Postfix: Using Microsoft 365 as SMTP Relay

Postfix mail server is available in almost all Linux distributions. You can use it as a simple relay (smart host) to send email messages from your local network to user mailboxes and forward email queues to SMTP servers outside your organization. In this article, we’ll show you how to set up an SMTP relay for Microsoft 365 (Office 365, Exchange Online) with postfix on Linux (using Ubuntu/Debian as an example).

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Outlook 2019/2016/365 Prompts for Microsoft Account Login

The new versions of Outlook 2019/2016/365 have the Direct Connect to Office 365 feature enabled by default. This feature can show an annoying Modern Auth prompt to sign in to Microsoft 365 (Office 365) with a Microsoft account. Even if you’re using Outlook on a domain computer with an on-premises Exchange Server (or even Gmail) mailbox profile configured, your Outlook will periodically prompt you for your Microsoft account credentials. Also, you may have problems sending and receiving emails from Exchange or non-Microsoft mailbox service.

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