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[I reformulated the question after the 1st comment]

I have a MacBook Pro (Retina, early 2015) with OS X 10.10.5 (Yosemite). I would like to upgrade the OS. The only reason is that some new programs and devices (eg Wacom tablet) are not compatible with Yosemite. Otherwise it works perfectly for all my needs (a research mathematician). This is the 1st time I am doing this since I acquired this laptop and would like to do it myself (we don't have good Apple support here).

Question: Can you give some advice/tips how to best perform this task?

Here are some comments revealing my ignorance, to help you Mac experts guide me:

  • I heard it is not a good idea to upgrade to the last OS (possible unresolved bugs, incompatible with some of my older programs). But I am not sure.

  • I am afraid that after upgrade some apps won't work or will be missing. Say Keynote. Or non-Apple programs, like Mathematica 9, or MikTex.

  • I am not sure the cloud services I am using, like Dropbox, will not work after the update. I have several of these, about 80GB on my MacBook Pro.

  • I am not sure where is a good place to download the update, especially if not the last one. Seems like Apple will only let you download the recent one, but I am not sure.

A great answer can be just a link to some good article or a similar question on this forum.

MUCHAS GRACIAS!!

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    This site works best as one question per question and you’ve got 7 there, several of which have already been addressed and others are to overly broad ( which programs/services) and many quite opinionated. Let’s narrow this down by focusing on one objective topic that you’re stuck on because research refinement, and even trial/error have yielded no results. – Allan Aug 15 '20 at 5:49
  • Welcome to Ask Different. To get you started: first of all, make a backup, see support.apple.com/HT201250 for more information. Then follow the steps in the 'How to get updates for earlier macOS versions' section at support.apple.com/HT201541. The App Store app will probably display a prominent banner recommending that you upgrade to a newer macOS version. Click the banner to download the installer. The installer will automatically launch, just follow the onscreen instructions. For a list of macOS versions, see support.apple.com/HT201260. – jaume Aug 15 '20 at 9:06
  • Thank you everybody. Upgrading from 10.10 to 10.14 was a success! You helped a lot. All the best. – Gil Bor Aug 16 '20 at 13:54
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Welcome to the world of upgrading! These days, both Operating Systems and applications are regularly updated to keep pace with progress.

'Not upgrading' has the advantage that you reached a static point where everything works (or at least has fixed, known bugs). The problem comes, as you've found out, when you want something new, and it requires a newer OS than yours.

Upgrading 'one big jump' from very old software is more difficult than just 'the next version', because the change is so much larger. You will almost certainly have to update all your apps to match the OS, so you should check that there is a version compatible with the latest macOS (Catalina) for each one.

The good news is that any company still in business is likely to have current versions. Apple, as you would expect, has current versions of KeyNote, Pages and Numbers. Dropbox and other cloud services all have current versions.

The bad news is that some companies may require payment for newer versions.

There will always be unresolved bugs in any OS. But now is a good time in the 'annual cycle' to update, as Catalina is on its sixth and final release, so it's as good as it's going to get.

You should always download from Apple and nowhere else. Apple does make it difficult to obtain 'non-current' versions of the OS. This article provides links to some earlier versions on the Mac App Store.

https://www.macworld.co.uk/how-to/mac-software/download-old-os-x-3629363/#toc-3629363-2

If you have any software that runs as 32-bit binaries, with no updates available to 64-bit versions, then you may prefer to run Mojave (10.14) instead of Catalina. Catalina can only run 64-bit executable code, and won't run older 32-bit code.

If you do have old apps that don't have upgrades available, then you have two options: either use a separate volume with the earlier OS and boot to that when you want to use those apps; or use Virtual Machine software, such as Parallels, VMWare or VirtualBox, to create an 'OS within an OS', where you can use the older software.

Generally, it's best to keep up (to some extent) with new versions regularly. You don't always have to be on the very latest: you can be '1 year behind', for instance. But keeping up ensures that you receive important security fixes, as well as bug fixes; and that you don't fall behind into the situation you are now in.

It can be a bit of a pain when every time you launch an app to do some work, there's an alert that a new version is available: do you want to install it now? But it's good to set a small amount of time to deal with 'software admin'. Some apps (and those from the Mac App Store) can be set to install silently in the background.

Relying on software that is not being maintained is not a great place to be. Old, unsupported software will require old hardware, which eventually break down and become hard to repair or replace.

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  • Great answer. Really. One question: you say "Upgrading 'several jumps' from very old software is more difficult than 'one jump', because the change is so much larger." Didn't you mean the other way around, i.e. 'one jump' is more difficult than 'several jumps'? – Gil Bor Aug 15 '20 at 14:03
  • @GilBor Sorry, perhaps that's not clear: I mean 'one big jump of several steps' rather than one small one, i.e. encompassing all the several updates between 10.10 and 10.15. I'll alter it. – benwiggy Aug 15 '20 at 14:17
  • Much clearer now, thanks. So to summarize: say I want to upgrade now from 10.10 to 10.14. You recommend I do it in 4 steps instead of a single one? from 10-11, 11-12, 12-13, 13-14? Is it worth the tedium? – Gil Bor Aug 15 '20 at 18:48
  • God No! Do it in one step. What I meant was that if you keep up to date, then updating the OS to the next version is very easy. But updating 5 OS versions in one go will inevitably require more changes to all your other software. – benwiggy Aug 15 '20 at 20:02
  • OK. All is clear now. Did the update in one go from 10.10 to 10.14. Was quite nervous but it went nice and easy, except one problem. Maple 17 does not run anymore. Dont remember how I acquired it (certainly did not pay for it). Oh well. – Gil Bor Aug 16 '20 at 13:50
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You can erase Macs easily and reinstall the older OS. Why not make a good backup and then test the upgrade?

Worst case, you find some things that break and erase and spend an hour reloading things from Time Machine. Best case, you now have a backup and things update and work.

If you are super concerned and your time is valuable, buy an external SSD and install the new os there. When it boots migrate your data and apps from the running system to the new external test. You don’t even risk your main system to do this test.

Apple has extensive support on choosing the specific installers you want:

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  • Thanks! Now I am following yr advice, backing up all my essential files on an external hard disk, about 100 GB. But it is very slow, about 5GB per hour, and getting slower by the minute. I must be doing something wrong. What? Disk brand is ADATA, seems very standrd. I am not using the time machine software. Just a simple copy/paste via the mac's Finder. All advice welcome!! – Gil Bor Aug 15 '20 at 19:16

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