diff --git a/Sources/FoundationEssentials/Data/Data+Writing.swift b/Sources/FoundationEssentials/Data/Data+Writing.swift
index af49745d6..51b54ed5e 100644
--- a/Sources/FoundationEssentials/Data/Data+Writing.swift
+++ b/Sources/FoundationEssentials/Data/Data+Writing.swift
@@ -171,7 +171,7 @@ private func createTemporaryFile(at destinationPath: String, inPath: PathOrURL,
             guard _mktemp_s(templateFileSystemRep, strlen(templateFileSystemRep) + 1) == 0 else {
                 throw CocoaError.errorWithFilePath(inPath, errno: errno, reading: false, variant: variant)
             }
-            let fd = String(cString: templateFileSystemRep).withCString(encodedAs: UTF16.self) {
+            let fd = try String(cString: templateFileSystemRep).withNTPathRepresentation {
                 openFileDescriptorProtected(path: $0, flags: _O_BINARY | _O_CREAT | _O_EXCL | _O_RDWR, options: options)
             }
 #else
diff --git a/Sources/FoundationEssentials/FileManager/FileManager+Directories.swift b/Sources/FoundationEssentials/FileManager/FileManager+Directories.swift
index 4371f24ad..0413087c8 100644
--- a/Sources/FoundationEssentials/FileManager/FileManager+Directories.swift
+++ b/Sources/FoundationEssentials/FileManager/FileManager+Directories.swift
@@ -257,36 +257,6 @@ extension _FileManagerImpl {
         try fileManager.createDirectory(atPath: path, withIntermediateDirectories: createIntermediates, attributes: attributes)
     }
 
-#if os(Windows)
-    /// If `path` is absolute, this is the same as `path.withNTPathRepresentation`.
-    /// If `path` is relative, this creates an absolute path of `path` relative to `currentDirectoryPath` and runs
-    /// `body` with that path.
-    private func withAbsoluteNTPathRepresentation<Result>(
-        of path: String,
-        _ body: (UnsafePointer<WCHAR>) throws -> Result
-    ) throws -> Result {
-        try path.withNTPathRepresentation { pwszPath in
-            if !PathIsRelativeW(pwszPath) {
-                // We already have an absolute path. Nothing to do
-                return try body(pwszPath)
-            }
-            guard let currentDirectoryPath else {
-                preconditionFailure("We should always have a current directory on Windows")
-            }
-
-            // We have a relateive path. Make it absolute.
-            let absoluteUrl = URL(
-                filePath: path,
-                directoryHint: .isDirectory,
-                relativeTo: URL(filePath: currentDirectoryPath, directoryHint: .isDirectory)
-            )
-            return try absoluteUrl.path.withNTPathRepresentation { pwszPath in
-                return try body(pwszPath)
-            }
-        }
-    }
-#endif
-    
     func createDirectory(
         atPath path: String,
         withIntermediateDirectories createIntermediates: Bool,
@@ -301,7 +271,7 @@ extension _FileManagerImpl {
         if createIntermediates {
             // `SHCreateDirectoryExW` requires an absolute path while `CreateDirectoryW` works based on the current working
             // directory.
-            try withAbsoluteNTPathRepresentation(of: path) { pwszPath in
+            try path.withNTPathRepresentation { pwszPath in
                 let errorCode = SHCreateDirectoryExW(nil, pwszPath, &saAttributes)
                 guard let errorCode = DWORD(exactly: errorCode) else {
                     // `SHCreateDirectoryExW` returns `Int` but all error codes are defined in terms of `DWORD`, aka
diff --git a/Sources/FoundationEssentials/FileManager/FileManager+SymbolicLinks.swift b/Sources/FoundationEssentials/FileManager/FileManager+SymbolicLinks.swift
index 5e4e00b12..5e3b643f8 100644
--- a/Sources/FoundationEssentials/FileManager/FileManager+SymbolicLinks.swift
+++ b/Sources/FoundationEssentials/FileManager/FileManager+SymbolicLinks.swift
@@ -64,7 +64,7 @@ extension _FileManagerImpl {
 
         try path.withNTPathRepresentation { lpSymlinkFileName in
             try destPath.withFileSystemRepresentation {
-                try String(cString: $0!).withCString(encodedAs: UTF16.self) { lpTargetFileName in
+                try String(cString: $0!).withNTPathRepresentation(relative: true) { lpTargetFileName in
                     if CreateSymbolicLinkW(lpSymlinkFileName, lpTargetFileName, SYMBOLIC_LINK_FLAG_ALLOW_UNPRIVILEGED_CREATE | (bIsDirectory ? SYMBOLIC_LINK_FLAG_DIRECTORY : 0)) == 0 {
