Our system is configured to overwrite files of the same name rather than appending numbers (_0, _1, etc.) like many applications do. We have noticed that whenever we try to overwrite a file of the same name, the media/node is updated, but the attached file entity does not update.
Our current solution is to purge the file paths manually. It is a bit cumbersome with 50+ users updating content, and running a full varnish clear isn't good practice in production.
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It's likely this issue predates Contrib.social: some issue and comment data are missing.
With the ability in Core to now replace files we might need to revisit this issue and possibly create a patch/merge request to add this feature.
Actually, would this module work? Purge File Module →
@emerham: We'd been using some custom code based #6, but switched to Purge File → a couple weeks ago and it seems to be working very well.