My long and painful ordeal upgrading macOS to Big Sur.

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I have tried to upgrade macOS Mojave to Big Sur three successive times last night and each attempt took one hour because it was a full download.
The first time ended with an error code that some application was missing. Never mind that, I tried again.
This time it downloaded everything again for another hour and at the end the installer asked me if I wanted to install.
I click a “go ahead” button (by some other name).
And it started to download again the 12.44 GB for another hour!
I tried again, and once the third full download ended, magically, the installer asked me if I wanted to proceed to install, I clicked affirmatively, It asked me to  accept the EULA, I did, etc. and then started to install and took some 50 minutes doing that.

Once back in business, I started by testing the things I most needed to use, my compilers. Sadly, they would not work.
So I thought, maybe if I used “Homebrew” to install them again I may get their Big Sur compatible versions, if there are such things?
But it turned out that also did not work. Looking around in the web, I decided to install missing tools with “xcode”, but first I had to install some other missing, or in Big Sur obsolete, versions of command tools. I did that, then tried again to use xcode and then to upgrade Homebrew.
It worked, only it took over an hour to get all that done, but first I had to create several directories that were missing for the Homebrew upgrade’s install to work.
That took another half hour, between figuring out what to do and doing it.
Then I tried running the two compilers to compile some source files, as a test. One worked right away.
The other needed to have a script modified using something I found, again, looking around in the Web.
Then, with the compilers working, I started testing various applications I use frequently and consequently need them to work.
No problems with those. So far.

So: not exactly “I started the download, then installed Big Sur, logged in and everything worked.”

Ex-Windows user (Win. 98, XP, 7); since mid-2017 using also macOS. Presently on Monterey 12.15 & sometimes running also Linux (Mint).

MacBook Pro circa mid-2015, 15" display, with 16GB 1600 GHz DDR3 RAM, 1 TB SSD, a Haswell architecture Intel CPU with 4 Cores and 8 Threads model i7-4870HQ @ 2.50GHz.
Intel Iris Pro GPU with Built-in Bus, VRAM 1.5 GB, Display 2880 x 1800 Retina, 24-Bit color.
macOS Monterey; browsers: Waterfox "Current", Vivaldi and (now and then) Chrome; security apps. Intego AV

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bassmanzam, DrBonzo

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@OscarCP – You were trying to go from Mojave to Big Sur, which means you “skipped over” Catalina? Was Big Sur offered to you through the software update? I don’t know what to say about your compiler issues, but I have noticed that quite often late night/early morning updates from the App Store just don’t work, and that also software update can’t make up its mind whether it should offer Big Sur to me or Safari and Catalina updates, or any combination of them. All of which is to say, I wonder if the Big Sur download was somehow corrupted due to some server trouble on Apple’s end.

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OscarCP

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When you are a version behind (you are on Catalina and Big Sur is the current version) Apple always offers the UPGRADE version at the top and athe UPDATES for your version below under “more information.”
So if you are on Catalina, the upgrade to Big Sur is at the top. You need to click on “More information” to see the updates for Catalina 10.15.x and Safari.
This has always been the way it’s done since I can remember – so not confusing.

If you want to download the installer, I believe it needs to be done through the App Store or with Safari (not Firefox, Waterfox, Chrome, etc). though I have never done it that way, but always through System Preferences\Software Updates.

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bassmanzam, OscarCP, DrBonzo

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You’re right, it’s not confusing when it works right. A couple weeks ago, though, I would check and sometime nothing was offered, sometimes Big Sur was offered (and sometimes not) and sometimes either and/or both a safari and Catalina security update would be offered (or not). This happened on both my Macs, and I could check again 10 minutes later and everything that should be offered was offered. But, I could go back again 10 minutes later still and have an incomplete offering. It happened a lot a couple weeks ago, happened before that and has happened again since then. But it always happens in the late evening/early morning hours, never during daytime hours. (I’m on the left coast) So, I suspected something was going on with their servers – or possibly my internet connection, although it always seemed stable while I was checking.

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OscarCP

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I wonder if going from Mojave to Big Sur is sequenced so that what was Catalina downloads first and then Big Sur?  Or is Big Sur in this case somehow bundled to include the Catalina update all in one?  In either case, it would be a large update.  How does Apple do this?  But it’s one reason I stay current except to maybe skip a major update and wait for the .1 update to follow, eg, skiped 11.5 and waited for 11.5.1.

iPhone 13, 2019 iMac(SSD)

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bassmanzam, OscarCP, DrBonzo

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pmcjr6142: That is a very good question and your reasoning might just explain the second and third downloads I had of the system, not the first one that failed. Although the three were of the same size, so that might be an argument against it.

