To close the loop on my issue. I spent a couple of hours making calls to LifeMiles support and Citi ThankYou support. The friendliness and help from LifeMiles was surprising and unexpected based on stories of heard about their call center. Although the overall experience was frustrating, they were great. I called them five times and never experienced a wait time, english speakers were clear and polite and eventually they told me "Citi has not sent the miles to your account." With that, I called Citi back up for the fourth time and spoke to a very competent agent who essentially redeposited my Citi points, tried the transaction again and they posted IMMEDIATELY.