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

I have got a water view King at Yacht club twice (same room) for my Farts trip,
Inquiring minds want to know - what is a Farts trip?

didn’t book that level, got a WL Fireworks King with a std view booked. Didn’t asked for it.
Key words, didn't ask for them. You are usually moved because it works for Disney operationally or the old room was being transferred to someone else for various reasons. Win-Win for Disney if they can make two guest groups happy while filling rooms.

Last Spring I did fax in a room request for my AKL stay. I had std view and asked for if possible a partial animal view. I mentioned that I was celebrating 5 years of being cancer free, got a Savannah view.
You didn't ask for an upgrade, you were asking for a particular group of rooms within the category you booked. That is just just location request, like floor level or close to bus stop. They likely bumped you because it worked for them and your celebration got you picked over someone else. A perfect storm for the room assignor.
 
I've never had the temerity to ask for an upgrade -- just for a particular location within the category I booked, and I'd say those have been granted about 3/4 of the time. Anecdotally, friends in hospitality tell me that people ask for free upgrades with such regularity (and in many cases, with such rudeness and/or a sense of entitlement) that they really don't give them to anyone on request anymore, unless it's a VIP or someone they have reason to want to do a favor for. (Case in point: my brother-in-law happened to strike up a conversation with a CM when he was checking into a standard room at Art of Animation a few years back, after noticing that the CM's home town on their name tag was the same small town in central NY that he had grown up in. It turned out they knew tons of the same people, and they had a good time reminiscing. By the end of the conversation, the CM offered to switch them to a family suite - for no additional charge - the following day, when a bunch of them were expected to become available. That's how my sister's family ended up with a huge upgrade!)

The last time we visited WDW, we received an unsolicited upgrade, from a garden view room to a beautiful water/fireworks view at Yacht Club. It may have had something to do with our celebration of our 20th wedding anniversary, which was marked on the reservation -- but then again, we've had all sorts of other celebrations on various reservations over the years (anniversaries, birthdays, etc.), and never got an upgrade before, so it may have been just a coincidence. If you are celebrating something, I would recommend noting it on the reservation or making mention of it in your room request: perhaps someone will be moved to pixie dust you!
 
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During the great recession, we stayed at the Polynesian Mid December. I asked them what was the hotel occupancy since the resort seemed so empty, they told me less then 20% that week. I asked them if I could possibly upgrade my room. The cast member said, absolutely(at no additional cost), and ended up putting us on the third floor of Tuvalu with a perfect view of the castle( sure beat the garden view). When my wife and I were celebrating our 20th anniversary, they upgraded us from the sugar loaf concierge to the main building concierge at the Grand Floridian( they did that at the front desk when they asked us if we were celebrating anything special during the trip). You never know, sometimes it doesn't hurt to ask, and sometimes they go the extra mile to make your stay more magical without having to ask :)
 


I’ve been upgraded twice - here’s how.

I wanted the cheapest room at a Disney hotel but only the more expensive rooms were available. I kept checking, often several times a day. As the day got close, a cheaper category of room suddenly became available. I booked this.

Both times I did this (once at Caribbean Beach Resort and once at Coronado Springs), I paid for the least expensive category of room but was placed in the most expensive category of room.
 
Disney and Free don't belong in the same sentence lol

But honestly, why would anyone even expect a free room upgrade at Disney right now? It happens at hotels that have loyalty rewards at certain statuses, but even then it isn't promised. I wouldn't even have the gumption to ask for a free upgrade, because I'm only entitled to what I paid for. Nothing more.
 
I have had it happen three times.
All three where because the prior guest.
damaged the room, not from asking.
Twice I was moved to another resort, once I was upgraded in both room size and View, 1br lake view to a two bd magic view …

I have never thought to just ask at check in
 


I would think that DVC properties are (maybe) the most unlikely to give an upgrade (so many owners clamoring for early entry, specific room requests etc.) The only time we got a better room was on a cash stay at BC. My DD had just graduated and when we checked in, we were asked if we were celebrating. DD chimed in and said she had graduated. Now if that made the difference from our standard view to a lakeview..... who knows. But we enjoyed it!
 
Last year we had a split stay due to a trip extension. We started at BRV, and were upgraded from a studio to a 1 bed with the new renovation. I about fell over when we entered. We were on rented points and this caused up to buy a contract there 🤣 We moved after 3 nights there over to WL hotel side and had a std view booked but were upgraded to a fireworks view. Serious luck for us that trip.

We’ve been upgraded to CL once also. Probably the reservation CM feeling sorry for us when I had to reschedule my DH’s birthday trip 3 times!

