diff --git a/src/nvim/os/fs.c b/src/nvim/os/fs.c
index 85588ed876..820e5cdc3d 100644
--- a/src/nvim/os/fs.c
+++ b/src/nvim/os/fs.c
@@ -1227,7 +1227,7 @@ bool os_fileinfo2(const char *path, FileInfo *info)
     info->rest_off = (size_t)(p - path);
     return true;
   }
-  if (p[0] == '?' || p[0] == '.') {
+  if (leading_slashes >= 2 && (p[0] == '?' || p[0] == '.')) {
     if (!vim_ispathsep_nocolon(p[1])) {
       return true;
     }
diff --git a/test/functional/vimscript/fnamemodify_spec.lua b/test/functional/vimscript/fnamemodify_spec.lua
index 65a1ec72e9..c9b93dd31d 100644
--- a/test/functional/vimscript/fnamemodify_spec.lua
+++ b/test/functional/vimscript/fnamemodify_spec.lua
@@ -182,6 +182,11 @@ describe('fnamemodify()', function()
       eq('//?/UNC/server', fnamemodify('//?/UNC/server', ':h'))
       eq('//?/UNC/server/share', fnamemodify('//?/UNC/server/share', ':h'))
       eq('//?/UNC/server/share/', fnamemodify('//?/UNC/server/share/foo', ':h'))
+
+      -- relative "./" and ".\" prefixes
+      eq('./path/to', fnamemodify('./path/to/hello.txt', ':h'))
+      eq('./path', fnamemodify('./path/to/hello.txt', ':h:h'))
+      eq('./path/to', fnamemodify([[.\path\to\hello.txt]], ':h'))
     end
   end)