diff --git a/acceptance/ssh/connection/out.stdout.txt b/acceptance/ssh/connection/out.stdout.txt
index 41cae5e7d16..e69de29bb2d 100644
--- a/acceptance/ssh/connection/out.stdout.txt
+++ b/acceptance/ssh/connection/out.stdout.txt
@@ -1 +0,0 @@
-Connection successful
diff --git a/acceptance/ssh/connection/out.test.toml b/acceptance/ssh/connection/out.test.toml
index 06079f65341..9d444f6ae49 100644
--- a/acceptance/ssh/connection/out.test.toml
+++ b/acceptance/ssh/connection/out.test.toml
@@ -1,4 +1,4 @@
-Local = false
+Local = true
 Cloud = false
 RequiresCluster = true
 EnvMatrix.DATABRICKS_BUNDLE_ENGINE = ["direct"]
diff --git a/acceptance/ssh/connection/output.txt b/acceptance/ssh/connection/output.txt
index e69de29bb2d..6c4551026b5 100644
--- a/acceptance/ssh/connection/output.txt
+++ b/acceptance/ssh/connection/output.txt
@@ -0,0 +1,29 @@
+
+>>> print_requests.py //api/2.2/jobs/runs/submit
+{
+  "method": "POST",
+  "path": "/api/2.2/jobs/runs/submit",
+  "body": {
+    "run_name": "ssh-server-bootstrap-[TEST_DEFAULT_CLUSTER_ID]",
+    "tasks": [
+      {
+        "existing_cluster_id": "[TEST_DEFAULT_CLUSTER_ID]",
+        "notebook_task": {
+          "base_parameters": {
+            "authorizedKeySecretName": "client-public-key",
+            "maxClients": "10",
+            "secretScopeName": "[USERNAME]-[TEST_DEFAULT_CLUSTER_ID]-ssh-tunnel-keys",
+            "serverless": "false",
+            "sessionId": "[TEST_DEFAULT_CLUSTER_ID]",
+            "shutdownDelay": "10m0s",
+            "version": "[CLI_VERSION]"
+          },
+          "notebook_path": "/Workspace/Users/[USERNAME]/.databricks/ssh-tunnel/[CLI_VERSION]/[TEST_DEFAULT_CLUSTER_ID]/ssh-server-bootstrap"
+        },
+        "task_key": "start_ssh_server",
+        "timeout_seconds": 86400
+      }
+    ],
+    "timeout_seconds": 86400
+  }
+}
diff --git a/acceptance/ssh/connection/script b/acceptance/ssh/connection/script
index 39e8b39ef4b..3e206bfbb01 100644
--- a/acceptance/ssh/connection/script
+++ b/acceptance/ssh/connection/script
@@ -1,6 +1,22 @@
+if [ -z "${CLOUD_ENV:-}" ]; then
+  # Local runs have no release artifacts and never execute the uploaded
+  # binaries, so stand in empty archives (dev name omits the version).
+  mkdir -p releases
+  : >releases/databricks_cli_linux_amd64.zip
+  : >releases/databricks_cli_linux_arm64.zip
+  CLI_RELEASES_DIR="$PWD/releases"
+fi
+
 errcode $CLI ssh connect --cluster=$TEST_DEFAULT_CLUSTER_ID --releases-dir=$CLI_RELEASES_DIR --user-known-hosts-file=known_hosts -- "echo 'Connection successful'" >out.stdout.txt 2>LOG.stderr
 
-if ! grep -q "Connection successful" out.stdout.txt; then
-  run_id=$(cat LOG.stderr | grep -o "Job submitted successfully with run ID: [0-9]*" | grep -o "[0-9]*$")
-  trace $CLI jobs get-run "$run_id" > LOG.job
+if [ -n "${CLOUD_ENV:-}" ]; then
+  # On cloud the connection runs the remote command; dump the run on failure.
+  if ! grep -q "Connection successful" out.stdout.txt; then
+    run_id=$(cat LOG.stderr | grep -o "Job submitted successfully with run ID: [0-9]*" | grep -o "[0-9]*$")
+    trace $CLI jobs get-run "$run_id" > LOG.job
+  fi
+else
+  # Locally the handshake can't complete (no compute); just assert the CLI
+  # submitted the right dedicated-cluster bootstrap job.
+  trace print_requests.py //api/2.2/jobs/runs/submit
 fi
diff --git a/acceptance/ssh/connection/test.toml b/acceptance/ssh/connection/test.toml
index 76965d3ae0e..e2a33c0a5b9 100644
--- a/acceptance/ssh/connection/test.toml
+++ b/acceptance/ssh/connection/test.toml
@@ -1,6 +1,17 @@
-Local = false
+Local = true
 Cloud = false
+
+# On cloud this needs a real dedicated single-user cluster; locally the default
+# test cluster stands in for it.
 RequiresCluster = true
 
+# Assert the dedicated-cluster bootstrap job the CLI submits on a local run.
+RecordRequests = true
+
+# Local runs stage stand-in release archives here; not part of the golden output.
+Ignore = [
+  "releases",
+]
+
 [EnvMatrix]
   DATABRICKS_BUNDLE_ENGINE = ["direct"]
diff --git a/libs/testserver/fake_workspace.go b/libs/testserver/fake_workspace.go
index 1c5d842f0f8..df9499c7e91 100644
--- a/libs/testserver/fake_workspace.go
+++ b/libs/testserver/fake_workspace.go
@@ -382,9 +382,15 @@ func NewFakeWorkspace(url, token string) *FakeWorkspace {
 		ModelRegistryModels:       map[string]ml.Model{},
 		ModelRegistryModelIDs:     map[string]string{},
 		Clusters: map[string]compute.ClusterDetails{
+			// A running dedicated single-user cluster: the shape `ssh connect --cluster`
+			// requires (ValidateClusterAccess rejects anything else), matching the cloud
+			// TEST_DEFAULT_CLUSTER_ID this stands in for.
 			TestDefaultClusterId: {
-				ClusterId:   TestDefaultClusterId,
-				ClusterName: "DEFAULT Test Cluster",
+				ClusterId:        TestDefaultClusterId,
+				ClusterName:      "DEFAULT Test Cluster",
+				State:            compute.StateRunning,
+				DataSecurityMode: compute.DataSecurityModeSingleUser,
+				SingleUserName:   TestUser.UserName,
 			},
 		},
 	}