Filename Update Not Working with Replace File feature in CMS

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How would I go about debugging the upload/replace feature that is included with the CMS?

I have a problem where the upload/replace feature doesn’t automatically update the filename in the ‘filename’ field. If I update the filename manually, the update is successful. Otherwise, the file seems to upload, but the update is not successful upon publish/save.

Additionally, the upload/replace feature seems to work for files with image extensions, but not for files with document extensions, such as .pdf or .docx.

I think that it’s designed to keep the older filename by default. You shouldn’t have to edit the filename to save though. Sounds like there might be a bug there which could be reported if you are experiencing this on a clean install, if you do find this is an actual issue with the CMS could you raise as an issue here Issues · silverstripe/silverstripe-asset-admin · GitHub