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Did you tried to upload iCloud file or local file? I am asking, because I have got a similar report from my friend regarding iCloud files which are not downloaded to the machine.
It looks like an internal Electron issue, but I will try to make more investigation.
I am also having this issue, but it is also with inline images. It doesn’t happen every time, but pretty frequently. Also happens with published pages. I am on macOS Catalina 10.15.2 (19C57), Publii version 0.35.3.
Please check if in the prerelease version of Publii this issue occurs too. I see that indeed the problem with uploading images occurs sometimes on v.0.35.3 but I am unable to reproduce it on the prerelease version: https://forum.getpublii.com/topic/publii-0-36-prerelease-3-come-help-us-make-it-better/ it has never Electron and sharp, what could solve this issue.