diff --git a/cmd/root.go b/cmd/root.go
index 0f105051..1e50dc08 100644
--- a/cmd/root.go
+++ b/cmd/root.go
@@ -122,9 +122,8 @@ func startEmulator(ctx context.Context, rt runtime.Runtime, cfg *env.Env, tel *t
 	}
 
 	notifyOpts := update.NotifyOptions{
-		GitHubToken:    cfg.GitHubToken,
-		UpdatePrompt:   appConfig.UpdatePrompt,
-		PersistDisable: config.DisableUpdatePrompt,
+		GitHubToken:  cfg.GitHubToken,
+		UpdatePrompt: appConfig.CLI.UpdatePrompt,
 	}
 
 	if isInteractiveMode(cfg) {
diff --git a/internal/config/config.go b/internal/config/config.go
index eea38fbf..021128bd 100644
--- a/internal/config/config.go
+++ b/internal/config/config.go
@@ -13,10 +13,14 @@ import (
 //go:embed default_config.toml
 var defaultConfigTemplate string
 
+type CLIConfig struct {
+	UpdatePrompt bool `mapstructure:"update_prompt"`
+}
+
 type Config struct {
-	Containers   []ContainerConfig            `mapstructure:"containers"`
-	Env          map[string]map[string]string `mapstructure:"env"`
-	UpdatePrompt bool                          `mapstructure:"update_prompt"`
+	Containers []ContainerConfig            `mapstructure:"containers"`
+	Env        map[string]map[string]string `mapstructure:"env"`
+	CLI        CLIConfig                    `mapstructure:"cli"`
 }
 
 func setDefaults() {
@@ -27,7 +31,7 @@ func setDefaults() {
 			"port": "4566",
 		},
 	})
-	viper.SetDefault("update_prompt", true)
+	viper.SetDefault("cli.update_prompt", true)
 }
 
 func loadConfig(path string) error {
@@ -110,7 +114,7 @@ func Set(key string, value any) error {
 }
 
 func DisableUpdatePrompt() error {
-	return Set("update_prompt", false)
+	return Set("cli.update_prompt", false)
 }
 
 func Get() (*Config, error) {
@@ -118,6 +122,9 @@ func Get() (*Config, error) {
 	if err := viper.Unmarshal(&cfg); err != nil {
 		return nil, fmt.Errorf("failed to unmarshal config: %w", err)
 	}
+	if !viper.InConfig("cli.update_prompt") && viper.InConfig("update_prompt") {
+		cfg.CLI.UpdatePrompt = viper.GetBool("update_prompt")
+	}
 	for i := range cfg.Containers {
 		if err := cfg.Containers[i].Validate(); err != nil {
 			return nil, fmt.Errorf("invalid container config: %w", err)
diff --git a/internal/output/events.go b/internal/output/events.go
index d9ea5116..ea8ddac9 100644
--- a/internal/output/events.go
+++ b/internal/output/events.go
@@ -122,6 +122,7 @@ type UserInputRequestEvent struct {
 	Prompt     string
 	Options    []InputOption
 	ResponseCh chan<- InputResponse
+	Vertical   bool
 }
 
 const (
diff --git a/internal/ui/app.go b/internal/ui/app.go
index 4185bd3b..e8d14721 100644
--- a/internal/ui/app.go
+++ b/internal/ui/app.go
@@ -95,6 +95,9 @@ func (a App) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 			return a, tea.Quit
 		}
 		if a.pendingInput != nil {
+			if a.pendingInput.Vertical {
+				return a.handleVerticalPromptKey(msg)
+			}
 			if opt := resolveOption(a.pendingInput.Options, msg); opt != nil {
 				a.lines = appendLine(a.lines, styledLine{text: formatResolvedInput(*a.pendingInput, opt.Key)})
 				responseCmd := sendInputResponseCmd(a.pendingInput.ResponseCh, output.InputResponse{SelectedKey: opt.Key})
@@ -110,7 +113,7 @@ func (a App) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 		if a.spinner.Visible() {
 			a.spinner = a.spinner.SetText(output.FormatPrompt(msg.Prompt, msg.Options))
 		} else {
-			a.inputPrompt = a.inputPrompt.Show(msg.Prompt, msg.Options)
+			a.inputPrompt = a.inputPrompt.Show(msg.Prompt, msg.Options, msg.Vertical)
 		}
 	case spinner.TickMsg:
 		var cmd tea.Cmd
@@ -295,6 +298,35 @@ func (a *App) flushBufferedLines() {
 	a.bufferedLines = nil
 }
 
