How to setup email sending via Office365 on the SecPoint Penetrator?

If you’re using Microsoft Outlook with the two-step verification (2FA) turned on, you’ll need to:

1. Go to the Security basics page and sign in to your Microsoft account.
2. Select more security options.
3. Under App passwords, select Create a new app password. A new app password is generated and appears on your screen.
4. Enter this app password where you would enter your normal password along with regular Outlook SMTP/IMAP settings: IMAP: imap-mail.outlook.com 
   Port: 993 
   SMTP: smtp-mail.outlook.com 
   Port: 587 
   With this setup you will be able to use your Microsoft Outlook account! 
    

When MFA is enabled, the regular password will not work for SMTP/Basic Auth, even if Authenticated SMTP is enabled.
Microsoft blocks the login unless you use an App Password instead.
 
 

Generate an App Password

Please ask the user to do the following:
 

1. Go to:

👉 https://mysignins.microsoft.com/security-info
 

2. Log in with:

[e-mail]
 

3. Click:

“Add method” → “App password”
 

4. Name it (e.g., SecPoint SMTP), then copy the generated password.

5. Use this new App Password instead of the regular one in:

• Penetrator email config

Step-by-step in Microsoft 365:

1. Log in to: https://admin.microsoft.com
2. Go to Users > Active Users
3. Click on [e-mail]
4. Go to Mail > Manage email apps
5. Ensure “Authenticated SMTP” is enabled

   If it's off, the SMTP login will silently fail even with correct password.