diff --git a/Sources/SWBUtil/CMakeLists.txt b/Sources/SWBUtil/CMakeLists.txt
index 8e490da2..0be8ed58 100644
--- a/Sources/SWBUtil/CMakeLists.txt
+++ b/Sources/SWBUtil/CMakeLists.txt
@@ -68,6 +68,7 @@ add_library(SWBUtil
   OutputByteStream.swift
   Pair.swift
   Path.swift
+  PathWindows.swift
   PbxCp.swift
   PluginManager.swift
   PluginManagerCommon.swift
diff --git a/Sources/SWBUtil/Library.swift b/Sources/SWBUtil/Library.swift
index 1c6fe064..c96072d8 100644
--- a/Sources/SWBUtil/Library.swift
+++ b/Sources/SWBUtil/Library.swift
@@ -33,7 +33,7 @@ public enum Library: Sendable {
     @_alwaysEmitIntoClient
     public static func open(_ path: Path) throws -> LibraryHandle {
         #if os(Windows)
-        guard let handle = path.withPlatformString(LoadLibraryW) else {
+        guard let handle = try path.withPlatformString({ p in try p.withCanonicalPathRepresentation({ LoadLibraryW($0) }) }) else {
             throw LibraryOpenError(message: Win32Error(GetLastError()).description)
         }
         return LibraryHandle(rawValue: handle)
diff --git a/Sources/SWBUtil/PathWindows.swift b/Sources/SWBUtil/PathWindows.swift
new file mode 100644
index 00000000..f20d909d
--- /dev/null
+++ b/Sources/SWBUtil/PathWindows.swift
@@ -0,0 +1,89 @@
+//===----------------------------------------------------------------------===//
+//
+// This source file is part of the Swift open source project
+//
+// Copyright (c) 2025 Apple Inc. and the Swift project authors
+// Licensed under Apache License v2.0 with Runtime Library Exception
+//
+// See http://swift.org/LICENSE.txt for license information
+// See http://swift.org/CONTRIBUTORS.txt for the list of Swift project authors
+//
+//===----------------------------------------------------------------------===//
+
+#if os(Windows)
+import WinSDK
+
+#if canImport(System)
+public import System
+#else
+public import SystemPackage
+#endif
+
+extension UnsafePointer where Pointee == CInterop.PlatformChar {
+    /// 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.
+    ///
+    /// - seealso: https://learn.microsoft.com/en-us/windows/win32/fileio/maximum-file-path-limitation
+    public func withCanonicalPathRepresentation<Result>(_ body: (Self) throws -> Result) throws -> Result {
+        // 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(self, 0, nil, nil)
+        return try withUnsafeTemporaryAllocation(of: WCHAR.self, capacity: Int(dwLength)) { pwszFullPath in
+            guard (1..<dwLength).contains(GetFullPathNameW(self, DWORD(pwszFullPath.count), pwszFullPath.baseAddress, nil)) else {
+                throw Win32Error(GetLastError())
+            }
+
+            // 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] == UInt8(ascii: "\\"),
+                base[1] == UInt8(ascii: "\\"),
+                base[2] == UInt8(ascii: "."),
+                base[3] == UInt8(ascii: "\\") {
+                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 = numericCast(PATHCCH_ALLOW_LONG_PATHS.rawValue)
+            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 Win32Error(WIN32_FROM_HRESULT(result))
+        }
+    }
+}
+
+@inline(__always)
+fileprivate func HRESULT_CODE(_ hr: HRESULT) -> DWORD {
+    DWORD(hr) & 0xffff
+}
+
+@inline(__always)
+fileprivate func HRESULT_FACILITY(_ hr: HRESULT) -> DWORD {
+    DWORD(hr << 16) & 0x1fff
+}
+
+@inline(__always)
+fileprivate func SUCCEEDED(_ hr: HRESULT) -> Bool {
+    hr >= 0
+}
+
+// This is a non-standard extension to the Windows SDK that allows us to convert
+// an HRESULT to a Win32 error code.
