27+ trips..NEVER an upgrade and I have traveled Peak times, Slow times and average times..heck I barely have gotten any of my room requests either.
Sorry - don't mean to laugh at you...more like WITH you. This is totally us. We have been a lot..all different times of the year...all different levels of resorts..and have never been upgraded. We have never asked and have no plans to ask.. I may be odd, but the thought of even asking for an upgrade makes me feel really uncomfortable. The good news... I book the category we want so we are always happy with the room we get. 

For those of you have had your room upgraded at check in, did you ask? How would you ask?
For those of you have had your room upgraded at check in, did you ask? How would you ask?
Thanks everyone for the advice. I am willing to pay for it. Savannah views were not available when we made the resi. I guess my biggest concern was not coming across as rude or greedy. I will be at Disney after all so I have nothing to complain about![]()
Sorry - don't mean to laugh at you...more like WITH you. This is totally us. We have been a lot..all different times of the year...all different levels of resorts..and have never been upgraded. We have never asked and have no plans to ask.. I may be odd, but the thought of even asking for an upgrade makes me feel really uncomfortable. The good news... I book the category we want so we are always happy with the room we get.
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We always do..I don't ask for upgrades and I don't expect them either.We generally book the category we want and that's about it.I have made room requests, and only once have gotten them .As long as my room is clean and not looking at a smelly,fly infested dumpster,It's all good
We were booked at Bay Lake Towers for our first trip with our then little ones (DS's second birthday and DD was 3 at the time, also had DD 13 at that time too) and when I booked the trip I didn't really understand "magic kingdom view". After reading about it on these boards I really wanted that MK view but when I called Disney none were available. When we went to check in DH mentioned that we would love a MK view b/c our kids were little and at least we could watch the fireworks from our room. He even offered to pay for the upgrade. The CM upgraded us to a 1 bedroom/2bath suite on the 14th floor of the CR (concierge level). It was amazing! Best first trip the little ones could have asked for! This was at the end of October and typically it is a "slow" time.
I've also heard that if you pay for an upgrade at the desk you may end up paying full rack rate for the upgraded category (i.e. you lose any discounts you had on your room rate before the upgrade)--so if you're sure you want the upgraded category, you should try to do it before you arrive at the hotel. FWIW we've been to Disney 6 times over the past 20 years and have never been upgraded for free (although we've always loved our rooms!).