                         throw CocoaError.errorWithFilePath(path, win32: GetLastError(), reading: false)
                     }
diff --git a/Sources/FoundationEssentials/FileManager/FileOperations.swift b/Sources/FoundationEssentials/FileManager/FileOperations.swift
index 3d9a769f4..1c28880ac 100644
--- a/Sources/FoundationEssentials/FileManager/FileOperations.swift
+++ b/Sources/FoundationEssentials/FileManager/FileOperations.swift
@@ -829,7 +829,7 @@ enum _FileOperations {
         try src.withNTPathRepresentation { pwszSource in
             var faAttributes: WIN32_FILE_ATTRIBUTE_DATA = .init()
             guard GetFileAttributesExW(pwszSource, GetFileExInfoStandard, &faAttributes) else {
-                throw CocoaError.errorWithFilePath(.fileReadNoSuchFile, src, variant: bCopyFile ? "Copy" : "Link", source: src, destination: dst)
+                throw CocoaError.errorWithFilePath(src, win32: GetLastError(), reading: true, variant: bCopyFile ? "Copy" : "Link", source: src, destination: dst)
             }
 
             guard delegate.shouldPerformOnItemAtPath(src, to: dst) else { return }
diff --git a/Sources/FoundationEssentials/String/String+Internals.swift b/Sources/FoundationEssentials/String/String+Internals.swift
index fdd6d4c6c..16193afda 100644
--- a/Sources/FoundationEssentials/String/String+Internals.swift
+++ b/Sources/FoundationEssentials/String/String+Internals.swift
@@ -23,7 +23,12 @@ import Darwin
 import WinSDK
 
 extension String {
-    package func withNTPathRepresentation<Result>(_ body: (UnsafePointer<WCHAR>) throws -> Result) throws -> Result {
+    /// Invokes `body` with a resolved and potentially `\\?\`-prefixed version of the pointee,
+    /// to ensure long paths greater than MAX_PATH (260) characters are handled correctly.
+    ///
+    /// - parameter relative: Returns the original path without transforming through GetFullPathNameW + PathCchCanonicalizeEx, if the path is relative.
+    /// - seealso: https://learn.microsoft.com/en-us/windows/win32/fileio/maximum-file-path-limitation
+    package func withNTPathRepresentation<Result>(relative: Bool = false, _ body: (UnsafePointer<WCHAR>) throws -> Result) throws -> Result {
         guard !isEmpty else {
             throw CocoaError.errorWithFilePath(.fileReadInvalidFileName, "")
         }
@@ -35,15 +40,42 @@ extension String {
         // leading slash indicates a rooted path on the drive for the current
         // working directory.
         return try Substring(self.utf8.dropFirst(bLeadingSlash ? 1 : 0)).withCString(encodedAs: UTF16.self) { pwszPath in
+            if relative && PathIsRelativeW(pwszPath) {
+                return try body(pwszPath)
+            }
+
             // 1. Normalize the path first.
+            // Contrary to the documentation, this works on long paths independently
+            // of the registry or process setting to enable long paths (but it will also
+            // not add the \\?\ prefix required by other functions under these conditions).
             let dwLength: DWORD = GetFullPathNameW(pwszPath, 0, nil, nil)
-            return try withUnsafeTemporaryAllocation(of: WCHAR.self, capacity: Int(dwLength)) {
-                guard GetFullPathNameW(pwszPath, DWORD($0.count), $0.baseAddress, nil) > 0 else {
+            return try withUnsafeTemporaryAllocation(of: WCHAR.self, capacity: Int(dwLength)) { pwszFullPath in
+                guard (1..<dwLength).contains(GetFullPathNameW(pwszPath, DWORD(pwszFullPath.count), pwszFullPath.baseAddress, nil)) else {
                     throw CocoaError.errorWithFilePath(self, win32: GetLastError(), reading: true)
                 }
 
-                // 2. Perform the operation on the normalized path.
-                return try body($0.baseAddress!)
+                // 1.5 Leave \\.\ prefixed paths alone since device paths are already an exact representation and PathCchCanonicalizeEx will mangle these.
+                if let base = pwszFullPath.baseAddress,
+                    base[0] == UInt16(UInt8._backslash),
+                    base[1] == UInt16(UInt8._backslash),
+                    base[2] == UInt16(UInt8._period),
+                    base[3] == UInt16(UInt8._backslash) {
+                    return try body(base)
+                }
+
+                // 2. Canonicalize the path.
