode != http.StatusOK {
+				output.Errorf(1, "download failed: HTTP %d", resp.StatusCode)
+			}
+
+			file, err := os.Create(destPath)
+			if err != nil {
+				output.Errorf(1, "create file: %v", err)
+			}
+
+			written, err := io.Copy(file, resp.Body)
+			file.Close()
+			if err != nil {
+				os.Remove(destPath)
+				output.Errorf(1, "download interrupted: %v", err)
+			}
+
+			green.Printf("Downloaded %s (%.1f MB)\n", filename, float64(written)/(1024*1024))
+			fmt.Println()
+
+			runPostInstall(destPath, deb, dim)
+
+			fmt.Println()
+			bold.Println("Next steps:")
+			dim.Println("  browseros-cli launch        # start BrowserOS")
+			dim.Println("  browseros-cli init --auto   # configure the CLI")
+		},
+	}
+
+	cmd.Flags().String("dir", ".", "Directory to download the installer to")
+	cmd.Flags().Bool("deb", false, "Download .deb package instead of AppImage (Linux only)")
+
+	rootCmd.AddCommand(cmd)
+}
+
+func resolveDownload(deb bool) (url, filename string) {
+	switch runtime.GOOS {
+	case "darwin":
+		return "https://files.browseros.com/download/BrowserOS.dmg", "BrowserOS.dmg"
+	case "windows":
+		return "https://files.browseros.com/download/BrowserOS_installer.exe", "BrowserOS_installer.exe"
+	case "linux":
+		if deb {
+			return "https://cdn.browseros.com/download/BrowserOS.deb", "BrowserOS.deb"
+		}
+		return "https://files.browseros.com/download/BrowserOS.AppImage", "BrowserOS.AppImage"
+	default:
+		output.Errorf(1, "unsupported platform: %s/%s\n  Download manually from https://browseros.com", runtime.GOOS, runtime.GOARCH)
+		return "", ""
+	}
+}
+
+func platformDisplayName() string {
+	switch runtime.GOOS {
+	case "darwin":
+		return "macOS"
+	case "windows":
+		return "Windows"
+	case "linux":
+		return "Linux"
+	default:
+		return runtime.GOOS
+	}
+}
+
+func runPostInstall(path string, deb bool, dim *color.Color) {
+	switch runtime.GOOS {
+	case "darwin":
+		installMacOS(path, dim)
+
+	case "linux":
+		if deb {
+			dim.Println("Install the .deb package:")
+			fmt.Printf("  sudo dpkg -i %s\n", path)
+		} else {
+			os.Chmod(path, 0755)
+			dim.Printf("AppImage is ready to run: ./%s\n", filepath.Base(path))
+		}
+
+	case "windows":
+		fmt.Println("Launching installer...")
+		if err := exec.Command("cmd", "/c", "start", "", path).Run(); err != nil {
+			dim.Printf("Could not launch installer automatically. Run: %s\n", path)
+		} else {
+			dim.Println("Follow the installer prompts to complete setup.")
+		}
+	}
+}
+
+// installMacOS mounts the DMG and copies BrowserOS.app to /Applications.
+func installMacOS(dmgPath string, dim *color.Color) {
+	fmt.Println("Mounting disk image...")
+	mountOut, err := exec.Command("hdiutil", "attach", dmgPath, "-nobrowse", "-quiet").Output()
+	if err != nil {
+		dim.Println("Could not mount DMG automatically.")
+		dim.Printf("  Open it manually: open %s\n", dmgPath)
+		return
+	}
+
+	// Find the mount point (last field of last line of hdiutil output)
+	mountPoint := ""
+	for _, line := range splitLines(string(mountOut)) {
+		fields := splitTabs(line)
+		if len(fields) > 0 {
+			mountPoint = fields[len(fields)-1]
+		}
+	}
+
+	if mountPoint == "" {
+		dim.Println("DMG mounted but could not determine mount point.")
