These steps worked for me, on my machine, but your results may vary and Apple may change things tomorrow and break this whole process.
So if you are in a similar situation and for some reason need to download new iOS simulators outside of the normal XCode download process, here is how you do it. Since I don’t know what is causing this error and I can’t fix anything on Apple’s servers, all I can do is find a work around. This error even happens to users with “fast” connections. Others have the same problem and there really doesn’t seem to be a noticeable correlation to internet connection speed. Googling around I can tell that I am not alone. After some long period of time trying to download a file, I get a “connection timed out” error. I’ve had problems when downloading iOS updates in iTunes and problems when downloading new simulators in XCode. Blame it on the internet gods (or probably Apple), but I have the hardest time downloading large (like gigabyte size) downloads from Apple’s servers.
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