Q: Songs not eligible for iTunes match cannot be synced to iPhone

There is a work around for this issue:

1. Create a smart playlist, match the following rule icloud    status    is    ineledgiable.

2. Click edit select all in the menu bar

3. Click Advanced in the menu bar and select: Create AAC version

4. The newly created AAC versions will now be eligable to match

The only downside to this is that the date added will be changed to the current date all other metadata i.e playcount remains intact.

Hope this helps

P.S

There is a setting in iTunes, if you click on your iDevice in the sidebar select summary and tick the box "convert higher bit rate songs to 128kbps"

1.Go to file in the iTunes menu bar and select New smart playlist you will see this window open:

2.Click on the tabs below "match the following rule" to match above.

This will create an "untiltiled" playlist in the iTunes sidebar:

3.Click on this and then on the iTunes menu bar select: edit, and then: sellect all.

4. Click on advanced in the iTunes menu bar, and select create AAC version.

5. Once the files have been converted to AAC the will match.

Does this include recordings that are above the size limit?

I have several DJ mixes that are 90-120 minutes long. I have converted them to AAC versions already.

No this work around is for songs that show as inelegiable because the bit rate is lower than the 96kbps limit.

You could convert your AAC files to a different format to make them smaller than the 200mb limit, but this would sacrifice sound quality.

This is indeed a work-around but it's ridiculous to expect customers to do this.  Apple - please fix ASAP. 

Apple can't hear you here, this is a user forum.

Send feedback here:

http://www.apple.com/feedback/macosx.html

For your "hard work" at lest you get tthe bonus of upgradeing the bit rate quality of your songs.

Thank you.  This string has been very helpful.  I have followed the directions to create the aac version, but nothing appears to happen (as in I cannot tell a difference in itunes and when I choose "get info" it still shows as an mp3).  What is going on?  What am I doing wrong?

If you chose to create an AAC, you end up with a copy of the original.  I don't know how you are viewing things in iTunes, but basically unless you've removed the original, there should be two versions of the same track.  If you highlight a track, then select create an AAC, you should in the title bar see it do its thing and then a second version should show up in iTunes next to the original track you still have highlighted.

This was very helpful! Thank you!