+		dim.Printf("  Open it manually: open %s\n", dmgPath)
+		return
+	}
+
+	// Look for BrowserOS.app in the mounted volume
+	appSrc := filepath.Join(mountPoint, "BrowserOS.app")
+	if _, err := os.Stat(appSrc); err != nil {
+		dim.Printf("DMG mounted at %s but BrowserOS.app not found inside.\n", mountPoint)
+		dim.Printf("  Check the volume manually: open %s\n", mountPoint)
+		exec.Command("hdiutil", "detach", mountPoint, "-quiet").Run()
+		return
+	}
+
+	appDest := "/Applications/BrowserOS.app"
+	fmt.Printf("Installing to %s...\n", appDest)
+
+	// Remove existing installation if present
+	os.RemoveAll(appDest)
+
+	// Copy using cp -R (preserves code signatures, symlinks, etc.)
+	if err := exec.Command("cp", "-R", appSrc, appDest).Run(); err != nil {
+		dim.Printf("Could not copy to /Applications (may need sudo).\n")
+		dim.Printf("  Try: sudo cp -R \"%s\" /Applications/\n", appSrc)
+		exec.Command("hdiutil", "detach", mountPoint, "-quiet").Run()
+		return
+	}
+
+	// Unmount
+	exec.Command("hdiutil", "detach", mountPoint, "-quiet").Run()
+
+	// Clean up DMG
+	os.Remove(dmgPath)
+
+	fmt.Println("BrowserOS installed to /Applications/BrowserOS.app")
+}
+
+func splitLines(s string) []string {
+	var lines []string
+	for _, line := range filepath.SplitList(s) {
+		lines = append(lines, line)
+	}
+	// filepath.SplitList uses : on unix, not newlines — use manual split
+	result := []string{}
+	start := 0
+	for i := 0; i < len(s); i++ {
+		if s[i] == '\n' {
+			line := s[start:i]
+			if len(line) > 0 {
+				result = append(result, line)
+			}
+			start = i + 1
+		}
+	}
+	if start < len(s) {
+		result = append(result, s[start:])
+	}
+	return result
+}
+
+func splitTabs(s string) []string {
+	result := []string{}
+	start := 0
+	for i := 0; i < len(s); i++ {
+		if s[i] == '\t' {
+			field := s[start:i]
+			if len(field) > 0 {
+				result = append(result, field)
+			}
+			start = i + 1
+		}
+	}
+	if start < len(s) {
+		field := s[start:]
+		if len(field) > 0 {
+			result = append(result, field)
+		}
+	}
+	return result
+}
diff --git a/packages/browseros-agent/apps/cli/cmd/launch.go b/packages/browseros-agent/apps/cli/cmd/launch.go
new file mode 100644
index 000000000..7454ab006
--- /dev/null
+++ b/packages/browseros-agent/apps/cli/cmd/launch.go
@@ -0,0 +1,287 @@
+package cmd
+
+import (
+	"fmt"
+	"net/http"
+	"os"
+	"os/exec"
+	"path/filepath"
+	"runtime"
+	"strings"
+	"time"
+
+	"browseros-cli/output"
+
+	"github.com/fatih/color"
+	"github.com/spf13/cobra"
+)
+
+// macOS bundle identifier — verified from BrowserOS.app/Contents/Info.plist
+const browserOSBundleID = "com.browseros.BrowserOS"
+
+func init() {
+	cmd := &cobra.Command{
+		Use:   "launch",
+		Short: "Launch the BrowserOS application",
+		Long: `Find and launch the BrowserOS application.
+
+Uses platform-native detection to find BrowserOS, launches it,
+and waits for the server to become ready.
+
+If BrowserOS is already running, reports the server URL.`,
+		Annotations: map[string]string{"group": "Setup:"},
+		Args:        cobra.NoArgs,
+		Run: func(cmd *cobra.Command, args []string) {
+			green := color.New(color.FgGreen)
+			dim := color.New(color.Faint)
+			waitSecs, _ := cmd.Flags().GetInt("wait")
+
+			if url := probeRunningServer(); url != "" {
+				green.Printf("BrowserOS is already running at %s\n", url)
+				return
+			}
+
+			if !isBrowserOSInstalled() {
+				output.Error("BrowserOS is not installed.\n\n"+
+					"  To install:  browseros-cli install", 1)
+			}
+
+			fmt.Println("Launching BrowserOS...")
