It was my experience (and quite a few others online, from what I've read), that the first transfer can often be lost indefinitely, or at least for many weeks. I made one transfer that never made it, followed by another one a couple hours later that posted instantly.
My advice: transfer the minimum number of points the very first time you transfer (currently 1k), and then transfer the balance that you need immediately.
Mine at least had a happy ending, as the points posted months later, and Citi was willing to refund the TYP to me after 15 days, so a nice bonus. Rep said he had never been able to cancel a points transfer before, but no issues when he tried for me.