diff --git a/pyinfra/operations/server.py b/pyinfra/operations/server.py
index 9264dd8b6..d51f2ee63 100644
--- a/pyinfra/operations/server.py
+++ b/pyinfra/operations/server.py
@@ -99,6 +99,12 @@ def wait_and_reconnect(state, host):  # pragma: no cover
 
     yield FunctionCommand(wait_and_reconnect, (), {})
 
+    # On certain systems sudo files are lost on reboot
+    def clean_sudo_info(state, host):
+        host.connector_data["sudo_askpass_path"] = None
+
+    yield FunctionCommand(clean_sudo_info, (), {})
+
 
 @operation(is_idempotent=False)
 def wait(port: int):
diff --git a/tests/operations/server.reboot/reboot.json b/tests/operations/server.reboot/reboot.json
index 061a5798d..9b8f5b216 100644
--- a/tests/operations/server.reboot/reboot.json
+++ b/tests/operations/server.reboot/reboot.json
@@ -6,7 +6,8 @@
             "command": "reboot",
             "success_exit_codes": [0, -1]
         },
-        ["wait_and_reconnect", [], {}]
+        ["wait_and_reconnect", [], {}],
+        ["clean_sudo_info", [], {}]
     ],
     "idempotent": false
 }