Hi, thanks for stopping by my blog. You may remember/know me from such places as:
• the xoxo festival slack since summer 2018
• stints in IT at the following companies:
• Urban Airship
• New Relic
• Conference talks from 2014-2016 at:
• Penn State Mac Admins (2014 and 2015)
• Mac Tech (2014)
• MacAD.UK (2016)
• The MacAdmins Slack (from May-Oct 2015)
• Being angry/weird on Twitter (since July 2009)
• The old Apple Mailing lists and Freenode ##osxserver channel (2012-2015)
• A number of odd jobs I've had
• Being that really angry redhead at the Pioneer Place Apple Store in Portland Oregon from 2005-2009
Or maybe you've never met me! Maybe a friend sent you this. Hurray!
Hi, I'm V, a bipolar woman in tech based out of Portland, OR. I've been using Macs daily since 1994, except for a 2.5 week stint when I was in Japan in 2002. I've supported macOS (OS X, Mac OS) professionally since 2005, and unprofessionally since 1999, when I tore apart the Computer Graphics lab at my high school to ensure me and my friend's Power Mac's had more RAM than the rest of the class.
Anyway! That doesn't matter, that isn't the content you're here for.
PLEASE NOTE: I am just a cranky former IT engineer/client systems engineer. This post is me being angry at all the employers I've had that have refused to allow users to upgrade when new versions of macOS come out, and at users who upgraded thoughtlessly. This post is not to be constituted as advice, suggestions, or recommended procedures for anyone. I will not be held liable for anyone following this "advice" as it were.
Catalina: Release date speculation
So it’s early October and we're still probably a few weeks out (at least a week or two) from macOS 10.15 Catalina's initial release — Apple has a few known issues that are pretty big, and they can't really release the OS just yet without a ton of bad press. This will be the first time since 2014 that we've had a new version of macOS drop in a month other than September, which is probably causing some level of havoc at 1 Infinite Loop.
At the very earliest we're looking at October 7th or 8th as the earliest possible release date. More likely we're looking at sometime after October 14th. If Apple plays it exceptionally safe the public release might get pushed back to October 21 or later.
Prepping for Catalina
OK, the IT person in me has to scream this:
DON'T JUST UPGRADE TO CATALINA FROM WHATEVER YOU'RE RUNNING NOW WITHOUT DOING PREP WORK. YOU WILL KICK YOURSELF IN THE ASS AFTERWARDS. DO NOT TRY TO RUN THE UPGRADE ON YOUR MAIN MAC OVER LUNCH, EVEN IF YOU'RE TAKING A LONG LUNCH, IT WILL INEVITABLY NOT BE DONE WHEN YOU GET BACK, IT NEVER IS.
IF THIS COMPUTER WORKING NORMALLY IS HIGHLY CRITICAL AND YOU ABSOLUTELY CANNOT AFFORD ANY ISSUES:
DON'T FUCKING UPGRADE UNTIL 10.15.2 AT THE EARLIEST. 10.15.3 WILL BE SAFER, IF YOU CAN WAIT.
SERIOUSLY. I AM NOT SHITTING YOU. I HAVE BEEN DOING THIS PROFESSIONALLY SINCE 2011. FFS LISTEN TO ME DAMMIT.
Upgrading to Catalina intelligently:§
1. BACK UP YOUR MAC. Or, at least BACK UP YOUR IMPORTANT FILES! This can be to iCloud, Dropbox, Google Drive, a flash drive, a Time Machine backup, an external hard drive -- make sure you back your system up. If this is a mission critical machine shut it down and boot to an external drive* and clone it with something like Carbon Copy Cloner. *if you're on a 2018 or later Mac you can't boot to an external drive because of the T2 security chip in your Mac. You may be able to perform some unholy dark arts with a USB drive mounted while booted to Internet (or internal) Recovery. Maybe just grab the important stuff and offload it somewhere, and accept that you might need to reinstall your apps.
2. No, seriously BACK UP YOUR SHIT. Make sure your password manager files are backed up. Make sure your photos are backed up somewhere. Make sure your tax files are backed up somewhere. Make sure your goddamn thesis is backed up, ESPECIALLY IF IT'S A WORK IN PROGRESS. Back critical shit up in at least 2 places, preferably with one in the cloud and one local. If you have the time and the money make a third backup and put it in a safety deposit box outside of your home city's limits, away from fault lines and volcanoes and tsunami zones.
3. Yep, you guessed it BACK STUFF UP. Don't risk this being the OS upgrade that deletes the last 20 years of your photos from photos.app. Don't risk losing all of those files on your desktop that you've been meaning to sort for the last few weeks but meh it's ok you’ll get to it eventually. BACK THAT SHIT UP. NOW.