+func (a App) handleVerticalPromptKey(msg tea.KeyMsg) (tea.Model, tea.Cmd) {
+	switch msg.Type {
+	case tea.KeyUp:
+		a.inputPrompt = a.inputPrompt.SetSelectedIndex(a.inputPrompt.SelectedIndex() - 1)
+		return a, nil
+	case tea.KeyDown:
+		a.inputPrompt = a.inputPrompt.SetSelectedIndex(a.inputPrompt.SelectedIndex() + 1)
+		return a, nil
+	case tea.KeyEnter:
+		idx := a.inputPrompt.SelectedIndex()
+		if idx >= 0 && idx < len(a.pendingInput.Options) {
+			opt := a.pendingInput.Options[idx]
+			a.lines = appendLine(a.lines, styledLine{text: formatResolvedInput(*a.pendingInput, opt.Key)})
+			responseCmd := sendInputResponseCmd(a.pendingInput.ResponseCh, output.InputResponse{SelectedKey: opt.Key})
+			a.pendingInput = nil
+			a.inputPrompt = a.inputPrompt.Hide()
+			return a, responseCmd
+		}
+	}
+	if opt := resolveOption(a.pendingInput.Options, msg); opt != nil {
+		a.lines = appendLine(a.lines, styledLine{text: formatResolvedInput(*a.pendingInput, opt.Key)})
+		responseCmd := sendInputResponseCmd(a.pendingInput.ResponseCh, output.InputResponse{SelectedKey: opt.Key})
+		a.pendingInput = nil
+		a.inputPrompt = a.inputPrompt.Hide()
+		return a, responseCmd
+	}
+	return a, nil
+}
+
 func formatResolvedInput(req output.UserInputRequestEvent, selectedKey string) string {
 	formatted := output.FormatPrompt(req.Prompt, req.Options)
 	firstLine := strings.Split(formatted, "\n")[0]
diff --git a/internal/ui/app_test.go b/internal/ui/app_test.go
index b2da93d8..dbb26f98 100644
--- a/internal/ui/app_test.go
+++ b/internal/ui/app_test.go
@@ -410,6 +410,44 @@ func TestAppEnterDoesNothingWithNonLetterLabel(t *testing.T) {
 	}
 }
 
+func TestAppEnterSelectsHighlightedVerticalOption(t *testing.T) {
+	t.Parallel()
+
+	app := NewApp("dev", "", "", nil)
+	responseCh := make(chan output.InputResponse, 1)
+
+	model, _ := app.Update(output.UserInputRequestEvent{
+		Prompt:     "Update lstk to latest version?",
+		Options:    []output.InputOption{{Key: "u", Label: "Update now [U]"}, {Key: "s", Label: "Skip this version [S]"}, {Key: "n", Label: "Never ask again [N]"}},
+		ResponseCh: responseCh,
+		Vertical:   true,
+	})
+	app = model.(App)
+
+	model, _ = app.Update(tea.KeyMsg{Type: tea.KeyDown})
+	app = model.(App)
+
+	model, cmd := app.Update(tea.KeyMsg{Type: tea.KeyEnter})
+	app = model.(App)
+	if cmd == nil {
+		t.Fatal("expected response command when enter is pressed on vertical prompt")
+	}
+	cmd()
+
+	select {
+	case resp := <-responseCh:
+		if resp.SelectedKey != "s" {
+			t.Fatalf("expected s key, got %q", resp.SelectedKey)
+		}
+	case <-time.After(time.Second):
+		t.Fatal("timed out waiting for response on channel")
+	}
+
+	if app.inputPrompt.Visible() {
+		t.Fatal("expected input prompt to be hidden after response")
+	}
+}
+
 func TestAppAnyKeyOptionResolvesOnAnyKeypress(t *testing.T) {
 	t.Parallel()
 
