cygwin sshd vs Win 10 'built-in' openSSh server

cygwin sshd vs Win 10 'built-in' openSSh server

[Evan Cooch]

Greetings --

Apologies if this should go to another list, but...

I've been using the cygwin sshd as a service under Windows (XP -> 7), for
*many* years. However, with the pending deprecatin of Win 7, and the IT
guys at my institution nagging me to upgrade to Win 10, that raises a
question -- are there relative pros/cons of sticking with cygwin sshd as a
service under Win 10 (assuming that is still possible), or enabling the
openssh server that is 'hidden' (relatively speaking) in Win 10 Pro an
Enterprise (not so sure about Win 10 Home)?

My preference would be to stick with cygwin (since I'm familiar with it,
and can tweak things as I need), but I'm uncertain as to how well it would
play with Win 10, which might be 'happier' if the MS approved openssh
approach was used.

Thoughts/opinions?  I have a couple of Win 10 installs in virtual machines,
and will try testing both approaches at some point, but wanted to collate
some information before that point.

Thanks in advance....

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Re: cygwin sshd vs Win 10 'built-in' openSSh server

[Brian Inglis]

On 2019-11-21 09:07, Evan Cooch wrote:
> I've been using the cygwin sshd as a service under Windows (XP -> 7), for 
> *many* years. However, with the pending deprecatin of Win 7, and the IT guys
> at my institution nagging me to upgrade to Win 10, that raises a question --
> are there relative pros/cons of sticking with cygwin sshd as a service under
> Win 10 (assuming that is still possible), or enabling the openssh server that
> is 'hidden' (relatively speaking) in Win 10 Pro an Enterprise (not so sure
> about Win 10 Home)?
> 
> My preference would be to stick with cygwin (since I'm familiar with it, and
> can tweak things as I need), but I'm uncertain as to how well it would play
> with Win 10, which might be 'happier' if the MS approved openssh approach was
> used.
> 
> Thoughts/opinions?  I have a couple of Win 10 installs in virtual machines, 
> and will try testing both approaches at some point, but wanted to collate 
> some information before that point.

With Cygwin you have documentation, familiarity, prompt support and fixes, and
support of standard cypher suites and key sizes.

What do you know about MS "hidden" ssh server and client, and interop with the
systems to which you want to connect?

What can you expect by way of support from your IT guys and MS?

Some wiki notes are less than informative and may be worrysome:
https://github.com/PowerShell/Win32-OpenSSH/wiki/SSH-remote-sessions-on-Windows
"A remote session opened via password authentication has the user credentials
attached to it and hence is capable of outbound authentication as the user.
A remote session opened via key based authentication does not have associated
user credentials and hence is not capable of outbound authentication as the
user. This is by design and goes by the rules of standard Windows security."
https://github.com/PowerShell/Win32-OpenSSH/wiki/ssh.exe-examples

-- 
Take care. Thanks, Brian Inglis, Calgary, Alberta, Canada

This email may be disturbing to some readers as it contains
too much technical detail. Reader discretion is advised.

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Re: cygwin sshd vs Win 10 'built-in' openSSh server

[Evan Cooch]

Thanks very much -- good points.

On 11/21/2019 3:47 PM, Brian Inglis wrote:
> On 2019-11-21 09:07, Evan Cooch wrote:
>> I've been using the cygwin sshd as a service under Windows (XP -> 7), for
>> *many* years. However, with the pending deprecatin of Win 7, and the IT guys
>> at my institution nagging me to upgrade to Win 10, that raises a question --
>> are there relative pros/cons of sticking with cygwin sshd as a service under
>> Win 10 (assuming that is still possible), or enabling the openssh server that
>> is 'hidden' (relatively speaking) in Win 10 Pro an Enterprise (not so sure
>> about Win 10 Home)?
>>
>> My preference would be to stick with cygwin (since I'm familiar with it, and
>> can tweak things as I need), but I'm uncertain as to how well it would play
>> with Win 10, which might be 'happier' if the MS approved openssh approach was
>> used.
>>
>> Thoughts/opinions?  I have a couple of Win 10 installs in virtual machines,
>> and will try testing both approaches at some point, but wanted to collate
>> some information before that point.
> With Cygwin you have documentation, familiarity, prompt support and fixes, and
> support of standard cypher suites and key sizes.
>
> What do you know about MS "hidden" ssh server and client, and interop with the
> systems to which you want to connect?
>
> What can you expect by way of support from your IT guys and MS?
>
> Some wiki notes are less than informative and may be worrysome:
> https://github.com/PowerShell/Win32-OpenSSH/wiki/SSH-remote-sessions-on-Windows
> "A remote session opened via password authentication has the user credentials
> attached to it and hence is capable of outbound authentication as the user.
> A remote session opened via key based authentication does not have associated
> user credentials and hence is not capable of outbound authentication as the
> user. This is by design and goes by the rules of standard Windows security."
> https://github.com/PowerShell/Win32-OpenSSH/wiki/ssh.exe-examples
>


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