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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?

Thank you!

Steve

closed as too broad by Ron Maupin Jul 15 '17 at 22:04

Please edit the question to limit it to a specific problem with enough detail to identify an adequate answer. Avoid asking multiple distinct questions at once. See the How to Ask page for help clarifying this question. If this question can be reworded to fit the rules in the help center, please edit the question.

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All you can conclude is that traceroute doesn't give you the information you wanted.

Many organizations' security policies break traceroute by denying ICMP or high port UDP packets. That has nothing to do with your application.

I can think of a few scenarios that would explain what you're seeing with the browser, but I would need to know more about your network and the remote app to give you any real advice.

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