Upgrade from macOS Mojave to macOS Monterey

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19 points

Upgrade from macOS Mojave to macOS Monterey

My operating system is macOS Mojave Version macOS 10.14.6 and I am thinking of upgrading to macOS Monterey.

But before I do I need to understand a few things.

My music files are stored in the Music/iTunes folder on my hard drive and my audiobooks are stored in Music/iTunes/iTunes Media/Audiobooks folder on my hard drive. I play both my music and audiobooks using iTunes.

My understanding is that iTunes is not included in Monterey and that Apple has separate apps in Monterey for Music and Books?

My questions for macOS Monterey are as follows:

1. If I should upgrade to Monterey, will my music and books that are stored in iTunes migrate into these separate apps?

2. What about Films and TV Shows downloaded and played through iTunes?

3. I assume that I can still listen to music and audiobooks by opening/playing the media via these apps?

4. What happens to my music playlists, are they maintained in the Music app?

5. I download audiobooks from Audible.com and the downloads are automatically added to the folder Music/iTunes/iTunes Media/Audiobooks. How will this work in Monterey?

6. I download the audiobooks onto my iPhone using iTunes, how does this work in Monterey?

7. I back up my phone onto my Mac using iTunes, I don’t store my backups in iCloud. If there is no iTunes, and other than doing this on my phone, how can I (a) check for upgrades to IOS and download it and (b) create an iPhone backup on my Mac?

8. Is it correct to assume that my documents, files and folders will be migrated so I can access them through a “Finder”?

9. Safari: will my bookmarks & passwords be migrated into Safari?

10. Does Key Chain work using macOS Monterey?

11. Is there a location I can use to view a full demonstration of Monterey?

iMac 21.5″, macOS 10.14

Posted on Feb 18, 2022 9:46 AM

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Answer 1

Best reply

leroydouglas

Community+ 2024

Level 10

183,960 points

Feb 18, 2022 10:24 AM in response to brian mck

brian mck wrote:

My operating system is macOS Mojave Version macOS 10.14.6 and I am thinking of upgrading to macOS Monterey.

Always have a current and redundant backup plan in place... only in this way can you fall back if the upgrade does not work out for you.

I would anticipate no issues.

It never pays to get too far behind in the macOS or the hardware...baby steps along the way compared to a giant leap.

Keep your Mac up to date - Apple Support

https://support.apple.com/guide/mac-help/get-macos-updates-mchlpx1065/mac

What happened to iTunes? - Apple Support

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Answer 2

brian mck Author

Level 1

19 points

Feb 27, 2022 6:44 AM in response to brian mck

My previous issue of apps, files, folders etc take much longer to launch in Catalina than in Mojave persists and I have restored Mojave onto my iMac.

Catalina - Audiobooks

Loading Books onto my iPhone is more cumbersome than using iTunes. Firstly the Finder takes a long time to load my iPhone and when looking at the Audiobooks tab, I cannot see any detail other than the file name. In iTunes the phone loaded much quicker and one could see all details before dragging and dropping onto the phone. In iTunes I selected books using the download date and just dragged the selection over my phone and the selected books were transferred to my phone.

I realise this forum is for the community and can only hope that an Apple developer or some technical Apple employee reads this post as iTunes is much simpler, quicker and more user friendly than the Audiobooks app that Catalina, and no doubt Big Sur & Monterey, use.

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Answer 3

lllaass

Level 10

210,417 points

Feb 18, 2022 10:39 AM in response to leroydouglas

Some users have experienced problem by sipping macOS versions. ome even from not fully update Big Sur before going to Monterey.

I also recommend you have backups in case something happens.

ALso I would incrementally upgrade to Monterey. That first go to Catalina, then to Big Sur and finally to Monterey.

You can get the installers for the older ones here:

How to get old versions of macOS - Apple Support

Note tha Mojave was the last macOS version to support 32 bit apps. If you have any 32 bit apps those will not work.

