> If I had to run Sage on Windows for some reason today, 
> I would use Docker or VirtualBox.

I’ve been using Sage for many years mainly on Windows. 
First with the Virtual box. This had many disadvantages. On 
the one hand the VirtualBox was error-prone and often did not 
work as expected. It also eats up a lot of memory and especially 
that worksheets are not stored directly on the host system 
proved to be a disadvantage. I had no joy with it. 

My experience changed dramatically when the SageMath binaries 
appeared in the Windows installable form. I never had a problem 
again, didn’t have to worry about other software and its quirks. 
And I had my Yupyter notebooks where I can search for them, 
in my Windows explorer. 

Regarding performance: in my applications I have never experienced 
a situation where I assumed to have any advantage if I used 
a Linux system. For my work it fits perfectly into Windows. 
I don’t feel the slightest need to interpose another layer 
again, whatever type it is. 

For someone who doesn’t care if Cygwin is "ugh-worthy" or 
"ohh-worthy" some remarks made in this thread do not reflect
the experience of a normal Windows user. 

I am aware that this is only because of extraordinary skills
and efforts by E. M. Bray and I would like to express my 
appreciation for it. 

Peter

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