Jython 2.5rc3 seems to behave differently to Python 2.5 and Jython 2.2.1 in the handling of absolute paths to files on Windows. In particular jython2.5rc3 seems to need to a drive prefix added unlike Jython2.2.1 and CPython2.5 The following show attempts to open and existing file /home/misc/jython/bug/t.txt The tests were run under Windows XP and similar results are obtained from the Windows cmd shell and cygwin/bash. Jython 2.5rc3 ============= C:\lib\jython2.5rc3>jython.bat Jython 2.5rc3 (Release_2_5rc3:6384:6385, May 26 2009, 15:51:41) [Java HotSpot(TM) Client VM (Sun Microsystems Inc.)] on java1.6.0_04 Type "help", "copyright", "credits" or "license" for more information. >>> file("/home/misc/jython/bug/t.txt", "r") Traceback (most recent call last): File "", line 1, in IOError: [Errno 2] ENOENT: '/home/misc/jython/bug/t.txt' >>> >>> file("c:/home/misc/jython/bug/t.txt", "r") >>> Jython 2.2.1 ============ C:\lib\jython221>jython.bat Jython 2.2.1 on java1.6.0_04 Type "copyright", "credits" or "license" for more information. >>> file("/home/misc/jython/bug/t.txt", "r") >>> >>> Python 2.5.1 ============ C:\lib\Python25>python Python 2.5.1 (r251:54863, Apr 18 2007, 08:51:08) [MSC v.1310 32 bit (Intel)] on win32 Type "help", "copyright", "credits" or "license" for more information. >>> file("/home/misc/jython/bug/t.txt", "r") >>>