diff --git a/moonraker/components/update_manager/app_deploy.py b/moonraker/components/update_manager/app_deploy.py
index ffe7567a..464ab1b4 100644
--- a/moonraker/components/update_manager/app_deploy.py
+++ b/moonraker/components/update_manager/app_deploy.py
@@ -169,6 +169,7 @@ def _configure_virtualenv(self, config: ConfigHelper) -> None:
             else:
                 self.log_info("Unable to locate pip executable")
         self.venv_args = config.get('venv_args', None)
+        self.pip_env_vars = config.getdict("pip_environment_variables", None)
 
     def _configure_dependencies(
         self, config: ConfigHelper, node_only: bool = False
@@ -411,11 +412,18 @@ async def _update_python_requirements(
         else:
             reqs = [req.replace("\"", "'") for req in requirements]
             args = " ".join([f"\"{req}\"" for req in reqs])
+        env: Optional[Dict[str, str]] = None
+        if self.pip_env_vars is not None:
+            self.log_info(
+                f"Running Pip with environment variables: {self.pip_env_vars}"
+            )
+            env = dict(os.environ)
+            env.update(self.pip_env_vars)
         self.notify_status("Updating python packages...")
         try:
             await self.cmd_helper.run_cmd(
                 f"{self.pip_cmd} install {args}", timeout=1200., notify=True,
-                retries=3
+                retries=3, env=env, log_stderr=True
             )
         except Exception:
             self.log_exc("Error updating python requirements")
diff --git a/moonraker/components/update_manager/common.py b/moonraker/components/update_manager/common.py
index 4ed92894..0d5971a8 100644
--- a/moonraker/components/update_manager/common.py
+++ b/moonraker/components/update_manager/common.py
@@ -32,6 +32,7 @@
         "system_dependencies": "scripts/system-dependencies.json",
         "host_repo": "arksine/moonraker",
         "virtualenv": sys.exec_prefix,
+        "pip_environment_variables": "SKIP_CYTHON=Y",
         "path": str(source_info.source_path()),
         "managed_services": "moonraker"
     },
diff --git a/moonraker/components/update_manager/update_manager.py b/moonraker/components/update_manager/update_manager.py
index 4c5651b4..caec8ef3 100644
--- a/moonraker/components/update_manager/update_manager.py
+++ b/moonraker/components/update_manager/update_manager.py
@@ -582,10 +582,14 @@ async def run_cmd(
         retries: int = 1,
         env: Optional[Dict[str, str]] = None,
         cwd: Optional[str] = None,
-        sig_idx: int = 1
+        sig_idx: int = 1,
+        log_stderr: bool = False
     ) -> None:
         cb = self.notify_update_response if notify else None
-        scmd = self.build_shell_command(cmd, callback=cb, env=env, cwd=cwd)
+        log_stderr |= self.server.is_verbose_enabled()
+        scmd = self.build_shell_command(
+            cmd, callback=cb, env=env, cwd=cwd, log_stderr=log_stderr
+        )
         for _ in range(retries):
             if await scmd.run(timeout=timeout, sig_idx=sig_idx):
                 break