macOS 10.13 High Sierra Upgrade to Anything 64-bit

2011 September

In later part of September 2021, recognize that increasingly reaching end of possibility to continue using 10.13 High Sierra.

Which has been absolutely “good enough” for years, including use of:

  • MS Office 2011
  • Adobe CS suite with perpetual license
  • MS Ergo 4000 keyboard, ok – been a bit of struggle for years but ControllerMate has done it working even on 10.13
    • Oh, one other thing that definitely will break going from macOS 10.13  is use of MS Ergo 4000 keyboard, the best keyboard ever created. (Got a bunch, as bought all remaining in stock at a store when realized it had been discontinued, now goes for $380 (!) on Amazon, Sep 2021).
    • Was actually only officially supported by Microsoft up to macOS to 10.7 Lion (2011-2012)
    • But did continue to work w/ Microsoft driver/software to macOS 10.10 Yosemite (2014-2017)
    • Then eventually been using ControllerMate up to including macOS 10.13 High Sierra (2017-2020)
    • This broke with macOS 10.15 Catalina, and with some twiddling finally got MS Natural Keyboard HID Handler to work.
      • Increasingly complex measures by Apple for locking down software, protection against malware, et c, makes installations on the level of drivers sometimes quite complicated, or even possibly impossible.
    • Also been able to get this to run on macOS 11 Big Sur (2020-..)
    • (Driver solution for Ergo 4000: blood, sweat, and tears; done it once but it’s not trivial, many manuals steps to enable and configure specialized hardware driver on any modern strong security-minded OS, and macOS is a bit tough one to get around.

So, actions:

  • As clearly HAVE reached end of life of 10.13 and 32 bit apps
    • Can’t use HomeBrew (brew) or MacPorts (ports) any longer,  support for at least brew must have stopped in last month or maybe just few weeks (don’t remember exactly when last used when still worked in 10.13)
    • Slack support is ending, actually ended Sep 1, 2021.
  • Started process of upgrading macOS from HighSierra 10.13 to Big Sur 11 generation
  • Taken inventory of what will happen and what I will need to look at fixing
    • More than 200 apps will break, most notably MS Office and Adobe Creative Suite – high-cost suites, but also
    • VMware hypervisor software,
      • Included VMs w/ Ubuntu for working with embedded systems and (e.g.) LIDAR sensors
      • Cisco AnyConnect (that was initially and continued to used for customer site access in Japan),
      • Ubiquity app ( for admin of their products
    • Continued using apps that worked “good enough”, no good reason to change as meeting requirements,
      BUT that now has to be replaced with some alternative, to be determined.
  • Cost estimates – separate column in table below
Area / Application Costs involved Plans (2021-09) Status
Hypervisor $80 (Parallels), $200 (Fusion) Trial of Parallels [√] 2021-09-27
 + 10.13 High Sierra VM blood, sweet, & tears Create VM, install 10.13 [√] 2021-09-27
MS Office (currently 2011) $250 / 1 pc (perpetual) Office 2011 into a VM [√] 2021-09-27 (10.13 VM)
MS Office 365 (…) Use a personal license [√] 2021-09-30
Adobe Creative Suite $600/yr subscr. CS into a VM [-] NOT doing on MBP17
VMware Fusion 12 Pro hypervisor $200 / 1 pc (perpetual)
### current license
Upgrade? [-] holding off for now
   as applicable, upgr. of VMs $0 (own work) As needed [-] -“-
KeePass $0 Fix!! (Broke ~Sep’21) [√] 2021-09-30


2021-09-27 Mon

  • General assessment and doing a bit inventory of what got, status
  • Hypervisor and VM for a macOS 10.13 appliance.
    • Re-evaluated hypervisors, not done in a while – VMware vs. Parallels, been heavy user of both earlier, incl. VirtualBox
    • Parallels gets a little bit more positive notch compared to Fusion and start a 14-day trial
    • Created a 10.13 VM from recovery partition, as still is using 10.13 (not upgraded machine yet).
    • Installed MS Office 2011, w/ Activation over phone (as earlier, activation server(s) have stopped responding year(s) ago(?))

2021-09-28 Tue – didn’t have time for any actions on this topic

2021-09-29 Wed

  • Download macOS 11 Big Sur installer and running it
    • 14:20 Start download, very quickly done (gigaservice)
    • 14:21 Start running installer, and at first progress bar moves slowly but at least moves, setting a couple of 30 min alarms and check on progress
    • 16:04 Looks like it’s been stuck at may 95% done, some 5 mm left on progress bar
    • 17:00 Same, no change, seems stuck…. Really concerning – stuck in installation of something as core as OS can be really problematic.
      • Researching topic, stuck in installing Big Sur, find other who has got into this, and with – many with continued problems also after tries but … – common recommendation seems to still power cycle computer.
    • 17:15 DO that – power cycle
    • 17:20 Yay, at least this computer IS booting up properly, and in Big Sur, new OS. So, just about 3 hours with unavailable computer.
  • Start first basic configuration steps with a new OS.

2021-09-30 Thu

  • Special Key Handler stuff (for Ergo 4000 keyboard)  – START
    • Using AppleScript based apps, which fails to be used as-is, new code signing requirements
  • Code signing research, need Xcode, plus CLI dev tools
  • Xcode installation –  1h20m
  • Command line developers tools (xcode-select –install) – 15 min
  • Finally able to save a first AppleScript application – took about 1 h 40 min to sort out saving the first AppleScript app on Big Sur.
  • Fixing handling of Ergo 400 keyboard (/is/macos/keyboards/)
  • Log into Office 365 (personal license), install local applications, start one (Word) to log into office 365 and enable use of apps on computer.
  • When try opening Parallels installed just two days ago, it won’t start, try multiple times.
    • End up reinstalling and then it asks for permissions to access multiple folders (Desktop, Documents, and Downloads), and after this it starts up nicely. And can access the also two-day old 32 10.13 High Sierra VM.
    • Plus, actually DO NEED TO RESTART host computer (MBP17; not Hypervisor and VM but host computer).
  • KeePass password manager, password repository handling – new research on what is working on Big Sur now.
    • Looks like KeePassXC is kept up to date, download latest now available (2.6.6, posted on Jun 12, 2021). And it works with existing pw file.
  • brew (HomeBrew) – not immediately getting to work but have to “unshallow”, then DO get it to work, installing a package (jq) as test.
  • – install config w/ keys info.


2011 November (IM2713)

Decided to move another workhorse computer (IM2713) t0 10.15 – last possible release to upgrade to on this generation of Apple iMac hardware – for the following reasons:

  • As getting use to struggling w/ Office 365 on other computers, can as well struggle on this… (Same goes for other 32-bit SW, run these inside VM(s))
  • Feels better to at least take this one up to latest available macOS release from Apple as long as they support it, and will be releasing security updates, et c.
  • (Also, for some time, have occasional problems with this computer and properly recognizing the Ergo 4000 keyboard (via USB-keyboard/peripheral switch) – see if will work better after upgrade. Nothing to loose anyway.)
  • The upgrade t0 10.15 also