For your Hotmail Account try unchecking the toggle for Use SSL with SMTP Server, I believe their documentation references it prefers using TLS. https://support.office.com/en-us/article/POP-IMAP-and-SMTP-settings-for-Outlook-com-d088b986-291d-42b8-9564-9c414e2aa040?ui=en-US&rs=en-US&ad=US For...