Also, soe printers do not work with monterey since no updated drivers are available.

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Answer 4

brian mck Author

Level 1

19 points

Feb 19, 2022 10:30 PM in response to lllaass

I have upgraded to macOS Catalina and am reasonable happy with the upgrade.

Catalina Dislikes:

The apps, files, folders etc take much longer to launch than in Mojave.
When visiting AppleID, Discussion Groups and iCloud Safari prompts for the user name/password differently to Mojave. In Catalina a drop down appears from the top of the screen and one has to look up the password for every visit. However in Mojave the browser prompted for user name/password in the main screen and I could populate both these from the passwords saved in my browser. I preferred the way Mojave prompted for user names/password.
System preferences takes quite a long time to load the Apple ID information and the speed of opening one of the links e.g. Energy Saver, is slower than in Mojave.
Loading Books onto my iPhone is more cumbersome than using iTunes. Firstly the Finder takes a long time to load my iPhone and when looking at the Audiobooks tab, I cannot see any detail other than the file name. In iTunes the phone loaded much quicker and one could see all details before dragging and dropping onto the phone. Im iTunes I selected books using the download date and just dragged the selection over my phone and the selected books were transferred to my phone. Much simpler, more user friendly and quicker than Catalina.

My plan was to upgrade to Big Sur followed by Monterey, but if the functionality to add audiobooks to one's iPhone is the same as in Catalina, I will most probably restore Mojave from my backup..

I can only hope & trust that the audiobooks transfer in Monterey is more user friendly and similar to iTunes. Otherwise

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Answer 5

Feb 18, 2022 10:37 AM in response to brian mck

First two notes:

1) NEVER Uprgrade without a solid backup; preferably, two, a Time Machine and a bootable clone, on separate drives

2) It is best to start fresh with a new OS, especially since you are skipping two intermediate versions. To that end, I recommend that after doing the backups, you create a bootable installer, erase the drive completely (using APFS with GUID Partition Map) and do a clean install, followed by transferring ONLY the user accounts (this include all your music, photos, documents...) but NOT applications, settings or other files.

That said:

All your music will still work as before, your albums, artwork, etc, all will be recognized.

It is just that the several functions that iTunes used to do are now assigned to different applications, which makes a lot of sense.

Its duties are subsumed by Music, TV, Podcasts and the Finder.

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Answer 6

CanukG4

Level 1

8 points

Feb 22, 2022 1:07 PM in response to brian mck

Great replies all around! There used to be software to tell you if apps would work in the upgrade, I guess there isn't such software or can someone point me to it if it exists?

One of you said 32 bit apps won't work any more, how can I tell if an app is 32 bit (Get-Info doesn't say)?

I use QuickTimePlayer 7 all the time, every day, I guess that wouldn't work any more?

I use FLVCrunch v15 all the time every day I'm sure that won't work so I won't be upgrading but I wish I could!

My Finale 26.3.1.643 with the great Apple sampler plugin probably won't work though I would love it if it would.

Can I create another user of the computer and only upgrade for that user?

Thanks for the great answers and thanks for the awesome forums to share and get answers!

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Answer 7

tbirdvet

Level 6

13,731 points

Feb 22, 2022 1:34 PM in response to CanukG4

If you upgrade it will be for all users on the Mac. You can download a free app called Go64 that will show all your apps that are 32 or 64 bit. Download from here:

https://www.macupdate.com/app/mac/61515/go64

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Answer 8

tbirdvet

Level 6

13,731 points

Feb 18, 2022 10:44 AM in response to brian mck

I went from Mojave to Big Sur to Monterey and no issues. I skipped Catalina.

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Answer 9

Feb 27, 2022 6:46 AM in response to brian mck

If I had to do it over, I would not update from Mojave. I did that 3 weeks ago and still trying to sort out sharing issues, network and photos. I may revert back to Mojave.

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Upgrade from macOS Mojave to macOS Monterey

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