Asking for free upgrade?

We were upgraded at GF once, and it was after I asked. However, I explained that there were only standard rooms available when we booked (true, because we booked with a TA that only had a block of standard rooms), and asked if they had any rooms with a better view available, and, if so, how much it would cost to upgrade. We were told no, but, by sheer luck, a manager was standing close enough to overhear, and she came over, got on the computer, and gave us a different room. I knew it would be good when the original CM’s eyebrows raised halfway up his forehead, and then he stammered that it was a really good view. And it was! Amazing view of the MK. But, it never would have happened if that manager hadn’t happened to be there. I think it also helped that we were, sincerely, asking to pay for an upgrade, too.

We’ve also gotten smaller upgrades, like asking if we could possibly have a room that didn’t overlook the parking lot, when we booked standard. So, not asking for an upgrade, per se, but asking if they can accommodate a particular request, which might mean a small bump to garden view, for example. I think they’re happy to make those changes when they can, and, if they can’t, no big deal.
 
I’ve been 8 times since 2007 and upgraded once. Like both of you, I was upgraded at BWI. It was a 5 night stay, just DH and I. I booked a standard room and was upgraded to a cottage suite! The trip was for my birthday (although this was not noted on the reservation). I was so happy, I cried! It was an amazing room...I wish I could actually afford to stay there. So maybe the trick is to stay at BWI?

Kidding aside, I think upgrades are luck of the draw and it’s probably unlikely that you’ll get one by asking.

Is that the room that’s two levels? I’ve always thought those were so cute!! What an awesome surprise!
 
Thank you everyone for the helpful feedback! Your responses seem much more how I imagined it works.

Pixie dust it is!

Years ago when I was planning our trip to bring our GD on her first visit I had way too much time on my hands and was studying every post on the DIS. After reading so many posts about complimentary surprise I was positive that once we arrived at AKL the CM would take one look at our beaming faces and upgrade us to CL. And then one down to Earth poster crushed my daydreaming self down to Earth by telling someone who dared to post what I was keeping to myself, and BOOM! I called my TA and had him upgrade our rooms to CL. I Book what you knwo you wil be happy with and book it when you know you want it.

FF to a few years ago when CSR still had it's version of CL, I was a cheap traveler trying to work an inexpensive trip in to say Goodbye to the Osborne Lights. I booked a room for us, and called a few days later to book CL. Nope, not there. YIKES! It never opened, and een when I asked at checkin, it was booked solid. No money could purchase what was not available.

Don't get me wrong, I still picture my family and I being whisked up to one of those fancy 2 Bdrm suites I have seen pictures, but never visited, but I know that this is a dream that is not my reality, much like the Hallmark Christmas Movie homes that I always picture as I drag my decorations out. WHat I picture is not what I end up with! LOL!
 
I've never asked and we've never been upgraded. I don't see a problem with asking but it's not something I would do.

I'm one of those people that is fine with whatever I book. If I book standard view and I get a view of a parking lot or a trash can it doesn't phase me because it's what I paid for. I don't book a lower category then put in requests for a water view room when it's not what I paid for.

We've always been happy with our rooms and vacation at Disney!
 

I've never asked and we've never been upgraded. I don't see a problem with asking but it's not something I would do.

I'm one of those people that is fine with whatever I book. If I book standard view and I get a view of a parking lot or a trash can it doesn't phase me because it's what I paid for. I don't book a lower category then put in requests for a water view room when it's not what I paid for.

We've always been happy with our rooms and vacation at Disney!

Agree!

Heck, I won't even fuss if the room does not meet my requests because I know they were just that - requests. (Of course that is also often because I arrive early and if the room is not ready I drop my luggage with bell services and head to the park and don'e get back until late when my room has been assigned and my luggage put in there. But generally I'm a "you get what you get and you don't get upset kind of person anyway as long as what I get is what I reserved and paid for.)

