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).

~        ~        ~

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?


Support your windbag!

This site is ad-free, because I think ads are ugly. That's why I rely on readers for support! If only one person per year gives me $5, then I'll have $5 more per year. Everyone wins!



  1. cardpediem says:

    Yes, I’ve run into the same issue. It’s absolutely ridiculous. I hope your blog post reaches a platform that can get this issue in front of the right people at Hilton. I’m linking to a post I wrote describing a similar issue: https://creditcardpediem.com/2017/02/14/careful-making-changes-hilton-free-night-certificate/

    Liked by 1 person

    1. Windbag Miles says:

      Jeez, your story is even worse! Not only did they apply “the policy” but they authorized your card for a huge points purchaes?!? My head would have exploded.


  2. Biggie F says:

    Ugh. I can’t help but think there is a common thread to all of this … and the thread seems to be that they don’t have any way in the system to indicate a free night. I am now reminded of the following:

    The last two times I have booked a free weekend night, I have then checked my reservations. And each time, it is there. But it does not show as a free night. It shows as a points night. Both times I was taken aback, and I think both times (or maybe only one, maybe I just remembered the second time) I called to say that there had been a mistake — that I had ever so clearly booked a free night with a weekend certificate, and yet it was showing as a points night.

    Well, close inspection revealed/reveals that no points were actually subtracted, and the first time at least — the second reservation is still awaiting the stay date — indeed I got a free night. But maybe their entry system somehow is coding these things as points stays which, for a person with less commitment to their job than we have to their job notwithstanding it is not our job, may translate into the idea that you need the requisite points stay to go through in order for the weekend award stay to post. Because maybe, in some kind of kludge programming, it does.

    It’s a theory.


    1. Windbag Miles says:

      Your theory is absolutely correct. As you were typing it out, I was updating the post with some more info I just received from a Hilton rep, and you pretty much nailed it.


  3. Pam says:

    Interesting “policy” considering if you actually use points to first book a room & then try & substitute that same res with a free nights cert the reps can’t do that, either! Like you, I “captured” a Standard room award while it was available by booking a room (but during the night when the res agents that handle free nights were’t there). The next morning I called to substitute my free night certificate for my points, & they can’t do it! Has to be a new res. Ridiculous & convuluted.


  4. Drew says:

    I had a similar issue last year – I tried to book a 5 night award and apply a certificate to one of the nights. The reps I spoke to on multiple occasions (including supervisors) kept saying it wasn’t possible (even though I had done it before earlier that year) since I didn’t have enough points for a 5 night stay (I had enough for 4 nights which should have been fine with the 5th night free anyway). Eventually they cancelled part of my reservation (I initially had a 3 night stay held since availability was tight and I held that stay before my certificate and more points posted) without me asking and almost screwed up my entire trip. It was only fixed when I contacted the hotel directly and they were nice enough to fix everything – Hilton itself wasn’t willing to even re-instate the reservation they cancelled without my permission.


  5. Adam B says:

    i don’t think there is anything new here about points equivalent of the certs for booking other than maybe poorly trained reps (i am still waiting for my amex cert to arrive so thank you for heads-up about future headache). i had a booking back in 2013 for 7 nights with 5 nights on points and 2 using citi certs. looking at that reservation email, it was coded as following:

    Reward Redemption Information:
    Redemption Type:
    HHonors Reward ID: 1166628 80,750 Points
    HHonors Reward ID: 11661031 80,750 Points
    HHonors Reward ID: 11758511 403,750 Points
    Total Number of Points per Stay: 565,250 Points


    1. Windbag Miles says:

      I’ve never noticed that on the redemption end before. It still seems like a convoluted process to me that the certificate doesn’t just become the equivalent amount in points but rather requires the points be added to your account for it to be redeemed.


  6. A great read. Hilton reps suck, but I didn’t know they were this bad.


  7. Army says:

    aw crap. They wont swap out a reward night cert for your already-booked award night stay??? Can anyone confirm???


  8. Army says:

    I meant, they wont let you use a free night cert instead of your award night booking if it was done with points? Its 1AM in Dubrovnik – excuse my sleepy grammar!


