Although this is not a KNM question per se, I think that it is relevant and of interest to forum members.
In a past post in 2016, forum members discouraged me from upgrading from El Capitan to Sierra, but I had to do so a few months later because of app update incompatibilities.
I was then discouraged from upgrading to High Sierra and never did so.
I am already encountering certain apps which only can be updated on High Sierra or later.
Should I stay with Sierra, or update to High Sierra or Mojave ?
thanks very much for your time and help
Hey @ronald,
I'm going to stay far away from Mojave for at least 6 months to a year.
Fortunately nothing is requiring me to give up Sierra (so far), but I'd probably go up to High Sierra before messing with Mojave.
Too many major changes have been made.
Too many unexplained issues with Keyboard Maestro and other software...
Meh...
-Chris
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My decision making on upgrading to a new macOS, is simply this:
Do I have a compelling reason to upgrade? Will it break my workflow?
This means will the upgrade either fix issues in, or offer material improvements to, my current workflow, without materially breaking any of my essential apps?
So, I'm currently running macOS Sierra, and do not see any compelling reasons to upgrade to either High Sierra or Mojave. Both of them had material adverse impacts to my workflow when they were released.
I do like several of the Mojave new features, but it has a major impact to AppleScripts and Keyboard Maestro. So I will stay with Sierra for at least several months until I see how things shake out with Mojave.
I am curious to know which apps can only be updated with High Sierra. Does the upgrade provide anything that you really need?
Don't rush your decision. While it is possible to downgrade after an update, it can be hard and painful, particularly if you want to downgrade some time after the update when you have created/updated many files.
Good luck, and please let us know your decision, and how it goes.
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@JMichaelTX @ccstone
thank you VERY much to both of you.
In view of your comments, I will stick to Sierra.
The app which is not Sierra compatible is outlineedit version 2 (a complete rewrite). I will just do without it.
On one hand, you are both obviously right. On the other hand it gets confusing for someone less experienced like me.
My gut reaction would be simply wait about 6 months after each new major release (El Capitan, Sierra, etc). In addition, as a precaution, I also ask in this forum and look at recommendations on other Internet forums.
My problems is that with High Sierra, the consensus has always been NO, do not upgrade. It just seems strange to skip an entire major upgrade. And as I mentioned earlier, I was advised many times not to upgrade from El Capitan to Sierra. Had I not been forced to upgrade, I would still be using El Capitan.
I am just saying that it's confusing.
FWIW I skipped Sierra and will probably skip Mojave (I’m certainly in no rush to upgrade) but have had no problem with High Sierra, and wasn’t even aware people were ever down on it.
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Thank you. I thought there were terrible problems when high Sierra came out due to encryption
Different users have different reasons to upgrade, or not upgrade. So, ultimately you have to weigh the comments of others, apply to your situation, and make your own decision. Personally, I would never make a major decision like OS upgrade based solely on what one person, or even several, said.
I too waited a long time before I upgraded from El Capitan to Sierra, and I don't regret a moment of it. It worked out very well for me. By the time I upgraded to Sierra the combination of Apple fixes and App fixes resulted in all of my essential apps working very well with Sierra.
At the time I upgraded to Sierra, I make one final check with the community here, and did not get anyone suggesting I should not upgrade. Unfortunately, I can't find the topic where I asked that question.
IMO, there is nothing wrong with skipping a macOS version, if that version does NOT offer you a compelling reason to upgrade. In fact, my nominal plan now is to upgrade from Sierra to Mojave, skipping High Sierra. But that won't happen for many months, maybe a year -- it just depends on the reports I see about Mojave and my essential apps.
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I upgrade to new Mac OS's on their release day, and I have zero regrets. My method?
First, I update all of my apps and utilities. I run a tight set of utilities—only three are necessities: Keyboard Maestro; Razer drivers for my mouse and Bartender for my menu bar. Before the upgrade, I check the utilities' sites for compatibility confirmations.
Second, using a reliable external drive, I back up my entire Mac. I recommend Carbon Copy Cloner.
Third, I do the upgrade. I run it through my standard practices. I try out all of my main apps. If all goes well (and thus far, it always has), I cheer and get on with my life.
