Technical question
This could be the most boring blog I’ve ever done, but boy, could it be useful to me.
This is a technical question about computers which I first posed on Twitter last year, but – naturally, Twitter being what it is – on that occasion I ended up with about 212 responses and didn’t know the correct arse from the actually-quite-misleading elbow. Now I’m going to raise this thorny issue again to the more select audience which tunes into this blog. If you don’t know the answer and aren’t ever likely to need to know the answer, then I must emphasise again – this blog is going to be absolute dogshit and you may as well go on some other webpage. Maybe Minchin’s site, or eBay, or www.thehungersite.com where you can click and give food to people.
For the rest of you:
I have iTunes. It’s on my old laptop. All my music is on there. From time to time I ‘sync’ the laptop with my iPhone. Nice and simple. For a long time I’ve been purchasing and listening to music in this manner. As I say -nice and simple.
But these days the laptop is old as Brucie. My wife has a new Mac. It would be nice to transfer the whole library from my phone, or computer, onto the new laptop. But you know. There’s all this business with ‘home sharing’ and ‘authorising computers’ and ‘if you just plug the phone into the new computer, it will wipe everything you’ve ever had’ and ‘you don’t really know what the hell you’re doing, Watson’.
So. The question really is this straightforward. How, please, do I get all my music onto the new computer so that I don’t lose it all and have an awful life, and so that I can continue plugging my phone into that new computer and so can my wife, and the world will continue very much as it is now?
I can only say again, sorry this was such a tedious, tedious blog, but if someone can just stick a Comment up explaining the best way – even if it’s something laborious like getting it all onto an external hard drive and then shoving that into the Mac – I would be bloody grateful.
I promise that tomorrow’s blog will be an awful lot nicer to read. If you have an outstanding ‘request’ for a subject which you think hasn’t been dealt with, remind me. Otherwise, the first Comment on this blog will win the right to dictate tomorrow’s blog. Which will not be about computers. Good.

Posted by Aislinn on January 5, 2011
Don’t know a thing about computers, though it appears everyone else does (handy), but I do like the fact you used the very Key-esque phrase ‘thorny issue’.
Posted by Lucy on January 4, 2011
Hi, homesharing is the way forward. Have both your macs switched on, and connected to the wifi.
On your wife’s mac, click turn on homesharing, and log in with YOUR iTunes email and password.
You should get a screen where you get an option to show only the tracks from your mac that are not already on your wife’s. then import them all. It may take a while, so just leave it going…
Posted by Anji on January 4, 2011
Mark you are a mind reader! I have just had a major clean up of 8 year old desk top pc, which had a number of songs in iTunes and that connected to old iPod. iPhone is connected to different laptop and I want to merge the two – anyways we have put everything on an external hard drive which was sort of in limbo while we figured out what was the next move!
so thank you Mark, and thank you wonderful all knowing people who have posted answers! You can all have gold stars!!
My next move is now to get my OH to read the helpful posts on here and get him busy
Posted by Steph on January 4, 2011
I don’t know about home sharing, but my laptop got wiped a few months ago and I had to get all the music off my ipod. I used Music Rescue (http://www.kennettnet.co.uk/products/musicrescue/). Just download it onto the mac then plug your ipod in and tell it to copy everything over. If you and your wife have some shared music then you can deselect any songs with a green dot next to them too so you don’t get duplicates. It’ll even rebuild your playlists and put ratings and stuff back if you get it to transfer the songs straight to itunes. It’s only £10 for a licence for the program (or you can use it for free but you have to press a button every 50 songs or so). If it all goes tits up then you’ll still have the music on your computer so it should be safe.
Posted by Rachael on January 4, 2011
Sounds awfully complicated, I will stick with CD’s.
Posted by Shell on January 4, 2011
I’ve just had to do this as my PC is dying! I can’t comment on the software as I’ve not tried it.
I have an external hard drive anyway so I copied the folder containing all my music and podcasts to that (Music/iTunes/iTunes Music) then installed iTunes on the laptop and copied the contents of that folder into the new empty one. I then used File – Add Folder to Library and it all appeared in the new iTunes.
My music is indeed all safe and I simply had to re-subscribe some podcasts so they’ll update. HOWEVER, I did lose all my playlists and will have to re-build them – the music is all there and listed in ‘Music’ and can be organised into albums etc but the Playlists are gone.
I ‘might’ have been better telling iTunes to Add folder to Library itself rather than placing it in there and I imagine there is an additional file that I could have transferred which might have transferred the playlist information too.
My playlists were mainly albums or artists rather than compilations anyway so easy to re-do.
If you are very anxious about losing your music I’d recommend saving it to an external hard drive in this way even if you find a software solution, as then at least you know it is all safe. DVDs are too time consuming – with the HD you just tell it to copy and walk away for a couple of hours.
Good luck. Please let us know how you get on.
