SAIDR

Connect Microsoft 365 / Outlook

Works for @outlook.com, @hotmail.com, @live.com, and any custom domain on Microsoft 365.

Recommended: Use OAuth instead. Go to Settings → Integrations and click Connect — no app password needed. Keep reading for the SMTP fallback.
You must have two-step verification enabled on your Microsoft account. For M365 work accounts, your admin may also need to turn on SMTP AUTH at the tenant level — see below.

1 · Turn on two-step verification

Skip this step if it's already on.

  1. 1
    Sign in at account.microsoft.com/security.
  2. 2
    Click Advanced security options → Two-step verification → Turn on.
  3. 3
    Follow the prompts to verify via the Microsoft Authenticator app or SMS.

2 · Generate the app password

  1. 1
    At account.microsoft.com/security, click Advanced security options.
  2. 2
    Scroll to App passwords and click Create a new app password.
  3. 3
    Microsoft shows a long string of lowercase letters. Copy it.
On a Microsoft 365 work/school account? The personal app-password page won't show it. Use mysignins.microsoft.com/security-info → Add sign-in method → App password. If that option is missing, your tenant admin has disabled it — ask them to enable app passwords, or enable modern-auth SMTP AUTH on your mailbox (admin center → Users → your user → Mail → Manage email apps → enable Authenticated SMTP).

3 · Paste into SAIDR

  • SMTP host: smtp.office365.com (for M365 / work domains) or smtp-mail.outlook.com (for personal @outlook / @hotmail)
  • SMTP port: 587
  • Use TLS: on
  • Username: your full email address
  • Password: the app password from step 2

4 · If “Test connection” fails

  • “SMTP AUTH is disabled for this tenant.” Your admin has to enable it. M365 Admin Center → Users → your user → Mail → Manage email apps → tick Authenticated SMTP.
  • “5.7.57 Client was not authenticated” — you pasted the regular account password. Generate an app password.
  • “Connection timed out” — you used port 465. Use 587 with STARTTLS.
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