diff --git a/winsup/cygwin/path.cc b/winsup/cygwin/path.cc
index 8615386aff..b1a088a9fd 100644
--- a/winsup/cygwin/path.cc
+++ b/winsup/cygwin/path.cc
@@ -709,6 +709,12 @@ path_conv::check (const char *src, unsigned opt,
 	      need_directory = 1;
 	      *--tail = '\0';
 	    }
+	  /* Special case for "/" must set need_directory, without removing
+	     trailing slash */
+	  else if (tail == path_copy + 1 && isslash (tail[-1]))
+	    {
+	      need_directory = 1;
+	    }
 	  path_end = tail;
 
 	  /* Scan path_copy from right to left looking either for a symlink
@@ -1248,6 +1254,7 @@ path_conv::check (const char *src, unsigned opt,
 		cfree (wide_path);
 	      wide_path = NULL;
 	    }
+
 	  if (need_directory)
 	    {
 	      size_t n = strlen (this->path);