I recently got a replacement Citi Double Cash card since I was upgraded to WEMC. Unfortunately, it looks like a contact EMV transaction is still required to activate the contactless interface. Citi still doesn't mention that on their website, either, other than a general statement about how you can still swipe or insert if tapping doesn't work.

Also, FWIW, we tapped the Citi Costco card at the gas pump today (on the insert/tap membership card prompt) and it does in fact skip basically all other prompts. The only prompt we got was the car wash one (since our nearby location has one).