Sending emails from Digital Pigeon via Microsoft Office 365

Please note: Our strong recommendation when configuring email sending is that we send emails from our servers with your domain as the sender, and you configure your SPF (DNS TXT) records in order for the email to be trusted and received without issue by your users/customers.

To set up your SPF records please see this KB article: Improve email delivery by updating your domains SPF Send Policy Framework DNS record

However, if this is not possible, we can instead connect to your email server and send mail directly from an account on your system.

There can be a number of obstructions that may affect our ability to connect to your email server and relay email. e.g.: If you host your own server, firewall ports may need to be opened.

We highly recommend using a dedicated user account (i.e.: 'Digital Pigeon') for the exclusive purpose of sending emails, rather than a regular user account (e.g. 'Jane Citizen').

If you are using Office365 (Exchange Online) then you may need to consider the following additional factors:

• SMTP Authentication may be disabled across your Microsoft tenant (e.g. if MS/Azure Security Defaults have recently been applied). You may need to manually enable SMTP Auth for the dedicated user account, that can be done as follows: 

• • Use the Microsoft 365 admin center to enable SMTP AUTH on specific mailboxes
    1. Open the Microsoft 365 admin center as an Exchange or Global Administrator and go to Users > Active users.
    2. Select the user, and in the flyout that appears, click Mail.
    3. In the Email apps section, click Manage email apps.
    4. Verify the Authenticated SMTP setting is checked (enabled).
    5. When you're finished, click Save changes.
    
    Source: https://learn.microsoft.com/en-us/exchange/clients-and-mobile-in-exchange-online/authenticated-client-smtp-submission#enable-smtp-auth-for-specific-mailboxes

• You should disable Multi-Factor Authentication for the Office365 Digital Pigeon user account.  However, if this is not possible and if MFA is enforced (e.g. via Conditional Access), you may need to create an 'App Password'.  This also avoids the problem of regular password changes that might be required for the account.  To create an App Password:

• • Use the My Account | Security Info page to create an App Password
    1. Sign into the Digital Pigeon user account and open the My Account page.
    2. Select Security info from the left navigation pane or from the link in the Security info block, and then select Add method from the Security info page
    3. On the Add a method page, select App password from the list, and then select Add.
    4. Type 'DigitalPigeon' as the name of the app that requires the app password, and then select Next.
    5. Copy the text from the Password box, and then in another browser window, paste it into the Digital Pigeon | Account Settings | Email | SMTP Password field.
    6. Click Save in Digital Pigeon, and then switch back to the Microsoft My Account page and select Done.

Source: https://support.microsoft.com/en-us/account-billing/create-app-passwords-from-the-security-info-preview-page-d8bc744a-ce3f-4d4d-89c9-eb38ab9d4137