diff --git a/gix-validate/tests/path/mod.rs b/gix-validate/tests/path/mod.rs
index 84950e787ca..1330ff4a9c7 100644
--- a/gix-validate/tests/path/mod.rs
+++ b/gix-validate/tests/path/mod.rs
@@ -1,9 +1,9 @@
 #[test]
 fn component_is_windows_device() {
-    for device in ["con", "CONIN$", "lpt1.txt", "AUX", "Prn", "NUL", "COM9"] {
+    for device in ["con", "CONIN$", "lpt1.txt", "AUX", "Prn", "NUL", "COM9", "nul.a.b "] {
         assert!(gix_validate::path::component_is_windows_device(device.into()));
     }
-    for not_device in ["coni", "CONIN", "lpt", "AUXi", "aPrn", "NULl", "COM"] {
+    for not_device in ["coni", "CONIN", "lpt", "AUXi", "aPrn", "NULl", "COM", "a.nul.b "] {
         assert!(!gix_validate::path::component_is_windows_device(not_device.into()));
     }
 }
@@ -53,10 +53,10 @@ mod component {
 
         mktest!(ascii, b"ascii-only_and-that");
         mktest!(unicode, "😁👍👌".as_bytes());
-        mktest!(backslashes_on_unix, b"\\", UNIX_OPTS);
+        mktest!(backslashes_on_unix, br"\", UNIX_OPTS);
         mktest!(drive_letters_on_unix, b"c:", UNIX_OPTS);
         mktest!(virtual_drive_letters_on_unix, "֍:".as_bytes(), UNIX_OPTS);
-        mktest!(unc_path_on_unix, b"\\\\?\\pictures", UNIX_OPTS);
+        mktest!(unc_path_on_unix, br"\\?\pictures", UNIX_OPTS);
         mktest!(not_dot_git_longer, b".gitu", NO_OPTS);
         mktest!(not_dot_git_longer_all, b".gitu");
         mktest!(not_dot_gitmodules_shorter, b".gitmodule", Symlink, NO_OPTS);
@@ -66,7 +66,7 @@ mod component {
         mktest!(dot_gitmodules_as_file, b".gitmodules", UNIX_OPTS);
         mktest!(
             starts_with_dot_git_with_backslashes_on_linux,
-            b".git\\hooks\\pre-commit",
+            br".git\hooks\pre-commit",
             UNIX_OPTS
         );
         mktest!(not_dot_git_shorter, b".gi", NO_OPTS);
@@ -82,6 +82,9 @@ mod component {
         mktest!(conin_without_dollar, b"conin");
         mktest!(not_con, b"com");
         mktest!(also_not_con, b"co");
+        mktest!(con_as_middle, b"x.CON.zip");
+        mktest!(con_after_space, b" CON");
+        mktest!(con_after_space_mixed, b" coN.tar.xz");
         mktest!(not_nul, b"null");
         mktest!(
             not_dot_gitmodules_shorter_hfs,
@@ -136,7 +139,7 @@ mod component {
         mktest!(dot_git_upper, b".GIT", Error::DotGitDir, NO_OPTS);
         mktest!(
             starts_with_dot_git_with_backslashes_on_windows,
-            b".git\\hooks\\pre-commit",
+            br".git\hooks\pre-commit",
             Error::PathSeparator
         );
         mktest!(dot_git_upper_hfs, ".GIT\u{200e}".as_bytes(), Error::DotGitDir);
@@ -225,10 +228,10 @@ mod component {
         mktest!(path_separator_slash_trailing, b"a/", Error::PathSeparator);
         mktest!(path_separator_slash_only, b"/", Error::PathSeparator);
         mktest!(slashes_on_windows, b"/", Error::PathSeparator, ALL_OPTS);
-        mktest!(backslashes_on_windows, b"\\", Error::PathSeparator, ALL_OPTS);
-        mktest!(path_separator_backslash_between, b"a\\b", Error::PathSeparator);
-        mktest!(path_separator_backslash_leading, b"\\a", Error::PathSeparator);
-        mktest!(path_separator_backslash_trailing, b"a\\", Error::PathSeparator);
+        mktest!(backslashes_on_windows, br"\", Error::PathSeparator, ALL_OPTS);
+        mktest!(path_separator_backslash_between, br"a\b", Error::PathSeparator);
+        mktest!(path_separator_backslash_leading, br"\a", Error::PathSeparator);
+        mktest!(path_separator_backslash_trailing, br"a\", Error::PathSeparator);
         mktest!(aux_mixed, b"Aux", Error::WindowsReservedName);
         mktest!(aux_with_extension, b"aux.c", Error::WindowsReservedName);
         mktest!(com_lower, b"com1", Error::WindowsReservedName);
@@ -248,6 +251,8 @@ mod component {
         mktest!(prn_mixed_with_extension, b"PrN.abc", Error::WindowsReservedName);
         mktest!(con, b"CON", Error::WindowsReservedName);
         mktest!(con_with_extension, b"CON.abc", Error::WindowsReservedName);
+        mktest!(con_with_middle, b"CON.tar.xz", Error::WindowsReservedName);
+        mktest!(con_mixed_with_middle, b"coN.tar.xz ", Error::WindowsReservedName);
         mktest!(
             conout_mixed_with_extension,
             b"ConOut$  .xyz",
@@ -261,7 +266,10 @@ mod component {
             Error::WindowsPathPrefix,
             ALL_OPTS
         );
-        mktest!(unc_path, b"\\\\?\\pictures", Error::PathSeparator, ALL_OPTS);
+        mktest!(unc_net_path, br"\\host", Error::PathSeparator, ALL_OPTS);
+        mktest!(unc_path, br"\\?\pictures", Error::PathSeparator, ALL_OPTS);
+        mktest!(unc_device_path, br"\\.\pictures", Error::PathSeparator, ALL_OPTS);
+        mktest!(unc_nt_obj_path, br"\??\pictures", Error::PathSeparator, ALL_OPTS);
 
         #[test]
         fn ntfs_gitmodules() {