Anyone every have any luck requesting a free upgrade at a Disney resort?

No. I have a friend who does the room assignments, she said they do not upgrade people who ask but do occasionally pixie dust someone. She said it’s the same reason I got a ton of pixie dust when I got engaged there. She said you never asked, didn’t wear a pin or the bridal ears. She said those people are clearly asking for something and are less likely to get anything other than a free cupcake at the end of a meal.

How would they know you were celebrating something like getting engaged unless you were wearing a button? I mean you could just come out and tell them, but that's kind of the same thing.

I do see her point regarding people who outright ask for something.
 
How would they know you were celebrating something like getting engaged unless you were wearing a button? I mean you could just come out and tell them, but that's kind of the same thing.

I do see her point regarding people who outright ask for something.
At check in they ask, “are we celebrating anything”
 
I would definitely not go in expecting or requesting it. The main reasons they upgrade in the first place is due to maintenance or them overbooking a category and sometimes, but rarely, due to pixie dust. In the 16 years we’ve been going we’ve been upgraded once and it was due to overbooking. We were booked at CBR during FD in a standard room in 2016. When we arrived they stated they overbooked so moved us to the pirate rooms but it was our anniversary so the CM stated a pirate room is not acceptable for a couple without kids on their anniversary. The CM proceeded to upgrade us to AKL but didn’t say which category. When we arrived we were given a Savannah View on the first floor, I was so shocked. I was crying in the car all the way from CBR to AKL because I was so shocked. We’ve never been upgraded again since, not even the room category and I’m ok with that. We book what we want and are happy with that.

To me to expect it or ask for it is just a sign of entitlement.
 
How would they know you were celebrating something like getting engaged unless you were wearing a button? I mean you could just come out and tell them, but that's kind of the same thing.

I do see her point regarding people who outright ask for something.
He proposed to me in MK in front of the castle during the fireworks and a Disney photo pass person captured it. I’m guessing he made a note in their system because we never said anything but anytime we scanned our magic bands the CM saw it on our file. If you are celebrating something and let Disney know, anytime you scan your magic band the CM can see it.
 

How would they know you were celebrating something like getting engaged unless you were wearing a button? I mean you could just come out and tell them, but that's kind of the same thing.

I do see her point regarding people who outright ask for something.
There is an option to add a celebration to your booking.
 
How would they know you were celebrating something like getting engaged unless you were wearing a button? I mean you could just come out and tell them, but that's kind of the same thing.

I do see her point regarding people who outright ask for something.
When we call in to make our reservation, most of the times they will ask if we are celebrating anything.
 
With Disney resorts often being quite full, it's not likely to happen. But something we say when going to Disney - it never, ever hurts to ask.... Just be respectful and unsurprised if the answer is no.
OP, if you're still reading this thread, if you ask for an upgrade, do NOT ask for a "free" upgrade. Ask how much it would cost to upgrade your room. The odds of them saying "nothing" are near zero.

We've been upgraded a few times, but not because we asked. It just happened and we weren't expecting it. This past May we were disappointed with the resort we booked and moved to a more expensive resort--and paid for the difference.

The only pixie-dust-like thing that we got was that resort #1 didn't charge us for the few hours we were there before we moved. We did not ask for this and weren't expecting it and were quite surprised by it.

The only time people are upgraded to a higher level resort is when Disney does it for any number of reasons--unplanned maintenance, overbooking, and hurricane are a few of the reasons I can think of offhand--but never because someone just asks Hey, can I be upgraded for free to a better resort? Don't do it.
 
A few years ago I was checking in at Caribbean Beach with my husband. The front desk lady said, "Lucky you" you've been upgraded to a pirate room... We start walking all the way to the end of the resort, what a hike it was !! We got to the room and started putting our stuff away and laid on the bed for a minute and the beds felt like rocks. We headed all the way back to the main check in area and asked to be "un-upgraded" out of a pirate room.... As its the furthest room away and the beds are awful... They were completely booked, so they moved us to Art of Animation to 1- Bedroom Suite... Now that was an upgrade :)
 
Years ago on our first trip with our daughter (who was turning 4), we had booked a room @ Poly (whatever the lowest category was) and at check in, someone met us and walked us over to the club lounge. We had been upgraded to a castle/fireworks view w club access. It was amazing. We spent every night on the balcony watching the water parade and fireworks as our daughter wanted to go to sleep early. Can't imagine a better club lounge than at the poly. I recall the high ceilings and big picture window.

And once at DL, we had a 1 night reservation @ the DL hotel so we could get early access for 2 mornings (we checked in at like 6am) after a few days @ HoJo's. They upgraded us from the standard view to a 1BR suite. We've never asked for upgrades when at Disney which makes the pixie dust even more magical. Don't know if we'll ever be upgraded again but it's already a treat just to be at a Disney resort.
 
Many stays, nothing. Except last time, last November - no room ready text as it was only noontime, so stopped at front desk at YC to see if she could get us in any room early. Going to Christmas party and just wanted to settle somewhere as soon as possible. Dont care where. Standard room booked with earliest room box checked in online check in. She did. Got to room, gorgious front facing water view.
 
As others have said, I don't recommend asking for a free room upgrade. Book a room that you would be happy with and then if you're upgraded - BONUS!

The only time we were upgraded was 2 years ago - on the way to the airport we got word that our flight was cancelled. Decided to turn the rental car around and stay another night in Disney- it was already 2:00pm. Booked a Little Mermaid room on the app - it was actually the cheapest available in all of Disney property. We received our room assignment right away and it turned out to be a Cars Suite. We loved it, but couldn't make really good use of it since we had to leave the next day mid-morning for the airport.
 



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