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SSL Issues and Connection Failures

SimpleHelp applications, like the Technician Console or Remote Support client, will refuse to connect to SimpleHelp servers over SSL if there is a problem with the server's SSL certificate. This guide details the messages you may see in these situations, and ways to work around the problem to get up and running.

Failure Messages

An application launch may fail with one of the following messages:

  • Unable to establish a valid SSL session.
  • SSL error. The server's certificate is not trusted.

These messages typically indicate that the SimpleHelp server could be reached, but a SSL connection to the server failed due to a certificate issue.

Possible Causes of SSL Issues

The SSL certificate that SimpleHelp is using may have one of the following issues that could result in failed SSL connections:

  • Certificate Path Issue - if the SSL certificate was uploaded in a store that didn't contain the intermediate certificates, then the client may be unable to create a path from the provided SSL certificate to a trusted root certificate. We suggest checking your SimpleHelp server with a SSL tool like Digicert to see if the intermediate certificates are missing. If they are, consult with your certificate provider as they will be able to provide the relevant intermediate certificates.
  • Expired Certificate - an expired SSL certificate will show an error in a web browser, and will cause applications to fail to connect to your SimpleHelp server.
  • Self-Signed Certificate - if SimpleHelp is using a self-signed certificate, then the applications will fail to establish a secure connection to the server.

Fixing a SSL Connection Issue

The following options will help to allow applications to connect to your SimpleHelp server over SSL:

  • Install a Certificate - install an existing SSL certificate by uploading to your SimpleHelp server, or if your server is accessible on port 80 you can request a Let's Encrypt certificate. See our SSL Guide for more information.
  • Download over http:// - applications will use the protocol that they were downloaded with to connect to the server. Download and launching an application using http:// instead of https:// will result in non-SSL connections being made to the server (although all data is still encrypted in transit). This is useful if you require access to your server to manage the server's certificate.