I can't configure my email in MS Outlook 2010 or 2013

OS type and version Ubuntu Linux 18.04.6
Webmin version 2.001
Virtualmin version 7.2-1 Pro
Related packages SUGGESTED


I’m writing because I just can’t see, to configure the email for one of my domains in Outlook. I currently have 26 domains on my server… I’ve successfully configured the email in all of them. This particular domain (artandcrafts.com) was previously on another server for a number of years and I just moved it to my in house server.

I can configure the email on my Iphone with no problem, it’s sending and receiving just fine. I can view it in roundcube with no problem. But every time I try to set it up in Outlook I get this response.

When I try to manually set it up and I specify port 993 for the incoming email (ssl) and port 587 (TLS) for the outgoing email, Outlook rejects it saying it can’t establish a secure connection and then it reverts back to port 143 and 25 for the outgoing.

I’ve set up dozens of other email accounts on my other domains on this server with no problem. What do you think the problem is with this one?

Dan Lewis


Looks like connection to the server can be estabilished, but the connection cant be secured.

First of all, I would try to disable login via SPA, as Dovecot does not support it and moreover it is outdated security option.

Which ciphers and TLS versions do you have actually enabled on your dovecot? MS outlook 2010/13 are pretty old and they might not work well with current TLSv1.2 or TLSv1.3. I would try to enable TLSv1 and TLSv1.1 as well.

The fact that connection works on other devices like iphone indicates that it will be most probably TLS version / cipher missmatch.

Is this the only installation of MS 2010/13 or do you have succesfully set it up on other devices?

Best regards,

things to check :

  • try a different+modern email client (eg. Thunderbird)

  • DNSSEC seems enabled on registrar, but not configured on server. might want to remove entry from registrar, or fix DNSSEC on house server.

  • you have an internal ip(192.168.xxx.xxx) as nameserver address. that is just wrong. this might be ok, checking email/addresses from your internal house LAN, but not going to work for external mail…

see if any of those things, help…

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