I've searched the Internet if someone successfully use the Office365 Microsoft Exchange Online without the use of TLS and SMTP Authentication . I found nothing, so I've decided to write this article so other administrators will benefit and save time. Hopefully give me credit of saving their precious time :) Office365 (Microsoft Exchange Online) a cloud based email powered by Microsoft Exchange Server with running latest version. SMTP Authentication and TLS protocol are required for your printer to scan and email the result to your corporate intended recipients. I've tested the SMTP Authentication and TLS settings using Toshiba eStudio printers , and works like a charm. It took a while to configure but it works. See the captured configuration. I enabled SMTP Client with all certificate without CA, the SSL/TLS as STARTTLS (this is the key to make scan to email using Office365 to work). My SMTP Server Address is pod51018.outlook.com . Microsoft recommend that you