4. Ok, did you finally back your Mac up? For real? Cool. Check for macOS updates. You can do this a number of ways:
• Apple Menu > About This Mac > Software Update
• System Preferences > Software Update
• Terminal.app > softwareupdate -la (this lists all available updates, use "-da" to download all, and "-ia" to install all. or just run softwareupdate and it’ll give you a pretty friendly help output into your terminal)
• Note: you may need to check for updates a couple times if you aren't good about updating your Mac. You mileage may vary on how to run updates if you're on a version of macOS before 10.13. Google “how to run software updates mac 10.x” with x being whatever version you’re on.
5. Have you finished updating macOS? Better run another backup! Seriously. Do it.
6. Ok, macOS is fully updated and backed up, and now we need to update your apps.
• Open the App Store app. Check for updates. Run them.
• Go to your Applications folder. You can do this by clicking on Finder and then pressing Command + Shift + A at the same time on your keyboard. Or clicking in the Sidebar of a new Finder Window. Or by going to the Go Menu in Finder and picking "Applications"
• Start opening apps. They should automagically check for software updates when you do that. If they don't, question why you are using these apps. Maybe throw them away.
• But seriously: open and update all critical apps that you need. Steam, whatever you use for video conferencing, Adobe products, Microsoft products—update them ∞
∞ If you're using illicit copies of Adobe Creative Suite Whatever or Microsoft Non Office365: friend, have you considered paying for software this decade? Like… you don't even need to buy a subscription to the Adobe or MS suites, go to MacRumors or AppleInsider and find something that is compatible with your files. DO NOT UPGRADE TO CATALINA UNTIL YOU FIND A SOLUTION OR YOU'LL BE SOL.
7. BACK THINGS UP. AGAIN. DO NOT QUESTION ME. I AM A PROFESSIONAL. THIS IS CALLED COVERING YOUR ASS. IF YOU AREN’T CYA’ING IN YOUR OWN JOB HOW ARE YOU SURVIVING?
8. Are you an engineer? Do you work with software? Do you know what a command line is? Is Homebrew critical to your work?
• UPDATE YOUR HOMEBREW ENVIRONMENT NOW:
• Seriously. This is the step literally every software engineer I have ever met will forget.
• Open Terminal.app (or iTerm or whatever it is you're using)
• Type in "brew update" without the quotes and press return
• Go get some coffee. This will probably take a while if you've got a full dev environment.
• Once Homebrew is updated run "homebrew upgrade" and maybe go grab a snack. Or offer to spend some time pair programming with a coworker. Or go share some memes on Slack. Untitled Goose Game is really popular lately, maybe make a meme?
• Eventually the updates will be done, yay! Huzzah! You're almost ready
9. Can you guess what 9 is? You're smart, I bet you can, its:
• BACK UP YOUR MAC, AGAIN. YES, DAMMIT. YOU’LL MAYBE ONLY ACTUALLY DO TWO OF THE UPDATES I ASKED FOR. I KNOW HUMANS. Y’ALL DON’T LISTEN.
10. Congrats, you can now safely upgrade to Catalina, after you download the installer app from the App Store and:
• BACK UP YOUR MAC, YET AGAIN. Ok maybe this time it’s a bit overkill, but that installer is big! Like 5-10GB! That sucks to re-download. Especially if your company doesn’t have caching servers, or you WFH, or Apple’s CDNs are slower than goddamn molasses launch week.
§ "But my IT department hasn't told me what I can doooooo" Please see the next section
IT hasn't said I can upgrade/forbade it/what is IT? A guide for Mac Users at Work.
Does your Mac have an Asset Tag on it? Was it purchased for you by your corporate overlords? Do you still desperately long to upgrade it to macOS 10.15 Catalina as soon as is humanly possible?
Well friends, do I have news for you: I can tell you whether or not it's even remotely possible to bypass what your IT people want. Because I am a former IT person, and there is no goddamn magician’s code or some bullshit to tell me what I can or cannot tell you.
Other IT people: y'all, the fuck are you doing if you aren't fully securing your endpoints AND communicating with your users in a TIMELY FASHION about OS upgrades? You deserve dealing with them, coming to me, learning the ways to bypass you in this delightful parody blog post.
Finding out: Are you pwned by IT?
(LA LA LA LA LA, THIS SECTION IS A JOKE AND IS NOT TO BE TAKEN SERIOUSLY BY ANY LIFE FORM, CARBON BASED OR OTHERWISE, LA LA LA)
Welcome, welcome my dears. Let me tell you how to check to see if your corporate overlords fully control your company issued Mac.
