WORKAROUND — Found a Way to Force iTunes Match to UPLOAD

I wanted to let everyone know that after months of living with incorrect matches (mainly The Beatles in Mono), I've finally found a semi-easy workaround to force uploads. I haven't found this anywhere else, but if someone else has documented it, I apologize. I posted this onto one of the many threads regarding the issue quite some time ago (~ 6 months), but I wanted to make sure it was seen by as many as possible. (Sorry for the long post—skip anything you're not interested in! 😉)

MY THEORY

The basis of this was noticing that there seemed to be discrete steps to the matching process (when adding via already-ripped FILES and not CD at least):

1. You add the files to iTunes
2. You can force a scan by right-clicking and selecting "Add to iCloud"
3. iTunes scans the new files
4. iTunes reports that it is sending the file data to Apple
5. iTunes waits for a "Matched" or "No Match" response from Apple
6. If the response is "No Match," then iTunes triggers the upload

After observing this for some time, I concluded that if (edited) files could be imported that would give a definite "No Match" result, there may be time in-between steps 4 and 6 to replace the files with the real ones (which had been triggering a false match in the past). To my delight, this worked. Here's what I did:

STEP-BY-STEP:

1. Deleted existing files from iTunes/iCloud, but kept the files on the computer. I then moved these to a different folder.
2. Took existing files and converted them with dBpoweramp. This will cost money but is well worth it if you are looking for a way to force an upload to iTunes Match. I converted them using the same AAC settings (this doesn't matter), but added the "reverse" DSP, which reverses the audio. This has been enough to foil iTunes into not matching the track, while ensuring that each file will contain unique audio data. This will be quick and painless, at least for the first time. I did it this way because it will retain all of the tags AND length of the file. iCloud will get the file length from this step, and will not change it afterward...so you probably want to use files of the same length as the real ones.
3. Now I have a copy of the files with audio gibberish but still having correct metadata, etc. I then put these files in my "Automatically Add to iTunes" folder.
4. Right-clicked on these files and selected "Add to iCloud." If you use "Sort Album" like I do, you can change it before this step and it will upload into iCloud with the correct sort information. If done afterward, it doesn't usually sort correctly on my iPhone.
5. After iTunes displayed the message "Sending information to Apple" (don't remember the exact message), I pasted the original (correct) files and replaced my audio gibberish files. It is important to note that the filenames must be the same, e.g. "01 Come Together.m4a" if a single-disc, or "1-01 Back in the USSR.m4a" if multidisc. iTunes will also truncate the file name at 36 characters (I believe) so this will all need to be done beforehand. I use various MP3tag actions that I'd be happy to share if anyone wants them. If you are starting with a file that has already existed in your iTunes library, this will already be done (provided iTunes is managing the library).
6. When Apple returns a "No Match" signal back to iTunes, it then begins to upload the files which I have just pasted.

This has worked for me 100% if doing the upload one time. In some rare cases, I may decide to EQ a file and then re-upload, or otherwise edit the file. Or perhaps I have more than one version (original/remastered, or original mix/remix) that I want to coexist in my library. In those cases, I have again utilized the dBpoweramp "VST Plug-in" DSP, where I use something like Freq Show to garble the audio. It is necessary for the garbled audio to be unique each time for this to work.

A FEW THINGS I HAVE LEARNED

1. If you delete a file and wish to re-upload it, you can use the same files from step 2 (provided you still have them) and iTunes will recognize them as the files previously uploaded. I am not sure how long this works, but your uploaded music remains in iCloud, though invisible, for some time — even if you selected "Delete from iCloud."
2. iTunes/iCloud evidently does use metadata (at least Album) to help determine if you've already uploaded a song within the same album. I ran into this when trying to test an EQ/level change I had made, and even though the audio content was completely different, iTunes would not upload or would flag as duplicate. If I altered the Album field in any way it would proceed. Other tags can be kept the same.
3. If you do have mono content, it is trivial to use the dBpoweramp "Channel Mapper" DSP to remove one channel during the conversion from lossless to AAC. The nice thing is, I encode with Nero AAC quality 0.65 (~250 kbps VBR) and this will reduce the file size significantly. There is no real advantage to keeping both channels, since you're doing a lossy conversion anyway. Sometimes the encoders (even very good ones) don't see the file as being mono, due to different artifacts and noise in the left and right channels. Or perhaps the mono tape was transfered with a stereo tape deck, etc. Try it yourself and see if it makes a difference. Also, iTunes will report the file as "mono" when you do "Get Info." I keep the FLAC disc image/tracks in stereo so it will exactly match the CD, but only encode one channel to lossy. If you know the source is mono for sure then there is no possible advantage to keeping both channels of a lossy conversion. (If you're not sure if the source is mono, use your favorite DAW, e.g. Audacity, to invert the phase of one channel before combining left and right. Once you do that, if all that is left is very low-level noise or other artifacts, then you know it is safe to encode as mono.)

IF YOU CARE ABOUT MASTERING

It is also worth noting that if you care about what mastering you have in your iTunes library, there is no other way I know of to guarantee you have the correct version in your iCloud library except to upload it. I found this out the hard way: I had a retail CD version of Paul McCartney's "RAM" album that was recently remastered. I put the CD in, added to my library, and iTunes Match quickly returned with "Matched" for all tracks. Some time later I was listening with headphones and noticed that some tracks had hardly any hiss at all, whereas others had a good amount of it. Since "RAM" is a rather hissy album, I investigated it against the CD and finally found that many of the tracks were being matched to other versions of the song (either from the earlier CD version or compilations with different mastering). So most of the tracks were hit with heavy noise reduction for the iCloud version. I had to follow this upload procedure to be sure that I got the right version. Purchasing the item(s) from the iTunes store would work also, but I had already paid $100 for the deluxe box set. This same problem occured with the Bob Dylan mono box. I was surprised to find that iTunes actually matched my mono versions to mono versions, and continued listening until one day the stereo version played on a certain track instead of the mono. So, even if the iTunes store has the mix/mastering that you are wanting to add to iCloud, the only sure way is to upload it (or purchase it from iTunes in the first place.) If given the choice going forward I would choose the latter, since I am not hung up on physical media and cannot tell a 256K iTunes store encode apart from a FLAC file in a double blind test (almost nobody can).

This has been bothering me for months. I'm really happy to be able to play my correct files on all my devices! For those of us who have unique versions or masterings of albums we prefer, this should be a workaround until Apple decides to give us a "force upload" option. I have tested this on Windows 7 primarily. Should work on any OS.

Hope everyone finds this useful!

Nick