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iTunes Match never connects on iTunes startup

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This is the lovely non-descript icon sitting next to my Music library every time I start up iTunes. After startup, I don't have the ability to add songs to, update or download from iTunes Match. I can click the icon and it starts swirling like a barber-shop pole, but stays that way forever. I have to actually turn iTunes Match off then turn it back on again to access my music in the cloud.


I've installed iTunes on other computers, as well as virtual machines on my current computer, and they all work flawlessly the first time.


I've uninstalled and reinstalled all Apple software (including all the little things like Bonjour... basically everything published by Apple has been deleted and reinstalled), nothing seems to work.


I suspected it was my WLAN card's drivers (I have an Alienware laptop with a Bigfoot Killer 1103), as they initially caused problems with iTunes 10.5, but after uninstalling them completely, shutting off my WLAN card and connecting via cable to my router, I still get the same problem.


My OS is Windows 7 x64. I installed iTunes on a Win 7 x64 virtual machine and it worked just fine, so I don't think it's the OS.


Has anyone else had the same problem?

Posted on Dec 2, 2011 1:48 PM

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37 replies

Feb 11, 2012 11:11 PM in response to zlightbulb80

I replaced one of my hybrid HDDs with an SSD and reinstalled Windows. I had to reinstall because I originally had two hybrid HDDs in RAID, and now I just have one SSD and one hybrid HDD, and Windows doesn't like it when you swap out the underlying disk system from underneath it 🙂


So in other words, my iTunes match works perfectly now. I will definitely be keeping an eye on it in one month to see if the problem returns like before.


The only thing I think we have here in common is Windows 7 64-bit, am I right? If so, it still wouldn't make much sense as to what the problem is, unless it is some kind of Windows subsystem that gets wonky and interferes with iTunes...

Feb 12, 2012 12:49 PM in response to Locust76

So, good news, sorta... the good news is that after upgrading my hybrid HDD to an SSD, iTunes Match now connects on startup like it should.


Strange, though, that it didn't work the first time I tried. I basically cloned my Windows partition from the 9th of February to my SSD today. When I booted from it, iTunes exhibited the same problem: iTunes pops up, thinks a little, craps out and shows the weird cloud icon.


I then closed iTunes, right-clicked the iTunes icon and chose "Run as Administrator." Same problem, so I turned iTunes Match off and then back on again and closed iTunes. After that, I opened up iTunes normally (not as Administrator) and it works!


So, I'm not 100% sure if that's the actual problem solution, or if it's a combination of getting rid of my hybrid HDD and then running it once as admin, turning match off and on again....


Maybe one of you could try that out and post the results here?

Feb 14, 2012 5:40 AM in response to sizemoresr

So we both had SSDs (well I had a hybrid, but it stands to reason that after ~1 month iTunes would have gotten cached to the flash memory) and we both had the same problem.


I wonder what it is about running as Admin that solved the problem? From what I know, all the iTunes files (library xml files, .plists, library content) are user-owned files, so iTunes when run as a user should have full access to all necessary files...


The only thing I can think of is that since I've been moving my iTunes library from computer to computer, that maybe some kind of permissions problem did actually manage to creep in. Sizemoresr, did you move your library from one computer to another as well?

Feb 14, 2012 6:04 AM in response to Locust76

I don't think the hard drive speed has anything to do with it. This has happened to me on every Windows machine that I've installed iTunes on, SSD or rotational. It seems like there is a problem with authenticating to the iTunes Match service on Windows iTunes after a few subsequent launches. It does not happen on any Mac that I use.


Here was a good experiment. I had a Windows 7 machine with iTunes loaded on it. iTunes Match was configured to run on it. After one or two launches, iTunes Match would fail every time I ran iTunes. I had to turn off and turn on iTunes Match on every launch. On the same network, with the same version of iTunes, a Mac never has the issue.


I really think it's a bug in the Windows iTunes code that relates to authentication with the service. It could be a bad SSL root certificate or something. If someone can get a network capture of the traffic when it happens it would probably go pretty far toward resolving the problem. I've since given up that Windows 7 machine to another employee and I'm using only the Mac. That solved my problem 🙂

Feb 14, 2012 11:03 AM in response to Locust76

My Windows 7 (64bit) and Windows 7(32bit) laptops both have this problem. I get the barber pole icon and greyed out "download" icons until I remove/readd Itunes Match. I've tried the Run as Administrator workaround and it didn't change the behavior. Update Match doesn't work. The 64bit Windows laptop is new and was added to the Itunes Match account just a month ago, the 32bit Windows laptop was added when I first setup Match in December.


My Macbook and Ipad never have this problem.


The remove/readd is fast and always works .. but a pain.

iTunes Match never connects on iTunes startup

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