diff --git a/internal/ui/components/input_prompt.go b/internal/ui/components/input_prompt.go
index 68d4bbb9..fa1feec8 100644
--- a/internal/ui/components/input_prompt.go
+++ b/internal/ui/components/input_prompt.go
@@ -8,19 +8,23 @@ import (
 )
 
 type InputPrompt struct {
-	prompt  string
-	options []output.InputOption
-	visible bool
+	prompt        string
+	options       []output.InputOption
+	visible       bool
+	selectedIndex int
+	vertical      bool
 }
 
 func NewInputPrompt() InputPrompt {
 	return InputPrompt{}
 }
 
-func (p InputPrompt) Show(prompt string, options []output.InputOption) InputPrompt {
+func (p InputPrompt) Show(prompt string, options []output.InputOption, vertical bool) InputPrompt {
 	p.prompt = prompt
 	p.options = options
 	p.visible = true
+	p.selectedIndex = 0
+	p.vertical = vertical
 	return p
 }
 
@@ -33,20 +37,31 @@ func (p InputPrompt) Visible() bool {
 	return p.visible
 }
 
+func (p InputPrompt) SelectedIndex() int {
+	return p.selectedIndex
+}
+
+func (p InputPrompt) SetSelectedIndex(idx int) InputPrompt {
+	if idx >= 0 && idx < len(p.options) {
+		p.selectedIndex = idx
+	}
+	return p
+}
+
 func (p InputPrompt) View() string {
 	if !p.visible {
 		return ""
 	}
 
-	lines := strings.Split(p.prompt, "\n")
+	if p.vertical {
+		return p.viewVertical()
+	}
 
+	lines := strings.Split(p.prompt, "\n")
 	firstLine := lines[0]
 
 	var sb strings.Builder
-
-	// "?" prefix in secondary color
 	sb.WriteString(styles.Secondary.Render("? "))
-
 	sb.WriteString(styles.Message.Render(firstLine))
 
 	if suffix := output.FormatPromptLabels(p.options); suffix != "" {
@@ -60,3 +75,25 @@ func (p InputPrompt) View() string {
 
 	return sb.String()
 }
+
+func (p InputPrompt) viewVertical() string {
+	var sb strings.Builder
+
+	if p.prompt != "" {
+		sb.WriteString(styles.Secondary.Render("? "))
+		sb.WriteString(styles.Message.Render(strings.TrimPrefix(p.prompt, "? ")))
+		sb.WriteString("\n")
+	}
+
+	for i, opt := range p.options {
+		if i == p.selectedIndex {
+			sb.WriteString(styles.NimboMid.Render("● " + opt.Label))
+		} else {
+			sb.WriteString(styles.Secondary.Render("○ " + opt.Label))
+		}
+		sb.WriteString("\n")
+	}
+
+	return sb.String()
+}
+
diff --git a/internal/ui/components/input_prompt_test.go b/internal/ui/components/input_prompt_test.go
index 18a8576e..58f26989 100644
--- a/internal/ui/components/input_prompt_test.go
+++ b/internal/ui/components/input_prompt_test.go
@@ -14,6 +14,7 @@ func TestInputPromptView(t *testing.T) {
 		name     string
 		prompt   string
 		options  []output.InputOption
+		vertical bool
 		contains []string
 		excludes []string
 	}{
@@ -21,12 +22,14 @@ func TestInputPromptView(t *testing.T) {
 			name:     "hidden returns empty",
 			prompt:   "",
 			options:  nil,
+			vertical: false,
 			contains: nil,
 		},
 		{
 			name:   "no options",
 			prompt: "Continue?",
 			options: nil,
+			vertical: false,
 			contains: []string{"?", "Continue?"},
 			excludes: []string{"(", "["},
 		},
@@ -34,6 +37,7 @@ func TestInputPromptView(t *testing.T) {
 			name:   "single option shows parentheses",
 			prompt: "Continue?",
 			options: []output.InputOption{{Key: "enter", Label: "Press ENTER"}},
+			vertical: false,
 			contains: []string{"?", "Continue?", "(Press ENTER)"},
 		},
 		{
@@ -43,12 +47,14 @@ func TestInputPromptView(t *testing.T) {
 				{Key: "y", Label: "Y"},
 				{Key: "n", Label: "n"},
 			},
+			vertical: false,
 			contains: []string{"?", "Configure AWS profile?", "[Y/n]"},
 		},
 		{
 			name:   "multi-line prompt renders trailing lines",
 			prompt: "First line\nSecond line\nThird line",
 			options: []output.InputOption{{Key: "y", Label: "Y"}},
+			vertical: false,
 			contains: []string{"?", "First line", "Second line", "Third line", "(Y)"},
 		},
 	}
@@ -67,7 +73,7 @@ func TestInputPromptView(t *testing.T) {
 				return
 			}
 
