I am trying to narrow down a problem with intermittent connectivity issues to a remote service hosted via HTTPS. The application frequently fails to establish the SSL tunnel during the CONNECT phase.
The odd thing is that when you open a web browser to the same url used by the application, the page loads. Even more interestingly is that once you do this in the browser, then retry the application starts working and is able to connect.
I ran a trace route and even when set to 200 hops, around hop 8 I start getting request timed out, it eventually hits 200 hops and fails to complete the trace, I started at 30, then 100, then 200.
I may have something to learn, and do not want to come to incorrect conclusions based on incorrect knowledge.
Am I correct to think that even with the timeouts along the route, if the route to the destination was correct it would still complete within a reasonable number of hops?
Can I safely draw a conclusion that something is misconfigured or failing when a trace route never completes, or is this potentially a perfectly valid response due to some sort of security measure in place at the destination?
Lastly, is there a reason why the act of browsing to the site works, and why after browsing to the site, the application is then able to work?