diff --git a/src/ssh/azext_ssh/custom.py b/src/ssh/azext_ssh/custom.py
index 4d2198f8af3..04e4ab4a74e 100644
--- a/src/ssh/azext_ssh/custom.py
+++ b/src/ssh/azext_ssh/custom.py
@@ -78,6 +78,7 @@ def _do_ssh_op(cmd, ssh_ip, public_key_file, private_key_file, username,
     proxy_path = None
     relay_info = None
     if is_arc:
+        _is_aad_extension_installed(cmd, resource_group_name, vm_name)
         proxy_path = _arc_get_client_side_proxy()
         relay_info = _arc_list_access_details(cmd, resource_group_name, vm_name)
     else:
@@ -379,3 +380,16 @@ def _check_if_arc_server(cmd, resource_group_name, vm_name):
     except ResourceNotFoundError:
         return False
     return True
+
+
+def _is_aad_extension_installed(cmd, resource_group_name, vm_name):
+    from azext_ssh._client_factory import cf_machine_extension
+    from azure.core.exceptions import ResourceNotFoundError
+    extension = "AADSSHLoginForLinux"
+    client = cf_machine_extension(cmd.cli_ctx)
+    try:
+        client.get(resource_group_name=resource_group_name, machine_name=vm_name, extension_name=extension)
+    except ResourceNotFoundError as e:
+        raise azclierror.ResourceNotFoundError(f"The extension {extension} must be installed in the target machine. "
+                                               f"Run \"az connectedmachine extension create --machine-name {vm_name} "
+                                               f"--resource-group {resource_group_name} --name {extension}\"") from e