A tidy naming rule can make two different files indistinguishable. Suppose scan-01.pdf and scan-02.pdf both become receipt.pdf in the same folder. The proposed names look reasonable one at a time; together they reveal a collision. Ask the AI for a plan before letting any tool apply it.
Review paths, not just attractive names
Request one row per original file, with its complete old path, proposed new path, and reason for the change. Check for repeated destinations and for destinations already occupied by files outside the selection. Even a pair of unique proposed names can be unsafe if the operation swaps two existing paths and the tool cannot handle that sequence.
Do not rely on letter case to separate files. Windows naming rules warn against assuming that Receipt.pdf and receipt.pdf are different names. Preserve the extension unless you deliberately planned a separate format change; renaming is not conversion.
A missing date should remain unresolved. An assistant should not turn an ambiguous filename into an invented creation date. If adding a sequence number avoids collisions, keep a stable ordering and record which original received each number.
Test the tool, then verify the files
PowerRename in Microsoft PowerToys for Windows provides a preview of original and proposed names. Inspect the actual tool's preview as well as the AI's plan: options and replacement rules can produce a different result. Start with disposable copies containing duplicate-looking names and punctuation.
Before applying the full operation, keep verified copies of the originals and save the old-to-new mapping. A mapping explains a rename but cannot restore file contents that were overwritten. Require the operation to stop on an occupied destination rather than silently replacing it.
Afterward, check file counts and the mapping. Compare content hashes where available to verify that each renamed file retains its bytes, and open important files. If the results differ from the plan, stop before further renames or cleanup.