    1. Windbag Miles says:

      You could probably get them to do it by first modifying your award stay and then applying the cert once the points are back in your account. You’d have to get a good agent, though.


    2. Adam B says:

      I have an upcoming stay for 6 consecutive nights booked all with points on Fri-Wed. Just got my Aspire cert and called to swap for one night and get the points back. Since I used 5th night free option I could only swap either the first or the last day. The agent knew well about the cert that apparently was visible on my account and explained that given my situation the last day is not an option since the cert is only weekend night (duh) so she can only play with the first day. Surprisingly she said she can actually modify my existing reservation by spiting it into 1+5 (i thought the whole thing will have to be re-booked entirely). The problem in my case was that over water villa I have reserved right now is no longer available on Fri that I need so she would have to book beach villa for me so I had to tell her to leave everything as is for now. I can probably contact the hotel and asked them to allow me stay in the same over water villa for the entire stay especially if my first night will be release back into the system after the change but I will wait for now to see if it will open up and call again. I don’t have hard proof yet but at least the agent didn’t dismiss and actually was willing (and sounded like able in their system) to modify the existing reservation to swap points for the Aspire cert.


  9. I just received my Hilton Surpass/Ascend’s anniversary award night certificate! My second year’s annual fee didn’t hit yet – I thought you get the cert once you pay that second year fee… would you happen to know if I *have to* pay the annual fee to use this or could I use it and cancel the card before it hits (and not have it get clawed back/have booking cancelled)??


    1. Windbag Miles says:

      With the Aspire, they made me wait around 9 weeks between when I got the card and when the certificate showed up. I figured that was designed to get me to pay the fee and then wait until after Amex’s fee refund window closed before I got the free night. I assumed it would be the same the second year, but maybe not? I guess it also could have been due to the Citi Reserve/Ascend changeover (even though you didn’t have a Reserve card before).


  10. Mark says:

    I had an issue with this too. It seemed like it was going smoothly and that the agent knew what they were doing, until i logged in and noticed that they had just booked the night with 95,000 points from my account….arg! Luckily the agent at the Diamond desk that i got transferred to when i called back knew what to do and fixed it. As it is now a regular potential benefit of of a couple of their cards, i hope they remedy the issue of not being able to book online.

    Liked by 1 person

  11. Adam B says:

    I am going to have to take my praise of Hilton reps back – encountered situation exactly as the article stated, in order to use the cert, the Hilton rep I was talking wanted to either lock my 95K points for the cost of one night or…. actually charge my credit card which would be $1.1K. Out of curiosity I asked when i will get my money back if I go with the credit card option on which she suggested to contact the property directly to inquiry when they will be able to release my points or cash. Hang up… dialed again…2 min and done – got my email confirmation with the reservation booked with free night cert, didn’t even need to provide my cert number – experienced rep vs. rookie.


  12. Joseph Pena says:

    I tried to use my American Express Free weekend night certificate and initially, the agent was all for it. I had first tried through Chat and that agent flat out said it was not possible until I was at the hotel and the hotel would take care of it. This is contrary to what HHonors says online that you call the phone number. So, I called the phone number and that agent tried to help me book a Sunday night with the certificate and Monday and Tuesday night using points. After the agent put me on hold and consulted with a help desk, the agent said we will book your Monday and Tuesday with points and you should try the next day to do the Sunday night because the system was updating. I told the agent that was just an excuse they were using to keep me from using my certificate and eventually I just said use my points for the Sunday night as well – all of which I could have done online myself and saved an hour and half of chat and phone calls. Not sure if I will ever be able to use the free weekend night certificate.


    1. Windbag Miles says:

      Don’t despair… the trick is to hang up the instant you get any resistance from the rep. Eventually you’ll get a good one.


      1. Joseph Pena says:

        I will try that when I get the urge to try using the certificate again. Thank you. One thing occurred to me though, that I should actually be grateful, because I believe the certificate if it is truly redeemable can be used at more expensive hotels than the one I was trying at first to use it for. Just 30000 points for the night, I should save the certificate for the ones that want like a 100000 points.


Leave a Comment

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s