Ahaahh! I have figured out what was going wrong on my end. After a few more Google searches and looking on the Chrome bug tracker I narrowed the problem down to my antivirus software (ofc!). I use Avast antivirus on my Windows 8.1 machine and it has a web shield that basically man-in-the-middles any https connection to check if the content contains malware (you can read more: http://security.stackexchange.com/a/73481). So I disabled that feature, connected to https://caddyserver.com and it worked! And thinking back, I ran into another problem with Avast preventing any Go programs I compiled from running. I had to turn off a ‘feature’ called DeepScan which scans unknown running files and stops anything ‘suspicious’. Now, I’d like to know why Avast is preventing the https connection to caddyserver.com and not the http one… More rabbit holes to chase!