Weird problem. I Have spend a lot of time searching answers in this site, But not one yet. Ispconfig 3 is working fine, webmail is working fine, outlook is receiving emails fine, but when I try to send mail via outlook its just stays in outbox and doesn't send? please advise
Please check the mail log file to see which error gets added there when you try to send an email with outlook. Does outlook shows any error message?
I checked but their is no errors in the log when i tried sending a test email. But the reason their is no issue shown in the log i think its because its not getting that far, the email just stays pending in the outbox in outlook. I also have the emails from my server setup on an mail client app on my phone, I also sent a test email from their but its fails to send. I have made one more test from outlook sending from one ispconfig email to another on the same server and that email worked fine. so their must be some issues around the imap plan text configuration that is not working when sending to external emails from outlook, I don't have this issues if sending from any webmail or sendmail to external emails, this issue only seems to be when sending from third party clients via imap. please advise
Imap is used only for receiving, sending is done with smtp, so this can't be an IMAP issue. Check the SMTP settings of outlook and ensure that it authenticates with plain or login mechanism when sending with smtp.