The only time I've been "upgraded" was a Marathon Weekend (might have been when I did Goofy, but I'm not 100% on that). I booked a standard room at CBR on a cast member rate since I worked at The Disney Store. On the Magical Express, I got my room info and it was a Pirate Room. Normally I would have been fine with it, but with the early hours and knowing I'd be tired and sore from the race(s), the last thing I wanted to deal with was the extra frame on the pirate beds, so I went to the desk when I got there to politely ask if I could be "downgraded" to what I had booked and give the pixie dust to a family who would love that room. As others have said, the CM had to get on the phone to the assigners to find out if I could be moved (and the CM at the next station said "I'm with you. That is the one upgrade I would not want, especially on a race weekend where you're participating."). A few minutes later, I had a new room that happened to still be an upgrade to a King in one of the preferred areas - but I would have been 100% fine with a plain old standard room.
 
Book what you want. Disney is so busy these days. Upgrades are rare. Not directed at OP but it seems people feel Disney owes them pixie dust- free upgrades, special occasion upgrades or treats,etc.

People wear buttons expecting freebies for every special event no matter how small. Everyone seems to have one on- sure it’s nice if you get something but to ask or expect is unreasonable.
 
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I'm one of those people that is fine with whatever I book. If I book standard view and I get a view of a parking lot or a trash can it doesn't phase me because it's what I paid for. I don't book a lower category then put in requests for a water view room when it's not what I paid for.

Me too. I don’t get people (not meaning the OP) who book a room, then start asking about upgrades or are disappointed when they get what they booked.
 
Is that the room that’s two levels? I’ve always thought those were so cute!! What an awesome surprise!

Yes! There’s a downstairs living area, kitchenette, and half bath, and the loft has a bed and bath (with a tub and separate shower). Plus those rooms have club level access. It was the best surprise ever!!
 
Agree!

Heck, I won't even fuss if the room does not meet my requests because I know they were just that - requests. (Of course that is also often because I arrive early and if the room is not ready I drop my luggage with bell services and head to the park and don'e get back until late when my room has been assigned and my luggage put in there. But generally I'm a "you get what you get and you don't get upset kind of person anyway as long as what I get is what I reserved and paid for.)

The only time I've been "upgraded" was a Marathon Weekend (might have been when I did Goofy, but I'm not 100% on that). I booked a standard room at CBR on a cast member rate since I worked at The Disney Store. On the Magical Express, I got my room info and it was a Pirate Room. Normally I would have been fine with it, but with the early hours and knowing I'd be tired and sore from the race(s), the last thing I wanted to deal with was the extra frame on the pirate beds, so I went to the desk when I got there to politely ask if I could be "downgraded" to what I had booked and give the pixie dust to a family who would love that room. As others have said, the CM had to get on the phone to the assigners to find out if I could be moved (and the CM at the next station said "I'm with you. That is the one upgrade I would not want, especially on a race weekend where you're participating."). A few minutes later, I had a new room that happened to still be an upgrade to a King in one of the preferred areas - but I would have been 100% fine with a plain old standard room.

I'm the same with the requests. I rarely put in requests and when I do I don't expect to get them. If I do it's a bonus but if I don't I don't even mention it to the CM. (we usually just request specific buildings) I honestly forget what I requested once I'm there. LOL I guess I'm just so happy to be there we just run off to check out the room.
 
We received two upgrades on our honeymoon split stay, but not by asking. First we were upgraded from standard to water view at the Beach Club (and we got a great king bed corner room that felt bigger than the regular BC rooms). We were then upgraded from a standard room to club level at the Grand Floridian.

Several vacations have passed since then, and it hasn't happened again.

I would never ask. Of course, I secretly hope an upgrade will happen again every time we check in after getting lucky once.
 
I stay in DVC studios when I go to WDW. I have never been upgraded....I expect it's because there is limited inventory
 
I've been upgraded several times. I have never asked.

First time was WL for our wedding/honeymoon. We booked 10 days in a standard room (part of our block of rooms) and got upgraded to one of the Honeymoon rooms on the Club Level floor! That was awesome, but we also spent $$$$ on our Disney wedding, so...

