diff --git a/Sources/SWBUtil/CMakeLists.txt b/Sources/SWBUtil/CMakeLists.txt
index eae57b98..9fa533e0 100644
--- a/Sources/SWBUtil/CMakeLists.txt
+++ b/Sources/SWBUtil/CMakeLists.txt
@@ -101,6 +101,7 @@ add_library(SWBUtil
   VFS.swift
   WaitCondition.swift
   WeakRef.swift
+  Win32.swift
   Win32Error.swift
   XCBuildDataArchive.swift
   Xcode.swift)
diff --git a/Sources/SWBUtil/Library.swift b/Sources/SWBUtil/Library.swift
index c8079482..a0174ad3 100644
--- a/Sources/SWBUtil/Library.swift
+++ b/Sources/SWBUtil/Library.swift
@@ -117,32 +117,3 @@ public struct LibraryHandle: @unchecked Sendable {
         self.rawValue = rawValue
     }
 }
-
-#if os(Windows)
-@_spi(Testing) public func SWB_GetModuleFileNameW(_ hModule: HMODULE?) throws -> String {
-#if DEBUG
-    var bufferCount = Int(1) // force looping
-#else
-    var bufferCount = Int(MAX_PATH)
-#endif
-    while true {
-        if let result = try withUnsafeTemporaryAllocation(of: WCHAR.self, capacity: bufferCount, { buffer in
-            switch (GetModuleFileNameW(hModule, buffer.baseAddress!, DWORD(buffer.count)), GetLastError()) {
-            case (1..<DWORD(bufferCount), DWORD(ERROR_SUCCESS)):
-                guard let result = String.decodeCString(buffer.baseAddress!, as: UTF16.self)?.result else {
-                    throw Win32Error(DWORD(ERROR_ILLEGAL_CHARACTER))
-                }
-                return result
-            case (DWORD(bufferCount), DWORD(ERROR_INSUFFICIENT_BUFFER)):
-                bufferCount += Int(MAX_PATH)
-                return nil
-            case (_, let errorCode):
-                throw Win32Error(errorCode)
-            }
-        }) {
-            return result
-        }
-    }
-    preconditionFailure("unreachable")
-}
-#endif
diff --git a/Sources/SWBUtil/POSIX.swift b/Sources/SWBUtil/POSIX.swift
index 9221bb6c..1d3576c6 100644
--- a/Sources/SWBUtil/POSIX.swift
+++ b/Sources/SWBUtil/POSIX.swift
@@ -26,22 +26,10 @@ public enum POSIX: Sendable {
     public static func getenv(_ name: String) throws -> String? {
         #if os(Windows)
         try name.withCString(encodedAs: CInterop.PlatformUnicodeEncoding.self) { wName in
-            let dwLength: DWORD = GetEnvironmentVariableW(wName, nil, 0)
-            if dwLength == 0 {
-                if GetLastError() == ERROR_ENVVAR_NOT_FOUND {
-                    return nil
-                }
-                throw POSIXError(errno, context: "GetEnvironmentVariableW", name)
-            }
-            return try withUnsafeTemporaryAllocation(of: WCHAR.self, capacity: Int(dwLength)) {
-                switch GetEnvironmentVariableW(wName, $0.baseAddress!, DWORD($0.count)) {
-                case 1..<dwLength:
-                    return String(decodingCString: $0.baseAddress!, as: CInterop.PlatformUnicodeEncoding.self)
-                case 0 where GetLastError() == ERROR_ENVVAR_NOT_FOUND:
-                    return nil
-                default:
-                    throw POSIXError(errno, context: "GetEnvironmentVariableW", name)
-                }
+            do {
+                return try SWB_GetEnvironmentVariableW(wName)
+            } catch let error as Win32Error where error.error == ERROR_ENVVAR_NOT_FOUND {
+                return nil
             }
         }
         #else
diff --git a/Sources/SWBUtil/Win32.swift b/Sources/SWBUtil/Win32.swift
new file mode 100644
index 00000000..3c19f65a
--- /dev/null
+++ b/Sources/SWBUtil/Win32.swift
@@ -0,0 +1,66 @@
+//===----------------------------------------------------------------------===//
+//
+// 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)
+public import WinSDK
+
+/// Calls a Win32 API function that fills a (potentially long path) null-terminated string buffer by continually attempting to allocate more memory up until the true max path is reached.