Happy New Year!
x
Posted by Meg on January 4, 2011
I used Home Sharing too and it is amazing. So simple once you’ve got it set up. You can simply transfer your entire library over to another computer that is connected to your computer using the same iTunes account. Here is how to do it: http://support.apple.com/kb/HT3819
I’ve always been a bit wary of just plugging my iPod into the computer because it would be a huge pain if everything was wiped. On the article regarding this method, it does says it does not apply to the iPod touch so I’m not sure whether that also means the iPhone. It’s sort of the same software isn’t it? In which case, it would probably be better not to risk it.
Posted by Josh on January 4, 2011
Well Mark, Home Sharing is for exactly this. I’m not sure how to activate it on a PC exactly, but under perhaps “Advanced” at the top of the screen, it should say “Turn On Home Sharing”. It’ll say that on a Mac, anyway. It’ll then prompt you to type in your iTunes account email/password, so do so. After doing this on both computers, if they are both on, at the sidebar thing in iTunes (from where you select what you want eg Music, Movies, TV Shows, iTunes Store etc) your other computer should appear under a “Shared” heading. Click on it, wait a few seconds, and your library from the other computer should appear on the screen. Then select all your songs (if you’re struggling to do this, select the top song, scroll to the bottom, hold down “Shift” and select the bottom song) and click “Import” on the bottom right. This will now start copying the songs across to your Mac, as long as that is the computer you have been using for this
It sounds very confusing, but is a lot easier than it sounds!
Posted by Tracey on January 4, 2011
Hi Mark. I wish I could be super intelligent and come up with a solution but, being a bit of a Luddite I can’t I’m sorry to say and can only hope you manage to sort it out. It looks as though plenty of other people have really good advice.Take care, Tracey x
Posted by max on January 4, 2011
This is gonna be long, but I spent these past holidays teaching ipods/iphones/itunes to my mom and dad, and I managed to make them understand it. So I can pretty much make a rock understand iTunes now.
I will bullet the most important points, so it’s easy for you to follow.
Let’s start with the basics,
1) The relationship between computer to ipod can be one to many, but the ipod to computer thing is only one to one.
This means that you can have multiple iPods connected to a single computer, but only one computer per iPod. This is the reason why when you sync a full ipod to a new computer, the computer will take ownership of it and delete all the previous files.
2) The authorization thing is only between computers and it’s only for songs you bought. I think the limit is 5 computers or so.
This means that 5 computers can share all the stuff you bought with your account. If you paid attention to point (1), it follows that all the authorized computers can have multiple iPods, so the number of “authorized” iPods can be much greater than 5.
3) Generally, iTunes keeps all the music in a directory of the form iTunes Music>Artist>Album. You generally don’t need to change a thing, and if the “Keep iTunes media organized” and “Copy files to iTunes media folder when adding to library” options are selected in the advanced preferences in iTunes are selected (which they are by default, I think) then you should not worry about the music.
All your music will be inside this folder in your laptop.
Assuming your iPhone has a greater capacity than this folder, then all your music is also in the iPhone. If not, then a selection of it is.
So. That’s the situation so far. You have a media library in your computer and a media library in the iphone. Now, how to go from there to the new mac?
The easiest way, without dealing with sharing libraries or networking the computer is an external hard drive.
How to do it:
a) Plug in the hard drive into the old laptop and copy the iTunes music directory to the new HD. You should be able to find the folder easily, in a mac it’s under the User>Music>iTunes directory. I dunno about windows, but it shouldn’t be too hard.
b) Plug in the hard drive to the mac.
c) Go to iTunes in the mac, choose File>Add to library and point to the music folder in the external HD. Make sure that the two options I mentioned in (3) are enabled. This will make sure the computer makes a local copy of all files.
d) Go make yourself some tea and wait for the thing to finish. You may get some questions from the computer (like, do you want me to organize the music or something), trust the mac. Tell her yes to all.
And that’s it. I think that the first time you try to play a song that you’ve bought through iTunes, the computer will ask you to authorize it. Do it and that’s it. You can now sync iphones/ipods from both computers, as you see fit.
4) Hard drives fail. Always keep a back up of your music and photos.
This is not trivial. This is important. You can use time machine in the new mac (that’s a whole other post, though) or you can just store the external HD with all the music in some drawer and pull it out the day something goes wrong.
The only complication with this approach is that you will now have two identical libraries in two different computers, but they will not be synced from now on.
This is something you must decide for now and stick to it. Will you always download music from one the computers? or will you randomly add stuff to any of the available libraries?
If you do so, remember that music you downloaded to one computer will not be available on the other unless you manually transfer it (via the external HD or through the network). I know it sounds trivial, but believe me it can get complicated pretty quick.
My own recommendation is that if you want to keep both libraries synced you shouldn’t wait until there’s a bunch of music to transfer. Every time you download something to one computer, just transfer it to the other computer too. If you wait too much you will not even remember what you downloaded.
(TIP: you can sort songs within iTunes by date added to library, this way you can see how much you added since the last sync).
You can download software to sync folders across computers, but I expect that is a wee bit too technical for the Watsons (no disrespect intended).
I think that’s about it. You should be able to do this!
