Tips needed to help a friend copy files off old Mac to give to an ex
December 29, 2020 1:45 PM   Subscribe

I am helping a friend who needs to give an ex-partner a large amount of files from a shared 2013 family iMac. The files that need to be copied to a new external HD and handed off will include plain old word docs, lots of photos, probably some Adobe or similar design files, music files (in iTunes), tax software files/records, and possibly a few others categories. Can you help me get this done completely so all parties are satisfied?

I haven’t owned a Mac since 2004 or so. I know where iTunes stores stuff, and I’m sure I can locate the equivalent of “my documents “. This handoff of files will be stressful and somewhat hostile, so I don’t think making a time machine backup is a good idea, as I think what is desired is easily browsable folders of files on the external HD, not a specially formatted backup of everything.

Any tips for where to look for files on a 2013 iMac would be much appreciated - or just tips for carrying this out simply! (It’s running os 10.14.1 if that matters.)
posted by chr1sb0y to Computers & Internet (7 answers total) 1 user marked this as a favorite
This could be incredibly simple or fiendishly complicated, depending on the circumstances.

Did Friend and Ex use the same user account, or did they have separate accounts?

Would Friend be OK if Ex gets all the documents on the shared computer, or does friend want to be selective and give Ex only some?

Did Friend and Ex use Photos for pictures, or some other program?

Did Friend and Ex create a filing system for documents, or did they save everything in the default Documents folder? Or worse, save everything to the Desktop?

Within a user's Home folder, the default MacOS folders are Desktop, Documents, Downloads, Movies, Music, Pictures, Public, and Sites, which are visible, plus Library, which is invisible. Some applications store user files in the Library, e.g. Mail, but it's mostly for caches, preferences, logs, and other things that a typical user shouldn't muck with.

The iTunes library will be in the Music folder. If that's all that's in it, copy the Music folder to the external HD. The Photos library will be in the Pictures folder. If Ex will also be using Photos on a Mac, they should be able to open the library; if not, you can open Photos, make sure that all files are visible, and then export them.

The rest is going to depend on the answers to the questions above. While threadsitting is discouraged here, it would be helpful if you could provide answers.
posted by brianogilvie at 2:40 PM on December 29, 2020

Oh: Also, did Friend and Ex use Dropbox, iCloud Drive, or some other file sharing service? Some newer apps really push saving documents to the cloud as a default.
posted by brianogilvie at 2:41 PM on December 29, 2020 [1 favorite]

You would start by going to the home directory for this person, easiest way to do this is, when you are in the Finder, go to the Go menu and select Home from the list. All of these directories are inside there.

That said, if this person had their own account on the computer, copying over their ENTIRE home directory will get everything and would be the optimum solution. Also if there's a possibility to just zip all this stuff up and put it on the cloud somewhere using something like WeTransfer, that might be best.

1. Word Docs will be in the Documents folder unless this person stored them elsewhere
2. Photos if they were in iPhoto or Photos would be in the Pictures folder. However, they're sort of buried in a proprietary lump called iPhoto Library or Photos Library. Might be better to go to the photo managing software and export all the photos into individual discrete files.
3. Just copy the entire iTunes directory that is in the Music directory
4. Tax files *might* be encrypted or have something weird there, so again this might be simple but could also be weird, so you might need more info to determine if a file export from within the software is preferable to just copying the files.

Clicking and dragging these over to an external hard drive (or, heck, I might just get a high-capacity USB drive depending on how many files we're talking about here) will copy them over.
posted by jessamyn at 2:51 PM on December 29, 2020 [1 favorite]

I know someone who was required to do something similar as part of their separation, in a similarly hostile situation.

Although this isn't necessarily a technically difficult task, based on that experience, I would recommend that you consider using a third-party service (especially if you are not super familiar with Macs these days). They may not do anything different to what you could do if you worked through it, but the blame can then be shifted if there are any accusations of issues with the files.

An alternative, depending on the circumstances, might be to allow access to the machine to the other party for them to copy what they wish (and then it falls on them if it is not done properly). You might find a neutral location for this to take place, rather than hand over the machine or have them in your friend's home.
posted by AnnaRat at 2:54 PM on December 29, 2020

Response by poster: I’m pretty sure it’s all one account and/ or Apple ID.
posted by chr1sb0y at 3:00 PM on December 29, 2020

+1 jessamyn's advice. I'd probably only use an internet-based transfer if I knew the total storage requirement was fairly low.

As a CYA measure, you could clone the entire hard drive, which would include the operating system and applications. These should not be necessary as part of the deal, but it should forestall any accusations that you left anything out. You'd need an external drive at least as big as the current total storage requirements and cloning software--check out Carbon Copy Cloner.
posted by adamrice at 3:13 PM on December 29, 2020 [3 favorites]

Not to threadsit myself, but I'd be grateful if you could respond to my questions above, which would help clarify this part of your original ask:

Can you help me get this done completely so all parties are satisfied? [my emphasis]

What does "completely" mean? If it's just a complete copy of all the user files, and they used only one account and AppleID, just (1) drag the user folder to the external HD, (2) go to the iCloud drive in Finder (if they used that) and drag all its files to the external HD, which may take a while, and (3) call it a day. If it's a complete copy of everything, including system files, use SuperDuper or Carbon Copy Cloner to make a bootable duplicate of the drive, including system files, etc. Note that if you do the latter, Ex will have a copy of the password keychains, and if they know the keychain passwords, they will have access to all of Friend's saved passwords.

Where it gets tricky has almost nothing to do with tech and almost everything to do with social relationships, i.e., what Friend and Ex want, and how much they commingled their lives on the shared computer. E.g., if Friend has a hobby and doesn't want Ex to have documents, photos, etc. relating to the hobby, you'll need to exclude those. If Friend has saved letters to or from friends and family that they don't want Ex to get, you'll need to exclude those. If this is a tense but not hostile breakup, that may not be an issue, but if there is open hostility and distrust, it could be a big deal.
posted by brianogilvie at 8:23 PM on December 29, 2020

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