diff --git a/Modules/signalmodule.c b/Modules/signalmodule.c
index ed0368329572ab..149e2f177c4f3b 100644
--- a/Modules/signalmodule.c
+++ b/Modules/signalmodule.c
@@ -244,6 +244,32 @@ trip_signal(int sig_num)
 
     Handlers[sig_num].tripped = 1;
 
+    if (!is_tripped) {
+        /* Set is_tripped after setting .tripped, as it gets
+           cleared in PyErr_CheckSignals() before .tripped. */
+        is_tripped = 1;
+        Py_AddPendingCall(checksignals_witharg, NULL);
+    }
+
+    /* And then write to the wakeup fd *after* setting all the globals and
+       doing the Py_AddPendingCall. We used to write to the wakeup fd and then
+       set the flag, but this allowed the following sequence of events
+       (especially on windows, where trip_signal runs in a new thread):
+
+       - main thread blocks on select([wakeup_fd], ...)
+       - signal arrives
+       - trip_signal writes to the wakeup fd
+       - the main thread wakes up
+       - the main thread checks the signal flags, sees that they're unset
+       - the main thread empties the wakeup fd
+       - the main thread goes back to sleep
+       - trip_signal sets the flags to request the Python-level signal handler
+         be run
+       - the main thread doesn't notice, because it's asleep
+
+       See bpo-30038 for more details.
+    */
+
 #ifdef MS_WINDOWS
     fd = Py_SAFE_DOWNCAST(wakeup.fd, SOCKET_T, int);
 #else
@@ -281,13 +307,6 @@ trip_signal(int sig_num)
             }
         }
     }
-
-    if (!is_tripped) {
-        /* Set is_tripped after setting .tripped, as it gets
-           cleared in PyErr_CheckSignals() before .tripped. */
-        is_tripped = 1;
-        Py_AddPendingCall(checksignals_witharg, NULL);
-    }
 }
 
 static void