Outlook 2013 - Can't Send Mail

[lsheen]

Hi, my user is "lordclic" on stevie.

 

I set up my mail in Outlook as per the settings below, and when I test the server settings, they check out. I can receive e-mail, but when I try to send a mail, Outlook says: "We can't complete this because we can't contact the server right now. Please try again later." (when I have 3 or more e-mail addresses in the To field). If I have 2 or 1 e-mail in the To field, it attempts to send it, but then keeps asking me for the password. Is something wrong with my settings?

 

 

IMAP

 

incoming mail server: stevie.heliohost.org - Port 143

outgoing mail server: stevie.heliohost.org - Port 465 over SSL

 

User: lukas@zillioncompany.com

Password: (e-mail password)

 

outgoing server authentication enabled

 

 

EDIT:

 

Ok I figured out that I should have used my overall account User "lordclic" as username, so I no longer get the pop up asking me to enter the password.

 

However, I still get the "We can't complete this because we can't contact the server right now..." message. It seems to only appear if I try to send a mail to an e-mail address that isn't yet recognized by outlook as an address I previously sent a mail to. Once I send an e-mail to that new address from another account, I can then also send a mail to that new address through the heliohost account.

 

Do you know what the issue is here?

 

Thanks.