iTunes match fails on upload, loops

I spent the past few days battling this exact problem and believe I have fixed it.

I believe this actually is an ISP related issue (even if that sounds like BS at first). I do not have these problems when I use the internet at work, or use my personal hotspot on my phone, but I do have them on my home internet (Comcast).

I believe that when iTunes Match begins uploading, it maxes out the uplink bandwidth of the Comcast connection, renders it useless and causes the connection to time out. iTunes Match thinks the connection died, and it stops, then restarts.

The way I fixed it was limiting my maximum upload bandwidth via my router. My router (Netgeard WNDR3700) has a setting that allows me to set up maximum uplink bandwidth. Speedtest.net told me my connection had 4-5mbps up, so I limited it via my router to 2mbps.

As soon as I did this, my uploads began working without timing out and restarting. They are slower than they could be, because I am limiting upload, but at least it isn't restarting!

I can confirm what rwthelen said works. Someone suggested it in a thread I started on the same topic. Ever since I did that, I haven't had any issues whatsoever.

my problem also turned out to be the isp. i have COMCAST. no luck... step 3 loop for about three days straight. went to the in-law's place (much slower internet there), and step 3 uploads fine, just slow... haha

If you've got a big data plan on your phone, I've found that works as well. I connect my laptop to my iPhone's wifi hotspot and then run iTunes Match - with LTE the upload is even faster than my ISP.

rwthelen is a genius - this worked perfectly for me. I've been trying to solve this for months and was about to drop the match service as a result - even called apple and had them on the line for about an hour trying to figure it out to no avail. They really need to get this info out there - I would imagine this would immediately fix the problem for most people (especially if Comcast is your ISP).

Thanks - you just made my day.

Too late. I've waited a year for Apple to fix this or at least acknowledge the problem. Nada. My service expires today and I won't be renewing.

I'm fine with syncing music to my iDevices manually, and in fact I prefer it anyway given that iOS provides next to no options for managing what remains on the device. Apple dropped the ball on this one.

After months of utter frustration I saw rwthelen's post. As soon as I turned on the VPN on my iMac (Hotspot Shield) everthing worked just like it's supposed to. Not one singe restart. My provider is Timer Warner - RoadRunner. Thanks rwthelen!

I had this issue due to a song that was a 400mb lossless m4a file. Deleted the song & it fixed the problem, converted the song to a mp3 (124mb) and all is well. I'm pointing this out for 2 reasons.

First because I don't know if it was the bandwidth issue described by rwthelen or not but given others may not have a router with QoS features, it's an alternative work-around to try.

Secondly, is there possibly a max song size for match?

Hi,

Max file size is 200mb.

Jim

I did succeed with a 240mb file... silly iTunes.

Thanks for this great tip. I have been struggling for 4 days and both Applecare and Comcast could not offer any useful help.

Your tip did the trick. I set my bandwith to 256 Kbps and the upload went without a problem.

If the cache deletion does not work for you, let me relay something that did work for me - and I was NOT the guy that figured it out. Reducing the upload speed from the problem computer was the trick - some folks do this in their routers with QOS settings, but I use a TimeCapsule and don't have that option. Download this free software:http://tools.chocoflop.com/entonnoir_en.html and then set the HTTPS port (443) to a maximum upload rate of 100 or so. Screenshot of my settings below. Some slightly quirky behavior in Entonnier though: You have to turn the throttling off to edit the settings, and once you enter a value into the text boxes below, you must hit <enter> or <return> on your keyboard for the settings to stick. Then turn throttling on with the button upper right, and watch iTunes. As I am sharing this solution my Mac is finally uploading the songs that have caused it to loop endlessly. It's quite possible that a higher setting would work but I only have 24 or so, so I'm not messing with it - it's working! Props to the guy that figured this out.

P.S. You're going to want to then turn the throttling OFF when you finish, or things like Gmail and others that use HTTPS to upload are going to crawl.

Thank you! I've been looking for a solution to this for a while and nothing worked until now!

iTunes Match was in an endless loop on my Mac also. I followed the advice, downloaded Entonnoir, ran it as advised (throttling port 443--I used 128) and have finally had success. Match went through steps 1 and 2 as before. Step 3 has been running for 16 hours (yesterday afternoon, overnight, this morning) at this point and has pasted the point of failure. It is "slow and steady". Since other features of iTunes are available and the Mac can be used normally, I am letting it run to completion.

Step 3 shows each file as its information is being uploaded. This is neat to see and also caused me to rethink by "never throw anything away" practive. (LOL!!!)

Thanks for sharing your fix. It surely looks like a solution to me.

Thanks, been having that dreaded loop for days now. COMCAST, set my UL speed to 2Mbps on the router and all good to go. Hopefully when it's done I get iTunes Radio to work on my iPhone 5s with no ads then I'll be happy.