diff --git a/src/deadline_test_fixtures/deadline/worker.py b/src/deadline_test_fixtures/deadline/worker.py
index d1a76bf..cb2b2ad 100644
--- a/src/deadline_test_fixtures/deadline/worker.py
+++ b/src/deadline_test_fixtures/deadline/worker.py
@@ -281,6 +281,7 @@ def send_command(self, command: str) -> CommandResult:
             ssm_waiter.wait(
                 InstanceId=self.instance_id,
                 CommandId=command_id,
+                WaiterConfig={"Delay": 5, "MaxAttempts": 30},
             )
         except botocore.exceptions.WaiterError:  # pragma: no cover
             # Swallow exception, we're going to check the result anyway
diff --git a/src/deadline_test_fixtures/models.py b/src/deadline_test_fixtures/models.py
index eda009e..ba70004 100644
--- a/src/deadline_test_fixtures/models.py
+++ b/src/deadline_test_fixtures/models.py
@@ -228,7 +228,7 @@ def install_command_for_windows(self) -> str:
             )
 
         if self.upgrade_pip:
-            cmds.append("pip install --upgrade pip")
+            cmds.append("python -m pip install --upgrade pip")
 
         cmds.append(
             " ".join(