-			p = p.Show(tc.prompt, tc.options)
+			p = p.Show(tc.prompt, tc.options, tc.vertical)
 			view := p.View()
 
 			for _, s := range tc.contains {
diff --git a/internal/ui/components/message.go b/internal/ui/components/message.go
index 4bf19e96..b28de421 100644
--- a/internal/ui/components/message.go
+++ b/internal/ui/components/message.go
@@ -14,6 +14,7 @@ func RenderMessage(e output.MessageEvent) string {
 
 func RenderWrappedMessage(e output.MessageEvent, width int) string {
 	prefixText, prefix := messagePrefix(e)
+
 	if prefixText == "" {
 		style := styles.Message
 		if e.Severity == output.SeveritySecondary {
diff --git a/internal/update/github.go b/internal/update/github.go
index 472fbdac..992f19bf 100644
--- a/internal/update/github.go
+++ b/internal/update/github.go
@@ -37,22 +37,30 @@ func githubRequest(ctx context.Context, url, token string) (*http.Response, erro
 	return http.DefaultClient.Do(req)
 }
 
-func fetchLatestVersion(ctx context.Context, token string) (string, error) {
+func fetchLatestRelease(ctx context.Context, token string) (*githubRelease, error) {
 	resp, err := githubRequest(ctx, latestReleaseURL, token)
 	if err != nil {
-		return "", err
+		return nil, err
 	}
 	defer func() { _ = resp.Body.Close() }()
 
 	if resp.StatusCode != http.StatusOK {
-		return "", fmt.Errorf("GitHub API returned %s", resp.Status)
+		return nil, fmt.Errorf("GitHub API returned %s", resp.Status)
 	}
 
 	var release githubRelease
 	if err := json.NewDecoder(resp.Body).Decode(&release); err != nil {
-		return "", err
+		return nil, err
 	}
 
+	return &release, nil
+}
+
+func fetchLatestVersion(ctx context.Context, token string) (string, error) {
+	release, err := fetchLatestRelease(ctx, token)
+	if err != nil {
+		return "", err
+	}
 	return release.TagName, nil
 }
 
diff --git a/internal/update/notify.go b/internal/update/notify.go
index bc9ccb6e..3db1c94e 100644
--- a/internal/update/notify.go
+++ b/internal/update/notify.go
@@ -12,12 +12,11 @@ import (
 type versionFetcher func(ctx context.Context, token string) (string, error)
 
 type NotifyOptions struct {
-	GitHubToken    string
-	UpdatePrompt   bool
-	PersistDisable func() error
+	GitHubToken  string
+	UpdatePrompt bool
 }
 