+@inline(__always)
+fileprivate func WIN32_FROM_HRESULT(_ hr: HRESULT) -> DWORD {
+    if SUCCEEDED(hr) { return DWORD(ERROR_SUCCESS) }
+    if HRESULT_FACILITY(hr) == FACILITY_WIN32 {
+        return HRESULT_CODE(hr)
+    }
+    return DWORD(hr)
+}
+#endif
diff --git a/Tests/SWBUtilTests/PathWindowsTests.swift b/Tests/SWBUtilTests/PathWindowsTests.swift
new file mode 100644
index 00000000..f81f7afb
--- /dev/null
+++ b/Tests/SWBUtilTests/PathWindowsTests.swift
@@ -0,0 +1,92 @@
+//===----------------------------------------------------------------------===//
+//
+// This source file is part of the Swift open source project
+//
+// Copyright (c) 2025 Apple Inc. and the Swift project authors
+// Licensed under Apache License v2.0 with Runtime Library Exception
+//
+// See http://swift.org/LICENSE.txt for license information
+// See http://swift.org/CONTRIBUTORS.txt for the list of Swift project authors
+//
+//===----------------------------------------------------------------------===//
+
+import Testing
+import SWBTestSupport
+import SWBUtil
+
+@Suite(.requireHostOS(.windows))
+fileprivate struct PathWindowsTests {
+    @Test func testCanonicalPathRepresentation_deviceFiles() throws {
+        #expect(try "NUL".canonicalPathRepresentation == "\\\\.\\NUL")
+        #expect(try Path("NUL").canonicalPathRepresentation == "\\\\.\\NUL")
+
+        #expect(try "\\\\.\\NUL".canonicalPathRepresentation == "\\\\.\\NUL")
+
+        // System.FilePath appends a trailing slash to fully qualified device file names
+        withKnownIssue { () throws -> () in
+            #expect(try Path("\\\\.\\NUL").canonicalPathRepresentation == "\\\\.\\NUL")
+        }
+    }
+
+    @Test func testCanonicalPathRepresentation_driveLetters() throws {
+        #expect(try Path("C:/").canonicalPathRepresentation == "C:\\")
+        #expect(try Path("c:/").canonicalPathRepresentation == "c:\\")
+
+        #expect(try Path("\\\\?\\C:/").canonicalPathRepresentation == "C:\\")
+        #expect(try Path("\\\\?\\c:/").canonicalPathRepresentation == "c:\\")
+    }
+
+    @Test func testCanonicalPathRepresentation_absolute() throws {
+        #expect(try Path("C:" + String(repeating: "/foo/bar/baz", count: 21)).canonicalPathRepresentation == "C:" + String(repeating: "\\foo\\bar\\baz", count: 21))
+        #expect(try Path("C:" + String(repeating: "/foo/bar/baz", count: 22)).canonicalPathRepresentation == "\\\\?\\C:" + String(repeating: "\\foo\\bar\\baz", count: 22))
+    }
+
+    @Test func testCanonicalPathRepresentation_relative() throws {
+        let root = Path.root.str.dropLast()
+        #expect(try Path(String(repeating: "/foo/bar/baz", count: 21)).canonicalPathRepresentation == root + String(repeating: "\\foo\\bar\\baz", count: 21))
+        #expect(try Path(String(repeating: "/foo/bar/baz", count: 22)).canonicalPathRepresentation == "\\\\?\\" + root + String(repeating: "\\foo\\bar\\baz", count: 22))
+    }
+
+    @Test func testCanonicalPathRepresentation_driveRelative() throws {
+        let current = Path.currentDirectory
+
+        // Ensure the output path will be < 260 characters so we can assert it's not prefixed with \\?\
+        let chunks = (260 - current.str.count) / "foo/bar/baz/".count
+        #expect(current.str.count < 248 && chunks > 0, "The current directory is too long for this test.")
+
+        #expect(try Path(current.str.prefix(2) + String(repeating: "foo/bar/baz/", count: chunks)).canonicalPathRepresentation == current.join(String(repeating: "\\foo\\bar\\baz", count: chunks)).str)
+        #expect(try Path(current.str.prefix(2) + String(repeating: "foo/bar/baz/", count: 22)).canonicalPathRepresentation == "\\\\?\\" + current.join(String(repeating: "\\foo\\bar\\baz", count: 22)).str)
+    }
+}
+
+fileprivate extension String {
+    var canonicalPathRepresentation: String {
+        get throws {
+            #if os(Windows)
+            return try withCString(encodedAs: UTF16.self) { platformPath in
+                return try platformPath.withCanonicalPathRepresentation { canonicalPath in
+                    return String(decodingCString: canonicalPath, as: UTF16.self)
+                }
+            }
+            #else
+            return self
+            #endif
+        }
+    }
+}
+
+fileprivate extension Path {
+    var canonicalPathRepresentation: String {
+        get throws {
+            #if os(Windows)
+            return try withPlatformString { platformPath in
+                return try platformPath.withCanonicalPathRepresentation { canonicalPath in
+                    return String(decodingCString: canonicalPath, as: UTF16.self)
+                }
+            }
+            #else
+            return str
+            #endif
+        }
+    }
+}