Hello, 

I am a client of Bell Sympatico in Canada.  Just purchased Office 365 and trying to configure Outlook.  I also installed Windows 8.1

Using the required POP3  information and required SMTP configuration, Outlook receives emails but no emails will get out.  Using the same configuration on Outlook 2010 on another computer everything works fine.  Bell Sympatico technicians could not figure out the problem even when they took control of my PC.  

Configuration :  outgoing mail server smtphm.sympatico.ca

Checked box regarding "My outgoing server (SMTP)requires authentication

Server port numbers  Incoming POP3 995

Checked box "this server requires an encrypted connection (SSL)

Outgoing server (SMTP) 25

Use the follwing type of encrypted connection : Auto

I can second this, I have the exact same error, any advice?

I have the same problem (but with Office Outlook 2010) same ISP Sympatico and I cant configure. I have been at it with 4 different TechReps from Bell and still can connect. Now using Outlook.com for messages

Same error here i.e. does not Work on Win 8.1 - but Works on Win 8. The user is a domain user with a romaing profile.

However tested with SMTP port set to 587 with TLS. Outlook responds with connection interrupted. No way to get it to Work? So on the Win 8.1. test machine roaming into a Win 8 machine if having to answer email.

Hi,

I don't know if this will help for your situation, but I've always had issues with the way sympatico.ca accounts work with the POP3 mail servers.  The functionality has always been somewhat limited.

Earlier this year, I discovered that if I set up my sympatico.ca or bell.net accounts as an outlook.com type of account using the server:

blu-m.hotmail.com

then everything works perfectly.  The sympatico.ca and bell.net email accounts work with more functionality compared to the POP3 setup.  I found this server from my iPad email configuration and it seems to work well (for some reason, the iPad was able to automatically find this correct server when setting it up as a Microsoft email account whereas Outlook did not???)

Please note that this setup was for Outlook 365 on Windows 8.  I have not tried it with Windows 8.1.

Hopefully it can work for you too.

I experienced the same issue, the Bell support guys are useless. It is a Windows 8.1 bug see:

http://social.msdn.microsoft.com/Forums/vstudio/en-US/5555297a-3b32-41f4-aedf-666825a9f0c0/cant-send-email-to-hotmail-on-windows-81-os

I found a great solution using Microsoft Office Outlook Hotmail Connector which creates a MAPI connection. Here is a link to download it and also gives you a great overview:

http://office.microsoft.com/en-ca/outlook-help/microsoft-office-outlook-hotmail-connector-overview-HA010222518.aspx

Hope it helps....