Second time was at BWI. I had booked a standard room using the military discount for 5 nights in mid May. We were upgraded to Club Level.

Third time was a view upgrade at BC, Club level. We had booked Standard View, Club Level and got a full on water view room right above Stormalong Bay.

Fourth time was at Coronado. We booked standard and got a preferred room.

Fifth time was at the Dolphin. Booked standard, got upgraded to upper level "Resort View" (at the center top of the triangle).

Sixth time was at the Disneyland hotel. Booked discounted standard room for 2 nights in July, upgraded to a 1 bedroom suite!

Once I booked a woods view room at WL and was given a handicap room on the ground floor that I didn't like (had a weird setup and was at the far end of the long hallway, and felt really dark/dingy). I went back to the front desk to ask for a different non handicap room on another floor (was solo and don't like ground floor access rooms in that situation) and was reassigned to a courtyard view room on the 5th floor.

Also, we were staying at GF in a Lagoon view room and they assigned us a dormer room in Big Pine Key without a daybed (which we needed). After a LONG time on the phone with the room assignor, ws were given a theme park view room in Boca Chica.

The ONE time I asked about an upgrade, I was quoted the rack rate upcharge. I said no thanks.
 
I am guessing your coworker likes to brag about a LOT of things regardless of whether or not they are true.

I know a girl (friend of a friend) that says she gets upgraded every time she goes on vacation (non Disney). But she asks and always gets it. She's a very pretty girl and I'm pretty sure she flirts her way around it. We all went on an Caribbean vacation together two years ago and she sure enough was upgraded to a suite from a standard room. She said before we left that she would get an upgrade because she "always" gets upgraded and sure enough she did.
 
IMO the days of talking your way to an upgrade or pitching a fit about your assigned room at WDW to get an upgrade are a relic of the past for a couple of reasons:
Occupancy is high, thus there’s less ability to move one group without impacting some other group’s stay. Rooms are supposedly assigned a couple of days before arrival (although w/ my recent Dec. stay I had 3 different villas assigned when I took my phone out of airplane mode - so some rearranging was happening day of before I got there!) and it’s like a giant jig saw puzzle, the check in person most likely doesn’t have the information they need to make a change w/out messing up the puzzle.
That said, sometimes people are upgraded for operational reasons - most often a bump up in view category - because Disney may over sell lower priced standard views planning to bump some up. In the past (but not recently) I’ve also read of people being bumped down to standard from preferred at the values.
Personally I’ve been upgraded twice in about a dozen trips, first about 10 years ago at POFQ to a water view because when we went to our assigned garden view room at 10 pm when we arrived the beds were unmade, trash was in the room from previous occupants, so they moved us to what was available which was water view. The second was around 5 years ago when I was upgraded to water view from garden view at the YC - it was a pre assigned upgrade - loved that room!
 
Yes! There’s a downstairs living area, kitchenette, and half bath, and the loft has a bed and bath (with a tub and separate shower). Plus those rooms have club level access. It was the best surprise ever!!
Oh that sounds amazing! *Added to bucket list* :)
 
As someone who works with the general public in a customer service role I can say I go out of my to “surprise and delight” those who do not ask. All I require is a pleasant experience with someone and I’ll do all I can to make them happy in return. In a Me Me Me society I reward those who don’t make it all about themselves and are just genuinely nice people (which seems to be the anomaly these days, sadly).

Just my .02. YMMV.

Good luck OP - here’s a little pixiedust: for you.
 
In the many times- to be honest I've lost track of how many- of all of the times we've stayed on site in the last 10 years or so and we've stayed at Values, Moderates, and Deluxe. The only time we were ever "upgraded" was when a Value was overbooked and they bumped us to a preferred location at another value. And it wasn't really an upgrade because of all of the screaming teens walking by our room on the way to the main building at all hours. Other than that, we have never received an upgrade. Even on our last trip to Animal Kingdom Lodge and we paid for a standard room and were given a partial savannah, that partial savannah was already assigned before we even walked through the door.
 



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