diff --git a/experimental/ssh/internal/client/client.go b/experimental/ssh/internal/client/client.go
index 07e6dd3af5..0e4777b9c6 100644
--- a/experimental/ssh/internal/client/client.go
+++ b/experimental/ssh/internal/client/client.go
@@ -279,7 +279,7 @@ func Run(ctx context.Context, client *databricks.WorkspaceClient, opts ClientOpt
 
 	if opts.ServerMetadata == "" {
 		cmdio.LogString(ctx, "Uploading binaries...")
-		sp := cmdio.NewSpinner(ctx)
+		sp := cmdio.NewSpinner(ctx, cmdio.WithElapsedTime())
 		sp.Update("Uploading binaries...")
 		err := UploadTunnelReleases(ctx, client, version, opts.ReleasesDir)
 		sp.Close()
@@ -581,7 +581,7 @@ func runSSHProxy(ctx context.Context, client *databricks.WorkspaceClient, server
 }
 
 func checkClusterState(ctx context.Context, client *databricks.WorkspaceClient, clusterID string, autoStart bool) error {
-	sp := cmdio.NewSpinner(ctx)
+	sp := cmdio.NewSpinner(ctx, cmdio.WithElapsedTime())
 	defer sp.Close()
 	if autoStart {
 		sp.Update("Ensuring the cluster is running...")
@@ -605,7 +605,7 @@ func checkClusterState(ctx context.Context, client *databricks.WorkspaceClient,
 // waitForJobToStart polls the task status until the SSH server task is in RUNNING state or terminates.
 // Returns an error if the task fails to start or if polling times out.
 func waitForJobToStart(ctx context.Context, client *databricks.WorkspaceClient, runID int64, taskStartupTimeout time.Duration) error {
-	sp := cmdio.NewSpinner(ctx)
+	sp := cmdio.NewSpinner(ctx, cmdio.WithElapsedTime())
 	defer sp.Close()
 	sp.Update("Starting SSH server...")
 	var prevState jobs.RunLifecycleStateV2State
@@ -674,7 +674,7 @@ func ensureSSHServerIsRunning(ctx context.Context, client *databricks.WorkspaceC
 			return "", 0, "", fmt.Errorf("failed to submit and start ssh server job: %w", err)
 		}
 
-		sp := cmdio.NewSpinner(ctx)
+		sp := cmdio.NewSpinner(ctx, cmdio.WithElapsedTime())
 		defer sp.Close()
 		sp.Update("Waiting for the SSH server to start...")
 		maxRetries := 30
@@ -684,6 +684,7 @@ func ensureSSHServerIsRunning(ctx context.Context, client *databricks.WorkspaceC
 			}
 			serverPort, userName, effectiveClusterID, err = getServerMetadata(ctx, client, sessionID, clusterID, version, opts.Liteswap)
 			if err == nil {
+				cmdio.LogString(ctx, "Health check successful, starting ssh WebSocket connection...")
 				break
 			} else if retries < maxRetries-1 {
 				time.Sleep(2 * time.Second)
diff --git a/libs/cmdio/io.go b/libs/cmdio/io.go
index da22c3b492..d54840d0f0 100644
--- a/libs/cmdio/io.go
+++ b/libs/cmdio/io.go
@@ -195,9 +195,9 @@ func RunSelect(ctx context.Context, prompt *promptui.Select) (int, string, error
 //
 // The spinner automatically degrades in non-interactive terminals (no output).
 // Context cancellation will automatically close the spinner.
-func NewSpinner(ctx context.Context) *spinner {
+func NewSpinner(ctx context.Context, opts ...SpinnerOption) *spinner {
 	c := fromContext(ctx)
-	return c.NewSpinner(ctx)
+	return c.NewSpinner(ctx, opts...)
 }
 
 type cmdIOType int
diff --git a/libs/cmdio/spinner.go b/libs/cmdio/spinner.go
index 9557710524..503a03ad64 100644
--- a/libs/cmdio/spinner.go
+++ b/libs/cmdio/spinner.go
@@ -2,6 +2,7 @@ package cmdio
 
 import (
 	"context"
+	"fmt"
 	"sync"
 	"time"
 
@@ -12,9 +13,10 @@ import (
 
 // spinnerModel is the Bubble Tea model for the spinner.
 type spinnerModel struct {
-	spinner  bubblespinner.Model
-	suffix   string
-	quitting bool
+	spinner   bubblespinner.Model
+	suffix    string
+	quitting  bool
+	startTime time.Time // non-zero when elapsed time display is enabled
 }
 
 // Message types for spinner updates.
@@ -23,8 +25,18 @@ type (
 	quitMsg   struct{}
 )
 
+// SpinnerOption configures spinner behavior.
+type SpinnerOption func(*spinnerModel)
+
+// WithElapsedTime enables an elapsed time prefix (MM:SS) on the spinner.
+func WithElapsedTime() SpinnerOption {
+	return func(m *spinnerModel) {
+		m.startTime = time.Now()
+	}
+}
+
 // newSpinnerModel creates a new spinner model.
-func newSpinnerModel() spinnerModel {
+func newSpinnerModel(opts ...SpinnerOption) spinnerModel {
 	s := bubblespinner.New()
 	// Braille spinner frames with 200ms timing
 	s.Spinner = bubblespinner.Spinner{
@@ -33,11 +45,13 @@ func newSpinnerModel() spinnerModel {
 	}
 	s.Style = lipgloss.NewStyle().Foreground(lipgloss.Color("10")) // Green
 
-	return spinnerModel{
-		spinner:  s,
-		suffix:   "",
-		quitting: false,
+	m := spinnerModel{
+		spinner: s,
+	}
+	for _, opt := range opts {
+		opt(&m)
 	}
+	return m
 }
 
 func (m spinnerModel) Init() tea.Cmd {
@@ -69,11 +83,16 @@ func (m spinnerModel) View() string {
 		return ""
 	}
 
+	var result string
+	if !m.startTime.IsZero() {
+		elapsed := time.Since(m.startTime)
+		result += fmt.Sprintf("%02d:%02d ", int(elapsed.Minutes()), int(elapsed.Seconds())%60)
+	}
+	result += m.spinner.View()
 	if m.suffix != "" {
-		return m.spinner.View() + " " + m.suffix
+		result += " " + m.suffix
 	}
-
-	return m.spinner.View()
+	return result
 }
 
 // spinner provides a structured interface for displaying progress indicators.
@@ -121,14 +140,18 @@ func (sp *spinner) Close() {
 //	sp := cmdio.NewSpinner(ctx)
 //	defer sp.Close()
 //	sp.Update("processing files")
-func (c *cmdIO) NewSpinner(ctx context.Context) *spinner {
+//
+// Use WithElapsedTime() to show a running MM:SS prefix:
+//
+//	sp := cmdio.NewSpinner(ctx, cmdio.WithElapsedTime())
+func (c *cmdIO) NewSpinner(ctx context.Context, opts ...SpinnerOption) *spinner {
 	// Don't show spinner if not interactive
 	if !c.capabilities.SupportsInteractive() {
 		return &spinner{p: nil, c: c, ctx: ctx}
 	}
 
 	// Create model and program
-	m := newSpinnerModel()
+	m := newSpinnerModel(opts...)
 	p := tea.NewProgram(
 		m,
 		tea.WithInput(nil),