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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.

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  • There is definitely not enough information here to troubleshoot this problem. For a start you need to compare packet captures from client and server to see which packets gets lost or corrupted in flight.
    – kasperd
    Nov 30, 2018 at 11:21
  • Something like a wireshark capture of opening the connection?
    – Spence
    Nov 30, 2018 at 12:16
  • That's a start. But you need to capture it on both client, load balancer, and server.
    – kasperd
    Nov 30, 2018 at 13:28
  • What’s the output of the SSL Labs test?
    – StackzOfZtuff
    Dec 1, 2018 at 22:22

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