Thanks. Looks like that would need some compat implementation of gettimeofday via GetSystemTime and SystemTimeToFileTime or something like that.

Would be nice if the OS provided a fix on the system level rather than requiring downstreams to come up with workarounds for its brokenness...

The funcion is already compat implemented here:

but when declaring

we are taking the timeval declaration from winsock2.h, that is a signed 32 bits.

Right. I need to fix the aggressive .gitignore...

If we're lucky, the diff below works. I'm unsure how posix_win.c ends up pulling in sys/time.h, perhaps it needs an explicit such include somewhere at the top.

diff --git a/include/compat/sys/time.h b/include/compat/sys/time.h
index 76428c1..2448969 100644
--- a/include/compat/sys/time.h
+++ b/include/compat/sys/time.h
@@ -8,6 +8,15 @@
 
 #ifdef _MSC_VER
 #include <winsock2.h>
+
+#define timeval libressl_timeval
+#define gettimeofday libressl_gettimeofday
+
+struct timeval {
+	long long	tv_sec;
+	long		tv_usec;
+};
+
 int gettimeofday(struct timeval *tp, void *tzp);
 #else
 #include_next <sys/time.h>

See #1078. It would be great if you could check if this addresses the issue.