diff --git a/libcxx/test/std/input.output/filesystems/class.directory_entry/directory_entry.cons/path.pass.cpp b/libcxx/test/std/input.output/filesystems/class.directory_entry/directory_entry.cons/path.pass.cpp
--- a/libcxx/test/std/input.output/filesystems/class.directory_entry/directory_entry.cons/path.pass.cpp
+++ b/libcxx/test/std/input.output/filesystems/class.directory_entry/directory_entry.cons/path.pass.cpp
@@ -153,7 +153,8 @@
   // reading directories; test using a special inaccessible directory
   // instead.
   const path dir = GetWindowsInaccessibleDir();
-  TEST_REQUIRE(!dir.empty());
+  if (dir.empty())
+    TEST_UNSUPPORTED();
   const path file = dir / "file";
   {
     std::error_code ec = GetTestEC();
diff --git a/libcxx/test/std/input.output/filesystems/class.directory_iterator/directory_iterator.members/ctor.pass.cpp b/libcxx/test/std/input.output/filesystems/class.directory_iterator/directory_iterator.members/ctor.pass.cpp
--- a/libcxx/test/std/input.output/filesystems/class.directory_iterator/directory_iterator.members/ctor.pass.cpp
+++ b/libcxx/test/std/input.output/filesystems/class.directory_iterator/directory_iterator.members/ctor.pass.cpp
@@ -92,7 +92,8 @@
     // reading directories; test using a special inaccessible directory
     // instead.
     const path testDir = GetWindowsInaccessibleDir();
-    TEST_REQUIRE(!testDir.empty());
+    if (testDir.empty())
+        TEST_UNSUPPORTED();
 #else
     scoped_test_env env;
     path const testDir = env.make_env_path("dir1");
diff --git a/libcxx/test/std/input.output/filesystems/class.rec.dir.itr/rec.dir.itr.members/ctor.pass.cpp b/libcxx/test/std/input.output/filesystems/class.rec.dir.itr/rec.dir.itr.members/ctor.pass.cpp
--- a/libcxx/test/std/input.output/filesystems/class.rec.dir.itr/rec.dir.itr.members/ctor.pass.cpp
+++ b/libcxx/test/std/input.output/filesystems/class.rec.dir.itr/rec.dir.itr.members/ctor.pass.cpp
@@ -93,7 +93,8 @@
     // reading directories; test using a special inaccessible directory
     // instead.
     const path testDir = GetWindowsInaccessibleDir();
-    TEST_REQUIRE(!testDir.empty());
+    if (testDir.empty())
+        TEST_UNSUPPORTED();
 #else
     scoped_test_env env;
     path const testDir = env.make_env_path("dir1");
diff --git a/libcxx/test/std/input.output/filesystems/fs.op.funcs/fs.op.exists/exists.pass.cpp b/libcxx/test/std/input.output/filesystems/fs.op.funcs/fs.op.exists/exists.pass.cpp
--- a/libcxx/test/std/input.output/filesystems/fs.op.funcs/fs.op.exists/exists.pass.cpp
+++ b/libcxx/test/std/input.output/filesystems/fs.op.funcs/fs.op.exists/exists.pass.cpp
@@ -78,7 +78,8 @@
     // reading directories; test using a special inaccessible directory
     // instead.
     const path p = GetWindowsInaccessibleDir();
-    TEST_REQUIRE(!p.empty());
+    if (p.empty())
+        TEST_UNSUPPORTED();
 #else
     scoped_test_env env;
     const path dir = env.create_dir("dir");
diff --git a/libcxx/test/support/filesystem_test_helper.h b/libcxx/test/support/filesystem_test_helper.h
--- a/libcxx/test/support/filesystem_test_helper.h
+++ b/libcxx/test/support/filesystem_test_helper.h
@@ -679,21 +679,36 @@
   std::error_code ec;
   const fs::path root("C:\\");
   fs::directory_iterator it(root, ec);
-  if (ec)
+  if (ec) {
+    fprintf(stderr, "Unable to iterate over %s, skipping tests regarding "
+                    "an inaccessible directory\n", root.string().c_str());
     return fs::path();
+  }
   const fs::directory_iterator endIt{};
   while (it != endIt) {
     const fs::directory_entry &ent = *it;
     if (ent == dir) {
       // Basic sanity checks on the directory_entry
-      if (!ent.exists())
+      if (!ent.exists() || !ent.is_directory()) {
+        fprintf(stderr, "The expected inaccessible directory \"%s\" was found "
+                        "but doesn't behave as expected, skipping tests "
+                        "regarding it\n", dir.string().c_str());
         return fs::path();
-      if (!ent.is_directory())
+      }
+      // Check that it indeed is inaccessible as expected
+      fs::exists(ent, ec);
+      if (!ec) {
+        fprintf(stderr, "The expected inaccessible directory \"%s\" was found "
+                        "but seems to be accessible, skipping tests "
+                        "regarding it\n", dir.string().c_str());
         return fs::path();
+      }
       return ent;
     }
     ++it;
   }
+  fprintf(stderr, "No inaccessible directory \"%s\" found, skipping tests "
+                  "regarding it\n", dir.string().c_str());
   return fs::path();
 }