Connect Outlook / Microsoft 365

Before you start

Open the Add mailbox dialog in AI Emaily. It has three tabs: Gmail, Outlook, and IMAP.

For Outlook and Microsoft 365 accounts, use the Outlook tab. It signs you in through Microsoft, so you never type a password into AI Emaily.

Microsoft has retired Basic Auth (app passwords over IMAP and SMTP) for Microsoft 365 and is phasing it out for personal accounts. The IMAP tab works only for the minority of personal Outlook.com or Hotmail accounts that still allow it.

Connect with one click (recommended)

1. 1

   Open the Outlook tab

   In the Add mailbox dialog, select the Outlook tab.

2. 2

   Start sign-in

   Select Connect with Microsoft. A Microsoft sign-in window opens.

3. 3

   Sign in to Microsoft

   Enter your Outlook.com, Hotmail, or Microsoft 365 address and complete sign-in, including any two-factor prompt.

4. 4

   Grant access

   Review the permissions AI Emaily requests and select Accept. The window closes and returns you to AI Emaily.

5. 5

   Wait for the first sync

   AI Emaily confirms the connection and begins importing your mail. Your mailbox appears in the sidebar when the first sync starts.

Fallback: connect with an app password (IMAP)

Use this only if your account is a personal Outlook.com or Hotmail account with two-step verification turned on and app passwords still available. Microsoft 365 work and school accounts cannot use this path.

First create an app password, then add it to AI Emaily on the IMAP tab.

1. 1

   Open Microsoft security settings

   Sign in to your Microsoft account and go to Security, then Advanced security options.

2. 2

   Confirm two-step verification is on

   App passwords are available only when two-step verification is enabled. Turn it on if it is not already.

3. 3

   Create an app password

   Under App passwords, create a new one. Microsoft shows a generated password once. Copy it now.

4. 4

   Open the IMAP tab in AI Emaily

   In the Add mailbox dialog, select the IMAP tab.

5. 5

   Enter your address and app password

   Type your full Outlook.com or Hotmail address. In the password field, paste the app password you just generated, not your login password.

6. 6

   Confirm the server settings

   Use IMAP host outlook.office365.com on port 993 (SSL) and SMTP host smtp.office365.com on port 587 (STARTTLS). Then select Add mailbox.

7. 7

   Let AI Emaily verify

   AI Emaily tests the connection before saving. If the test fails, a hint indicates which setting is likely wrong.

Server settings

Troubleshooting

• Authentication failed: you likely entered your normal login password. The IMAP tab needs an app password, which requires two-step verification turned on.
• Sign-in works but no app password option appears: your account does not support app passwords. Use the Outlook tab and connect with Microsoft instead.
• Microsoft 365 work or school account rejects IMAP: Basic Auth is retired for these accounts. The Outlook one-click path is the only supported option.
• IMAP must be enabled: if your account or organization has disabled IMAP, the connection cannot complete. Enable IMAP in Outlook settings, or use the Outlook tab.
• Connection refused or times out: confirm IMAP host outlook.office365.com on port 993 (SSL) and SMTP host smtp.office365.com on port 587 (STARTTLS).
• Still failing: remove the mailbox and reconnect through the Outlook tab, which avoids passwords entirely.