There have been a number of great flights come up recently (thanks for those who've posted them) where if you pay via CC there are additional fees, but if by POLI or Paypal not so much.
According to the citibank Signature cc terms, if you pay for the tickets with the card you will receive complimentary travel insurance.
How about if you pay via PayPal, but choose the CC in question to make the payment? Would you be entitled to the insurance or not? Would they see that as paying for the tickets or simply paying the PayPal bill?
I'm loathe to call Citibank and ask as I'll get switched from person to person and in the end I'll just get someone who will read me the terms and conditions.
(This is what happened when I called them to clarify another issue)
Any ideas? Obviously you wouldn't want to just assume, have something go wrong and find you're not covered.
It is my understanding that credit card companies can only see who charged your card, not what you bought. So all Citibank will see is a charge from PayPal, not AirAsia or some other airline, and no mention of a flight. My inclination is that it would be risky - they may allow you to provide further proof of the transaction to demonstrate that it qualifies, eg. PayPal invoice, but they may not. My guess is that in normal situations they would determine eligibility based on which company charged your card.