-const checkTimeout = 500 * time.Millisecond
+const checkTimeout = 2 * time.Second
 
 func CheckQuietly(ctx context.Context, githubToken string) (current, latest string, available bool) {
 	return checkQuietlyWithVersion(ctx, githubToken, version.Version(), fetchLatestVersion)
@@ -25,6 +24,7 @@ func CheckQuietly(ctx context.Context, githubToken string) (current, latest stri
 
 func checkQuietlyWithVersion(ctx context.Context, githubToken string, currentVersion string, fetch versionFetcher) (current, latest string, available bool) {
 	current = currentVersion
+	// Skip update check for dev builds
 	if current == "dev" {
 		return current, "", false
 	}
@@ -59,21 +59,21 @@ func notifyUpdateWithVersion(ctx context.Context, sink output.Sink, opts NotifyO
 		return false
 	}
 
-	return promptAndUpdate(ctx, sink, opts.GitHubToken, current, latest, opts.PersistDisable)
+	return promptAndUpdate(ctx, sink, opts, current, latest)
 }
 
-func promptAndUpdate(ctx context.Context, sink output.Sink, githubToken string, current, latest string, persistDisable func() error) (exitAfter bool) {
-	output.EmitWarning(sink, fmt.Sprintf("Update available: %s → %s", current, latest))
+func promptAndUpdate(ctx context.Context, sink output.Sink, opts NotifyOptions, current, latest string) (exitAfter bool) {
+	releaseNotesURL := fmt.Sprintf("https://github.com/%s/releases/latest", githubRepo)
+
+	output.EmitNote(sink, fmt.Sprintf("New lstk version available! %s → %s", current, latest))
+	output.EmitSecondary(sink, fmt.Sprintf("> Release notes: %s", releaseNotesURL))
 
 	responseCh := make(chan output.InputResponse, 1)
 	output.EmitUserInputRequest(sink, output.UserInputRequestEvent{
-		Prompt: "A new version is available",
-		Options: []output.InputOption{
-			{Key: "u", Label: "Update"},
-			{Key: "s", Label: "SKIP"},
-			{Key: "n", Label: "Never ask again"},
-		},
+		Prompt:     "Update lstk to latest version?",
+		Options:    []output.InputOption{{Key: "u", Label: "Update now [U]"}, {Key: "r", Label: "Remind me next time [R]"}, {Key: "s", Label: "Skip this version [S]"}},
 		ResponseCh: responseCh,
+		Vertical:   true,
 	})
 
 	var resp output.InputResponse
@@ -89,20 +89,18 @@ func promptAndUpdate(ctx context.Context, sink output.Sink, githubToken string,
 
 	switch resp.SelectedKey {
 	case "u":
-		if err := applyUpdate(ctx, sink, latest, githubToken); err != nil {
+		if err := applyUpdate(ctx, sink, latest, opts.GitHubToken); err != nil {
 			output.EmitWarning(sink, fmt.Sprintf("Update failed: %v", err))
 			return false
 		}
 		output.EmitSuccess(sink, fmt.Sprintf("Updated to %s — please re-run your command.", latest))
 		return true
-	case "n":
-		if persistDisable != nil {
-			if err := persistDisable(); err != nil {
-				output.EmitWarning(sink, fmt.Sprintf("Failed to save preference: %v", err))
-			}
-		}
+	case "r":
 		return false
-	default:
+	case "s":
+		output.EmitNote(sink, "Skipping version " + latest)
 		return false
 	}
+
+	return false
 }
diff --git a/internal/update/notify_test.go b/internal/update/notify_test.go
index 62ba9e35..ae784256 100644
--- a/internal/update/notify_test.go
+++ b/internal/update/notify_test.go
@@ -124,29 +124,20 @@ func TestNotifyUpdatePromptSkip(t *testing.T) {
 	assert.False(t, exit)
 }
 
-func TestNotifyUpdatePromptNever(t *testing.T) {
+func TestNotifyUpdatePromptRemind(t *testing.T) {
 	server := newTestGitHubServer(t, "v2.0.0")
 	defer server.Close()
 
-	persistCalled := false
-
 	var events []any
 	sink := output.SinkFunc(func(event any) {
 		events = append(events, event)
 		if req, ok := event.(output.UserInputRequestEvent); ok {
-			req.ResponseCh <- output.InputResponse{SelectedKey: "n"}
+			req.ResponseCh <- output.InputResponse{SelectedKey: "r"}
 		}
 	})
 
