Hi,

> On 1 Mar 2018, at 17:39, ⁨ɹןʇnqן⁩ <⁨lbutler+roundc...@covisp.net⁩> wrote:
> 
> Mar  1 09:27:02 mail submit-tls/smtpd[86118]: connect from 
> localhost[127.0.0.1]
> Mar  1 09:27:02 mail submit-tls/smtpd[86118]: SSL_accept error from 
> localhost[127.0.0.1]: 0
> Mar  1 09:27:02 mail submit-tls/smtpd[86118]: warning: TLS library problem: 
> error:14094418:SSL routines:ssl3_read_bytes:tlsv1 alert unknown 
> ca:/usr/src/crypto/openssl/ssl/s3_pkt.c:1493:SSL alert number 48:
> Mar  1 09:27:02 mail submit-tls/smtpd[86118]: lost connection after STARTTLS 
> from localhost[127.0.0.1]
> Mar  1 09:27:02 mail submit-tls/smtpd[86118]: disconnect from 
> localhost[127.0.0.1] ehlo=1 starttls=0/1 commands=1/2

The 'SSL alert number 48' indicates that the server certificate cannot be 
verified due to being issued by an unknown CA. This is probably caused by a 
missing, outdated or improperly configured CA bundle on the machine running 
Roundcube. You should be able to reproduce the problem with openssl s_client 
from that machine.

Kind regards,

-- 
Sebastiaan Hoogeveen

NederHost
https://www.nederhost.nl/
KvK: 34099781
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