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I've just upgraded my company server to 1.10.0-dev from 1.9.3 and most attachments from issues were gone from the file-system (they were still there in the attachment
table). Lucky me I had a good backup at hand and recovered them all, so no worries there. However, this is something we should definite look into.
I've checked what migration steps new to 1.10 are related to attachments and I've found this step from #6068:
gitea/models/migrations/v96.go
Line 16 in 3810fa4
I'm not sure about the reasoning of the function, but it seems to me that it deletes all but those related to releases (EDIT: or comments; those deleted were from issues or PR).