Got a work around that works for me:
Made a Smart Playlist of all Waiting under 320kbps
Highlight 4000 files and selected Create AAC Version
Without clicking anything else (while the original 4000 were selected), clicked Delete and removed these from my system
Highlighted the 4000 new AAC files and NOW I have the ability to Add to Icloud
These are now also showing up as Matched and not Uploaded so I will probably go in and delete the new AAC files and redownload as 256k DRM free version
How to Fix Step 2 and Step 3 Errors in iTunes: Music Media Formats, and Checking Firewall
This solution assumes that you do not have corruption in your iTunes library database. To fix that follow the steps in Apple Support KB ht1251 above.
Step 1, 2, or 3 Hangs: Problems with Media Formats.
If you have heterogenous media formats in your music files, some of them will FAIL iTunes match, causing it to hang. This is a software error in iTunes match, which should mark the files as "Not eligible" instead of remaining stuck in an endless loop. These errors never occur if all the songs in the music library are unprotected AAC 256 kbps music files encoded by iTunes 10.5.1.
There are two basic ways to upgrade your song media formats to iTunes 10.5.1 AAC encoding - encode all of them at once, or do them selectively. In either method, you must delete the original version from iTunes and your file system. If you previously loaded them to iCloud, get rid of them there also.
You will be able to see a hung file in OS/X under Activity Monitor -> iTunes -> Inspect Process -> Open Files and Ports. In Windows you will have to use standard Task Manager inspections.
In my iTunes library, I found that certain AAC (m4a) files which were encoded in before 2011 were stuck, and m4p Protected AAC files. I had already fixed the encoding of MP3s, so I was suprised that music previously encoded by iTunes was hanging up.
You may convert all files which were not encoded at 256 kbps AAC with a right-mouse click. Find them:
1) individually in iTunes as you discover them in Open Files and Ports trace, or
2) by creating a sort smart playlist that matches their pattern. For example, a playlist with bit-rate < 256k.
After converting them, you MUST delete the previous file(s) from your iTunes library. I suggest you move the actual file to trash, and delete the trash. Archive the files if you wish. If any of them were already matched to iTunes Match, you must delete them there also.
After getting rid of older media formats, re-run iTunes match. Step 2 should complete, and your Open Files and Ports window should no longer show any music file open in your iTunes library. If it does show, convert it and remove the old file from your library.
If you have converted your music library and Step 3 is still stuck, it is likely a Firewall problem. Check the last line in Open Files and Ports, and use the information in the last rows to check your firewall settings. The upload port is shown in this form, 192.168.1.1:53089->22.214.171.124:https. If you see this type of row, but nothing is being uploaded, a firewall or other issue is blocking that port.
In my case the block was created by my broadband modem settings. Check with the installation guide for your modem - typically they can be managed by a http:// address such as http://192.168.1.254. Change the firewall settings as needed.
My main iTunes library is on a old PPC machine running 10.5.8, and iTunes Match has required a TON of handholding for a relatively small library. This is in addition to the problems other have been reporting (matches failing, oddly uploading some podcasts, etc).
Just to add a few more data points to this:
I have had a very difficult time with Step 3 failing with the last ~150/6000 songs in my library. In my experience:
It is not a firewall issue
It is not a bit rate issue
I suspect it MAY be a bug in iTunes for PPC machines and/or System 10.5.8. In my case songs that would hang iTunes would upload just fine when added to a different machine running 10.6.8 and uploaded to iTunes Match from that machine. No bitrate conversion was required. These files would not load to iTunes Match from a PPC machine but loaded fine from an Intel machine.
Also, when my PPC machine was getting stuck, it was not getting stuck with any particular song file, the only file open was the iTunes Cache.db file, and rebuilding that cache file did not solve the problem.
Also, the "Add to iCloud" context menu option does not appear to be available from 10.5.8.
UPDATE: I had all but given up on this problem. Was just going to let Match sit there until an iTunes update is released. Out of sheer curiosity and coincidence I went and checked that statuses of all the remainging songs left to be uploaded (labeled "Waiting"). To my surprise they had all been uploaded. I don't know how this happened since I had "stopped" iTunes Match a couple of days ago. So, at least for me this problem solved itself. I don't know how. I don't know why. For this I am grateful.
I was trying to upload a 7000 song library to itunes match. I was experiencing many of the things that were described here. I tried many of what was described here. What finally worked for me was I took the hard drive that I had my library on to work where I have a T1 connection. I instructed itunes to open the library on the hard drive and everything went beautifully. In 2-3 hours, everything was done.
This really makes me think that it was the internet connection. At home, I have a relatively fast connection with Charter Cable. But almost everything that others were describing was happening to me. But not on my fast ethernet connection at work.
How to solve stage 3 lockups, yes it does work been doing it myself.
Choose an album that has tracks waiting, delete the whole album but keep files.
Add files back into ITunes then highlight the whole album.
Right click and go to add to icloud. Bingo it loads the album to the cloud.
Before you ask, yes you have double the tracks, but when it uploads the old ones go.
go to iTunes - click on music - then click on 'time' to sort from longest to shortest song.
some of my 'songs' are over 1 hour long e.g. particularly on albums that have continuous play, iTunes is not recogising them as tacks.
my iTunes match looks like it is taking a long time to upload these and hence, looks like it is stalling.
not sure if this is whats going on, but maybe.
The tip about using the Activity Monitor to inspect the iTunes process and then using the "Open Files and Ports" view to see which song was hanging up the iTunes Music Match upload process worked like a charm. I was able to spot the offending song title and file location after scrolling down through the "Open Files and Ports" window. I removed that song, restarted iTunes and the process was able to complete all 3 steps within just a few seconds.
- - Initially I had problems with step 3 freezing after only 1 song had been uploaded (although at times it was just a large file that took time to upload). After trying the below (suggested in this order) any issues seemed to be resolved and I am now the happy owner of 13,000+ songs in the cloud (around 5,000 of which were uploaded)
- - Steps to follow if step 3 freezes:
- Update to the latest version of iTunes (recent updates have included fixes for iTunes match, so I would suggest doing this first if you have issues uploading)
- If the above doesn’t fix your issue, you can delete out your whole library and re-load it: I had to do this a couple of times and each time it then proved better at uploading the remaining tracks
- If neither of the above work then you can delete out the whole library and re-add certain albums (and try adding each album to the iCloud one by one)
- - iCould statuses and my interpretations:
- Matched: matched with the same song in the iTunes catalogue and no need for upload, but available in the iCloud
- Uploaded: not matched and therefore uploaded to the iCloud
- Error: this looks to be files that haven’t uploaded correctly, possibly due to timing out (due to size) but also other reasons – sometimes adding this again to iCloud fixes this issue (once the majority of your catalogue has been uploaded), but at other times the file just does not want to upload and there were certain tracks that I had to re-purchase from iTunes in order for the file to be available in the iCloud
- Waiting: iTunes match is waiting to match/upload the file – usually this will be one that is waiting to upload and will do so once the catalogue has been checked
- Ineligible: this either relates to
- the file size (more than 200MB)
- or the bit rate (less than 96kbps. Hopefully not many files will be this low quality: for me it was 5 albums from thousands)
- or if the files in your library were purchased with another iTunes account that hasn’t been authorised on your computer (once authorised, these files can be matched)
- or the file is a (music) video