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Troubleshooting “Session is invalid” error or “Security Certificate presented by inSync Server was issued by a certificate authority not trusted by your Operating System”

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Overview

This article explains the steps to be performed in case you receive the error- “Session is invalid” error or “Security Certificate presented by inSync Server was issued by a certificate authority not trusted by your Operating System”.

Cause

  • This error occurs due to various reasons, but primarily it occurs if SSL traffic is being blocked to the Master. (Generally if SSL traffic on port 80 is blocked or a third party application blocking SSL traffic from the client.)
  • Mostly this issue is observed on inSync Cloud.

Troubleshooting

  • Are you using any kind of Proxy in the environment ? If yes, is it a SSL terminating Proxy?
  • Name of proxy server (make, brand, version)
  • Type of authentication used (kerberos/ntlm/basic)
  • Check if you are able to perform a Telnet to Server (telnet <cloud.druva.com/serverIP  80/443/6061)
  • Check the client version. (Client below 5.4.2 release will not work on port 443)
  • Check if SSL scan works on the defined port. If it fails, that means SSL traffic is getting blocked somewhere. You can also use openSSL, which you can download using this link.
openssl s_client -CAfile C:\inSync4\ca-certificates.crt –connect cloud.druva.com:80/6061/443 –debug
  • Download SSL tool from this link.
  • Extract the zip file to desktop.
  • Open Command prompt with admin rights and navigate to the extracted folder in step 2.
  • Run the following command and send the screenshot of the cmd prompt to Druva Technical support:
SSLScan.exe --no-failed cloud.druva.com/serverIP:80/443/6061
  • For Mac machines, run the following command:
openssl s_client -CAfile /Users/<username>/Library/Application Support/inSync/ca-certificates.crt -connect cloud.druva.com:80/6061/443 –debug

Note:All the above points need to be collected, to get the issue investigated.