From 05ce2d18a6f568001518429b4a0cff7ccf384d2a Mon Sep 17 00:00:00 2001
From: JxxIT <110342008+JxxIT@users.noreply.github.com>
Date: Sat, 5 Apr 2025 09:02:09 +0200
Subject: [PATCH] Fix utime sometimes failing

---
 osxphotos/fileutil.py | 22 +++++++++++++++++++++-
 1 file changed, 21 insertions(+), 1 deletion(-)

diff --git a/osxphotos/fileutil.py b/osxphotos/fileutil.py
index 6e59c7495..7f04e7438 100644
--- a/osxphotos/fileutil.py
+++ b/osxphotos/fileutil.py
@@ -8,6 +8,7 @@
 import typing as t
 from abc import ABC, abstractmethod
 from tempfile import TemporaryDirectory
+import fcntl
 
 from .imageconverter import ImageConverter
 from .platform import is_macos
@@ -163,7 +164,26 @@ def rmdir(cls, dirpath):
     def utime(cls, path, times):
         """Set the access and modified time of path."""
         path = normalize_fs_path(path)
-        os.utime(path, times=times)
+        
+        fd = None
+        try:
+            # Open file and set F_NOCACHE to prevent filesystem cache interference
+            fd = os.open(path, os.O_RDONLY)
+            fcntl.fcntl(fd, fcntl.F_NOCACHE, 1)
+            
+            os.utime(path, times)
+            return True
+        finally:
+            if fd is not None:
+                try:
+                    # Clear F_NOCACHE flag before closing
+                    fcntl.fcntl(fd, fcntl.F_NOCACHE, 0)
+                    os.close(fd)
+                except:
+                    try:
+                        os.close(fd)
+                    except:
+                        pass
 
     @classmethod
     def cmp(cls, f1, f2, mtime1=None):