1. Open System Preferences > Check to see if "Profiles" exists.
• If Profiles does not exist, you are likely not pwned. You can probably install whatever the heck you want on this Mac. "Do no harm and do what thou whilst" as the old saying goes.
• If Profiles does exist:
Woo. Your IT team figured out how to do some basic Mac management. Open up Profiles and see if you can delete whatever is there!
• If you can't delete it: Sorry, you are at the whim of your IT team. Politely supplicate on Slack in the IT channel, or do a drive by of your favorite IT person to find out their poison of choice so you can be an early adopter of Catalina.
• LA LA LA TOTALLY NOT RECOMMENDING BRIBING IT STAFF WITH THINGS, NOPE NOPE NOPE!
• If you can delete it: Congrats, your IT folks are inept! You can do whatever you want, until they have physical possession of your computer again (and, uh, you delete Jamf.)
2. If you work someplace that has had a sizable Mac fleet since 2009 there is a decent chance they're running Jamf Pro on your computer. To check this, open Terminal.app and run "which jamf"—if it responds with anything, you've got Jamf.
• Removing Jamf:
• Assuming you've got an Admin account, you can run "sudo jamf removeFramework" and it'll pull the Jamf client software off your Mac.
• IF YOU DO THIS FEIGN IGNORANCE TO YOUR IT TEAM. THEY MAY BELIEVE YOU. JAMF BREAKS ALL THE TIME, AND THEY PROBABLY DON'T HAVE ALERTING/REPORTING SET UP RIGHT ANYWAY, OR ARE USE TO FALSE POSITIVES FROM BAD/OUTDATED DESIGN SCHEMAS.
• DO NOT WIPE AND REINSTALL YOUR MAC AFTER THIS POINT IF YOUR COMPUTER HAD A REMOVABLE PROFILE. THE PROFILE MAY COME BACK, AND MAY NOT BE REMOVABLE IF YOUR IT TEAM LEARNED ANYTHING IN THE PAST FEW YEARS.
• No admin account?
• welll… you're probably SOL. If your Mac is a pre 2018 model you can probably boot it into Single User Mode to force on an admin account by removing .AppleSetupDone—unless your IT folks were smart enough to turn on a firmware password and not share it with you. Also if your IT folks did finally set up DEP and mobile device management after your Mac was deployed this could actually make your Mac check into DEP so don’t take my word for this, go google it your damn self.
• Other device management platforms:
Look cats and kittens, I've only really run into places that use Jamf on end user deployed hardware. I've heard rumors of folks running FileWave, or Fleetsmith, or other management platforms on Macs issued to users but I personally haven't seen them in the wild. I am sure there is someone someplace with guides on removing them. I'm just taking out the biggest most annoying platform.
la la la I am not telling you how to bypass you employer's controls over your computer, la la la I am just an innocent satirist who is exhausted from the better part of a decade supporting Macs professionally without vacations and backup and la la la why yes I have worked many long hours uncompensated because I was salaried and had to support out of hours emergencies without hazard pay, or pay commensurate to the stress I was under.
Blah blah blah if you found this post entertaining or something I am n3philim on paypal and cash. I don't have kofi or soundcloud or whatever the latest side hustle app is. If you like inane banter and occasional hilarity you can follow me @the_nephilim on twitter. No, I don't have Mastodon. No, I won't like your facebook page. Please, for the love of cthulhu, don’t send me a goddamned linkedin connection request. And for the sake of hell please don’t act like we’re long lost bosom buddies because my screen name/handle is nephilim: the mounds back east were built by a Native American society called the mound builders not some fucking lost tribe of israel or human/angel/alien hybrids who survived a localized flood that hit Mesopotamia 6000 years ago—I got my screen name from a race of goddamn cat people in a Mac OS 7 shareware game that was a loving riff off of old school RPGs like Ultima—the cat people were outcasts and so was I and goddamn it I only riffed off the weird biblical part buying my domain name because that seemed like the edgy cool thing to do as a self proclaimed gnostic discordian when I was in university so just back off, ancient aliens/mysterious lost white people of north america/angel enthusiasts.
(ffs, employers of the world: please don't sue me. I swear this is just a joke)
Bats and liches,
-V., cranky life long Mac user who took her goddamn username from a race of cat people, ok? You know now. Stop thinking it’s goddamn ancient aliens. And honestly Zamzummim as I understand the translation means “the ones that buzz/hum” and my birth first name’s best definition is a genus of butterflies, and the Japanese kanji for my name transliterates to “the sound of insect wings” so zamzummim is an elaborate in joke I came up with for myself because my birth name is inexplicably linked to bugs and bug wing sounds in Japanese.
Comments are open. I fear that may be a mistake.