Hilton Honors Gold and Diamond members normally receive complimentary upgrades at check-in, subject to availability.
Going forward, Hilton will be enhancing how those upgrades are processed. Gold and Diamond members will be notified of their space-available upgrade 72 hours prior to arrival, and will be able to pre-select their upgraded room directly when they check-in via the app.
While it all sounds promising, you might want to temper your expectationsโฆ
Hilton Honors now offers automatic upgrades

Hilton Gold and Diamond members will receive an email and push notification from the Hilton Honors app informing them of their upgrade, within 72 hours of arrival. They will then be able to choose their specific room within the upgraded category within 36 hours of arrival.
All stays of up to six nights are eligible for this early confirmation, which will be available โ in the coming monthsโ at all Hilton brands globally where space-available upgrades are offered, namely Waldorf Astoria Hotels & Resorts, LXR Hotels & Resorts, Conrad Hotels & Resorts, Canopy by Hilton, Hilton Hotels & Resorts, Curio Collection by Hilton, DoubleTree by Hilton, Signia by Hilton and Tapestry Collection by Hilton.
On the one hand, itโs good that the upgrade process will be automated. Under the previous system, it wasnโt uncommon to meet front desk associates completely ignorant of the Hilton Honors T&Cs, who would simply assign elite members the same category they booked.
On the other, itโs not like youโll suddenly be chilling out in the presidential suite. Inventory control still remains very much in the hands of hotels, which presumably set aside a certain number of rooms for upgrades. If the hotel doesnโt block out those rooms, the system canโt automatically assign them.
Hilton Honorโs upgrade policy remains weak

The bigger problem lies with the weak language the Hilton T&Cs adopt with regards to upgrades. While Hyatt and Marriott explicitly state that top-tier elites will receive upgrades to suites where available, Hilton simply says:
Upgrades for Diamond Hilton Honors Members may include upgrades up to โjuniorโ, โstandardโ or โone-bedroomโ suites. Upgrades exclude executive suites, villas and specialty accommodations/floors/towers (which may include, but not limited to, โVista,โ โVilla,โ or โClubโ accommodation types), subject to the discretion of the hotel
This leaves a lot of discretion on the hotelโs side, and consequently, my experience as a Hilton Diamond is that suite upgrades are nowhere as common as my Starwood Platinum days.
Of course, there are hotels which do go above and beyond when it comes to upgrades. Then there are also hotels which will insist theyโre fulfilling their obligations by placing you on a higher floor. Itโs a classic YMMV situation, and I donโt see an automated system changing that.
My experience with automatic upgrades
Hilton has been trialing the automated upgrade feature at selected properties, and I happened to encounter it during my recent VTL trip to Munich. I had booked the Hilton Munich City for one night, and received an email about my room upgrade a couple of days before arrival.
It made me feel warm and fuzzy, but in reality the upgrade was anything but impressive.My room was upgraded from a King Guest Room to a King Executive Room, similar in every way except with lounge access- which I already have by virtue of my Diamond status.


This is exactly what I was referring to in the previous section: if a hotel isnโt inclined to give actual upgrades, then an automated system wonโt change much. If anything, it might even be better to check-in the old fashioned way, where the front desk staff may be empowered to offer elite members something better.
Conclusion
Hiltonโs new automated system takes some of the uncertainty out of the upgrades process, but itโs still up to the hotel how generous they want to be. A reader once emailed the Hilton Singapore to enquire about suite upgrades, and was told they simply didnโt exist at this property!
โIn regards to your request for an upgrade to one of our suites room. As the complimentary upgrade for Honors Diamond member may include upgrades up to โjuniorโ, โstandardโ or โone-bedroomโ suites.
As above categories are no available in our property. We may offer discounted price for Honors Diamond member to guarantee the Family Suite / Executive Suite room upgraded. Our suites are very popular and sell out quickly.
If hotels want to play games with nomenclature, thereโs very little an automated system will do to change that.
Such a shitty reply from Hilton Singapore, shame on them!
We shall spread this nice reply to the world to let the whole world know our Hilton Singaporeโs hospitality
That particular โHilton Singaporeโ will be no longer (good riddance) and a new โHilton Singaporeโ, a completely different property, coming online in Jan 2022.
Though come to think about it, if you are only buying a entry deluxe room why should they give you the suite upgrade if they can sell them. Shame on the person who blames the hotel for following the groupโs T&C. For me as a HH Diamond, i always take upgrades as a pinch of salt and get surprises more often than not, in a good way.