So much frustration to unpack:
So I went with a travel agent (first time) who booked us 12 nights between two resorts. She talked about booking stuff for us (dining etc). I expected I’d get a reminder that my 60 days was coming up, and an offer to help book stuff. It’s on me that I totally miscalculated our 60 days, and realized on day 60 at 10:55 pm. I dashed online and realized that I could only book for the first part of our split stay, not the second. Emailed travel agent who said, correct, you or I can call Disney in the morning to see if they’ll extend your window. I called Disney and got through and the CM said sorry, can only book for the first half. So I asked the CM, wait, so if I book another room for the entire duration will I be able to reserve 60+10? And CM said, sure, you can totally do that. Not wanting to miss ANOTHER morning attempting to book, I got online and quickly booked ASSp for the entire duration of our stay to get my 10 days. But then when I tried to book dining online it still only let me book for the first half of the split stay.
I called Disney again and while I was on the phone, magically my (now)59+10 window appeared! Woo hoo! So I booked something we wanted at 59+9, so I told the CM, “no problem, all sorted out!” Hung up the phone, when to book something else, and now I can’t book anything past the first half of our split stay. And phones are closed now. I’ve tried logging out, logging in, clearing cache, rebooting. Nada.
So many morals to the story.
- It’s your job to know your own timeline, don’t rely on a travel agent.
- Beware the split stay curse on dining booking windows.
- Try to figure out stuff online when Disney phone lines are open, otherwise waiting to get stuff sorted out is basically torture.
- Disney IT is SUPER glitchy. Like, atrocious by comparison given how amazing so much of the their other systems level stuff is.
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Sorry you had such a hard time. Hope you get it all worked out tomorrow.
Yes, Disney IT is definitely glitchy.
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Thanks for the sympathy! It’s a totally first world problem and it’s also totally on me for not planning better. I’m just kicking myself and now I have to get up in a few hours to try to get a human on the phone to get it sorted out… and it’ll actually all turn out just fine. 
(Except now it won’t even let me book dining for during my FIRST stay. )
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Grrrr. You’re correct, it will all work out.
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Are you using the app? It works better for me.
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Your TA volunteered to call to see if they would extend the window? I ask because although the rule has been “tow windows” there have been lots of recent reports of being transferred to “guests services” to open the whole window.
Just finished with Guest Services. Although I have a 12 night stay at ASSp to get the full window she said, “You’re not going to stay at two hotels” then offered to book a couple dining reservations during our stay. I asked about extending the booking window so I can do it myself and she chuckled and said, “No can do.” In good news my phone screen wasn’t working so I couldn’t leave feedback because I would have been unkind and I know the poor CM on the phone was just trying to do her job.
In good news, we’re going to Disney and we will be fed.
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Oh my gosh! I didn’t even know I could book from the app! Thanks for the tip! <3
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No problem - search for the restaurant and book from its page.
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The other trick is try to go incognito and/or a differnet browser. The booking wi dow is notorious for opening and closing. Disney afds so many cookie they can’t figure iut ehat yiy are entitled to.
Of.course my booking day, I opened each ADR in an incognito window and Disney algorithms thought my acciunt had been hacked and shut me down 
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Okay last follow up - I actually got pretty much what I wanted and had no reason to be so grumpy on the phone (I’m sure I was) so I sent Disney Guest Services an email with references (time of phone call and reservation reference numbers) and asked them to track down the poor CM and apologize and thank her for the help. Also, thanks @missoverexcited - the App works great!
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