+			if err := startBrowserOS(); err != nil {
+				output.Errorf(1, "failed to launch: %v", err)
+			}
+
+			fmt.Print("Waiting for server")
+			url, ok := waitForServer(time.Duration(waitSecs) * time.Second)
+			fmt.Println()
+
+			if !ok {
+				output.Error("BrowserOS launched but server didn't respond within "+
+					fmt.Sprintf("%d seconds.\n", waitSecs)+
+					"  Check if BrowserOS is fully loaded, then retry.", 1)
+			}
+
+			green.Printf("BrowserOS is ready at %s\n", url)
+			fmt.Println()
+			dim.Println("Next: browseros-cli init --auto")
+		},
+	}
+
+	cmd.Flags().Int("wait", 30, "Seconds to wait for server to start")
+	rootCmd.AddCommand(cmd)
+}
+
+// ---------------------------------------------------------------------------
+// Server probing
+// ---------------------------------------------------------------------------
+
+// probeRunningServer checks server.json, config, and common ports for a running server.
+func probeRunningServer() string {
+	check := func(baseURL string) bool {
+		client := &http.Client{Timeout: 2 * time.Second}
+		resp, err := client.Get(baseURL + "/health")
+		if err != nil {
+			return false
+		}
+		resp.Body.Close()
+		return resp.StatusCode == 200
+	}
+
+	// 1. server.json — written by BrowserOS on startup with the actual port
+	if url := loadBrowserosServerURL(); url != "" && check(url) {
+		return url
+	}
+
+	// 2. Saved config / env var
+	if url := defaultServerURL(); url != "" && check(url) {
+		return url
+	}
+
+	// 3. Probe common BrowserOS ports as last resort
+	for _, port := range []int{9100, 9200, 9300} {
+		url := fmt.Sprintf("http://127.0.0.1:%d", port)
+		if check(url) {
+			return url
+		}
+	}
+
+	return ""
+}
+
+// ---------------------------------------------------------------------------
+// Platform-native installation detection
+// ---------------------------------------------------------------------------
+
+// isBrowserOSInstalled checks if BrowserOS is installed using platform-native methods.
+//
+// macOS:   `open -Ra "BrowserOS"` — queries Launch Services (finds apps anywhere)
+// Linux:   checks /usr/bin/browseros (.deb), browseros.desktop, or AppImage files
+// Windows: checks executable at %LOCALAPPDATA%\BrowserOS\Application\BrowserOS.exe
+//          and registry uninstall key (per-user Chromium install pattern)
+func isBrowserOSInstalled() bool {
+	switch runtime.GOOS {
+	case "darwin":
+		// open -Ra checks if Launch Services knows about the app without launching it.
+		// Works regardless of where the app is installed.
+		return exec.Command("open", "-Ra", "BrowserOS").Run() == nil
+
+	case "linux":
+		// .deb install puts `browseros` in /usr/bin/
+		if _, err := exec.LookPath("browseros"); err == nil {
+			return true
+		}
+		// .deb also creates browseros.desktop
+		for _, dir := range []string{
+			"/usr/share/applications",
+			filepath.Join(userHomeDir(), ".local/share/applications"),
+		} {
+			if _, err := os.Stat(filepath.Join(dir, "browseros.desktop")); err == nil {
+				return true
+			}
+		}
+		// AppImage — user may have it in ~/Downloads, ~/Applications, etc.
+		return findLinuxAppImage() != ""
+
+	case "windows":
+		// Chromium per-user install: %LOCALAPPDATA%\BrowserOS\Application\BrowserOS.exe
+		if exePath := windowsBrowserOSExe(); exePath != "" {
+			if _, err := os.Stat(exePath); err == nil {
+				return true
+			}
+		}
+		// Fallback: check uninstall registry (per-user install uses HKCU)
+		for _, root := range []string{"HKCU", "HKLM"} {
+			key := root + `\Software\Microsoft\Windows\CurrentVersion\Uninstall\BrowserOS`
+			if exec.Command("reg", "query", key, "/v", "DisplayName").Run() == nil {
+				return true
+			}
+		}
+		return false
+	}
+
+	return false
+}
+
+// ---------------------------------------------------------------------------
+// Platform-native launch
+// ---------------------------------------------------------------------------
+
+// startBrowserOS launches BrowserOS using platform-native methods.
