diff --git a/Sources/FoundationEssentials/FileManager/FileManager+Directories.swift b/Sources/FoundationEssentials/FileManager/FileManager+Directories.swift
index 0413087c..1573b2d6 100644
--- a/Sources/FoundationEssentials/FileManager/FileManager+Directories.swift
+++ b/Sources/FoundationEssentials/FileManager/FileManager+Directories.swift
@@ -489,22 +489,13 @@ extension _FileManagerImpl {
     
     var currentDirectoryPath: String? {
 #if os(Windows)
-        var dwLength: DWORD = GetCurrentDirectoryW(0, nil)
-        guard dwLength > 0 else { return nil }
-
-        for _ in 0 ... 8 {
-            if let szCurrentDirectory = withUnsafeTemporaryAllocation(of: WCHAR.self, capacity: Int(dwLength), {
-                let dwResult: DWORD = GetCurrentDirectoryW(dwLength, $0.baseAddress)
-                if dwResult == dwLength - 1 {
-                    return String(decodingCString: $0.baseAddress!, as: UTF16.self)
-                }
-                dwLength = dwResult
-                return nil
-            }) {
-                return szCurrentDirectory
-            }
+        // Make an initial call to GetCurrentDirectoryW to get a buffer size estimate.
+        // This is solely to minimize the number of allocations and number of bytes allocated versus starting with a hardcoded value like MAX_PATH.
+        // We should NOT early-return if this returns 0, in order to avoid TOCTOU issues.
+        let dwSize = GetCurrentDirectoryW(0, nil)
+        return try? FillNullTerminatedWideStringBuffer(initialSize: dwSize >= 0 ? dwSize : DWORD(MAX_PATH), maxSize: DWORD(Int16.max)) {
+            GetCurrentDirectoryW(DWORD($0.count), $0.baseAddress)
         }
-        return nil
 #else
         withUnsafeTemporaryAllocation(of: CChar.self, capacity: FileManager.MAX_PATH_SIZE) { buffer in
             guard getcwd(buffer.baseAddress!, FileManager.MAX_PATH_SIZE) != nil else {
diff --git a/Sources/FoundationEssentials/WinSDK+Extensions.swift b/Sources/FoundationEssentials/WinSDK+Extensions.swift
index f0eb3ed9..54f3cb78 100644
--- a/Sources/FoundationEssentials/WinSDK+Extensions.swift
+++ b/Sources/FoundationEssentials/WinSDK+Extensions.swift
@@ -81,6 +81,10 @@ package var ERROR_FILENAME_EXCED_RANGE: DWORD {
     DWORD(WinSDK.ERROR_FILENAME_EXCED_RANGE)
 }
 
+package var ERROR_INSUFFICIENT_BUFFER: DWORD {
+    DWORD(WinSDK.ERROR_INSUFFICIENT_BUFFER)
+}
+
 package var ERROR_INVALID_ACCESS: DWORD {
     DWORD(WinSDK.ERROR_INVALID_ACCESS)
 }
@@ -288,4 +292,34 @@ internal func WIN32_FROM_HRESULT(_ hr: HRESULT) -> DWORD {
     return DWORD(hr)
 }
 
+/// 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.
+internal 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(ERROR_INSUFFICIENT_BUFFER)
+}
+
 #endif