I’m coming from CrashPlan Home. With CP I could tell it to keep backups until the disk was full (or the quota reached) and then old versions would be deleted. Does Duplicati have a way to handle this?
Unfortunately not. There is a --quota-size parameter however it is currently only used as a placeholder if the destination doesn’t report one.
It would be nice to have, though… 
What happens when the remote side gets full? Does Duplicati just error out?
Is there a way to manually tell Duplicati to prune versions?
You’d probably be interested in the latest few canary builds which now have the “retention policy” feature, which does (IMHO) the best possible version pruning, i.e. it progressively thins out backup jobs in a completely configurable manner over an arbitrary (configurable) number of timespans. Using this, and keeping your destination reasonably monitored, I’d think it should be really easy to avoid a situation where you suddenly slam into a storage limit, at least in most common use cases.
No and yes.
Duplicati should notice the space issue and stop thus leaving the backup “paused” but on a usable state. There is a delete command which can be used to manually debate specific backup versions (but too be confused with purge which works on specific files).
You might be interested in this discussion:
Though personally I do as @drakar2007 suggested so am not too worried about destination space.
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