Windbag Miles is a blog about points, miles, credit cards, travel, and general windbaggery.

Hilton is making it difficult to redeem free weekend night certificates, and it's driving me nuts.

Sometimes I wish my blog had a bigger platform, and not just because I crave the validation of thousands of strangers. When you have a well-known blog, you can put companies on blast about bad policies (or policy abuse), and it very often effects meaningful changes. Right now, I'm way too small for Hilton to care either way what I have to say, and I wish there were some way to get them to see this and actually respond, rather than just brushing it off as another #hater complaining on the internet. In the past year, I have earned three free weekend night certificates -- two from completing the minimum spend on my now-canceled Citi Hilton card, and one from opening the new Amex Hilton Aspire card. Amex made me wait around ten weeks to receive the award this time around, during which time I've had my eye on a particular redemption. When I finally got the email from Hilton with my certificate ID, I called immediately to try to book the stay while there was still a standard room reward available.

The first pain point is that Hilton makes you call in to redeem the certificate, rather than letting you do it online like IHG or Hyatt. I feel like it would save them time and money to invest in this functionality, but I guess they aren't there just yet. I went ahead and called, and the phone rep I reached took twenty minutes just to confirm that my certificate existed. He insisted first that I had an Amex gift card and not a free night certificate, and then that I had to call Amex to redeem it. Frustrated at having to defend myself when I was objectively right while he showed almost no interest in changing his mind, I explained that Hilton sent me the certificate and told me to call the normal Honors number. He muttered to himself for a minute or so and then put me on hold for the third time. When he finally came back, he said, "good news, I was able to get you approved to use your certificate," in a tone like he was doing me a favor.

So we finally got down to booking the award, at which point he said, "Unfortunately, you don't have enough points in your account to use the certificate." I asked him what the hell he was talking about and he explained that the terms and conditions of the reward certificate state that you need to have enough points in your account to book an award stay at the hotel in order to use the certificate. In other words, you can use the certificate to book a room instead of using points, but it's invalid unless you already have enough points for the award.

This is obviously non-sensical, and the terms and conditions absolutely do not say anything to that effect. I kept pushing him, more out of annoyance than anything else, because I knew he wasn't going to relent. I asked him to email me the terms and conditions he was reading, and he said he couldn't do that. I asked for a supervisor, and he said that the supervisor would tell me the same thing, since it's clearly written in the terms (the ones he couldn't send to me).

Here's the thing: this is the second time I have run into this issue when redeeming a free night certificate. It's an obvious hang-up-call-back situation, but now I'm wondering why multiple Hilton reps are refusing to let people redeem their free night certificates based on a non-existent policy. The first time it happened, I went back and forth with the rep and then her supervisor for 45 minutes before calling back, talking to a different rep, and redeeming the certificate in under five minutes. Hilton, you're officially on blast: WHY ARE YOUR REPS INVENTING A RESTRICTION ON FREE NIGHT CERTIFICATES?

Has anyone else run into this? The idea that you'd need to have enough points to pay for a stay in order to use a certificate that entitles you to a free stay is a ridiculous policy, but someone somewhere is communicating it to Hilton reps, and they're making what should be a simple process into a serious headache. More frustratingly, I earned those certificates -- Hilton didn't just give them to me to be nice. I paid $450 for a credit card in order to get this one, and it's really shitty of them to make it so difficult to use.

Of course that leaves aside the long argument I needed to have in order to get the rep to even admit that the free night certificate was a real thing and not an Amex gift card or something. I recognize there are bad apples, and if it were a one-off, I'd probably let it go. However, my track record is now two-for-three with Hilton reps refusing to honor the free night. I've been really happy with all my Hilton stays recently, so it's a shame that their call center stands in such stark opposition to their on-property staff when it comes to providing service to their members.

PS: In case you were wondering, at no point did I bring up my Diamond status as a reason I should get my way, because I may be easily irritated, but I'm still a ways from becoming the "DO YOU KNOW WHO I AM?!" guy...

Anyway, I'll let you know if I ever hear from Hilton, although I'm not confident. If anyone else has dealt with this, I'd love to collect more examples of it (although I feel bad for you that you had to deal with it too).

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Update: Immediately after posting this, I contacted Hilton to try again to redeem my certificate, and I found out some interesting info. Happily, the rep I spoke to was able to book the stay for me with no pushback whatsoever, which at least put this particular headache to rest. After I got the confirmation number, I asked him if he had ever heard of the "you need the equivalent cost in points" policy, and here's what he told me... Apparently, in their system, a free night certificate stay looks like a points stay. As a result, in order to apply the certificate, you need to book the room on points and then redeem the certificate, which credits the points back to the account. So it's not that it's a policy requiring you to have points in order to redeem the certificate or anything -- it's more of an IT issue.

To get around this, experienced reps know an internal procedure to "borrow" points, which forces the reservation through the system far enough that they can apply the certificate to complete the booking. However, as he was explaining this, he kind of chuckled and said that since it's uncommon for people to call in with the certificate, there are a lot of reps who don't understand the borrowing procedure and flat-out refuse to make the booking due to the system not letting them. (This explains why, when I dealt with this issue the first time, a supervisor told me that the system physically prevented her from making the booking, even though a different rep was able to do it without issue.)

Now I think I understand what's going on here... the problem is that Hilton isn't adequately training their phone reps in the process around free night certificates, which is causing phone reps to cite terms and conditions that are different from what the customer sees when they click on the full terms and conditions of the reward certificate. (I now also understand why the first rep I spoke to today couldn't send me the terms he was referring to, since they weren't "terms" as much as the reality of the IT system he was working with.) It's not some nefarious plot to swindle people out of their certificates, it's just corporate bureaucracy creating friction between customer expectations and operational realities. Yay?

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