Mojave to Monterey

My late 2015 i7 27 inch iMac wants to upgrade via software update directly to 12.1 from 10.14.6.
Is this wise? I have been waiting for an audio app to update, but have now given up hope.
I am a 26+ year Mac user and have only ever updated each year in the past, this would be 3 years if I go ahead.
Any views as to which of the 2 ways I proceed would be appreciated.

My habit is to stand back a step or two from the bleeding edge, but this time I waited until the security updates stopped.
MacBook Pro, mid 2014: 10.14.6 → 11.5.2 → 11.6.2 (Software Update presumably wanted to adjust the firmware)
Mac mini (2018): 10.14.6 and Software Update offered 12.1, so I did a clean install of 11.6.2.

I found this site helpful:

No problems so far. Good luck with it.

No need to go to a private link database like this unless you want an older release of a particular macOS version.

Apple provides links to the latest release of each version from their own pages.

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I updated my 2019 iMac 5k from Mojave directly to Monterey a few months ago with no problems. As a precaution, I emptied out my mail accounts before making the update. It might be helpful to peruse Howard Oakley’s site ( to gain insight into the major changes that will occur with your Mac, especially with respect to APFS. I’ve been quite pleased with performance and features.

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@holty43 Monterey is for my taste still too young. I stay with BigSur for a little longer. Your 10.14.6 is the last version that runs 32-bit software. Do check that everything you need is available as 64-bit SW.

I searched Apple Support for ‘Big Sur installer’ ‘macOS 11.6’ etc. and got no hits at all. Deeply frustrating.
How did you find that page ?

MDS is a free third party app that will download any installer from the Apple servers.
It will also make a bootable installer using creatinstallmedia.

Sometimes you just follow your nose:

I started with the Support tab on Then I selected the Mac section, then MacOS, then Reinstall macOS. The last section on that page entitled ’ Other macOS installation options’ had a bullet item ’ * Use the App Store or a web browser to download and install an earlier macOS.’ which had a link to the Apple page describing how to get the installer from the App Store.

Interestingly, searching directly for macOS BigSur on the App Store does not show it.

" . . .just follow your nose:"

Thanks, Alan. I think I’ll just follow my nose to the back of the class . . .

I guess I got lucky. It’s the first hit when searching for “old macos installer”:

Searching for individual macOS releases is less reliable, because Apple doesn’t have a separate support page for each release - they only have pages for some of the oldest versions. The rest are special links to App Store pages.

The usual make sure you have a couple of backups. I ran Monterey on a 2013 MBP and it worked fine (not that you asked). One thing I used to do is install on another boot drive, but that has become a real pain because Apple requires you to authorize, add iCloud, etc, so you end up with another device (in other words another boot drive on the same computer makes it a new device in Apple’s mind). The precaution on checking for 32 bit apps is good. Triple check for ways to run your outdated app. I had one, Intaglio, that people had found a work around for. Was OK for occasional use. But I upgraded to an M1 and that was a step too far. Not clear on why someone emptied their email. And Monterey is pretty mature—no one mentioned any ongoing problems, although no doubt there are a few. Lastly, be patient, sometimes nothing seems to be happening and a couple of hours later, the step is done. But on some upgrades (although I don 't think this happened with Monterey), you have to force reboot. Going from 10 to 12 is not a big step—double check, but don’t think there were any major changes under the hood between 11 and 12.

I upgraded my iMac (2019, 27-inch) from Mojave directly to Monterey just a couple of weeks ago and I have been pleasantly surprised that it went quite smoothly. There is one app that is no longer working: Maintain’s Cocktail app. It doesn’t detect my main hard drive—only my Time Machine drive. But, I think that is due to some odd restructuring of volumes. At any rate, Monterey is running smoothly and I’m happy I finally took the plunge to upgrade.

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Cocktail creates a new edition for each major OS version and does frequent updates of it. The current Monterey-specific edition is 15.2.1. I’m on a 2020 27" iMac and it fines the boot drive and all connected drives just fine.

Yes, I do have the Monterey version of Cocktail. The issue is with my particular hard drive. I had once (while using Mojave) tried to create a partition to try out the latest version of On The Job (Stunt Software) in Catalina and then reverted back to Mojave. I deleted that partition with the help of an Apple rep, but Cocktail is unable to detect my HD. I’ve attached a screenshot to show the drive hierarchy in Disk Utility. I’ve written to Cocktail several times, but they have been unresponsive. It’s not such a big deal. I just won’t be purchasing Cocktail updates anymore.
Disk Utility 2022-01-25 17-54-53

I updated a 2014 Mac Mini from High Sierra to Mojave last weekend. (I replaced the hard drive with an SSD previously). It is working well. Several older apps were no longer usable. It did hang on “less than one minute remaining” for at least 20 minutes, possibly an hour or more.

I’ve been hanging back on this upgrade, so this thread is encouraging. My 2019 iMac (27", 1 TB SSD) is still on Mojave (10.14.6). I’m getting some oddball little problems, and the one I called Apple about just got a response of “upgrade the OS.” Maybe it’s time. The only real loss would be DVD Player. No TV, and we occasionally watch a DVD on this Mac. I think my Samsung DVD player may be 32-bit as well as the DVD Player app, but Samsung no longer has any info about my player online. There are some other 32-bit apps on the iMac, but none of them are currently being used. Two questions: (1) Is it necessary to delete the unused 32-bit apps to get a smooth upgrade? (2) Any recommendations for replacing the DVD software and player? Thanks.

DVD Player still exists in Monterey. It’s on the Boot drive and is Universal (Intel and Apple Silicon versions together). Here’s the Info for it from my 2020 iMad running Monterey 12.1:

DVDPlayer Info.pdf (303.8 KB)

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Wow! Thanks. I had no idea DVD Player came back in Monterey.


It never went away. Apple moved it out of the /Applications folder (on my Big Sur system, it’s in /System/Library/CoreServices/Applications).

It should auto-launch when you insert a video DVD into a drive (it does on my Mac mini with an Apple SuperDrive), so you shouldn’t need to know where it is.

Thank you. It must be my Samsung SE-218 drive then. I just tried it on a MacBook Pro running Big Sur. The drive got a blinking light indicating it was getting power from the usb connection, but it wouldn’t open to accept a disk.

But looking for the system library item brought up another issue. I can’t figure out how to get to the system library! In every OS through Mojave, the internal drive was represented by a desktop icon. In Catalina and now in Big Sur there’s no such icon. The Finder icon doesn’t reveal anything at the system level. Clearly Apple doesn’t want us messing with the system, but at times you need to know what’s there. How do you get to the system files?