+                // This will add the \\?\ prefix if needed based on the path's length.
+                var pwszCanonicalPath: LPWSTR?
+                let flags: ULONG = PATHCCH_ALLOW_LONG_PATHS
+                let result = PathAllocCanonicalize(pwszFullPath.baseAddress, flags, &pwszCanonicalPath)
+                if let pwszCanonicalPath {
+                    defer { LocalFree(pwszCanonicalPath) }
+                    if result == S_OK {
+                        // 3. Perform the operation on the normalized path.
+                        return try body(pwszCanonicalPath)
+                    }
+                }
+                throw CocoaError.errorWithFilePath(self, win32: WIN32_FROM_HRESULT(result), reading: true)
             }
         }
     }
diff --git a/Tests/FoundationEssentialsTests/FileManager/FileManagerTests.swift b/Tests/FoundationEssentialsTests/FileManager/FileManagerTests.swift
index efb13e4d1..833566543 100644
--- a/Tests/FoundationEssentialsTests/FileManager/FileManagerTests.swift
+++ b/Tests/FoundationEssentialsTests/FileManager/FileManagerTests.swift
@@ -1072,4 +1072,92 @@ final class FileManagerTests : XCTestCase {
             XCTAssertEqual($0.contents(atPath: "a\u{301}/test"), data)
         }
     }
+
+    /// Tests that Foundation can correctly handle "long paths" (paths of 260 to 32767 chacters long) on Windows.
+    func testWindowsLongPathSupport() throws {
+        #if !os(Windows)
+        throw XCTSkip("This test is not applicable for this platform")
+        #else
+        // Create a directory with the absolute maximum path _component_ length of 255;
+        // this will guarantee the full playground path is well over 260 characters.
+        // Throw some Unicode in there for good measure, since only wide-character APIs support it.
+        let dirName = String(repeating: UUID().uuidString, count: 7) + "你好！"
+        XCTAssertEqual(dirName.count, 255)
+        XCTAssertEqual(dirName.utf16.count, 255)
+
+        try FileManagerPlayground {
+            Directory(dirName) {
+            }
+        }.test {
+            // Call every function that can call into withNTPathRepresentation with an overlong path and ensure it succeeds.
+            let fileName = UUID().uuidString
+            let cwd = try XCTUnwrap($0.currentDirectoryPath)
+
+            XCTAssertTrue($0.createFile(atPath: dirName + "/" + fileName, contents: nil))
+
+            let dirURL = URL(filePath: dirName, directoryHint: .checkFileSystem)
+            XCTAssertTrue(dirURL.hasDirectoryPath)
+
+            let fileURL = URL(filePath: dirName + "/" + fileName, directoryHint: .checkFileSystem)
+            XCTAssertFalse(fileURL.hasDirectoryPath)
+
+            XCTAssertTrue($0.fileExists(atPath: dirName + "/" + fileName))
+            XCTAssertTrue($0.isReadableFile(atPath: dirName + "/" + fileName))
+            XCTAssertTrue($0.isWritableFile(atPath: dirName + "/" + fileName))
+
+            // SHGetFileInfoW is documented to be limited to MAX_PATH, but appears to support long paths anyways (or at least does for SHGFI_EXETYPE).
+            // https://learn.microsoft.com/en-us/windows/win32/api/shellapi/nf-shellapi-shgetfileinfow
+            XCTAssertNoThrow(try Data().write(to: URL(fileURLWithPath: dirName + "/" + fileName + ".bat")))
+            XCTAssertTrue($0.isExecutableFile(atPath: dirName + "/" + fileName + ".bat"))
+            XCTAssertFalse($0.isExecutableFile(atPath: dirName + "/" + fileName))
+
+            XCTAssertNoThrow(try $0.attributesOfItem(atPath: dirName + "/" + fileName))
+            XCTAssertNoThrow(try $0.setAttributes([.modificationDate: Date()], ofItemAtPath: dirName + "/" + fileName))
+            XCTAssertNoThrow(try $0.attributesOfFileSystem(forPath: dirName + "/" + fileName))
+
+            XCTAssertNoThrow(try Data(contentsOf: URL(fileURLWithPath: dirName + "/" + fileName)))
+
+            XCTAssertNoThrow(try Data("hello".utf8).write(to: URL(fileURLWithPath: dirName + "/" + fileName)))
+            XCTAssertNoThrow(try Data("hello".utf8).write(to: URL(fileURLWithPath: dirName + "/" + fileName), options: .atomic))
+
+            XCTAssertNoThrow(try Data("hello".utf8).write(to: URL(fileURLWithPath: dirName + "/" + fileName + ".v2")))
+            XCTAssertTrue($0.contentsEqual(atPath: dirName + "/" + fileName, andPath: dirName + "/" + fileName + ".v2"))
+
+            XCTAssertEqual(try $0.subpathsOfDirectory(atPath: dirName).sorted(), [
+                fileName,
+                fileName + ".bat",
+                fileName + ".v2"
+            ])
+
+            XCTAssertNoThrow(try $0.createDirectory(at: URL(fileURLWithPath: dirName + "/" + "subdir1"), withIntermediateDirectories: false))
+
+            // SHCreateDirectoryExW's path argument is limited to 248 characters, and the \\?\ prefix doesn't help.
