diff --git a/core/libs/prx/libkernel/File/src/Stdio.cpp b/core/libs/prx/libkernel/File/src/Stdio.cpp
index bf22e21d02..adce983db2 100644
--- a/core/libs/prx/libkernel/File/src/Stdio.cpp
+++ b/core/libs/prx/libkernel/File/src/Stdio.cpp
@@ -662,6 +662,15 @@ int File::DuplicateFrom(int fd, int start) {
 }
 
 static int LookupError(const std::filesystem::path& native) {
+#ifdef _WIN32
+    const auto named = native.has_filename() ? native : WithoutTrailingSeparator(native);
+    const DWORD attributes = GetFileAttributesW(named.c_str());
+    if (attributes != INVALID_FILE_ATTRIBUTES && (attributes & FILE_ATTRIBUTE_REPARSE_POINT) != 0) {
+        FileStat target{};
+        if (!File::TryFillFileStat(named, &target)) return SceErrorFromErrno(errno) & 0xffff;
+        return native.has_filename() || (target.st_mode & 0170000) == 0040000 ? 0 : GUEST_ENOTDIR;
+    }
+#endif
     std::error_code error;
     const auto status = std::filesystem::status(native, error);
     if (std::filesystem::exists(status)) return native.has_filename() || std::filesystem::is_directory(status) ? 0 : GUEST_ENOTDIR;
diff --git a/core/libs/tests/GuestFilesystem.cpp b/core/libs/tests/GuestFilesystem.cpp
index 9eb5a65154..f57ce71a30 100644
--- a/core/libs/tests/GuestFilesystem.cpp
+++ b/core/libs/tests/GuestFilesystem.cpp
@@ -634,6 +634,27 @@ int main() {
     Require(chflags_nid_postfix(file.string().c_str(), 0x200000) == -1 && *__error_nid_postfix() == 1);
     Require(ChflagsThrows(file, 0x2, "UF_IMMUTABLE"));
     Require(ChflagsThrows(file, 0x1000 | 0x40000, "UF_READONLY|SF_APPEND"));
+    const auto chflagsDangling = root / "dangling.link";
+    const auto chflagsPointing = root / "file.link";
+#ifdef _WIN32
+    const bool chflagsLinked = CreateSymbolicLinkW(chflagsDangling.wstring().c_str(), L"missing.bin", SYMBOLIC_LINK_FLAG_ALLOW_UNPRIVILEGED_CREATE) != 0 &&
+        CreateSymbolicLinkW(chflagsPointing.wstring().c_str(), L"file.txt", SYMBOLIC_LINK_FLAG_ALLOW_UNPRIVILEGED_CREATE) != 0;
+#else
+    std::error_code chflagsLinkError;
+    std::filesystem::create_symlink("missing.bin", chflagsDangling, chflagsLinkError);
+    if (!chflagsLinkError) std::filesystem::create_symlink("file.txt", chflagsPointing, chflagsLinkError);
+    const bool chflagsLinked = !chflagsLinkError;
+#endif
+    if (chflagsLinked) {
+        Require(chflags_nid_postfix(chflagsDangling.string().c_str(), 0) == -1 && *__error_nid_postfix() == 2);
+        Require(chflags_nid_postfix(chflagsPointing.string().c_str(), 0) == 0);
+        Require(chflags_nid_postfix((chflagsPointing.string() + "/").c_str(), 0) == -1 && *__error_nid_postfix() == 20);
+        Require(chflags_nid_postfix(chflagsPointing.string().c_str(), 0x20) == -1 && *__error_nid_postfix() == 45);
+        Require(unlink_nid_postfix(chflagsDangling.string().c_str()) == 0 && unlink_nid_postfix(chflagsPointing.string().c_str()) == 0);
+    } else {
+        unlink_nid_postfix(chflagsDangling.string().c_str());
+        std::fprintf(stderr, "symbolic links unavailable: the chflags link cases not tested\n");
+    }
     const int flagged = open_nid_postfix(file.string().c_str(), 0, 0);
     Require(flagged >= 0 && fchflags_nid_postfix(flagged, 0) == 0);
     Require(fchflags_nid_postfix(flagged, 0x20) == -1 && *__error_nid_postfix() == 45);