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SSL not fully trusted on ports 993 and 587 of our mail server by Zendesk

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brandonperdue

We have our own mail server running using iRedMail on Apache. It's been working for us for a number of years and there haven't been any issues with the SSL until now. One of our clients is trying to connect their smtp credentials to their Zendesk account and Zendesk is rejecting the connection because it doesn't fully trust the SSL. Zendesk support sent us to https://www.sslshopper.com/ssl-checker.html. When we test the domain on there without any ports it gets a full pass. If we put a ":587" or ":993" on the test we get the following error:

The certificate is not trusted in all web browsers. You may need to install an Intermediate/chain certificate to link it to a trusted root certificate. Learn more about this error. You can fix this by following Sectigo's Certificate Installation Instructions for your server platform (use these instructions for InstantSSL). Pay attention to the parts about Intermediate certificates.

We've ran tests on the ssl through ssllabs as well and both the imap. and smtp. addresses get A+ grades. Does anybody have any ideas about how to get this to work? Are there any port settings that we may not be thinking of?

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Steffen Ullrich avatar
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Steffen Ullrich
*"We've ran tests on the ssl through ssllabs as well and both the imap. and smtp. addresses get A+ grades. "* - IMAP, SMTP, HTTP are different ports with different servers and different configurations. SSLLabs only checks HTTP, so the results cannot be used to make assumptions about the configuration on IMAP and SMTP ports. Based on the error messages either the certificate used is wrong, the domain name to access the IMAP/SMTP servers is wrong or the proper chain certificates are not configured. Impossible to tell with only this error message, i.e. the exact domain name is needed to check.
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