+/// This is especially useful for protecting against race conditions like with GetCurrentDirectoryW where the measured length may no longer be valid on subsequent calls.
+/// - parameter initialSize: Initial size of the buffer (including the null terminator) to allocate to hold the returned string.
+/// - parameter maxSize: Maximum size of the buffer (including the null terminator) to allocate to hold the returned string.
+/// - parameter body: Closure to call the Win32 API function to populate the provided buffer.
+///   Should return the number of UTF-16 code units (not including the null terminator) copied, 0 to indicate an error.
+///   If the buffer is not of sufficient size, should return a value greater than or equal to the size of the buffer.
+private func FillNullTerminatedWideStringBuffer(initialSize: DWORD, maxSize: DWORD, _ body: (UnsafeMutableBufferPointer<WCHAR>) throws -> DWORD) throws -> String {
+    var bufferCount = max(1, min(initialSize, maxSize))
+    while bufferCount <= maxSize {
+        if let result = try withUnsafeTemporaryAllocation(of: WCHAR.self, capacity: Int(bufferCount), { buffer in
+            let count = try body(buffer)
+            switch count {
+            case 0:
+                throw Win32Error(GetLastError())
+            case 1..<DWORD(buffer.count):
+                let result = String(decodingCString: buffer.baseAddress!, as: UTF16.self)
+                assert(result.utf16.count == count, "Parsed UTF-16 count \(result.utf16.count) != reported UTF-16 count \(count)")
+                return result
+            default:
+                bufferCount *= 2
+                return nil
+            }
+        }) {
+            return result
+        }
+    }
+    throw Win32Error(DWORD(ERROR_INSUFFICIENT_BUFFER))
+}
+
+private let maxPathLength = DWORD(Int16.max) // https://learn.microsoft.com/en-us/windows/win32/fileio/maximum-file-path-limitation
+private let maxEnvVarLength = DWORD(Int16.max) // https://devblogs.microsoft.com/oldnewthing/20100203-00/
+
+@_spi(Testing) public func SWB_GetModuleFileNameW(_ hModule: HMODULE?) throws -> String {
+    try FillNullTerminatedWideStringBuffer(initialSize: DWORD(MAX_PATH), maxSize: maxPathLength) {
+        GetModuleFileNameW(hModule, $0.baseAddress!, DWORD($0.count))
+    }
+}
+
+public func SWB_GetEnvironmentVariableW(_ wName: LPCWSTR) throws -> String {
+    try FillNullTerminatedWideStringBuffer(initialSize: 1024, maxSize: maxEnvVarLength) {
+        GetEnvironmentVariableW(wName, $0.baseAddress!, DWORD($0.count))
+    }
+}
+
+public func SWB_GetWindowsDirectoryW() throws -> String {
+    try FillNullTerminatedWideStringBuffer(initialSize: DWORD(MAX_PATH), maxSize: maxPathLength) {
+        GetWindowsDirectoryW($0.baseAddress!, DWORD($0.count))
+    }
+}
+#endif
diff --git a/Tests/SwiftBuildTests/ConsoleCommands/CLIConnection.swift b/Tests/SwiftBuildTests/ConsoleCommands/CLIConnection.swift
index 5624e529..f97d7891 100644
--- a/Tests/SwiftBuildTests/ConsoleCommands/CLIConnection.swift
+++ b/Tests/SwiftBuildTests/ConsoleCommands/CLIConnection.swift
@@ -328,20 +328,7 @@ fileprivate func swiftRuntimePath() throws -> Path? {
 
 fileprivate func systemRoot() throws -> Path? {
     #if os(Windows)
-    let dwLength: DWORD = GetWindowsDirectoryW(nil, 0)
-    if dwLength == 0 {
-        throw Win32Error(GetLastError())
-    }
-    return try withUnsafeTemporaryAllocation(of: WCHAR.self, capacity: Int(dwLength)) {
-        switch GetWindowsDirectoryW($0.baseAddress!, DWORD($0.count)) {
-        case 1..<dwLength:
-            return Path(String(decodingCString: $0.baseAddress!, as: CInterop.PlatformUnicodeEncoding.self))
-        case 0:
-            throw Win32Error(GetLastError())
-        default:
-            throw Win32Error(DWORD(ERROR_INSUFFICIENT_BUFFER))
-        }
-    }
+    return try Path(SWB_GetWindowsDirectoryW())
     #else
     return nil
     #endif