diff --git a/Sources/FoundationEssentials/URL/URL.swift b/Sources/FoundationEssentials/URL/URL.swift
index aa0e58d81..5d006d1d7 100644
--- a/Sources/FoundationEssentials/URL/URL.swift
+++ b/Sources/FoundationEssentials/URL/URL.swift
@@ -13,8 +13,18 @@
 public struct URLResourceKey {}
 #endif
 
-#if os(Windows)
+#if canImport(Darwin)
+import Darwin
+#elseif canImport(Android)
+@preconcurrency import Android
+#elseif canImport(Glibc)
+@preconcurrency import Glibc
+#elseif canImport(Musl)
+@preconcurrency import Musl
+#elseif os(Windows)
 import WinSDK
+#elseif os(WASI)
+@preconcurrency import WASILibc
 #endif
 
 #if FOUNDATION_FRAMEWORK
@@ -2199,17 +2209,30 @@ extension URL {
 
 #if !NO_FILESYSTEM
     private static func isDirectory(_ path: String) -> Bool {
+        guard !path.isEmpty else { return false }
         #if os(Windows)
         let path = path.replacing(._slash, with: ._backslash)
-        #endif
-        #if !FOUNDATION_FRAMEWORK
-        var isDirectory: Bool = false
-        _ = FileManager.default.fileExists(atPath: path, isDirectory: &isDirectory)
-        return isDirectory
+        return (try? path.withNTPathRepresentation { pwszPath in
+            // If path points to a symlink (reparse point), get a handle to
+            // the symlink itself using FILE_FLAG_OPEN_REPARSE_POINT.
+            let handle = CreateFileW(pwszPath, GENERIC_READ, FILE_SHARE_READ | FILE_SHARE_WRITE | FILE_SHARE_DELETE, nil, OPEN_EXISTING, FILE_FLAG_BACKUP_SEMANTICS | FILE_FLAG_OPEN_REPARSE_POINT, nil)
+            guard handle != INVALID_HANDLE_VALUE else { return false }
+            defer { CloseHandle(handle) }
+            var info: BY_HANDLE_FILE_INFORMATION = BY_HANDLE_FILE_INFORMATION()
+            guard GetFileInformationByHandle(handle, &info) else { return false }
+            if (info.dwFileAttributes & FILE_ATTRIBUTE_REPARSE_POINT) == FILE_ATTRIBUTE_REPARSE_POINT { return false }
+            return (info.dwFileAttributes & FILE_ATTRIBUTE_DIRECTORY) == FILE_ATTRIBUTE_DIRECTORY
+        }) ?? false
         #else
-        var isDirectory: ObjCBool = false
-        _ = FileManager.default.fileExists(atPath: path, isDirectory: &isDirectory)
-        return isDirectory.boolValue
+        // FileManager uses stat() to check if the file exists.
+        // URL historically won't follow a symlink at the end
+        // of the path, so use lstat() here instead.
+        return path.withFileSystemRepresentation { fsRep in
+            guard let fsRep else { return false }
+            var fileInfo = stat()
+            guard lstat(fsRep, &fileInfo) == 0 else { return false }
+            return (mode_t(fileInfo.st_mode) & S_IFMT) == S_IFDIR
+        }
         #endif
     }
 #endif // !NO_FILESYSTEM
diff --git a/Tests/FoundationEssentialsTests/URLTests.swift b/Tests/FoundationEssentialsTests/URLTests.swift
index 049285462..3f7c84507 100644
--- a/Tests/FoundationEssentialsTests/URLTests.swift
+++ b/Tests/FoundationEssentialsTests/URLTests.swift
@@ -399,6 +399,44 @@ final class URLTests : XCTestCase {
         }
     }
 
+    func testURLFilePathDoesNotFollowLastSymlink() throws {
+        try FileManagerPlayground {
+            Directory("dir") {
+                "Foo"
+                SymbolicLink("symlink", destination: "../dir")
+            }
+        }.test {
+            let currentDirectoryPath = $0.currentDirectoryPath
+            let baseURL = URL(filePath: currentDirectoryPath, directoryHint: .isDirectory)
+
+            let dirURL = baseURL.appending(path: "dir", directoryHint: .checkFileSystem)
+            XCTAssertTrue(dirURL.hasDirectoryPath)
+
+            var symlinkURL = dirURL.appending(path: "symlink", directoryHint: .notDirectory)
+
+            // FileManager uses stat(), which will follow the symlink to the directory.
+
+            #if FOUNDATION_FRAMEWORK
+            var isDirectory: ObjCBool = false
+            XCTAssertTrue(FileManager.default.fileExists(atPath: symlinkURL.path, isDirectory: &isDirectory))
+            XCTAssertTrue(isDirectory.boolValue)
+            #else
+            var isDirectory = false
+            XCTAssertTrue(FileManager.default.fileExists(atPath: symlinkURL.path, isDirectory: &isDirectory))
+            XCTAssertTrue(isDirectory)
+            #endif
+
+            // URL uses lstat(), which will not follow the symlink at the end of the path.
+            // Check that URL(filePath:) and .appending(path:) preserve this behavior.
+
+            symlinkURL = URL(filePath: symlinkURL.path, directoryHint: .checkFileSystem)
+            XCTAssertFalse(symlinkURL.hasDirectoryPath)
+
+            symlinkURL = dirURL.appending(path: "symlink", directoryHint: .checkFileSystem)
+            XCTAssertFalse(symlinkURL.hasDirectoryPath)
+        }
+    }
+
     func testURLRelativeDotDotResolution() throws {
         let baseURL = URL(filePath: "/docs/src/")
         var result = URL(filePath: "../images/foo.png", relativeTo: baseURL)