SSL connection error but works if you telnet port first

I'm troubleshooting a connection to an application (Citrix Netscaler), between several countries in a complex network. There are definitely firewalls along the route.

• Machine is pingable
• tracert is successful along the route.
• Hostname resolves correctly.
• If you try to open the website, you immediately receive a "Secure connection failed" at the browser.
• If you open telnet to the hostname on port 443, then connect with the browser, the SSL connection succeeds and the website opens.

If anyone has seen something like this before and could give me a clue where to look it would be greatly appreciated.