Manual migration from Sierra to Monterey: How to transfer iTunes and Mails data?

[danqi]

I am planning on upgrading from my 2010 Mac Pro with Sierra to a new Mac Studio. I want to avoid using the Migration Assistant because a manual migration feels cleaner and I am not sure the Migration Assistant would work correctly due to the big OS gap.

Most files I can just drag over, but I am unsure about iTunes and Mail data.

Mail:
I have probably around 100k mails across dozens of accounts, many IMAP, some POP3 and a bunch of local archives. I assume I won't be able to just drag the Mail folder from the Library over, right? What would be the most elegant way to transfer this?

iTunes:
I have used iTunes for 20 years and have lot's of stuff in there that I don't want to loose. Since iTunes doesn't exist anymore I have no idea how to migrate everything over. I have read that podcasts are stored very differently now, for example.

I am especially concerned about the following:

- Podcasts: I have a huge amount of downloaded podcasts that don't exist in their feeds anymore. How can I migrate those, ideally with their status (played/unplayed) intact?

- Audiobooks: The vast majority of Audiobooks I have imported myself, not bought from Apple.

- Music: Almost all of my music I have imported myself, adding album art and correct metadata by hand. I have never subscribed to Apple Music, because I was always afraid it could mess my library up.

Btw, my iTunes library is located on an external HDD.

Appreciate any help!

 

[Fishrrman]

"I have probably around 100k mails across dozens of accounts, many IMAP, some POP3 and a bunch of local archives. I assume I won't be able to just drag the Mail folder from the Library over, right? What would be the most elegant way to transfer this?"

100,000 emails?
A question (and yes, it's serious):
Do you really, REALLY need to keep 100k emails on an "active" internal drive?

Why not just "archive them" on an external drive?
(with a backup, or two backups, of course)

Having said that, if you must do it, I'd do it this way:
1. copy the "Mail" folder (in home/library/mail) to an external drive
2. after you get your new email account set up on the new Mac, connect the drive
3. now, "import" mail from the external drive
4. it will go into an "imported" folder, you'll have to manually re-arrange the subfolders inside.

But again, I'd consider "archiving" this old email onto an external drive.

"I have used iTunes for 20 years and have lot's of stuff in there that I don't want to loose. Since iTunes doesn't exist anymore I have no idea how to migrate everything over. I have read that podcasts are stored very differently now, for example."

Are you aware that you can KEEP USING iTunes with the new Mac (and new OS)?
There's a free utility (by a very creative guy) called "Retroactive" that can do this for you.
Get it here:

GitHub - cormiertyshawn895/Retroactive: Retroactive has been discontinued. You should transition from Retroactive to supported apps such as Music, iTunes for Windows, iMazing, Photos, Darktable, Lightroom Classic, and DaVinci Resolve.

Retroactive has been discontinued. You should transition from Retroactive to supported apps such as Music, iTunes for Windows, iMazing, Photos, Darktable, Lightroom Classic, and DaVinci Resolve. - ...

github.com

It will download and install iTunes (I think you can even pick the version you want installed).

Since your iTunes library is already on an external drive, this makes things easy.
Just connect that drive to the new Mac.

If you've installed iTunes via Retroactive, put the iTunes icon into the dock.
Then, hold down the option key as you click the dock icon.
iTunes will open with a dialog that allows you to "choose [the] library" to use.
Select the iTunes music folder on the external drive, and things should work as they worked before (on the old Mac).

I don't use the new "Music.app" at all.
My primary interest with iTunes was the "radio tuner" for free internet radio streams, and (of course) Apple left that out with Music.app ...

 

[danqi]

"I have probably around 100k mails across dozens of accounts, many IMAP, some POP3 and a bunch of local archives. I assume I won't be able to just drag the Mail folder from the Library over, right? What would be the most elegant way to transfer this?"

100,000 emails?
A question (and yes, it's serious):
Do you really, REALLY need to keep 100k emails on an "active" internal drive?

Why not just "archive them" on an external drive?
(with a backup, or two backups, of course)

The size of those mails is not really that big compared to modern storage and I frequently need to reference old mails for work. But I will think about if there is a way to simplify/archive some of them.

Having said that, if you must do it, I'd do it this way:
1. copy the "Mail" folder (in home/library/mail) to an external drive
2. after you get your new email account set up on the new Mac, connect the drive
3. now, "import" mail from the external drive
4. it will go into an "imported" folder, you'll have to manually re-arrange the subfolders inside.

I didn't realise I could "import" straight from the Mail Library folder. Thanks!

Are you aware that you can KEEP USING iTunes with the new Mac (and new OS)?
There's a free utility (by a very creative guy) called "Retroactive" that can do this for you.
Get it here:

GitHub - cormiertyshawn895/Retroactive: Retroactive has been discontinued. You should transition from Retroactive to supported apps such as Music, iTunes for Windows, iMazing, Photos, Darktable, Lightroom Classic, and DaVinci Resolve.

Retroactive has been discontinued. You should transition from Retroactive to supported apps such as Music, iTunes for Windows, iMazing, Photos, Darktable, Lightroom Classic, and DaVinci Resolve. - ...

github.com

It will download and install iTunes (I think you can even pick the version you want installed).

Since your iTunes library is already on an external drive, this makes things easy.
Just connect that drive to the new Mac.

If you've installed iTunes via Retroactive, put the iTunes icon into the dock.
Then, hold down the option key as you click the dock icon.
iTunes will open with a dialog that allows you to "choose [the] library" to use.
Select the iTunes music folder on the external drive, and things should work as they worked before (on the old Mac).

I don't use the new "Music.app" at all.
My primary interest with iTunes was the "radio tuner" for free internet radio streams, and (of course) Apple left that out with Music.app ...

I wasn't aware of this but I must admit that I am a little bit skeptical. I just like to keep things simple and robust and keeping iTunes alive using special utilities seems finicky and not very future proof. I'll have a closer look at that tool, but how long can that really work for if iTunes isn't coming back? Also, how well does it sync with an iPhone?

 

[Fishrrman]

Can't help with the iPhone.
I don't own a smartphone (of any kind).

 

[gilby101]

I have probably around 100k mails across dozens of accounts, many IMAP, some POP3 and a bunch of local archives. I assume I won't be able to just drag the Mail folder from the Library over, right? What would be the most elegant way to transfer this?

Make sure you have everything stored safely in a backup.

I would start by just copying the Mail folder to the new macOS and see what happens. With a bit of luck Mail will convert everything to the current folder structure. You will, not sure when, need to enter mail addresses and passwords.

If that fails:

IMAP: Best practice for IMAP email is to connect Mail to the accounts and let it download everything.

Local mail folders: Import from your backup.

POP3: Be very careful in case your POP settings have deleted messages on the server as you downloaded them. My inclination would be to treat these the same as the local folders and do an import.