diff --git a/rsconnect/bundle.py b/rsconnect/bundle.py
index 9824ce95..0ff27c38 100644
--- a/rsconnect/bundle.py
+++ b/rsconnect/bundle.py
@@ -1432,6 +1432,15 @@ def fake_module_file_from_directory(directory: str):
     return join(directory, app_name + ".py")
 
 
+def is_python_enabled_on_server(connect_details):
+    """
+    Returns whether or not the Connect server has Python itself enabled.
+
+    :error: The Posit Connect server does not have Python enabled.
+    """
+    return any(connect_details.get("python", {}).get("versions", []))
+
+
 def are_apis_supported_on_server(connect_details):
     """
     Returns whether or not the Connect server has Python itself enabled and its license allows
diff --git a/rsconnect/main.py b/rsconnect/main.py
index ee473204..97e412a3 100644
--- a/rsconnect/main.py
+++ b/rsconnect/main.py
@@ -40,6 +40,7 @@
 from . import api, VERSION, validation
 from .api import RSConnectExecutor, RSConnectServer, RSConnectClient, filter_out_server_info
 from .bundle import (
+    is_python_enabled_on_server,
     are_apis_supported_on_server,
     create_python_environment,
     default_title_from_manifest,
@@ -1306,7 +1307,7 @@ def deploy_app(
         (
             ce.validate_server()
             .validate_app_mode(app_mode=app_mode)
-            .check_server_capabilities([are_apis_supported_on_server])
+            .check_server_capabilities([is_python_enabled_on_server, are_apis_supported_on_server])
             .make_bundle(
                 make_api_bundle,
                 directory,