I had been asking a closely related question myself before making the upgrade from Mojave: do I need to upgrade first to Catalina (that I was skipping because it was repeatedly commented as being rather flaky) to make things ready for Big Sur?

Well, the answer now seems rather more likely to be “Yes” than “No”, after the experience I had going directly from Mojave to Big Sur yesterday.

I also should add to my previous comment that yet another thing I did yesterday, after finally installing Big Sur, was to change from what has been the new default system user shell in macOS since Catalina, and so now also in Big Sur, called “zsh”, back to my preferred one, “bash”, that was the default one since October of 2003, when “Panther” was introduced as the 10.3 version of OS X (later renamed macOS), and for sixteen years remained the default shell all the way through Mojave.

So another good question this opens up now is whether the version of “bash” in macOS I am using is a recent one, or an old one that might no longer be appropriate to use, or have installed, in some circumstances. I guess I’ll find out. Probably the hard way. Unless someone here knows the answer and is kind enough to let all of us know.

Ex-Windows user (Win. 98, XP, 7); since mid-2017 using also macOS. Presently on Monterey 12.15 & sometimes running also Linux (Mint).

MacBook Pro circa mid-2015, 15" display, with 16GB 1600 GHz DDR3 RAM, 1 TB SSD, a Haswell architecture Intel CPU with 4 Cores and 8 Threads model i7-4870HQ @ 2.50GHz.
Intel Iris Pro GPU with Built-in Bus, VRAM 1.5 GB, Display 2880 x 1800 Retina, 24-Bit color.
macOS Monterey; browsers: Waterfox "Current", Vivaldi and (now and then) Chrome; security apps. Intego AV

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bassmanzam, pmcjr6142

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I’ve got a Kaby Lake iMac4K that is still on Catalina. After the Aug Patch Tues updates for the Parallels VMs running Windows 8.1/10 on that machine, and being sure my version of Parallels runs on Big Sur, I will back up the VMs and try the upgrade. I know I will have to update several programs to later versions – TrendMicro, Paragon NTFS for Mac, and maybe more.

I have a Haswell MacBook Pro on Catalina that is also eligible for BigSur, but I will have to wait till the end of the collegiate diving season in Feb to upgrade that one. I run the diving meets for the local university from that laptop in a Win VM, and I’m not sure the diving s/w will be able to use the MacBook’s hardware to correctly communicate with the Daktronics console and scoreboard from Big Sur.
If it doesn’t work with Big Sur, it will give me an excuse to retire from the diving scene. I’ve been running diving meets since the 1993-1994 season.

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OscarCP

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PK, good luck and with the upgrade when you get to it and, please, let us know how it goes with that upgrade as far as your general ability to use a VM on a Mac goes. I am very much interested in installing a VM in mine.

Ex-Windows user (Win. 98, XP, 7); since mid-2017 using also macOS. Presently on Monterey 12.15 & sometimes running also Linux (Mint).

MacBook Pro circa mid-2015, 15" display, with 16GB 1600 GHz DDR3 RAM, 1 TB SSD, a Haswell architecture Intel CPU with 4 Cores and 8 Threads model i7-4870HQ @ 2.50GHz.
Intel Iris Pro GPU with Built-in Bus, VRAM 1.5 GB, Display 2880 x 1800 Retina, 24-Bit color.
macOS Monterey; browsers: Waterfox "Current", Vivaldi and (now and then) Chrome; security apps. Intego AV

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PKCano wrote:

If it doesn’t work with Big Sur, it will give me an excuse to retire from the diving scene

Or an excuse to fix it and write about it here. 

cheers, Paul

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Not familiar with MacOS but with Windows and almost all Linux distros (MacOS seems to be a derivative), I’ve always done better doing an ISO “reinstall” rather than skipping a version with an update.  I use third party router firmware and the same recommendation is usually given, update one version, reinstall for more than one.

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OscarCP

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I’m on Catalina on my IMac.  I have my eye on the new Imac which I would purchase in a year or two.  I like everything about it except it has less ports than my Imac 21.5 inc. 2017.  I wonder if I should bother with the hassle of updating to Big Sur or just wait for my new purchase to come with the latest version a few years from now.  I have very little on the computer and it is compatible with what is on the computer.  Should I let well enough alone?  I’m asking because I’m taking a lesson from Oscar that if I want Big Sur I would be better off getting it before the next big update.

