My certificate was late in the fall of 2019. It was the first renewal of the Aspire card that was upgraded in the fall of 2018 from the Ascend card (or whatever the lower level card was called), before that it was the Citi Reserve card. So, figuring out the anniversary date is tricky. I called both Amex and Hilton several times. The last time I called Amex after their own deadline for issuing such a certificate expired: I was issued a certificate manually. It arrived in a day or two. Then a few days later another Hilton certificate arrived. I believe that was the one that was supposed to arrive automatically. Nonetheless, I quickly applied both of them for two nights at Conrad Tokyo and even finished my stay there last month.