Send Sometimes Doesn't Work.

So subject isn't really a good descriptor of the issue. Send works fine as long as I sign all character in at about the same time. But if say I sign into my friends account to tribox 12 hours after I signed in my main two characters, send won't work to his account. It'll still work between my two, just not the one signed in at a different time. I've had the same issue between my two before if one got dc'd and not the other, but it's fairly inconsistent there. Logging off all accounts and signing back in fixes it, but now that I'm trying to tribox voidwatch it's a bit annoying having to log all the way off and back on again with three accounts. Is this a known issue? And any workaround for it?

Its a windower update. You are using a different version of send 12 hours later basically. So it wont be compatible sent from a character firs tlogged on. However you should be able to use it on the more recent character to control characters who have been logged on for longer.
Basically when u open windower on ur friends account and u see the downloading bar, then you already know it wont work.

It's more deep rooted of a problem than that. Afaik, it was looked into and can't be fixed.