diff --git a/connect.c b/connect.c
index 15b72b644903e6..0e7aa7d91e2e79 100644
--- a/connect.c
+++ b/connect.c
@@ -915,6 +915,10 @@ static enum protocol parse_connect_url(const char *url_orig, char **ret_host,
 
 	if (protocol == PROTO_LOCAL)
 		path = end;
+	else if (protocol == PROTO_FILE && *host != '/' &&
+		 !has_dos_drive_prefix(host) &&
+		 offset_1st_component(host - 2) > 1)
+		path = host - 2; /* include the leading "//" */
 	else if (protocol == PROTO_FILE && has_dos_drive_prefix(end))
 		path = end; /* "file://$(pwd)" may be "file://C:/projects/repo" */
 	else
diff --git a/t/t5500-fetch-pack.sh b/t/t5500-fetch-pack.sh
index 1c71c0ec770cd5..b477be9ed07998 100755
--- a/t/t5500-fetch-pack.sh
+++ b/t/t5500-fetch-pack.sh
@@ -708,13 +708,22 @@ do
 	# file with scheme
 	for p in file
 	do
-		test_expect_success "fetch-pack --diag-url $p://$h/$r" '
+		test_expect_success !MINGW "fetch-pack --diag-url $p://$h/$r" '
 			check_prot_path $p://$h/$r $p "/$r"
 		'
+		test_expect_success MINGW "fetch-pack --diag-url $p://$h/$r" '
+			check_prot_path $p://$h/$r $p "//$h/$r"
+		'
+		test_expect_success MINGW "fetch-pack --diag-url $p:///$r" '
+			check_prot_path $p:///$r $p "/$r"
+		'
 		# No "/~" -> "~" conversion for file
-		test_expect_success "fetch-pack --diag-url $p://$h/~$r" '
+		test_expect_success !MINGW "fetch-pack --diag-url $p://$h/~$r" '
 			check_prot_path $p://$h/~$r $p "/~$r"
 		'
+		test_expect_success MINGW "fetch-pack --diag-url $p://$h/~$r" '
+			check_prot_path $p://$h/~$r $p "//$h/~$r"
+		'
 	done
 	# file without scheme
 	for h in nohost nohost:12 [::1] [::1]:23 [ [:aa