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Using offlineEnabled plus a timeout of 10 didn't help, but that plus a timeout of 60 did. 

Unfortunately, due to the need to continue tracking un-upgraded versions of the app, we can't turn on offline tracking on the report suite. Apparently that'd cause the server to drop all of those tracking requests, since they don't include a timestamp. So... I shall continue to dig. 

Edit: actually, would it hurt anything to enable offline tracking in the app but not on the server?