Outlook not sending or receiving mail; roundcube is

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rwzdoorn

Verified User
Joined
Jun 2, 2015
Messages
18
Hi,

We are facing issues after updating dovecot / exim. Roundcube is working, but using outlook with port 993 and 587 is not anymore.

I already checked the mainlog (/var/log/exim/mainlog) but this does not show the emails I tried to send from outlook. I already did a clean build with exim, exim_conf, dovecot and dovecot.conf.

Any clues how I can check what's going on?
 
From my scrap book
Code: 
cd /usr/local/directadmin/custombuild
./build update
./build exim
./build exim_conf
mv /etc/dovecot /etc/dovecot~moved 
./build dovecot
./build dovecot_conf
Otherwise try to revert to older version of dovecot & exim
 
What version of Windows and Outlook? Is SSL configuration set to Intermediate? (I have had some older versions of Outlook stop working if set any higher.)
 
rwzdoorn said:
but this does not show the emails I tried to send from outlook
Click to expand...
Did you also check the rejectlog?
If totally nothing is shown, check /var/log/maillog, if you don't see anything there either, then the pc (outlook) is not making a connection to the server otherwise always something is shown, even if it's an error.
 
Hi,

I've checked: /var/log/exim/rejectlog ; It gave me a lot of brazillian 'hackers' trying to authenticate, but not our outlooks. So, it looks like outlook isn't connecting to the server? We checked 'Mac Mail' (macOS) and that client is working.
 
rwzdoorn said:
Hi,

I've checked: /var/log/exim/rejectlog ; It gave me a lot of brazillian 'hackers' trying to authenticate, but not our outlooks. So, it looks like outlook isn't connecting to the server? We checked 'Mac Mail' (macOS) and that client is working.
Click to expand...
ONE OUTLOOK "client
To many wrong password try's?
Then IP blocked?
If CSF try to find of ip from clients is blocked.

Or if mixed ipv4 and ipv6 check the complet route route and network test you can do here internet.nl for mail https://en.internet.nl/ and do from client side the connection test on that website

Older versions OUTLOOK Windows YUP have problem tls ssl of ciphers , you can change that only with tools or in registry. ( log files on client)

So before that check first with en new version of outlook and windows.
 
Hi Ikkeben,

Thanks for hint towards https://en.internet.nl ! I've checked and there are a few issues (https://en.internet.nl/mail/runtrainer.com/723033/) I'm not familiar with. We are using Outlook for Mac (latest version), Thunderbird for Windows (latest version). Both don't work. When connecting the account to outlook I get a warning "Secure connection not available, still want to proceed?"

The credentials are correct.
 
What is the output of

Code: 
cd /usr/local/directadmin/custombuild
cat options.conf | grep "ssl"

and

Code: 
/etc/dovecot/conf
cat ssl.conf

What version did you upgrade from?

Any errors in /var/log/dovecot-lmtp.log
?

Also what is your exim.conf version (in ./build versions)
 
Okay, I think I solved the issue which was of cource a certificate issue (... man I hate those!).

Anyway: I normally use the auto renewal option of Letsencrypt. It looks like Letsencrypting is renewing our mail.domain.com address, but is not exporting the ca+cert & key to the exim.cert and exim.key!

Does anyone know why letsencrypt is not saving the cert to exim?
 
rwzdoorn said:
Does anyone know why letsencrypt is not saving the cert to exim?
Click to expand...
No that's odd. Should normally do all automatically. They did changed key locations in the latest DA version, maybe that has something to do with it.

Does it get fixed if you rebuild like @Active8 mentioned in #4?
 
rwzdoorn said:
but using outlook with port 993 and 587 is not anymore.
Click to expand...
You have to open your ports in the firewall.
I just tested and at least port 587 is not open. Neither is port 25 so probably also other important ports are closed.
Check your firewall. If you're using CSF/LFD, restart it and see if it works then.
 
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