I am new in mikrotik, I have been only using webproxy in mikrotik.
When i am configuring outlook on lan (which is connected to mikrotik) it does not get connected, when i bypass it (direct connect to internet) it works.
I don’t know what is blocking it to connect however, i don’t have any firewall rule and just webproxy is activated.
Outlook uses port 110 for POP3 accounts and 143 for IMAP access. For sending mail it usually uses port 25 (if using unencrypted acces - for ssl enabled servers tere are other ports).
Webproxy only passes web traffic on port 80.
So this can not work.
You have to forward or NAT the correct ports for outlook and use the webproxy only for browsing the internet.