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Anonymous, just over a year from now, in September or October of 2022, a new version of macOS will replace Monterrey, the newest one coming out later this year and that shall be also the third macOS version from Catalina, counting Catalina as the first. You have to upgrade to Big Sur or to Monterrey before that, otherwise your Mac is no longer going to be eligible for further upgrades, if my understanding of this is correct. A “three strokes, and if you do nothing after that, you are out” kind of deal.

On the other hand, if you look carefully into what difference for the better may upgrading to Big Sur mean to you, given whatever it is that you need your Mac for, it might turn out that there is no great need for you to upgrade to Big Sur after all. If you remain determined to buy a new iMac, that will certainly come with the latest software, including the latest version of the operating system, and to do this in a year from now, then giving Big Sur a miss will be a reasonable course of action for someone like you to follow, in my opinion.

Ex-Windows user (Win. 98, XP, 7); since mid-2017 using also macOS. Presently on Monterey 12.15 & sometimes running also Linux (Mint).

MacBook Pro circa mid-2015, 15" display, with 16GB 1600 GHz DDR3 RAM, 1 TB SSD, a Haswell architecture Intel CPU with 4 Cores and 8 Threads model i7-4870HQ @ 2.50GHz.
Intel Iris Pro GPU with Built-in Bus, VRAM 1.5 GB, Display 2880 x 1800 Retina, 24-Bit color.
macOS Monterey; browsers: Waterfox "Current", Vivaldi and (now and then) Chrome; security apps. Intego AV

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Thanks Oscar for your thoughtful reply.  I’m leaning towards staying with Catalina until I purchase the “latest and greatest” IMac.  I’m going to check today what the improvements are from Catalina to Big Sur and if they speak to me enough to update.

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I would agree with that as well.  If the new Mac will come with Monterey and you aren’t concerned with keeping the current Mac up to date for use as a second Mac, I’d probably wait as well.  I have a 2019 iMac that came with Catalina and I updated to Big Sur after a couple of months spent looking at many youtube videos describing Big Sur.  To me, the upgrades that were meaningful to me were minimal and not difficult at all to get familiar with.  I do think there is value in keeping a Mac up to date, though, and I will upgrade to Monterey after I go thru the youtube exercise again.  Catalina to Big Sur was my first Mac  major OS upgrade except for the Catalina point updates, and, as I’ve said before, I was nervous in doing it.  But it went without a hitch.  Waiting had another advantage in that the early adopters had already done it and the Apple servers weren’t all that busy.

iPhone 13, 2019 iMac(SSD)

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Normally I would be in favor of waiting at least four months from the first time a new version is released, to give Apple time to fix the worst bugs, for example in Big Sur’s case, that would have been release 11.3.1, in April of 2021, some five months after the first one, 11.0.1, came out in December of 2020. Even with that precaution, there is no guarantee that the installation or the use of the system afterwards shall be trouble-free, as I think my own case shows amply here, but waiting a few months is a good practice to follow, even if it does not mean things are guaranteed to be trouble-free. I also remember that waiting after the few first updates are out has been the advice of some AskWoody Mac experts. Also when buying a new Mac, it would be safer to buy it some months after a new system came out, so the Mac comes with the later and safer version of macOS pre-installed.

My own reason for waiting much longer than four months to install Big Sur was that, although the changes most users may notice are largely cosmetic, Big Sur is the result of a very extensive redesign of the system under the hood, so it could have taken Apple longer than usual to get rid of its most serious bugs and glitches. I don’t expect such a big change to happen again for quite a while.

As an example of the problems that early adopters of a new version of macOS may have, according to this paragraph in the “macOS Big Sur” entry in Wikipedia:

” The rollout of Big Sur came with several problems. Upgrading to the initial public release of Big Sur (version 11.0.1) bricked some computers, rendering them unusable. Many of these were 2013 and 2014 MacBook Pros, though problems were also observed on a 2019 MacBook Pro and an iMac from the same year. The initial rollout also disrupted Apple’s app notarization process, causing slowdowns even on devices not running Big Sur. Users also reported that the update was slow or even might fail to install.”

For some more information:

https://en.wikipedia.org/wiki/MacOS_Big_Sur

(I should add, for fairness’ sake, that except for the more than three hours unexpectedly taken by those three repeated installs, of which the first two were failures, the rest of my problems were caused by the changes in the operating system and closely related software  that took place “under the hood” and that I had to deal with because of how I use my Mac. Most people probably would not have to face any of that, because they use applications developed by programmers that, most likely, have already taken care of such things, so they are not likely to affect the use of their software, especially if the users stay up to date with the updates.)

