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"sync-files" role fails if no backup was made previously

The problem is in the step "pull initial files from backup". It applies a previous backup if the backed file doesn't exist on the host. However, if the file exist on the host, but not in the backup, this step fails because it cannot find the backup.

You have to create a dummy for the backed up file manually, which maybe isn't what we want, or is it?

To upload designs, you'll need to enable LFS and have an admin enable hashed storage. More information