If you can't connect your Outlook or Live accounts through the application's special login option, try the following:
Outlook Login Issue:
- Logging in through the Live option
- Logging in through the IMAP option
Live Login Issue:
- Logging in through the Outlook option
- Logging in with the IMAP option
Here's a link where you can check for issues logging in via IMAP and other possible issues: I can't connect my mail via the IMAP option (or I have a 2-step login).