I'm (as of this week) running the public version of 10.5.1 and was still having issues until the fix. Did you enable iTunes Match in the Store menu item? Also it looks like if I select tracks that have already been matched and others that are waiting, I don't get the "Add to iCloud". Did you enable the menus in Step 2? Other than that futz around with it a bit starting and stopping iTunes Match...there doesn't seem to be a foolproof way to get it working other than tinkering.
Ok and yes, I did enable Match in Store -- it's the only way you can enable the iCloud columns to view track status (waiting, matched, etc). When I had Match turned on (I have since given up and am waiting for a refund/cancellation of service from Apple) I did start/stop several times and still couldn't see "Add to iCloud" when right-clicking a track or a selection of tracks on "waiting" status. That was the final straw before I gave up on Match.
The steps as outlined by Andrew Gould has just worked for me. I am on a Windows 7 PC. Did not restart itunes or computer. Simply right clicked on "error" and "waiting" files and selected "add to icloud". Like he said not a fool proof, official, or even neat solution but it just got the job done for me and for that I am grateful. Hope it works out for you guys. I also hope that apple fixes this issue so that when other files get added or when match ups it cap to 50,000 (i can dream can I?) this problem will not occur again. Thanks!
I had the same problem on my iMac - Enabled iTunes Match it appeared to setup. Next day I launched iTunes and the process ran again. This time it got "stuck" or "hung" at step 1.
After trying a couple of differnet things, the "fix" for me was that I needed to re-create the iTunes Database:
Ater re-creating the iTunes Database, the whole iTunes match setup completed in 4 hours - I have a 17K iTunes music library.
Here's a brief summary of how I would enable iTunes Match:
1. In iTunes, disable the Genuis.
2. Run the Disk Uility and rebuild the disk permissions.
3. Restart your Mac.
4. Re-create the iTunes database per the above referenced KB article.
5. In iTunes, enable the Genuis - wait for it to finsih BEFORE continuing.
6. In iTunes, enable iTunes Match.
7. When iTunes Match has completed setting itself up - you will see a completed screen that you click <Done> on.
8. Restore your iOS apps, books, custom rings tones, moives, TV Shows, etc. to the iTunes library. For some reason iTunes ony re-creates your music library and doesn't include any other media. It doesn't delete it, just doesn't recreate it in the library. You can manually add it by going to the following path:
In the above ~ = your Users home directory on Macintosh HD
Once inside the iTunes Music directory you will see folders for each type of iTunes media. All you need to do is open the folders, select all and drag and drop into the iTunes Library in the iTunes Application.
9. Check for App updates for your iOS apps in iTunes.
10. Enable iTunes match on your iOS devices or other computers.
I followed the above and had success after running into problems.
I would also recommend that you DO NOT run any other appliactions on your Mac while setting up iTunes Match. iTunes says you can, but it slows down the setup process. It is somewhat CPU intensive and once you start uploading music to the cloud, that IS NOT in the iTunes store, it likes bandwidth.
On a Win 7 machine and no matter how many times I try, iTunes always freezes on Step 3. I've tried everything. Like others, I too DO NOT have the "add to iCloud" option under the righ-click ,menu. to force the uploads. Why is that and how do I fix it?
And YES, I have activated everything, turned on all the columns, have all the updates, etc, etc.
*edit, oh wait, while typing this, 1 item uploaded. only 6555 to go. That 1 item took 10 minutes. 15,000+ did match though so that's good. At this rate only another 650,000 minutes to go. WooHoo!!
BTW, it's not a bandwidth issue, I have 40M down and 30M up.
iTunes Match DOES NOT LIKE certain MP3 encodings.
I have tried all suggestions since I originally posted this "stuck at Step 3" post, nothing worked.. until I checked the bitrates.
Thinking that iTunes Match might "digest" AAC encoded songs more readily than MP3s I've acquired, I did get it working with the following.
1. Backup and physically delete ineligible songs (I did this 4 days ago, but I think it is important)
2. Reveal bitrate
3. Sort on bitrate
4. HIghlght all songs with bitrate <128kbps, if any. I had about 250 songs that were at 127 kbps or less for some reason.
5. Right-click "Convert to AAC"
6. After encoding completes, delete the highlighted songs & empty trash
7. Resume iTunes match
After performing this procedure, and my songs are uploading successfullly at Step 3.
Firewall notes. I temporarily shut down all firewall restrictions until I got iTunes Match Step 3 to work. I am not sure of the port and protocols that have to be unblocked in the iTunes match upload process.
I did want to share that you have to check not only your software firewall (Norton, OS/X system preferences, Windows XP etc.), but your broadband modem settings.
In my case, those settings are managed on ATT Gateway2 Broadband modem via a management interface IP address, http://192.168.1.254.
I cannot be sure whether an individual port or protocol block was preventing upload, because their were other problems I fixed after unrestricting the ports.