diff --git a/System/Directory/Internal/Posix.hsc b/System/Directory/Internal/Posix.hsc
--- a/System/Directory/Internal/Posix.hsc
+++ b/System/Directory/Internal/Posix.hsc
@@ -81,14 +81,10 @@
     allocaBytes (pathMax + 1) (realpath >=> action)
   where realpath = throwErrnoIfNull "" . c_realpath path
 
-canonicalizePathWith :: ((OsPath -> IO OsPath) -> OsPath -> IO OsPath)
-                     -> OsPath
-                     -> IO OsPath
-canonicalizePathWith attemptRealpath path = do
-  let realpath (OsString path') =
-        Posix.withFilePath path'
-          (`withRealpath` ((OsString <$>) . Posix.peekFilePath))
-  attemptRealpath realpath path
+realPath :: OsPath -> IO OsPath
+realPath (OsString path') =
+  Posix.withFilePath path'
+    (`withRealpath` ((OsString <$>) . Posix.peekFilePath))
 
 canonicalizePathSimplify :: OsPath -> IO OsPath
 canonicalizePathSimplify = pure
diff --git a/System/Directory/Internal/Windows.hsc b/System/Directory/Internal/Windows.hsc
--- a/System/Directory/Internal/Windows.hsc
+++ b/System/Directory/Internal/Windows.hsc
@@ -356,7 +356,8 @@
       | (toChar <$> [c1, c2, c3, c4]) == "\\\\?\\" ->
       case path of
         c5 : c6 : c7 : subpath@(c8 : _)
-          | (toChar <$> [c5, c6, c7, c8]) == "UNC\\" -> pack subpath
+          | (toChar <$> [c5, c6, c7, c8]) == "UNC\\" ->
+            os "\\" <> pack subpath
         drive : col : subpath
           -- if the path is not "regular", then the prefix is necessary
           -- to ensure the path is interpreted literally
@@ -407,10 +408,8 @@
     Left proposedSize -> peekTStringWith proposedSize cFunc
     Right result      -> pure result
 
-canonicalizePathWith :: ((OsPath -> IO OsPath) -> OsPath -> IO OsPath)
-                     -> OsPath
-                     -> IO OsPath
-canonicalizePathWith attemptRealpath = attemptRealpath getFinalPathName
+realPath :: OsPath -> IO OsPath
+realPath = getFinalPathName
 
 canonicalizePathSimplify :: OsPath -> IO OsPath
 canonicalizePathSimplify path =
diff --git a/System/Directory/OsPath.hs b/System/Directory/OsPath.hs
--- a/System/Directory/OsPath.hs
+++ b/System/Directory/OsPath.hs
@@ -10,7 +10,7 @@
 --
 -- System-independent interface to directory manipulation.
 --
--- @since 1.2.8.0
+-- @since 1.3.8.0
 --
 -----------------------------------------------------------------------------
 
@@ -872,7 +872,7 @@
    (`ioeSetOsPath` path)) `modifyIOError` do
     -- simplify does more stuff, like upper-casing the drive letter
     dropTrailingPathSeparator . simplify <$>
-      (canonicalizePathWith attemptRealpath =<< prependCurrentDirectory path)
+      (attemptRealpath realPath =<< prependCurrentDirectory path)
   where
 
     -- allow up to 64 cycles before giving up
diff --git a/changelog.md b/changelog.md
--- a/changelog.md
+++ b/changelog.md
@@ -1,6 +1,13 @@
 Changelog for the [`directory`][1] package
 ==========================================
 
+## 1.3.8.3 (Jan 2024)
+
+  * Relax `Win32` version bounds to support 2.14.0.0.
+    ([#166](https://github.com/haskell/directory/issues/166))
+  * Fix regression in `canonicalizePath` on Windows UNC paths.
+    ([#170](https://github.com/haskell/directory/issues/170))
+
 ## 1.3.8.2 (Dec 2023)
 
   * Relax `base` version bounds to support 4.19.
diff --git a/directory.cabal b/directory.cabal
--- a/directory.cabal
+++ b/directory.cabal
@@ -1,6 +1,6 @@
 cabal-version:  2.2
 name:           directory
-version:        1.3.8.2
+version:        1.3.8.3
 license:        BSD-3-Clause
 license-file:   LICENSE
 maintainer:     libraries@haskell.org
@@ -19,11 +19,13 @@
     config.status
     HsDirectoryConfig.h
 
+extra-doc-files:
+    README.md
+    changelog.md
+
 extra-source-files:
     HsDirectoryConfig.h.in
-    README.md
     System/Directory/Internal/*.h
-    changelog.md
     configure
     configure.ac
     directory.buildinfo
@@ -61,7 +63,7 @@
         base     >= 4.11.0 && < 4.20,
         time     >= 1.8.0 && < 1.13
     if os(windows)
-        build-depends: Win32 >= 2.13.3 && < 2.14
+        build-depends: Win32 >= 2.13.3 && < 2.15
     else
         build-depends: unix >= 2.8.0 && < 2.9
 
diff --git a/tests/CanonicalizePath.hs b/tests/CanonicalizePath.hs
--- a/tests/CanonicalizePath.hs
+++ b/tests/CanonicalizePath.hs
@@ -160,3 +160,14 @@
     vldn <- canonicalizePath "verylongdirectoryname"
     vldn2 <- canonicalizePath "VERYLONGDIRECTORYNAME"
     T(expectEq) () vldn vldn2
+
+  let isWindows =
+#if defined(mingw32_HOST_OS)
+        True
+#else
+        False
+#endif
+
+  when isWindows $ do
+    -- https://github.com/haskell/directory/issues/170
+    T(expectEq) () "\\\\localhost" =<< canonicalizePath "\\\\localhost"
diff --git a/tests/FindFile001.hs b/tests/FindFile001.hs
--- a/tests/FindFile001.hs
+++ b/tests/FindFile001.hs
@@ -28,13 +28,15 @@
   for_ (List.permutations ["qux", "bar", "."]) $ \ ds -> do
 
     let (match, noMatch) = List.partition (== "qux") ds
+    match0 : _ <- pure match
+    noMatch0 : _ <- pure noMatch
 
-    T(expectEq) ds (Just (List.head match </> "foo")) =<<
+    T(expectEq) ds (Just (match0 </> "foo")) =<<
       findFileWith f ds "foo"
 
     T(expectEq) ds ((</> "foo") <$> match) =<< findFilesWith f ds "foo"
 
-    T(expectEq) ds (Just (List.head noMatch </> "foo")) =<<
+    T(expectEq) ds (Just (noMatch0 </> "foo")) =<<
       findFileWith ((not <$>) . f) ds "foo"
 
     T(expectEq) ds ((</> "foo") <$> noMatch) =<<