Middle Age Miles

Amex Hilton Ascend – Free Weekend Night and Upgrade Strategies

amex hilton ascend strategies strategy free weekend night certificate double dip benefits upgrade downgrade aspire ascend
Middle Age Miles’ next stay using a Hilton Free Weekend Night Certificate from the Amex Hilton Ascend card will be at the elegant Waldorf Astoria Las Vegas (pictured: 23rd-floor Skybar)


Last week, we published an article about Hilton Free Weekend Night Certificates earned through $15k spend in a calendar year on the mid-tier Amex Hilton Ascend card.

In that article, we covered three key data points:

  • Our most recent Free Weekend Night certificate arrived just 3 days after we hit the $15k spend mark
  • Resort fees are waived when you use a Free Weekend Night certificate
  • You might be able to book a room past the expiration date of a certificate, if you call in before the certificate expires

In response to that article, we received an excellent comment from reader Rob, which led to a fun dialogue about Amex Hilton Ascend free night and upgrade strategies. We believed the exchange and strategies were article-worthy. So, with all appropriate hat tips and props to Rob, who’s certainly a co-author of this article, let’s review our thoughts on Amex Hilton Ascend strategies.

Strategy 1 from Rob – Spend Close to $15k on the Amex Hilton Ascend During the Year, then Wait to Hit $15k Until the Last Minute or When You Need the Certificate

The main topic of our article was how quickly Hilton Free Weekend Night certificates arrive once you hit $15k spend during the calendar year. An ancillary point here is that once the certificates are issued, they are good for one year only, and then they expire (we also explored that Hilton may be willing to extend the certificates under certain limited circumstances if you call before the certificate expires and have a reason and redemption in mind).

Rob hit upon a valuable strategy to “extend” the time in which you can use your certificates – spend close to $15k on the card during the calendar year, and then wait. You can spend the last few dollars on the card late in the year, or if you have a good use for a certificate in the meantime, you can spend the last few dollars when you need the certificate. Here’s Rob’s comment (slightly edited):

We have 3 Ascends between my wife and I and I’ve taken all of them up to about $14,800 of spend. Since most of our travel is already booked for this year, I figure I can just charge $200+ per card toward the end of the year and delay the onset of the 1 yr expiration clock. But if something pops up in the meantime where I think the certs will come in handy, I can always spend the extra $200 when I need it, get the cert and use it. So it’s almost like extending the life of the certificates by 7 months if you play it this way.

We love this strategy. It gives you a lot of optionality on either delaying the start of the 1-year expiration clock on the certificate, or pouncing quickly when you see a good redemption opportunity.

Strategy 2 from Middle Age Miles – Also Use Strategic Opportunities to Upgrade to the Aspire Card, and Pursue a Downgrade/Upgrade Strategy

We love Rob’s strategy, but we ourselves hadn’t quite followed it. We actually hit our $15k spend in mid-May, even though we didn’t have an immediate use for the Free Weekend Night certificate. Why would we do that? It’s part of a larger strategy to pursue a strategic downgrade/upgrade strategy with our Ascend and Aspire cards.

Our comment replying to Rob explains:

Hi Rob – Thanks for the insightful comment. Brilliant strategy. I did something similar but with a slight twist. Like you, I took it up to about $14,800 early in the year and waited. Why did I strike with the last $200+ to cross $15k now instead of waiting further? It’s part of an upgrade-downgrade strategy. My Aspire hits its 1-year anniversary around July 1. When the AF [annual fee] hits, I want to downgrade it to Ascend, and then I’ll start working on spending $15k on that card to get another free night. In the meantime, I’ll be hoping for an upgrade offer on my current Ascend. I wanted to have already hit the $15k so I can upgrade on a moment’s notice if I get the upgrade offer. If no upgrade offer comes along, I’ll just sit tight and then upgrade right before I have a Hilton stay where Diamond status would make a difference to us.
I went ahead and hit the $15k this week because I wanted to leave plenty of time to receive the certificate before my current Ascend goes on the “upgrade watch clock” on July 1. I figured 6 weeks would leave plenty of time for any complications to work themselves out. Turned out I needn’t have worried! I easily could have given myself another month or more.

