Ethereum Wallet not sending on cheapest? Anyone else with this issue?

I know its silly, but it all adds up in the end...

Everytime I try to send via the cheapest option, it fails to go through.

I update my time, update geth and then try to send. If I choose the default speed or fastest, it goes through no problem. If I choose cheapest, it fails no matter how many times I try to send.

Any ideas?