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"disk is full" error only once per connection?
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> idle the app in a loop that checks free space until the user has freed up enough space for the app to continue

Noting that free space is not, on all OS/filesystem combinations, and indication that the user can actually use that space. If FS quotas are in effect, a typical space-free check will not indicate that. Similarly, some OS/FS combinations allow the superuser to reserve, at filesystem-formatting time, some percentage of the space for superuser-only use. Thus apps may start failing due to filesystem-is-full errors even though 10% of the filesystem is ostensibly free.