-	exit := notifyUpdateWithVersion(context.Background(), sink, NotifyOptions{
-		UpdatePrompt: true,
-		PersistDisable: func() error {
-			persistCalled = true
-			return nil
-		},
-	}, "1.0.0", testFetcher(server.URL))
+	exit := notifyUpdateWithVersion(context.Background(), sink, NotifyOptions{UpdatePrompt: true}, "1.0.0", testFetcher(server.URL))
 	assert.False(t, exit)
-	assert.True(t, persistCalled)
 }
 
 func TestNotifyUpdatePromptCancelled(t *testing.T) {
@@ -157,6 +148,11 @@ func TestNotifyUpdatePromptCancelled(t *testing.T) {
 	sink := output.SinkFunc(func(event any) {
 		events = append(events, event)
 		if req, ok := event.(output.UserInputRequestEvent); ok {
+			assert.Equal(t, "Update lstk to latest version?", req.Prompt)
+			assert.Len(t, req.Options, 3)
+			assert.Equal(t, "u", req.Options[0].Key)
+			assert.Equal(t, "r", req.Options[1].Key)
+			assert.Equal(t, "s", req.Options[2].Key)
 			req.ResponseCh <- output.InputResponse{Cancelled: true}
 		}
 	})
@@ -164,3 +160,4 @@ func TestNotifyUpdatePromptCancelled(t *testing.T) {
 	exit := notifyUpdateWithVersion(context.Background(), sink, NotifyOptions{UpdatePrompt: true}, "1.0.0", testFetcher(server.URL))
 	assert.False(t, exit)
 }
+
diff --git a/test/integration/start_test.go b/test/integration/start_test.go
index 008f27d7..dd4aded6 100644
--- a/test/integration/start_test.go
+++ b/test/integration/start_test.go
@@ -207,7 +207,7 @@ func TestStartCommandSetsUpContainerCorrectly(t *testing.T) {
 	t.Run("http health endpoint", func(t *testing.T) {
 		resp, err := http.Get("http://localhost.localstack.cloud:4566/_localstack/health")
 		require.NoError(t, err)
-		defer resp.Body.Close()
+		defer func() { require.NoError(t, resp.Body.Close()) }()
 		assert.Equal(t, http.StatusOK, resp.StatusCode)
 	})
 
@@ -221,7 +221,7 @@ func TestStartCommandSetsUpContainerCorrectly(t *testing.T) {
 		}
 		resp, err := client.Get("https://localhost.localstack.cloud/_localstack/health")
 		require.NoError(t, err)
-		defer resp.Body.Close()
+		defer func() { require.NoError(t, resp.Body.Close()) }()
 		assert.Equal(t, http.StatusOK, resp.StatusCode)
 	})
 }
diff --git a/test/integration/update_test.go b/test/integration/update_test.go
index c5da4890..2221f870 100644
--- a/test/integration/update_test.go
+++ b/test/integration/update_test.go
@@ -247,7 +247,7 @@ func TestUpdateNotification(t *testing.T) {
 
 	t.Run("prompt_disabled", func(t *testing.T) {
 		configFile := filepath.Join(t.TempDir(), "config.toml")
-		require.NoError(t, os.WriteFile(configFile, []byte("update_prompt = false\n"), 0o644))
+		require.NoError(t, os.WriteFile(configFile, []byte("[cli]\nupdate_prompt = false\n"), 0o644))
 
 		ctx, cancel := context.WithTimeout(context.Background(), 30*time.Second)
 		defer cancel()
@@ -278,7 +278,7 @@ func TestUpdateNotification(t *testing.T) {
 
 	t.Run("skip", func(t *testing.T) {
 		configFile := filepath.Join(t.TempDir(), "config.toml")
-		require.NoError(t, os.WriteFile(configFile, []byte("update_prompt = true\n"), 0o644))
+		require.NoError(t, os.WriteFile(configFile, []byte("[cli]\nupdate_prompt = true\n"), 0o644))
 
 		ctx, cancel := context.WithTimeout(context.Background(), 30*time.Second)
 		defer cancel()
@@ -298,7 +298,7 @@ func TestUpdateNotification(t *testing.T) {
 		}()
 
 		require.Eventually(t, func() bool {
-			return bytes.Contains(output.Bytes(), []byte("new version is available"))
+			return bytes.Contains(output.Bytes(), []byte("New lstk version available"))
 		}, 10*time.Second, 100*time.Millisecond, "update notification prompt should appear")
 
