diff --git a/.cirrus.yml b/.cirrus.yml
index 8e0ae69bee..05a2ef2655 100644
--- a/.cirrus.yml
+++ b/.cirrus.yml
@@ -437,7 +437,11 @@ task:
     cd src/tools/msvc
     %T_C% perl vcregress.pl ecpgcheck
 
-  on_failure: *on_failure
+  on_failure:
+    <<: *on_failure
+    crashlog_artifacts:
+      path: "crashlog-**.txt"
+      type: text/plain
 
 
 task:
diff --git a/src/backend/main/main.c b/src/backend/main/main.c
index 9124060bde..3d67ce9dce 100644
--- a/src/backend/main/main.c
+++ b/src/backend/main/main.c
@@ -22,6 +22,10 @@
 
 #include <unistd.h>
 
+#if defined(WIN32)
+#include <crtdbg.h>
+#endif
+
 #if defined(__NetBSD__)
 #include <sys/param.h>
 #endif
@@ -237,8 +241,55 @@ startup_hacks(const char *progname)
 			exit(1);
 		}
 
-		/* In case of general protection fault, don't show GUI popup box */
-		SetErrorMode(SEM_FAILCRITICALERRORS | SEM_NOGPFAULTERRORBOX);
+		/*
+		 * By default abort() only generates a crash-dump in *non* debug
+		 * builds. As our Assert() / ExceptionalCondition() uses abort(),
+		 * leaving the default in place would make debugging harder.
+		 *
+		 * MINGW's own C runtime doesn't have _set_abort_behavior(). When
+		 * targetting Microsoft's UCRT with mingw, it never links to the debug
+		 * version of the library and thus doesn't need the call to
+		 * _set_abort_behavior() either.
+		 */
+#if !defined(__MINGW32__) && !defined(__MINGW64__)
+		_set_abort_behavior(_CALL_REPORTFAULT | _WRITE_ABORT_MSG,
+							_CALL_REPORTFAULT | _WRITE_ABORT_MSG);
+#endif							/* !defined(__MINGW32__) &&
+								 * !defined(__MINGW64__) */
+
+		/*
+		 * SEM_FAILCRITICALERRORS causes more errors to be reported to
+		 * callers.
+		 *
+		 * We used to also specify SEM_NOGPFAULTERRORBOX, but that prevents
+		 * windows crash reporting from working. Which includes registered
+		 * just-in-time debuggers, making it unnecessarily hard to debug
+		 * problems on windows. Now we try to disable sources of popups
+		 * separately below (note that SEM_NOGPFAULTERRORBOX did not actually
+		 * prevent all sources of such popups).
+		 */
+		SetErrorMode(SEM_FAILCRITICALERRORS);
+
+		/*
+		 * Show errors on stderr instead of popup box (note this doesn't
+		 * affect errors originating in the C runtime, see below).
+		 */
+		_set_error_mode(_OUT_TO_STDERR);
+
+		/*
+		 * In DEBUG builds, errors, including assertions, C runtime errors are
+		 * reported via _CrtDbgReport. By default such errors are displayed
+		 * with a popup (even with NOGPFAULTERRORBOX), preventing forward
+		 * progress. Instead report such errors stderr (and the debugger).
+		 * This is C runtime specific and thus the above incantations aren't
+		 * sufficient to suppress these popups.
+		 */
+		_CrtSetReportMode(_CRT_ERROR, _CRTDBG_MODE_FILE | _CRTDBG_MODE_DEBUG);
+		_CrtSetReportFile(_CRT_ERROR, _CRTDBG_FILE_STDERR);
+		_CrtSetReportMode(_CRT_ASSERT, _CRTDBG_MODE_FILE | _CRTDBG_MODE_DEBUG);
+		_CrtSetReportFile(_CRT_ASSERT, _CRTDBG_FILE_STDERR);
+		_CrtSetReportMode(_CRT_WARN, _CRTDBG_MODE_FILE | _CRTDBG_MODE_DEBUG);
+		_CrtSetReportFile(_CRT_WARN, _CRTDBG_FILE_STDERR);
 
 #if defined(_M_AMD64) && _MSC_VER == 1800