I truly feel like letting CM’s pixie dust you on their own, I’d never ask. They deal with so much from entitled guests these days don’t take the joy out of the pixie dust!
 
We've never asked for a 'better' room, but we have asked what else was available in the same category. Last week, we were booked at the Poly. The room wasn't ready, it was on the second floor, a bit further from the monorail and was facing construction. We asked if there was anything else available and we got a room that was ready, on the first floor (with a patio), closer to the main building and didn't have too much construction going on. To us, those were all 'upgrades' even though it was the same room type.
 
The only thing I'm gonna request for our upcoming AKL stay is something close to the lobby, I'd consider that a win lol.

At Riverside in '19 when we checked in the CM upgraded us to one of the princess rooms but I didn't ask for anything. I have two boys hah, but they were pretty little so still thought the light up headboards were cool.

I wouldn't ever ask for an actual upgrade in room class unless I changed my mind at check in and was going to pay for it. I still don't even like asking for a military discount at places, but I'll gladly accept if they offer.
 
My sister and I were upgraded to a preferred room our past trip not long ago! It was one of the best things that could have happened.
We did not ask for it, it came about from a conversation with our driver on the golf cart from bell Services!! He stated he could make a call and next thing we"re off to our "new" room,
 
NOTE: We have been going to WDW for years and I know requests are not guaranteed and I NEVER expect to be upgraded.
This is just based on our experience in 40+ trips we have received a room upgrade a number of times. i.e. Standard to garden or pool, garden view to water view etc. First, I do not just go to the CM and ask for a room upgrade, and like all the previous posts mentioned I also believe you will be told no. When we make our resort reservation, we always add a couple of room requests and if the room assigned to us is not close to where I was hoping, then I will try and get a better room. Last year is a good example, we were staying at POP and was texted our room # towards the beginning of our 7.5 HR drive to WDW and it was not where we were hoping to be. Once we arrived, I went to the front desk and was hoping (not expecting) to get a better location and not a room upgrade. I told the CM that we added a request for a room "near Hippidy Dippidy pool" and the room we were assigned was pretty far away (Bldg 7) and I was hoping there may a different room that may be closer to that pool? She said that she will check and after looking for a minute on her PC, she excused herself and walked over to the manager. When she came back she said they can switch us to a room closer to the pool area, I told her that would be great and our DDs will be excited about it. Our new room was #4133 and it ended up being a preferred room category.
I will say that for me personally I would have been happy with building #7 because it was a LOT closer to the parking lot where we had to unload all of our luggage. LOL
 
We have never asked for an upgrade. Occasionally we have been moved up one room category, such as standard to preferred at a value, but it was total pixie dust on the part of Disney. I never book hoping I will get upgraded, and I wouldn’t ask unless I was asking for a paid upgrade.

Only once in dozens of trips have we received what I would call a genuine free upgrade. We were booked at CR in late September just before one of the big anniversaries (I think maybe the 25th). We were there for ten days, checking out on the 30th of September. We were moved from the cheapest garden wing room to a multi room suite, and didn’t realize until we went into the room. We always figured that there was some VIP coming in for the anniversary and they wanted a guest in that room who would be checking out the day the VIP checked in. We really enjoyed that upgrade!
 
In 2018 I was at All Star Movies with my young kids. We were unfortunate enough to be in the same building as a large tour group and it was a nightmare. They kept us up all night. The next day I went to the front desk and explained what happened (I had also been there in the middle of the night) and asked if we could be moved to Coronado. However, I was very nice and said I'd be happy to pay the difference. The CM got me a room at CSR for free and even paid for a cab to take us over.

I certainly would never expect a free upgrade, and I don't think I have the chutzpah to ask directly for it! But we've had some really great CMs over the years give us some amazing pixie dust.
 
Never asked for a free upgrade but we've been pixie dusted four times! First time we booked a standard view at the Polynesian and got upgraded to a theme park view! Second time we booked 4 waterview rooms at BC and were upgraded to club level, third time we booked Sugarloaf CL at GF and were upgraded to the Main CL and last time we booked standard view at YC and were upgraded to CL.

Now this was 4 times in 28 trips so it wasn't something we were expecting!
That’s cool! Even once was awesome. We also once got to tour the inside of the castle and I thought I took pictures only to realize I never put film in the camera!
 
About 10 years ago we had a Contemporary club level bay view reserved. We mentioned we were celebrating our 46th anniversary and asked if there was any pixie dust. We were given a MK view club.
 
My parents were upgraded twice, both times from the least expensive view to concierge. They didn't ask, but they were celebrating their anniversary both times, over 60 years. There may be a joke somewhere in there about marriage and upgrades.
 

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