Important: to guarantee service security, we are enforcing high-grade encryption level for sending emails via POP/IMAP mailboxes. SSLv2 and SSLv3 are no longer supported. Outlook 2011 for Mac won't work with POP/IMAP mailboxes anymore since it does not have required TLS encryption used to establish the connection.
Use Outlook for Mac 2016 to connect your Mac to POP/IMAP mailbox. Read the Knowledge Base article on How Do I Configure Outlook 2016 For Mac To Connect To POP/IMAP Mailbox? for setup instructions.