Reimburseable expenses are not tax related event.

Honestly surprised Tim has to pay anything at all, given the massive write offs that come with luxurious work/pleasure trips.

My hands do not like it.

I think we’ve only paid a couple times during years where we took some capital gains hits. Don’t remember there being any drama but we never waited until two outs in the bottom of the ninth.

You could always file for extension with IRS just in case. That way avoid double payment. But you're probably fine.