Without knowing the site it's hard to confirm this. My guess is that Windows has blacklisted the SSL certificate (or root cert) and thus the error.
WyUpdate not updating over HTTPS
I currently have my application updating over HTTP, and I wanted to move it to HTTPS to satisfy a company requirement. I enabled SSL on my webserver, and I can browse to it over HTTPS with no problems. I used a startssl.com certificate, instead of a self-signed.
Before I put this change into WyBuild, I wanted to make sure it would work. So I ran WyUpdate:wyupdate -server="https://mysite.com/updates/wyserver.wys"
The WyUpdate pauses for a while, and then provides this error message in the details:Error trying to save file: Error downloading "https://mysite.com/updates/wyserver.wys": The underlying connection was closed: An unexpected error occurred on a send.
From that same machine, I can request https://mysite.com/updates/wyserver.wys and the browser prompts me to save the file.
In my Apache access logs, I only see the following:50.91.104.44 - - [05/Mar/2013:09:46:16 -0500] "-" 408 3362 "-" "-"50.91.104.44 - - [05/Mar/2013:09:46:37 -0500] "-" 408 3362 "-" "-"50.91.104.44 - - [05/Mar/2013:09:46:57 -0500] "-" 408 3362 "-" "-"50.91.104.44 - - [05/Mar/2013:09:47:18 -0500] "-" 408 3362 "-" "-"
The interesting thing, is that if I force the HTTPS over a tunnel with a trusted root certificate (using Fiddler2), it updates just fine. This would lead me to suspect that WyUpdate has an issue with certificates from startssl.com, but I see the line of code that allows even un-signed certificates past.
Am I doing something wrong?