+            // https://learn.microsoft.com/en-us/windows/win32/api/shlobj_core/nf-shlobj_core-shcreatedirectoryexw
+            XCTAssertThrowsError(try $0.createDirectory(at: URL(fileURLWithPath: dirName + "/" + "subdir2" + "/" + "subdir3"), withIntermediateDirectories: true))
+
+            // SetCurrentDirectory seems to be limited to MAX_PATH unconditionally, counter to the documentation.
+            // https://learn.microsoft.com/en-us/windows/win32/api/winbase/nf-winbase-setcurrentdirectory
+            // https://github.com/MicrosoftDocs/feedback/issues/1441
+            XCTAssertFalse($0.changeCurrentDirectoryPath(dirName + "/" + "subdir1"))
+
+            XCTAssertNoThrow(try $0.createSymbolicLink(atPath: dirName + "/" + "lnk", withDestinationPath: fileName))
+            XCTAssertNoThrow(try $0.createSymbolicLink(atPath: dirName + "/" + "lnk2", withDestinationPath: cwd + "/" + dirName + "/" + fileName))
+            XCTAssertEqual(try $0.destinationOfSymbolicLink(atPath: dirName + "/" + "lnk"), fileName)
+            XCTAssertEqual(try $0.destinationOfSymbolicLink(atPath: dirName + "/" + "lnk2"), cwd + "\\" + dirName + "\\" + fileName)
+
+            XCTAssertEqual((cwd + "/" + dirName + "/" + "lnk").resolvingSymlinksInPath, (cwd + "/" + dirName + "/" + fileName).resolvingSymlinksInPath)
+
+            XCTAssertNoThrow(try $0.createDirectory(at: URL(fileURLWithPath: dirName + "/" + "subdir2"), withIntermediateDirectories: false))
+            XCTAssertNoThrow(try $0.createDirectory(at: URL(fileURLWithPath: dirName + "/" + "subdir2" + "/" + "subdir3"), withIntermediateDirectories: false))
+            XCTAssertNoThrow(try Data().write(to: URL(fileURLWithPath: dirName + "/" + "subdir2" + "/" + "subdir3" + "/" + "somefile")))
+            XCTAssertNoThrow(try Data().write(to: URL(fileURLWithPath: dirName + "/" + "subdir2" + "/" + "subdir3" + "/" + "somefile2")))
+            XCTAssertNoThrow(try $0.moveItem(atPath: dirName + "/" + "subdir2" + "/" + "subdir3" + "/" + "somefile2", toPath: dirName + "/" + "subdir2" + "/" + "subdir3" + "/" + "somefile3"))
+            XCTAssertNoThrow(try $0.moveItem(atPath: dirName + "/" + "subdir2" + "/" + "subdir3", toPath: dirName + "/" + "subdir2" + "/" + "subdir3.delete"))
+            XCTAssertNoThrow(try $0.linkItem(atPath: dirName + "/" + "subdir2" + "/" + "subdir3.delete", toPath: dirName + "/" + "subdir2" + "/" + "subdir3.delete.lnk"))
+            XCTAssertNoThrow(try $0.linkItem(atPath: dirName + "/" + "subdir2", toPath: dirName + "/" + "subdir2.lnk"))
+            XCTAssertNoThrow(try $0.removeItem(atPath: dirName + "/" + "subdir2" + "/" + "subdir3.delete" + "/" + "somefile3"))
+            XCTAssertNoThrow(try $0.removeItem(atPath: dirName + "/" + "subdir2"))
+        }
+        #endif
+    }
 }