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os.path.existsreturns true for things that aren't files, such as directories. This gives false positives. See the other answers that recommendos.path.isfile.filepathwith the right timing, and BAM, you overwrite the target file. You should doopen(filepath, 'wx')in atry...exceptblock to avoid the issue.OSErroriffilepath + '.old'already exists: "On Windows, if dst already exists, OSError will be raised even if it is a file; there may be no way to implement an atomic rename when dst names an existing file."os.replaceportably performs silent replacement of the destination file (it's identical toos.rename's Linux behavior) (it only errors if the destination name exists and is a directory). So you're stuck on 2.x, but Py3 users have had a good option for several years now.renameexample: It should still be done withtry/except.os.rename(oros.replaceon modern Python) is atomic; making it check then rename introduces an unnecessary race and additional system calls. Just dotry: os.replace(filepath, filepath + '.old') except OSError: pass