diff --git a/NEXT_CHANGELOG.md b/NEXT_CHANGELOG.md
index f26e1ea1afc..17bd35390ef 100644
--- a/NEXT_CHANGELOG.md
+++ b/NEXT_CHANGELOG.md
@@ -6,6 +6,7 @@
 
 ### CLI
 * Show a once-per-day notice after a command when a newer CLI release is available, with a link to the release and the upgrade command for the detected install method. Suppressed for non-interactive/CI runs, JSON output, the Databricks Runtime, and development builds, and can be disabled with `DATABRICKS_CLI_DISABLE_UPDATE_CHECK` ([#5470](https://github.com/databricks/cli/pull/5470)).
+* Increase the SSH server startup timeout from 10 to 45 minutes when a GPU accelerator is requested via `databricks ssh connect --accelerator` ([#5569](https://github.com/databricks/cli/pull/5569)).
 
 ### Bundles
 * Remove API enum values and types that are still in development from the `databricks-bundles` Python package; these were never accepted by the backend ([#5484](https://github.com/databricks/cli/pull/5484)).
diff --git a/experimental/ssh/cmd/connect.go b/experimental/ssh/cmd/connect.go
index 2c1af41c5c8..6daaca6db7a 100644
--- a/experimental/ssh/cmd/connect.go
+++ b/experimental/ssh/cmd/connect.go
@@ -90,6 +90,12 @@ Connect to a dedicated cluster:
 		if connectionName == "" && clusterID == "" && !proxyMode {
 			connectionName = client.GenerateDefaultConnectionName(wsClient.Config.Host, accelerator)
 		}
+		// Serverless GPU compute can take much longer to provision than CPU compute,
+		// so allow extra time for the SSH server job to start.
+		startupTimeout := taskStartupTimeout
+		if accelerator != "" {
+			startupTimeout = gpuTaskStartupTimeout
+		}
 		opts := client.ClientOptions{
 			Profile:              wsClient.Config.Profile,
 			ClusterID:            clusterID,
@@ -103,7 +109,7 @@ Connect to a dedicated cluster:
 			HandoverTimeout:      handoverTimeout,
 			ReleasesDir:          releasesDir,
 			ServerTimeout:        max(serverTimeout, shutdownDelay),
-			TaskStartupTimeout:   taskStartupTimeout,
+			TaskStartupTimeout:   startupTimeout,
 			AutoStartCluster:     autoStartCluster,
 			ClientPublicKeyName:  clientPublicKeyName,
 			ClientPrivateKeyName: clientPrivateKeyName,
diff --git a/experimental/ssh/cmd/constants.go b/experimental/ssh/cmd/constants.go
index edf95494b75..64c99b5bd48 100644
--- a/experimental/ssh/cmd/constants.go
+++ b/experimental/ssh/cmd/constants.go
@@ -9,12 +9,13 @@ const (
 	defaultHandoverTimeout    = 30 * time.Minute
 	defaultEnvironmentVersion = 4
 
-	serverTimeout        = 24 * time.Hour
-	taskStartupTimeout   = 10 * time.Minute
-	serverPortRange      = 100
-	serverConfigDir      = ".ssh-tunnel"
-	serverPrivateKeyName = "server-private-key"
-	serverPublicKeyName  = "server-public-key"
-	clientPrivateKeyName = "client-private-key"
-	clientPublicKeyName  = "client-public-key"
+	serverTimeout         = 24 * time.Hour
+	taskStartupTimeout    = 10 * time.Minute
+	gpuTaskStartupTimeout = 45 * time.Minute
+	serverPortRange       = 100
+	serverConfigDir       = ".ssh-tunnel"
+	serverPrivateKeyName  = "server-private-key"
+	serverPublicKeyName   = "server-public-key"
+	clientPrivateKeyName  = "client-private-key"
+	clientPublicKeyName   = "client-public-key"
 )