Uploading files - overwriting previous version

Uploading a newer version of a file it asks if I want to replace the previous one., promising to update email links accordingly. It doesn’t - all it does is remove the file from the links and the new file does not even appear in the file link dropdown. I have to delete the old file, upload and re-connect manually. What am I doing wrong?

Ugh that’s a bummer. Where in Infusionsoft are you seeing the option to replace/update a file?

On the file load screen it says “Confirm File Replace”. It has just worked on for a .xlsx but has failed a few times for a .pdf