TLS configuration for IMAP/SMTP not working with self-signed certificate

  • Thread starter Thread starter floring67
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floring67

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Hello,

After posting in the community forum, a moderator suggested me to repost my issue in the tech forum.

've been trying to setup my e-mail account in Outlook (Office 2019 Pro) on Windows 10 Pro (build 1809), and can't get it to work. What I know so far:
- the server uses STARTTLS, on ports 993 and 143 for IMAP, and 2525 for SMTP

- the server certificate is self-signed and not expired

- the configuration I am trying in Outlook works without any problem in Thunderbird (but there I have the option "STARTTLS (Accept all certificates)" ) which is missing in Outlook 2019 where I only have STARTTLS.

- I've tried installing the server certificate, didn't help.

- what I get is connection refused no matter what combination I try (secure password authentication or not, SSL/TLS or STARTTLS, port 143 or 993, 25 or 2525 for SMTP)


It looks like Outlook 2019 simply rejects the server certificate and therefore doesn't connect. While the certificate is not installed, I get the classic warning that the certificate is untrusted, if I install it the warning disappears, but still no connection for Outlook. Is there anything that can be done, or simply Microsoft disabled connecting with untrusted certificates with no possibility to bypass this? I've had Outlook 2010 before and didn't have this issue.


Thanks,

Florin

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