I tried sending Shaw emails to somebody’s Outlook live account:
    
Setup Email in Windows Live Mail

https://community.shaw.ca/docs/DOC-2113

After connecting, it says “update in progress”, but it seems to be stuck on that.
When you click on edit, the default ports are 110 and 587.

I instead tried what was on the Shaw documentation page:

POP Settings

 
Incoming server information
Server type    POP
Server address    pop.shaw.ca
User Name    Shaw email without @shaw.ca
Password    Your email password
Security type    SSL
Port    995
        
Outgoing server information
Server address    mail.shaw.ca
User Name    Shaw email without @shaw.ca
Password    Your email password
Security type    TLS
Port    587
-    -

(There is only one encryption field, so I guessed SSL).

It still gives you an “update in progress”.

http://i.imgur.com/P1AMYnj.png

Gmail on the other hand seems to work fine.
I think that I only had to put the Shaw email and password.

POP.shaw.ca and 995 is put in for you.

Also, if you decide to enable the option of being labelled as Shaw when you send a message, the following information is filled.

>Secured connection on port 587 using TLS

Instead of Outlook Live’s “update in progress”, Gmail shows status updates after you connect an account:

>Last checked: 19 minutes ago.200 mails fetched.View history  161 mails remaining.

I tried sending my Gmail account emails to my Outlook live account, and it worked:

http://i.imgur.com/1a8aqbp.png

I’m confused as to why I have a different “connecting additional email accounts” page than that person in the first example (sending Shaw mails to Outlook live).

On the top left for me, it says outlook.com.
For him, it says outlook mail (preview).