 		_, err = ptmx.Write([]byte("s"))
@@ -307,47 +307,9 @@ func TestUpdateNotification(t *testing.T) {
 		_ = cmd.Wait()
 		<-outputCh
 
-		assert.Contains(t, output.String(), "Update available: 0.0.1")
+		assert.Contains(t, output.String(), "New lstk version available")
 	})
 
-	t.Run("never", func(t *testing.T) {
-		configFile := filepath.Join(t.TempDir(), "config.toml")
-		require.NoError(t, os.WriteFile(configFile, []byte("update_prompt = true\n"), 0o644))
-
-		ctx, cancel := context.WithTimeout(context.Background(), 30*time.Second)
-		defer cancel()
-
-		cmd := exec.CommandContext(ctx, tmpBinary, "--config", configFile)
-		cmd.Env = env.Without(env.AuthToken).With(env.AuthToken, "fake-token").With(env.APIEndpoint, mockServer.URL)
-
-		ptmx, err := pty.Start(cmd)
-		require.NoError(t, err, "failed to start command in PTY")
-		defer func() { _ = ptmx.Close() }()
-
-		output := &syncBuffer{}
-		outputCh := make(chan struct{})
-		go func() {
-			_, _ = io.Copy(output, ptmx)
-			close(outputCh)
-		}()
-
-		require.Eventually(t, func() bool {
-			return bytes.Contains(output.Bytes(), []byte("new version is available"))
-		}, 10*time.Second, 100*time.Millisecond, "update notification prompt should appear")
-
-		_, err = ptmx.Write([]byte("n"))
-		require.NoError(t, err)
-
-		_ = cmd.Wait()
-		<-outputCh
-
-		assert.Contains(t, output.String(), "Update available: 0.0.1")
-
-		// Verify config was updated to disable future prompts
-		configData, err := os.ReadFile(configFile)
-		require.NoError(t, err)
-		assert.Contains(t, string(configData), "update_prompt = false")
-	})
 
 	t.Run("update", func(t *testing.T) {
 		// Copy binary since it will be replaced during the update
@@ -357,7 +319,7 @@ func TestUpdateNotification(t *testing.T) {
 		require.NoError(t, os.WriteFile(updateBinary, data, 0o755))
 
 		configFile := filepath.Join(t.TempDir(), "config.toml")
-		require.NoError(t, os.WriteFile(configFile, []byte("update_prompt = true\n"), 0o644))
+		require.NoError(t, os.WriteFile(configFile, []byte("[cli]\nupdate_prompt = true\n"), 0o644))
 
 		ctx, cancel := context.WithTimeout(context.Background(), 2*time.Minute)
 		defer cancel()
@@ -377,7 +339,7 @@ func TestUpdateNotification(t *testing.T) {
 		}()
 
 		require.Eventually(t, func() bool {
-			return bytes.Contains(output.Bytes(), []byte("new version is available"))
+			return bytes.Contains(output.Bytes(), []byte("New lstk version available"))
 		}, 10*time.Second, 100*time.Millisecond, "update notification prompt should appear")
 
 		_, err = ptmx.Write([]byte("u"))
@@ -388,7 +350,7 @@ func TestUpdateNotification(t *testing.T) {
 
 		out := output.String()
 		require.NoError(t, err, "update should succeed: %s", out)
-		assert.Contains(t, out, "Update available: 0.0.1")
+		assert.Contains(t, out, "New lstk version available")
 		assert.Contains(t, out, "Updated to")
 
 		// Verify the binary was actually replaced