diff --git a/libcxx/src/filesystem/directory_iterator.cpp b/libcxx/src/filesystem/directory_iterator.cpp
--- a/libcxx/src/filesystem/directory_iterator.cpp
+++ b/libcxx/src/filesystem/directory_iterator.cpp
@@ -124,7 +124,8 @@
       ec = detail::make_windows_error(GetLastError());
       const bool ignore_permission_denied =
           bool(opts & directory_options::skip_permission_denied);
-      if (ignore_permission_denied && ec.value() == ERROR_ACCESS_DENIED)
+      if (ignore_permission_denied &&
+          ec.value() == static_cast<int>(errc::permission_denied))
         ec.clear();
       return;
     }
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
@@ -148,6 +148,8 @@
 
 TEST_CASE(path_ctor_cannot_resolve) {
   using namespace fs;
+#ifndef _WIN32
+  // Windows doesn't support setting perms::none to trigger failures
   scoped_test_env env;
   const path dir = env.create_dir("dir");
   const path file = env.create_file("dir/file", 42);
@@ -179,6 +181,48 @@
     TEST_CHECK_NO_THROW(directory_entry(sym_in_dir));
     TEST_CHECK_NO_THROW(directory_entry(sym_out_of_dir));
   }
+#else
+  const path dir("C:\\System Volume Information");
+  {
+    std::error_code ec;
+    const path root("C:\\");
+    directory_iterator it(root, ec);
+    if (ec)
+      return;
+    const directory_iterator endIt{};
+    bool found = false;
+    while (it != endIt) {
+      const directory_entry &ent = *it;
+      const path &p = *it;
+      if (p == dir) {
+        TEST_CHECK(ent.exists());
+        TEST_CHECK(ent.is_directory());
+        found = true;
+        break;
+      }
+      ++it;
+    }
+    if (!found)
+      return; // No point in proceeding if the directory doesn't exist
+  }
+  // We have a dir that exists (in a directory listing), but we can't
+  // access it (e.g.
+  {
+    std::error_code ec = GetTestEC();
+    TEST_CHECK(exists(dir, ec) == false);
+    TEST_CHECK(ErrorIs(ec, std::errc::permission_denied));
+  }
+  const path file = dir / "file";
+  {
+    std::error_code ec = GetTestEC();
+    directory_entry ent(file, ec);
+    TEST_CHECK(ErrorIs(ec, std::errc::no_such_file_or_directory));
+    TEST_CHECK(ent.path() == file);
+  }
+  {
+    TEST_CHECK_NO_THROW(directory_entry(file));
+  }
+#endif
 }
 
 TEST_SUITE_END()
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
@@ -87,6 +87,9 @@
 TEST_CASE(access_denied_test_case)
 {
     using namespace fs;
+#ifndef _WIN32
+    // Windows doesn't support setting perms::none to trigger failures
+    // reading directories.
     scoped_test_env env;
     path const testDir = env.make_env_path("dir1");
     path const testFile = testDir / "testFile";
@@ -100,6 +103,31 @@
     }
     // Change the permissions so we can no longer iterate
     permissions(testDir, perms::none);
+#else
+    const path testDir("C:\\System Volume Information");
+    {
+        std::error_code ec;
+        const path root("C:\\");
+        directory_iterator it(root, ec);
+        if (ec)
+            return;
+        const directory_iterator endIt{};
+        bool found = false;
+        while (it != endIt) {
+            const directory_entry &ent = *it;
+            const path &p = *it;
+            if (p == testDir) {
+                TEST_CHECK(ent.exists());
+                TEST_CHECK(ent.is_directory());
+                found = true;
+                break;
+            }
+            ++it;
+        }
+        if (!found)
+            return; // No point in proceeding if the directory doesn't exist
+  }
+#endif
 
     // Check that the construction fails when skip_permissions_denied is
     // not given.
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
@@ -88,6 +88,9 @@
 TEST_CASE(access_denied_test_case)
 {
     using namespace fs;
+#ifndef _WIN32
+    // Windows doesn't support setting perms::none to trigger failures
+    // reading directories.
     scoped_test_env env;
     path const testDir = env.make_env_path("dir1");
     path const testFile = testDir / "testFile";
@@ -102,6 +105,31 @@
 
     // Change the permissions so we can no longer iterate
     permissions(testDir, perms::none);
+#else
+    const path testDir("C:\\System Volume Information");
+    {
+        std::error_code ec;
+        const path root("C:\\");
+        directory_iterator it(root, ec);
+        if (ec)
+            return;
+        const directory_iterator endIt{};
+        bool found = false;
+        while (it != endIt) {
+            const directory_entry &ent = *it;
+            const path &p = *it;
+            if (p == testDir) {
+                TEST_CHECK(ent.exists());
+                TEST_CHECK(ent.is_directory());
+                found = true;
+                break;
+            }
+            ++it;
+        }
+        if (!found)
+            return; // No point in proceeding if the directory doesn't exist
+  }
+#endif
 
     // Check that the construction fails when skip_permissions_denied is
     // not given.
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
@@ -73,10 +73,17 @@
 
 TEST_CASE(test_exists_fails)
 {
+#ifndef _WIN32
+    // Windows doesn't support setting perms::none to trigger failures
+    // reading directories.
     scoped_test_env env;
     const path dir = env.create_dir("dir");
     const path file = env.create_file("dir/file", 42);
     permissions(dir, perms::none);
+#else
+    // Actually a directory, not a file
+    const path file("C:\\System Volume Information");
+#endif
 
     std::error_code ec;
     TEST_CHECK(exists(file, ec) == false);