Has anyone managed to get the Match Bank Data reconciliation rules to work with Custom Transaction types? I don't see anything in the documentation that says that they aren't supported, but I haven't been able to get any auto matching to occur against custom transactions.

Did you check if the Show All Transaction Types in Reconciliation preference is enabled in the Accounting Preferences?

Yep, that didn't seem to make a difference.

Silly question here: is the custom transaction already POSTING?