Ex-Windows user (Win. 98, XP, 7); since mid-2017 using also macOS. Presently on Monterey 12.15 & sometimes running also Linux (Mint).

MacBook Pro circa mid-2015, 15" display, with 16GB 1600 GHz DDR3 RAM, 1 TB SSD, a Haswell architecture Intel CPU with 4 Cores and 8 Threads model i7-4870HQ @ 2.50GHz.
Intel Iris Pro GPU with Built-in Bus, VRAM 1.5 GB, Display 2880 x 1800 Retina, 24-Bit color.
macOS Monterey; browsers: Waterfox "Current", Vivaldi and (now and then) Chrome; security apps. Intego AV

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pmcjr6142

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After installing Big Sur I have noticed, with the help of Intego’s NetBarrier –an application that monitors what in the Mac, for example the mystery software I am going to tell you about, is sending and receiving data over the Internet. The application in question is called “Address Book” and, for reasons unknown to me, exchanges information with the rest of the world, but is nowhere to be found using simple procedures, such as looking for it in Finder/Applications or in Finder/Applications/Utilities.

Looking around the Web, the information I have managed to find something that may not even be about this particular ghost of an application, because its name is so vague and ambiguous: it might be something that keeps the addresses of my email contacts and lets me update them from my email client, for example from “Mail”. But nothing about communicating online with whatever this one communicates with, or why it does that.

So: does anyone know what “Address Book” is doing online?

As seen in this screenshot, “Address Book” is among the applications being watched with NetBarrier as they access the Web. One of the applications (mDNSreponder, that tries to connect with other gadgets in my non-existing network — nothing bad with that) can be seen receiving data from somewhere (orange arrows) and sending data elsewhere (blue arrows). It is very hard to catch any of the monitored applications doing that, so I am attaching this picture just to give you an idea of how this looks like:

Ex-Windows user (Win. 98, XP, 7); since mid-2017 using also macOS. Presently on Monterey 12.15 & sometimes running also Linux (Mint).

MacBook Pro circa mid-2015, 15" display, with 16GB 1600 GHz DDR3 RAM, 1 TB SSD, a Haswell architecture Intel CPU with 4 Cores and 8 Threads model i7-4870HQ @ 2.50GHz.
Intel Iris Pro GPU with Built-in Bus, VRAM 1.5 GB, Display 2880 x 1800 Retina, 24-Bit color.
macOS Monterey; browsers: Waterfox "Current", Vivaldi and (now and then) Chrome; security apps. Intego AV

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Today, doing a search on the Web, I found a solution to a potential problem presented by the mystery application “Address Book”, already mentioned in my previous comment here, that turns out to be something of an avatar of “Contacts”, the application that saves and then retrieves as needed, the addresses of people, organizations and businesses one corresponds, or has corresponded with. When addressing a new email, it is “Contacts” what makes the full address pop up when one types in the first two or three letters of the intended recipient’s address.

I was not comfortable with my address book having big conversations over the Internet with unknown parties. What I found in my Web search is this: if one goes to Mac/System Preferences/Apple id/list of applications, one of the items there marked “on” by default as allowed access to the Cloud is “Contacts.” I disabled there both iCloud (*) and “Contacts” from using, or being available to use the Web.  After that, “Address Book” has disappeared from the list of software downloading or uploading information to the Web. But my email continues to function normally.

(*) It is not necessary to disable “iCloud” as well. I did it because I am allergic to things with “Cloud” in the name, but this is not needed to stop “Contacts” from having conversations with unknown participants and possibly babbling to them on my personal use of email. For that is enough to disable only “Contacts.”

Ex-Windows user (Win. 98, XP, 7); since mid-2017 using also macOS. Presently on Monterey 12.15 & sometimes running also Linux (Mint).

MacBook Pro circa mid-2015, 15" display, with 16GB 1600 GHz DDR3 RAM, 1 TB SSD, a Haswell architecture Intel CPU with 4 Cores and 8 Threads model i7-4870HQ @ 2.50GHz.
Intel Iris Pro GPU with Built-in Bus, VRAM 1.5 GB, Display 2880 x 1800 Retina, 24-Bit color.
macOS Monterey; browsers: Waterfox "Current", Vivaldi and (now and then) Chrome; security apps. Intego AV

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