diff --git a/ext/standard/http_fopen_wrapper.c b/ext/standard/http_fopen_wrapper.c
index fb987c82e5cc2..e4c63a957003e 100644
--- a/ext/standard/http_fopen_wrapper.c
+++ b/ext/standard/http_fopen_wrapper.c
@@ -219,7 +219,7 @@ static php_stream *php_stream_url_wrap_http_ex(php_stream_wrapper *wrapper,
 #ifndef PHP_WIN32
 		const double timeoutmax = (double) PHP_TIMEOUT_ULL_MAX / 1000000.0;
 #else
-		const double timeoutmax = (double) LONG_MAX / 1000000.0;
+		const double timeoutmax = (double) LONG_MAX + 0.999999;
 #endif
 
 		if (d > timeoutmax) {
diff --git a/main/network.c b/main/network.c
index d4938a4a08c1e..df42f57358655 100644
--- a/main/network.c
+++ b/main/network.c
@@ -319,6 +319,14 @@ static inline void php_network_set_limit_time(struct timeval *limit_time,
 		struct timeval *timeout)
 {
 	gettimeofday(limit_time, NULL);
+# ifdef PHP_WIN32
+	/* cap timeout (we're not picky regarding usec) */
+	if (limit_time->tv_sec > (LONG_MAX - timeout->tv_sec) + 1) {
+		limit_time->tv_sec = LONG_MAX;
+		limit_time->tv_usec = 999999;
+		return;
+	}
+# endif
 	limit_time->tv_sec += timeout->tv_sec;
 	limit_time->tv_usec += timeout->tv_usec;
 	if (limit_time->tv_usec >= 1000000) {