Ask the iTunes Guy

Kirk McEl­hearn an­swers your iTunes ques­tions

iPad&iPhone user - - CONTENTS -

iTunes is great at stor­ing all your mu­sic and other me­dia, but only if you let it. If, like one cor­re­spon­dent, you have a num­ber of hard drives with old iTunes Me­dia fold­ers, you need to do some work to con­sol­i­date them. In other news, iTunes has changed the way you delete files from your li­brary, but not from the cloud. And if iTunes dis­plays a ‘ses­sion ex­pired’ di­a­log, here’s how to fix it.

I’ll also be ad­dress­ing a few high-level ques­tions about iTunes; these are ques­tions I get very of­ten, but gen­er­ally don’t cover in the col­umn.


I have mul­ti­ple iTunes Mu­sic fold­ers from dif­fer­ent old hard drives that were dy­ing, and they all now re­side on an ex­ter­nal HD. One of them is in my iTunes Me­dia folder, oth­ers are named Mu­sic 2, 3, and so on. I am strug­gling to find an ef­fi­cient way to con­sol­i­date all the mu­sic into the iTunes Me­dia folder. Cur­rently I have to open two Fin­der win­dows high­light­ing two dif­fer­ent Mu­sic fold­ers to man­u­ally com­pare con­tents, se­lect the cor­rect con­tent and then drag it into the cor­rect folder; then delete the artist and al­bum from Mu­sic 2, and then re­peat this dozens of times. Is there a bet­ter way?


There are lots of rea­sons that peo­ple end up with mul­ti­ple mu­sic fold­ers. In some cases, iTunes will lose track of a li­brary, and prompt a user to cre­ate a new one. In oth­ers, peo­ple have thought it was a good idea to seg­re­gate mu­sic, man­u­ally man­ag­ing it and spend­ing a lot of time jug­gling files and fold­ers.

I get these ques­tions a lot, and there’s only one real an­swer. De­cide which is go­ing to be your mas­ter iTunes li­brary, open it, then drag the top-level fold­ers that con­tain the mu­sic from the dif­fer­ent li­braries or drives onto the iTunes win­dow. This will add all the tracks to the mas­ter iTunes li­brary. This may take a while; hours if you have a lot of mu­sic.

When you’re fin­ished, you’ll likely have a lot of du­pli­cates, but you can sort through these with Doug Adams’ $15 Dupin. This app lets you sort by a num­ber of cri­te­ria, such as bit rate, in case you have files of dif­fer­ent qual­ity, keep­ing the best ver­sions of your tracks.

The down­side to mass-com­bin­ing iTunes li­braries or mu­sic fold­ers is that you’ll lose any play counts, last played dates, rat­ings, and playlists. But it’s prob­a­bly bet­ter to just start from scratch, and con­sol­i­date the mu­sic once and for all.


I was sort­ing through my mu­sic li­brary, which uses iCloud Mu­sic Li­brary. I wanted to delete some songs to free up space. When I pressed delete, I did not get the usual mes­sage ask­ing if I wanted to re­move the down­load or delete the track from the cloud, but I got a mes­sage ask­ing if I wanted to delete the track en­tirely. Is this new?


This is new. I don’t know ex­actly when this started, but pre­vi­ously, if you se­lected one or more tracks and pressed Delete, iTunes dis­played a di­a­log ask­ing if you wanted to delete a track from your li­brary or from the cloud. Now, the process is very dif­fer­ent.

You can still choose to delete items from your lo­cal li­brary by right-click­ing on a track and choos­ing Delete from Li­brary. Note that as re­cently as last month, there were two Delete op­tions is the con­tex­tual menu, when you right-clicked on a track in a playlist. One would of­fer to delete the item from the playlist, and the

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