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
@@ -8,8 +8,6 @@
 
 // UNSUPPORTED: c++03
 
-// XFAIL: LIBCXX-WINDOWS-FIXME
-
 // <filesystem>
 
 // class directory_entry
@@ -155,7 +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
@@ -8,8 +8,6 @@
 
 // UNSUPPORTED: c++03
 
-// XFAIL: LIBCXX-WINDOWS-FIXME
-
 // <filesystem>
 
 // class directory_iterator
@@ -94,7 +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
@@ -8,8 +8,6 @@
 
 // UNSUPPORTED: c++03
 
-// XFAIL: LIBCXX-WINDOWS-FIXME
-
 // <filesystem>
 
 // class directory_iterator
@@ -95,7 +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
@@ -8,8 +8,6 @@
 
 // UNSUPPORTED: c++03
 
-// XFAIL: LIBCXX-WINDOWS-FIXME
-
 // <filesystem>
 
 // bool exists(file_status s) noexcept
@@ -91,7 +89,8 @@
     // 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
@@ -678,22 +678,28 @@
   const fs::path dir("C:\\System Volume Information");
   std::error_code ec;
   const fs::path root("C:\\");
-  fs::directory_iterator it(root, ec);
-  if (ec)
-    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())
-        return fs::path();
-      if (!ent.is_directory())
-        return fs::path();
-      return ent;
+  for (const auto &ent : fs::directory_iterator(root, ec)) {
+    if (ent != dir)
+      continue;
+    // Basic sanity checks on the directory_entry
+    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();
     }
-    ++it;
+    // Check that it indeed is inaccessible as expected
+    (void)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;
   }
+  fprintf(stderr, "No inaccessible directory \"%s\" found, skipping tests "
+                  "regarding it\n", dir.string().c_str());
   return fs::path();
 }