Even more Hilton Honors IT nonsense

Back in September, 2018, Robert Dwyer wrote at Milenomics about all the real and potential problems you might encounter redeeming Hilton Honors free weekend night certificates. Having re-read that post, I thought I was locked, loaded, and ready to redeem my own Hilton Honors Ascend free weekend night certificate for an upcoming trip to New York City.

It didn’t work out that way.

Good news: free weekend night awards may have gotten easier to book

Going into this call, my assumption was that I’d run into one of the same obstacles Robert did: I didn’t have enough points in my account to book a night entirely with points, even though I didn’t intend to use any points at all.

That did not end up being my problem. After I identified myself, the phone rep was able to find and apply my free weekend night certificate and complete the reservation without any problem, even though I had less than 6,000 Hilton Honors points in my account, so they seem to have fixed Robert’s ninth obstacle.

Interestingly, the phone rep was willing to let me use my free weekend night award to book any standard room award. Now that Hilton has started charging different prices for different “standard” rooms on the same night this is potentially a big advantage, for a couple of reasons.

First, for reservations booked entirely with free weekend night certificates, it may increase the value of the certificate by letting you book a larger room or one with more beds for a single “price.”

But second, depending on the property, it may also increase the value of your points when combining a points reservations with a free weekend night award reservation. That’s for the simple reason that under many circumstances a hotel may prefer to let you stay in a “better” room for multiple nights rather than force you to move every day and their housekeeping staff to turn over multiple rooms multiple times.

Your experience will vary, but using a free weekend night award for the first night of a stay may be one strategy for working your way into a larger or better room for the entire length of your stay.

Bad news: points are not available instantly after awards are cancelled

This is not exactly a new problem, so much as one Hilton has never really figured out how they want to handle. When I wrote about the issue in 2017, I advised cancelling, instead of changing, award redemptions since changing reservations did not redeposit the price difference in your account.

But now the problem has gotten worse, with award cancellations not immediately redepositing points either. I ran into this exact problem yesterday trying to rebook a 3-night award stay as a 2-night award stay (with the first night replaced with my weekend night award). I waited patiently for the points to be redeposited so I could rebook the last two nights, but they never were (and still haven’t been).

My pet theory having only looked into it over the course of a frustrating evening is that these developments are connected. When I opened my free weekend night award reservation, I saw that instead of simply saying a certificate or award had been used, instead my reservation stated that 67,000 points had been redeemed. If free weekend awards are being converted into points before being applied to reservations, that would mean you could theoretically book any standard night at any of the most expensive Hilton properties, cancel the reservation, and receive 95,000 points redeposited in your account.

If they really implemented free weekend night awards in such a crude way, adding a level of scrutiny to those free weekend night reservations necessarily means applying the same scrutiny to all cancelled award reservations. That is an issue that’s trivial to work around, but only if you know it exists.

And now you know.