Fix utime sometimes failing

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):