diff --git a/include/ghc/filesystem.hpp b/include/ghc/filesystem.hpp
index 25f270e..eb01524 100644
--- a/include/ghc/filesystem.hpp
+++ b/include/ghc/filesystem.hpp
@@ -805,7 +805,10 @@ class GHC_FS_API_CLASS directory_entry
 {
 public:
     // [fs.dir.entry.cons] constructors and destructor
-    directory_entry() noexcept = default;
+    directory_entry() noexcept
+        : _last_write_time((file_time_type::min)())
+    {
+    }
     directory_entry(const directory_entry&) = default;
     directory_entry(directory_entry&&) noexcept = default;
 #ifdef GHC_WITH_EXCEPTIONS
@@ -4687,7 +4690,7 @@ GHC_INLINE void last_write_time(const path& p, file_time_type new_time, std::err
 #ifdef GHC_OS_WINDOWS
     detail::unique_handle file(::CreateFileW(GHC_NATIVEWP(p), FILE_WRITE_ATTRIBUTES, FILE_SHARE_DELETE | FILE_SHARE_READ | FILE_SHARE_WRITE, NULL, OPEN_EXISTING, FILE_FLAG_BACKUP_SEMANTICS, NULL));
     FILETIME ft;
-    auto tt = std::chrono::duration_cast<std::chrono::microseconds>(d).count() * 10 + 116444736000000000;
+    const auto tt = std::chrono::duration_cast<std::chrono::duration<int64_t, std::ratio<1, 10000000>>>(d).count() + 116444736000000000LL;
     ft.dwLowDateTime = static_cast<DWORD>(tt);
     ft.dwHighDateTime = static_cast<DWORD>(tt >> 32);
     if (!::SetFileTime(file.get(), 0, 0, &ft)) {
diff --git a/test/filesystem_test.cpp b/test/filesystem_test.cpp
index 8244d37..9c89277 100644
--- a/test/filesystem_test.cpp
+++ b/test/filesystem_test.cpp
@@ -2574,9 +2574,9 @@ TEST_CASE("fs.op.last_write_time - last_write_time", "[filesystem][operations][f
     const auto preciseTime = nt + std::chrono::milliseconds(123);
     CHECK_NOTHROW(fs::last_write_time("foo", preciseTime, ec));
     REQUIRE(!ec);
-    CHECK(fs::last_write_time("foo") == preciseTime);
+    CHECK(std::abs(std::chrono::duration_cast<std::chrono::nanoseconds>(fs::last_write_time("foo") - preciseTime).count()) < 1000000);
     const fs::directory_entry preciseEntry("foo");
-    CHECK(preciseEntry.last_write_time() == preciseTime);
+    CHECK(std::abs(std::chrono::duration_cast<std::chrono::nanoseconds>(preciseEntry.last_write_time() - preciseTime).count()) < 1000000);
     if (is_symlink_creation_supported()) {
 #if !defined(GHC_OS_WINDOWS) && !defined(GHC_OS_WEB)
         struct ::stat linkStatBefore;