If an upgrade were available, why WOULDN'T the FD want to give it to someone. After all, it's not going to come out of his/her hide, and I know of no hotel that rewards it's staff for the number of upgrades they deny.

Because it's called revenue management, and you can't sell a room later in the night that you already gave away.

I feel that browbeating them into it is demeaning.

Front Office managers rely on line employees to lie about this kind of stuff. If you ask to speak to the manager on duty, they'll probably give you whatever you want. (At least, that's how it worked when I was at Hyatt and the managers never backed up line employees."

1. I pull out the Hilton App and show them the availability, adding there must be an error, please check with the manager. (85% success )
2. If they claim it is at their discretion, I get HHonors on the line, lets see what the rule actually is.
3. If that does not work, I request an appointment with the properties actual GM in the morning, hoping he/she can explain to me why this Diamond isn't getting the upgrade he is entitled to, as there is space available. I have never had an unsuccessful result if I managed to meet the GM. Would not help for the 1st night, but fixes things going forward as well as usually gets me a super room for the stay.

The trickier issue is if the next level up is sold out, but other levels are available. IMO, if we all did this, the issue would cease.

Color me self-entitled!

Indeed. It's demeaning for them to force me to browbeat for the entitled upgrade.

Agreed! Having to beg for an upgrade that's supposedly part of the program which we bought into to the tune of dozens of nights and thousands of dollars is not exactly my idea of hospitality, and when I'm doing so I certainly don't feel like a valued customer.

An empty room is not necessarily an available room. An available room is one someone at the hotel wishes to offer. Very many staff and managers at properties view Diamond members with disdain if not contempt. You would do well not validate those reactions. Quite a few property owners and managers have told their staff to upgrade a gold member who has stayed at their property say 8 times in the past few months before they upgrade a diamond member they've never seen before.

"Space-available upgrade to a preferred room"

Like I mentioned, upgrades are a privilege, not an entitlement. Higher floor, corner room, better views are all upgrades. It does not mean at least a one-category up always.

Why would we "do well not validate those reactions"? Are you saying it would be in our best interest to forgo entitled upgrades and allow the properties to violate Honors program rules at will?

You do realize the hotel could put you in the exact category of room you booked on the other side of the hotel and call it an upgrade because it has a different view and they would be fulfilling the letter of the benefit, don't you? An upgrade, per the benefits, does not need to be a suite? There are lots of ways they can give you and "upgrade" and not much you could do, other than complain and it would fall on deaf ears. you could go to another chain and I guarantee you Hilton will never miss you.

depends what level you are. Some hotels sell their schemes on the basis of getting upgrades at a certain level. In that case - although they are always "subject to availability" - they ARE an entitlement (subject to availability).

If it is important to me, I check availability of higher category rooms before checking in, will ask for an upgrade if it is not offered and will politely ask them to "double check" or ask management if they say "fully booked" and I know it not to be true.
I will let them know my disappointment at check out and also respond accordingly in any survey's I'm send.
The loyalty program and benefits are a key reason I stay at chain hotels. Some hotel managers want the benefits of belonging to a chain, but don't want to provide the elite benefits to elites who don't stay with that property regularly. That's not how the big chains work - elite is based on stays with the company not with the specific property. If that's the management's attitude they should remain independent - nobody forced them to join Hilton (insert whatever chain)...
I will not stay at hotels with poor elite treatment again - and I stay less with chains who don't enforce elite benefits across properties, simple really...

I call it more of a promise if available. It is absolutely not a "privilege".

If higher cat rooms are available to book online, does that mean they are available?
Just thinking about the "website is wrong".....