+//
+// macOS:   `open -b com.browseros.BrowserOS` — launches by bundle ID
+// Linux:   runs `browseros` binary or AppImage directly
+// Windows: runs BrowserOS.exe from the known install path
+func startBrowserOS() error {
+	switch runtime.GOOS {
+	case "darwin":
+		// Launch by bundle ID via Launch Services — no hardcoded paths needed.
+		return exec.Command("open", "-b", browserOSBundleID).Run()
+
+	case "linux":
+		// .deb install: browseros is in PATH
+		if p, err := exec.LookPath("browseros"); err == nil {
+			return startDetached(p)
+		}
+		// AppImage: run it directly
+		if appImage := findLinuxAppImage(); appImage != "" {
+			return startDetached(appImage)
+		}
+		// .desktop file: use gtk-launch (not xdg-open, which opens by MIME type)
+		if _, err := exec.LookPath("gtk-launch"); err == nil {
+			return exec.Command("gtk-launch", "browseros").Run()
+		}
+		return fmt.Errorf("BrowserOS found but could not determine how to launch it")
+
+	case "windows":
+		if exePath := windowsBrowserOSExe(); exePath != "" {
+			if _, err := os.Stat(exePath); err == nil {
+				return startDetached(exePath)
+			}
+		}
+		return fmt.Errorf("BrowserOS.exe not found at expected location")
+
+	default:
+		return fmt.Errorf("unsupported platform: %s", runtime.GOOS)
+	}
+}
+
+// ---------------------------------------------------------------------------
+// Helpers
+// ---------------------------------------------------------------------------
+
+// startDetached starts a process in the background without inheriting stdio.
+func startDetached(path string, args ...string) error {
+	cmd := exec.Command(path, args...)
+	cmd.Stdout = nil
+	cmd.Stderr = nil
+	cmd.Stdin = nil
+	return cmd.Start()
+}
+
+// windowsBrowserOSExe returns the expected BrowserOS.exe path on Windows.
+// Chromium per-user installs go to %LOCALAPPDATA%\<base_app_name>\Application\<binary>.
+// base_app_name = "BrowserOS" (from chromium_install_modes.h)
+func windowsBrowserOSExe() string {
+	localAppData := os.Getenv("LOCALAPPDATA")
+	if localAppData == "" {
+		return ""
+	}
+	return filepath.Join(localAppData, "BrowserOS", "Application", "BrowserOS.exe")
+}
+
+// findLinuxAppImage searches common locations for a BrowserOS AppImage.
+func findLinuxAppImage() string {
+	home := userHomeDir()
+	if home == "" {
+		return ""
+	}
+	for _, dir := range []string{
+		home,
+		filepath.Join(home, "Applications"),
+		filepath.Join(home, "Downloads"),
+		"/opt",
+	} {
+		entries, err := os.ReadDir(dir)
+		if err != nil {
+			continue
+		}
+		for _, e := range entries {
+			name := e.Name()
+			if strings.HasPrefix(name, "BrowserOS") && strings.HasSuffix(name, ".AppImage") {
+				return filepath.Join(dir, name)
+			}
+		}
+	}
+	return ""
+}
+
+// userHomeDir returns the home directory or empty string.
+func userHomeDir() string {
+	home, err := os.UserHomeDir()
+	if err != nil {
+		return ""
+	}
+	return home
+}
+
+// waitForServer polls until a BrowserOS server responds or timeout.
