When did Hilton get so bad at processing award stays?

I'm no thought leader in travel, so I'm not going to paint this as a symbolic or meaningful decline in the quality of the Hilton Honors program, but I had a pair of experiences this weekend that together formed one hell of a coincidence. My mom was visiting from Oregon, and together we drove to the Maryland coast to get out of the city for the weekend.

Hilton Honors award reservations are easy for hotels to screw up

Being a travel hacker means never having to share a hotel room with your parents, so I booked us two all-points award stays at a Doubletree property in the Annapolis suburbs, one with my partner as the "additional guest" and one with my mom as the additional guest. The stay went smoothly, but when the folios were emailed to me on the morning we checked out, only one of the rooms had been zeroed out; the other showed a charge to my credit card for the two nights of $480 or so.

The next night, I had booked my mom a room at the Hilton Garden Inn near Washington National Airport, again with her as the additional guest on the reservation, and got a text from her asking whether the stay was a points stay or a points and cash stay. I thought this was a pretty strange question, but she said the front desk clerk had been confused. Sure enough, the next morning the e-mailed folio showed the full room rate had been charged to my credit card!

If it hadn't happened two nights in a row it probably wouldn't have even registered with me; there are all sorts of things you have to call a hotel about to follow up on after a stay, and it only took two 2-minute phone calls to get both sets of charges reversed. The fact that it happened under identical circumstances, however, makes me think there may really be a Hilton reservation issue when the "additional guest" checks in on an award stay without the primary guest. There's no rule against booking such stays (I do it all the time), and the charges are easy to reverse, but the pattern is certainly suggestive.

A more serious concern would be if you booked an award stay for someone and they provided their own credit card on check-in, and that credit card was charged the full price of the stay. If they were nervous talking about money, like many Americans, they might simply pay the charge thinking you'd stiffed them! And of course if the reservation were held with a debit card, you could experience serious cashflow issues or even overdrafts while the refund was being processed, which can take several days.

Conclusion

I don't have any grand unified theories about the source of this issue, and don't have any idea whether it originates on Hilton's side as a reservation software issue or on the properties' side as a training issue or even an attempt to grift unwitting guests. The solution is simply to be aware of it, check your Hilton folio as soon as they e-mail it to you, fix the issue before you check out if possible, and call as soon as you discover it if not!