Posted by Jamie/James on January 4, 2011
Technically you can’t transfer music from an iphone/ipod to itunes…
But there’s a software called mytunes redux that’s designed to circumvent the restrictions set on itunes so you can download from your iphone/ipod. It also, if i remember correctly, has the ability to go onto other people’s itunes libraries that are wirelessly shared on your laptop and take their music.
It’s been around for a while, so not sure whether it still works with the latest versions of itunes, but it’s definitely worth a try.
Posted by Tibbs on January 4, 2011
I’d forgotten all about the hunger site! I used to try to get on there once a day. And there was some other site like that, where you donated cups of rice for every word you defined correctly. I never knew if that one was legitimate though.
Anyway, it seems like earlier commenters have already given you much better (and more legal) tips than I can provide. I hope the advice proves useful!
Posted by ChrisP on January 3, 2011
A few more things…
1. That help page does look really useful.
2. The New Pornographers CD is in the post. This had better be good, Mark! (And today’s blog shows why CDs will always be better than downloads).
3. A blog on cheese would be great. I’ve recently discovered Roulé. And Jarlsberg. Happy days.
Posted by Joe on January 3, 2011
Mark, if nobody asks before me, here’s a suggestion for tomorrow’s blog:
Since it’s referred to in countless interviews and press cuttings, please could you tell us a bit about ‘Far Too Happy’, your critically acclaimed Cambridge Footlights tour show? What were the most memorable sketches, and how did the writing process back then compare to the process of composing an amusing novel chapter or a witty stand-up routine now?
Thanks!
Posted by Josh on January 3, 2011
The way I’d do it would be to find out where the actual files were (ctrl click properties or something along those lines) then pick all of them up and put them in some sort of portable hard disk or something.
Or just, you know… something else.
Posted by Kathryn on January 3, 2011
This blog is not boring because I’ve freaked out about this in the past. In fact, it’s the reason I still buy CDs, so that I have almost everything in hard copy. Can’t offer any advice but previous comments seem helpful.
Posted by Beth (Bloomability) on January 3, 2011
I only wish this blog had happened sooner, since I had the exact same problem. But since that was several months ago, so I decided to just wipe everything and try again… and have consequently f**ked up my entire iPod/iTunes, and most of the songs have little ‘!”s next to them. Plus, all of the .mp3 files on my laptop all have names like HGFU and OCFE. I had 10,000 songs too, and now only 500
Sorry to complain, but it truly is a right bugger.
Posted by Dan on January 3, 2011
Can I request that you tell us what your favourite cheese is? This has become a bizarre obsession of mine recently. As well as being slightly interested in what’s popular (I have a ridiculous chart going right now), it actually can tell you quite a lot about people.
Posted by ChrisP on January 3, 2011
There’s a few ways of doing it.
My top recommendation would be to back the who lot up onto a massive pile of DVDs (which can then be kept for future use). Do this using iTunes [File -> Library -> Back up to disc] and you will have a backup you can keep forever and easily upload to the new computer without too many troubles. (But it is time and DVD consuming). Boring as hell though. May have to ‘authorise’ new computer to get iTunes purchases uploaded.
This is good for large amounts of music.
Second (but very efficient) option: Backup using iTunes onto your iPod. When the iPod is plugged into in iTunes, enable disc space and backup the music onto the iPod (this only works if the amount of data you are transferring is less than half the capacity of the ipod, assuming the music is also all on there; once in music form and once in data form). Less expensive and if done well, quicker and easier (if the iPod is big enough.
This is good for smaller amounts of music.
Really time consuming method but easy: copy individual files/folders across network.
Tracks downloaded from the iTunes store are an absolute ‘mare. I’ve had to burn them to audio CD and then rip them again onto new PC to get them across, it’s the only way to get past that 5 computers bollocks.
Top tip: make sure the files are being organised all nice and tidy on the new computer before you put them in [iTunes -> Edit -> Preferences -> Keep iTunes Media Files Organised]. This will make your life a lot easier in future.
Posted by Adam on January 3, 2011
http://support.apple.com/kb/HT1329?viewlocale=en_US
This is what I did if I remember correctly
Posted by Misha on January 3, 2011
In theory, just plug the phone in. Itunes is clever enough to copy it over.
HOWEVER. If you’re nervous about loosing everything, then you want to copy over the entire itunes library onto an external HD or similar, and copy it to the new mac.
The slow route is just to do it all manually, which is what I did in order to clean up my itunes of all the junk I liked at 13.
Hope that helps!
Posted by Adam on January 3, 2011
Hi Mark,
I havent commented much lately, but I’ve still been reading everyday. However, I think I can help you with this. I have done this only around a year ago, moving my music from old computer to new laptop. I can’t remember how I did it exactly, but I think it was just by moving things over using an external hard drive. This may cause a problem for you if you are using music you have bought from itunes though, though maybe not. My biggest recommendation (provided nobody else has a solution) is to go on to the itunes help forum and have a look around on there, they really are a helpful bunch on there and browsing the relevant pages for a few minutes could probably sort your problem