diff --git a/experimental/ssh/internal/client/client.go b/experimental/ssh/internal/client/client.go
index 1df157a7c6..e20ce8ac62 100644
--- a/experimental/ssh/internal/client/client.go
+++ b/experimental/ssh/internal/client/client.go
@@ -26,6 +26,8 @@ import (
 	"github.com/databricks/cli/internal/build"
 	"github.com/databricks/cli/libs/cmdio"
 	"github.com/databricks/cli/libs/log"
+	"github.com/databricks/cli/libs/telemetry"
+	"github.com/databricks/cli/libs/telemetry/protos"
 	"github.com/databricks/databricks-sdk-go"
 	"github.com/databricks/databricks-sdk-go/retries"
 	"github.com/databricks/databricks-sdk-go/service/compute"
@@ -283,6 +285,9 @@ func Run(ctx context.Context, client *databricks.WorkspaceClient, opts ClientOpt
 
 	version := build.GetInfo().Version
 
+	isReconnect := opts.ServerMetadata != ""
+	var serverStartTimeMs int64
+
 	if opts.ServerMetadata == "" {
 		cmdio.LogString(ctx, "Uploading binaries...")
 		sp := cmdio.NewSpinner(ctx, cmdio.WithElapsedTime())
@@ -292,10 +297,13 @@ func Run(ctx context.Context, client *databricks.WorkspaceClient, opts ClientOpt
 		if err != nil {
 			return fmt.Errorf("failed to upload ssh-tunnel binaries: %w", err)
 		}
+		serverStartTime := time.Now()
 		userName, serverPort, clusterID, err = ensureSSHServerIsRunning(ctx, client, version, secretScopeName, opts)
 		if err != nil {
+			logSshTunnelEvent(ctx, opts, false, isReconnect, 0)
 			return fmt.Errorf("failed to ensure that ssh server is running: %w", err)
 		}
+		serverStartTimeMs = time.Since(serverStartTime).Milliseconds()
 	} else {
 		// Metadata format: "<user_name>,<port>,<cluster_id>"
 		metadata := strings.Split(opts.ServerMetadata, ",")
@@ -332,6 +340,8 @@ func Run(ctx context.Context, client *databricks.WorkspaceClient, opts ClientOpt
 		cmdio.LogString(ctx, "Connected!")
 	}
 
+	logSshTunnelEvent(ctx, opts, true, isReconnect, serverStartTimeMs)
+
 	if opts.ProxyMode {
 		return runSSHProxy(ctx, client, serverPort, clusterID, opts)
 	} else if opts.IDE != "" {
@@ -704,3 +714,33 @@ func ensureSSHServerIsRunning(ctx context.Context, client *databricks.WorkspaceC
 
 	return userName, serverPort, effectiveClusterID, nil
 }
+
+func logSshTunnelEvent(ctx context.Context, opts ClientOptions, isSuccess, isReconnect bool, serverStartTimeMs int64) {
+	computeType := protos.SshTunnelComputeTypeDedicated
+	if opts.IsServerlessMode() {
+		computeType = protos.SshTunnelComputeTypeServerless
+	}
+
+	var clientMode protos.SshTunnelClientMode
+	switch {
+	case opts.ProxyMode:
+		clientMode = protos.SshTunnelClientModeProxy
+	case opts.IDE != "":
+		clientMode = protos.SshTunnelClientModeIDE
+	default:
+		clientMode = protos.SshTunnelClientModeSSH
+	}
+
+	telemetry.Log(ctx, protos.DatabricksCliLog{
+		SshTunnelEvent: &protos.SshTunnelEvent{
+			ComputeType:       computeType,
+			AcceleratorType:   opts.Accelerator,
+			IdeType:           opts.IDE,
+			ClientMode:        clientMode,
+			IsReconnect:       isReconnect,
+			AutoStartCluster:  opts.AutoStartCluster,
+			ServerStartTimeMs: serverStartTimeMs,
+			IsSuccess:         isSuccess,
+		},
+	})
+}
diff --git a/libs/telemetry/protos/frontend_log.go b/libs/telemetry/protos/frontend_log.go
index 7e6ab1012b..816297a8ee 100644
--- a/libs/telemetry/protos/frontend_log.go
+++ b/libs/telemetry/protos/frontend_log.go
@@ -19,4 +19,5 @@ type DatabricksCliLog struct {
 	CliTestEvent      *CliTestEvent      `json:"cli_test_event,omitempty"`
 	BundleInitEvent   *BundleInitEvent   `json:"bundle_init_event,omitempty"`
 	BundleDeployEvent *BundleDeployEvent `json:"bundle_deploy_event,omitempty"`
+	SshTunnelEvent    *SshTunnelEvent    `json:"ssh_tunnel_event,omitempty"`
 }
diff --git a/libs/telemetry/protos/ssh_tunnel.go b/libs/telemetry/protos/ssh_tunnel.go
new file mode 100644
index 0000000000..42be8233b7
--- /dev/null
+++ b/libs/telemetry/protos/ssh_tunnel.go
@@ -0,0 +1,47 @@
+package protos
+
+type SshTunnelComputeType string
+
+const (
+	SshTunnelComputeTypeUnspecified SshTunnelComputeType = "TYPE_UNSPECIFIED"
+	SshTunnelComputeTypeDedicated   SshTunnelComputeType = "DEDICATED"
+	SshTunnelComputeTypeServerless  SshTunnelComputeType = "SERVERLESS"
+)
+
+type SshTunnelClientMode string
+
+const (
+	SshTunnelClientModeUnspecified SshTunnelClientMode = "TYPE_UNSPECIFIED"
+	SshTunnelClientModeSSH         SshTunnelClientMode = "SSH_CLIENT"
+	SshTunnelClientModeProxy       SshTunnelClientMode = "PROXY"
+	SshTunnelClientModeIDE         SshTunnelClientMode = "IDE"
+)
+
+// SshTunnelEvent is emitted when a user establishes an SSH tunnel connection
+// via the Databricks CLI.
+type SshTunnelEvent struct {
+	// Type of compute: dedicated cluster or serverless.
+	ComputeType SshTunnelComputeType `json:"compute_type,omitempty"`
+
+	// GPU accelerator type for serverless compute.
+	AcceleratorType string `json:"accelerator_type,omitempty"`
+
+	// IDE that initiated the connection (e.g., "vscode", "cursor").
+	IdeType string `json:"ide_type,omitempty"`
+
+	// How the client is used: SSH client, proxy mode, or IDE mode.
+	ClientMode SshTunnelClientMode `json:"client_mode,omitempty"`
+
+	// Whether this is a reconnection to an existing session.
+	IsReconnect bool `json:"is_reconnect,omitempty"`
+
+	// Whether the cluster was auto-started by the CLI.
+	AutoStartCluster bool `json:"auto_start_cluster,omitempty"`
+
+	// Time in milliseconds spent starting the SSH server.
+	// Zero if server was already running.
+	ServerStartTimeMs int64 `json:"server_start_time_ms"`
+
+	// Whether the connection was successful.
+	IsSuccess bool `json:"is_success,omitempty"`
+}