Let’s break this down a little more. We hold both of the Amex Hilton fee cards, the mid-level Ascend and the premium Aspire. We figure that if we upgrade the Ascend to Aspire mid-year and downgrade the Aspire to Ascend, we can take advantage of each card’s features twice each year. For example, we can spend $15k on each card during the time period when it’s an Ascend and end up with 2 Free Weekend Night certificates that way. In addition, when we upgrade the Ascend to Aspire, we should get another Free Weekend Night certificate, an additional $250 airline fee credit to be used during that calendar year, and hopefully an additional $250 resort credit (although that one’s based on cardholder year, so it may be a bit more tricky).

We’d love to have more Hilton Free Weekend Night certificates to use at the spectacular Waldorf Astoria, Beverly Hills!

The other tricky part is whether or not we can get an upgrade offer for an Ascend card, once we downgrade an Aspire. This will necessitate a period where we have 2 Ascends and no Aspire (because we won’t get an upgrade offer for the Ascend while we hold an Aspire, as best I can tell from all research and data points we’ve read), and hoping for the best.

We’ve read some data points of people routinely receiving offers to upgrade Ascend to Aspire after downgrading, within 3 months or so. That would be ideal in our situation. On the other hand, Rob noted that he’s been waiting more than a year for an Ascend-to-Aspire upgrade offer that has never come:

I’ve been keeping my wife’s 2 Ascends hoping for an upgrade to Aspire to come along, but she hasn’t gotten any upgrade offer for Aspire. I too was thinking if she gets an upgrade offer for Aspire, I would then finish the spend on the Ascend, get the [free night] certificate for $15k, then accept the upgrade offer to Aspire and get the free certificate that comes with that one also.
Unfortunately, I’ve been waiting over a year for an upgrade offer for either one of her Ascends and nothing so far. I was half wondering if spending 15k on each of them is acting as a deterrent, like maybe Amex thinks they don’t need to offer an upgrade because we are already spending nicely on both of her Ascend cards.

We hope we have better luck with an Ascend-to-Aspire upgrade offer than Rob’s wife!

But while an Ascend-to-Aspire upgrade offer would be nice, eventually we would choose to upgrade our original Ascend to Aspire anyway, with plenty of time before year-end to get the free night certificate that comes upon approval or upgrade to Aspire, plus use the Aspire yearly credits.

For now, this is all a thought experiment, not yet implemented in practice – but we believe it should work, based on all we know about how these cards and their benefits operate.

We hope you’ve found this article to be interesting and thought-provoking. As we go forward with implementing the downgrade-upgrade strategy (experiment?) we’ve identified here, we’ll continue to publish articles to provide you with data points. Hopefully things will work out well and we can double-dip on the benefits from both the Aspire and Ascend cards within the same calendar year!

And finally, many thanks to Rob for the great comments and helping us out with this article!

What do you think of the strategies we’ve outlined here? Do you have any data points that would reflect on likely success or failure of our strategies? Please share with us and other Middle Age Miles readers in the Comments!

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3 thoughts on “Amex Hilton Ascend – Free Weekend Night and Upgrade Strategies

  1. Rob

    Great job! Thanks for the shout out. Hopefully the upgrade offers will come along and then I’ll try the MAM downgrade/upgrade strategy too!

    1. Craig at Middle Age Miles Post author

      Thanks Rob. Your comments and thoughts provided great insight for the article. I really appreciate it. We’ll keep our fingers crossed for good upgrade offers to come! ~Craig

    2. Craig at Middle Age Miles Post author

      Hi Rob – I wanted to let you know that I just successfully upgraded my Ascend to Aspire, using the link that Doctor of Credit provided in this article from yesterday: https://www.doctorofcredit.com/publicly-available-upgrade-you-american-express-hilton-honors-to-the-ascend-or-aspire-and-get-150000-bonus-points-ymmv/

      I’m going to write about it and break down the offer terms, but I wanted to let you know right away in light of our conversation a couple of weeks ago when you mentioned that you were hoping for an upgrade offer for one or both of your wife’s 2 Ascend cards.

      Good luck and let me know how it goes! ~Craig

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