Thanks to Alvaro's help, I was able to finally track down the issue.  
Windows, and all related programs and utilities such as browsers, 
Powershell, etc knew that my server was not behind the proxy(not sure how - 
there are no ENV variables set such as no_proxy).   Programs unrelated to 
Windows, such as the curl executables that come with Vagrant do not have 
access to this inside knowledge and therefore tried to use the proxy to 
reach my internal server.  This was the root cause and setting "no_proxy" 
for this server fixed it.

Thanks Alvaro!

On Wednesday, October 24, 2018 at 2:36:45 PM UTC-4, Nc Diesel wrote:
>
> So my company wants to host their own boxes; all the while supporting 
> versioning.   This turned out to be pretty simple, but I can not get 
> "vagrant box add" to work using a UR and I was hoping some of you folks 
> could help.  The symptom is the download just hangs for about 80 seconds 
> and then dies.  The error I get is
>
> curl: (35) OpenSSL SSL_connect: SSL_ERROR_SYSCALL in connection to 
> mymachine.mydomain:443
>
> General info:
>
>    - Running Vagrant 2.2.0 on Windows 10 machine
>    - curl successfully puls the resources when invoked from the same 
>    power sheel window immediately after the Vagrant failure
>    - My proxy's certificates were added to the end of cacert.pem in 
>    Vagrants embedded sub-directory
>    
> Important part of debug log:
>
> * Connected to proxy.mymachine.mydomain(<snip for privacy>) port 8080 (#0)
> * allocate connect buffer!
> * Establish HTTP proxy tunnel to mymachine.mydomain:443
> > CONNECT mymachine.mydomain:443 HTTP/1.1
> > Host: mymachine.mydomain:443
> > User-Agent: Vagrant/2.1.5 (+https://www.vagrantup.com; ruby2.4.4) 
> > Proxy-Connection: Keep-Alive
> > 
> < HTTP/1.1 200 Connection established
> < 
> * Proxy replied 200 to CONNECT request
> * CONNECT phase completed!
> * ALPN, offering h2
> * ALPN, offering http/1.1
> * Cipher selection: 
> ALL:!EXPORT:!EXPORT40:!EXPORT56:!aNULL:!LOW:!RC4:@STRENGTH
> * successfully set certificate verify locations:
> *   CAfile: C:\HashiCorp\Vagrant\embedded\cacert.pem
>   CApath: none
> * TLSv1.2 (OUT), TLS header, Certificate Status (22):
> } [5 bytes data]
> * TLSv1.2 (OUT), TLS handshake, Client hello (1):
> } [512 bytes data]
>   0     0    0     0    0     0      0      0 --:--:-- --:--:-- --:--:--  
>    0
>
> DEBUG subprocess: stderr: * CONNECT phase completed!
> DEBUG subprocess: stderr:   0     0    0     0    0     0      0      0 
> --:--:--  0:00:02 --:--:--     0  0     0    0     0    0     0      0      
> 0 --:--:--  0:00:03 --:--:--     0
>
> this last line repeats, with no progress noted (except elapsed seconds of 
> course) until the error shows up.  
>
> Thanks for any assistance!!!
>
>
>
>
>

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