Unfortunately these steps which appeared to run successfully haven’t solved the problem. This started after restarting local, now on an iMac and a Macbook Pro after both updated to the latest MacOS Catalina 10.15.2 over the holiday
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Hi Clay,
I also had the same issue and it was driving me bananas.
Thank you a million times over for helping me to resolve this issue!!!
I can’t, for the life of me figure out why this happened in the first place, however.
I did have Docker Desktop (along w/ Kubernetes set to the ‘context’ of Docker Desktop on my machine…as opposed to Minikube) running some separate (unrelated) containers/projects. I thought that maybe there might have been some conflict with Docker Desktop running concurrently with Local running on Docker Machine/VirtualBox, so I stopped running everything except for Local, but the issue was not resolved until regenerating the certs with the commands that you have provided above.
…stumped on the initial cause…
But, all is at least running again.
Cheers and thanks for saving my day 
Juliette
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What/where is the “docker machine CLI” and do I have to install it in a particular location?
And what commands do I run if on Windows?
Ironically I only started having issues after I installed the new Local (v5.?) - but could’t use it.
Site import failed - because it "couldn’t find home or siteurl or something like. Probably because the database I use isn’t named “Local” and your import site process cannot handle it. So it uninstalls and deletes the directory - it cannot even finish the import/install.
So I went back to v3.
First time, I think it worked after I let it update the hosts file. I think I had to re-trust the ssl certificate or something too. Not sure which site it was for - the same as the one I tried importing to v5, or if that was for a different site.
Anyway, that site I tried exporting that site again, after updating home and siteurl in the Local database.
Somewhere along the line it had issues. I couldn’t stop the site - just ran endlessly.
So Quit Local.
Restarted.
Now local won’t start at all.
Endless Regenerating Cert. loop.
Quit, restart doesn’t help.
But I’m on Windows 10.
Latest version of Local by Flywheel - 3.3 I think?
I installed docker machine CLI, but I still get
bash: docker-machine: command not found
when I try to run the 1st command:
docker-machine stop local-by-flywheel;
Well, good news is, after last reboot (required after installing docker desktop)), I no longer get the “regenerating docker machine” loop when I try to run Local.
BAD NEWS:
Instead I get like 6 error pop-ups in a row (VirtualBox, Hyper-V, E_FAIL messages), and then it just silently NEVER finishes starting. I don’t even get momentary flashes of my sites list anymore. Nope just completely broken.
So I guess it may not matter that THE docker-machine command wasn’t recognized in either git bash or powershell 
I’m in Flywheel Hell.