Found the solution to be downgrading to Tortoise 1.9.7. After doing 
certificate authorization  and handing over to BasicAuth worked as 
expected. A post in the Tortoise-Dev group pointed me to the solution and 
chased it down to a regression in OpenSSL. 

On Friday, September 27, 2019 at 6:50:27 AM UTC-5, Kyle Echols wrote:
>
>
> I've got a requirement to implement Certificate based authentication using 
> the users certificate stored in the Windows Certificate Store and I'm not 
> allowed to have them export the certificate to place it in the appropriate 
> folders for Tortoise to see it. Is there some extra configuration needed to 
> tell Tortoise to look at the Windows Cert Store and prompt for the 
> certificate?  Basic Auth works, but I don't get prompted by Tortoise to 
> pick the certificate, when browsing the same URL in a browser, I am 
> prompted.  
>
>

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