If I ever experience issues, Carbon Copy Cloner can have me safely back to the moment I made my back up.
Upgrading is easy if you prepare well and have patience and technical knowledge. I used to do tech support for a department of three hundred—upgrades are not a huge deal from my perspective. Good luck with whatever decision you make.
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thank you. And I in turn rely on experts like you. I will upgrade to Mojave when you feel it's OK.
thanks
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That is a very smart approach. I have not used CCC, but it looks great, and is on my short list to review/try/buy.
My biggest challenge is that my iMac-27 has a 2TB drive. While my current storage is no where near that, I need to think about the future. I have noticed recent discounts on SSD drives, so getting one of those and a drive box is a thought. A thunderbolt drive would be the best, but a USB-3 drive might be fast enough for backups/emergency use.
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I don't think anyone can answer for you as only you can determine the risk or lack thereof. I seem to be in a bit of a different place than many who responded. I enjoy upgrading as soon as is feasible. Something I do, is to check the programs I use all the time and can't live without. If any are not compatible but are working on it, I wait. If some are not going to be compatible, I replace them.
This go around with Mojave, I waited a little. Then took the seamless plunge. All is working just fine. Moreover, I'm happy I did it as there is much to love about it.
I have mitigated this with slower drives by scheduling backups while I sleep. The drive doesn't need to be fast for my needs—just reliable.
That said, I have a different perspective on hard drives. My first hard drive was 20MB (not a typo) and it cost me $1000. When I bought my LaCie Rugged 4TB USB-C for a fraction of that, well, I have no regrets. 
@ronald asked: "Should I stay with Sierra, or update to High Sierra or Mojave ?"
Lots of good advice here about updating or waiting.
But if you do decide to update your El Cap installation and haven't already managed to download the High Sierra installer* or can't get a copy of the installer from a trusted source, Apple has already decided for you what to update to: when they released Mojave, they removed High Sierra from the App Store. This is their standard behavior when issuing new macOS releases. So, your only update option is Mojave.
- My, and many others' attempts to download the High Sierra installer (see macintouch.com forums) resulted in downloading only a stub app, which when run would then download the full installer. It seems that for some Macs, the stub app was required to install firmware or other updates before installing the OS update. I tried several times to download it on my 2014 MacBook Pro running Yosemite, and every time, got only the stub app. I would love to be able to put High Sierra on it, but Apple won't let me.
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Hrm… that's odd. I was able to download them recently, but I don't doubt that you've had those problems.
However, I believe that the installers can be used even if they were downloaded by someone else.
I have all of the installers since Lion, and would be happy to make them available to you if you'd like. Send me a direct message with your email address and I can send you a link (the installer app is zipping right now).
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I rarely make recommendations, but in combination with the excellent CCC, the Samsung SSD T3 (now T5) external drive is outstanding in terms of speed, size, weight and reliability ... if you can find it at a good price.
You can get 1TB SSDs at a good price ~$150, but 2TB (the size of my iMac-27) are still very high.
To @Jim's point, for a drive you only need for backup and emergency boot, this 2TB drive looks very attractive for only $64:
WD 2TB Elements Portable External Hard Drive - USB 3.0
But I'm not buying anything now until Black Friday / Cyber Monday.
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I have not noticed any issues with KM after upgrading to Mojave, wouldn't recommend to update to Mojave as the system is new and no one knows when to expect any kind of issues.
Any machine connected to the internet should have at least the latest version of the previous version of the current OS. If you need to run an OS version more that one revision behind the current version, put it on a portable computer that you can keep off the internet, relying on sneakernet to retrieve data for it. Currently, I have High Sierra on a 2010 MacBook Air and MacOS 10.2.8 on a 2003 17-inch PowerBook. Both are disconnected from the internet, they use USB thumb drives for sneakernet -- and both run just fine.
I'm not sure I understand the need/rationale for this.
I have often ran a macOS two major versions behind the current, including right now: I'm still running Sierra: macOS 10.12.6
I've never had an issue with this, and continue to receive minor (dot) updates to Sierra.