+func waitForServer(maxWait time.Duration) (string, bool) {
+	client := &http.Client{Timeout: 2 * time.Second}
+	deadline := time.Now().Add(maxWait)
+
+	for time.Now().Before(deadline) {
+		// server.json is written by BrowserOS on startup with the actual port
+		if url := loadBrowserosServerURL(); url != "" {
+			resp, err := client.Get(url + "/health")
+			if err == nil {
+				resp.Body.Close()
+				if resp.StatusCode == 200 {
+					return url, true
+				}
+			}
+		}
+		fmt.Print(".")
+		time.Sleep(1 * time.Second)
+	}
+	return "", false
+}
diff --git a/packages/browseros-agent/apps/cli/cmd/root.go b/packages/browseros-agent/apps/cli/cmd/root.go
index a8f1e18f5..d7a704971 100644
--- a/packages/browseros-agent/apps/cli/cmd/root.go
+++ b/packages/browseros-agent/apps/cli/cmd/root.go
@@ -167,10 +167,17 @@ func envBool(key string) bool {
 }
 
 func defaultServerURL() string {
+	// 1. Explicit env var always wins
 	if env := normalizeServerURL(os.Getenv("BROWSEROS_URL")); env != "" {
 		return env
 	}
 
+	// 2. Live discovery file from running BrowserOS (most current)
+	if url := loadBrowserosServerURL(); url != "" {
+		return url
+	}
+
+	// 3. Saved config (may be stale if port changed)
 	cfg, err := config.Load()
 	if err == nil {
 		if url := normalizeServerURL(cfg.ServerURL); url != "" {
@@ -178,10 +185,6 @@ func defaultServerURL() string {
 		}
 	}
 
-	if url := loadBrowserosServerURL(); url != "" {
-		return url
-	}
-
 	return ""
 }
 
@@ -225,6 +228,9 @@ func validateServerURL(raw string) (string, error) {
 	}
 
 	return "", fmt.Errorf(
-		"BrowserOS server URL is not configured.\n  Open BrowserOS -> Settings -> BrowserOS MCP and copy the Server URL.\n  Then run: browseros-cli init",
+		"BrowserOS server URL is not configured.\n\n" +
+			"  If BrowserOS is running:  browseros-cli init --auto\n" +
+			"  If BrowserOS is closed:   browseros-cli launch\n" +
+			"  If not installed:         browseros-cli install",
 	)
 }
diff --git a/packages/browseros-agent/apps/cli/mcp/client.go b/packages/browseros-agent/apps/cli/mcp/client.go
index d40b1f1d7..8321633fd 100644
--- a/packages/browseros-agent/apps/cli/mcp/client.go
+++ b/packages/browseros-agent/apps/cli/mcp/client.go
@@ -44,7 +44,10 @@ func (c *Client) connect(ctx context.Context) (*sdkmcp.ClientSession, error) {
 
 	session, err := sdkClient.Connect(ctx, transport, nil)
 	if err != nil {
-		return nil, fmt.Errorf("cannot connect to BrowserOS at %s: %w\n  Is the server running? Try: browseros-cli init", c.BaseURL, err)
+		return nil, fmt.Errorf("cannot connect to BrowserOS at %s: %w\n\n"+
+			"  If BrowserOS is running on a different port:  browseros-cli init --auto\n"+
+			"  If BrowserOS is not running:                  browseros-cli launch\n"+
+			"  If not installed:                             browseros-cli install", c.BaseURL, err)
 	}
 	return session, nil
 }
@@ -184,7 +187,10 @@ func (c *Client) Status() (map[string]any, error) {
 func (c *Client) restGET(path string) (map[string]any, error) {
 	resp, err := c.HTTPClient.Get(c.BaseURL + path)
 	if err != nil {
-		return nil, fmt.Errorf("cannot connect to BrowserOS at %s: %w\n  Try: browseros-cli init", c.BaseURL, err)
+		return nil, fmt.Errorf("cannot connect to BrowserOS at %s: %w\n\n"+
+			"  If BrowserOS is running on a different port:  browseros-cli init --auto\n"+
+			"  If BrowserOS is not running:                  browseros-cli launch\n"+
+			"  If not installed:                             browseros-cli install", c.BaseURL, err)
 	}
 	defer resp.Body.Close()