Outlook

Use Outlook when you want Drip Drop to send email through a Microsoft mailbox. Outlook can be connected with Microsoft OAuth or with an App Password.

Note
Use OAuth when you can. Use App Passwords only when that is the intended Microsoft account setup and the mailbox allows them.
  • You want email messages to come from a Microsoft-hosted mailbox such as Outlook or Microsoft 365.
  • You want a mailbox-based sender rather than an API email service such as SendGrid or Mailgun.
  • You need sending now, and may also want reply handling through the Outlook OAuth inbox subscription flow.
  • Confirm you can sign in to the Microsoft account you want to connect.
  • If using OAuth, be ready to approve Microsoft authorization prompts for mail access.
  • If using an App Password, confirm the account supports app passwords and that two-step verification is already enabled.
    Note
    Create or choose a safe test contact for the first email send.

The Outlook provider form supports two connection methods.

OAuth: Starts a Microsoft authorization flow and stores the connected mailbox in Drip Drop.
App Password: Uses the mailbox email address and an Outlook/Microsoft app password entered directly into the provider form.

Connect with Microsoft OAuth

  1. Open Dashboard → Admin → Integrations.
  2. Click New Integration and choose Outlook.
  3. Keep the authentication method set to OAuth.
  4. Select Connect with Microsoft and complete the Microsoft sign-in and consent flow.
  5. Return to Drip Drop and confirm the provider shows as connected.

After a successful connection, Drip Drop stores the connected Outlook mailbox and can show its connected state inside the provider form. If the Microsoft authorization later expires, the form switches to a reconnect flow.

Connect With an App Password

  1. Open Dashboard → Admin → Integrations.
  2. Click New Integration and choose Outlook.
  3. Switch the authentication method to App Password.
  4. Enter the mailbox email address and password.
  5. Save the provider and confirm it appears in the Integrations list.
    1. To edit or see provider information click on the Provider Name to open the Edit Window.
Note
Use an App Password here, not the normal Microsoft account password. Drip Drop links to the Microsoft security area where admins can create or revoke app passwords when their account type allows it.
  • Once saved, the provider can be selected anywhere Drip Drop needs an email-capable sender.
  • Outlook sending is mailbox-based, so choose the mailbox that should appear as the sender for your flows or templates.
    Note
    OAuth and App Password connections both support sending, but only the OAuth path includes the Outlook inbox subscription flow described below.

Outlook reply handling is tied to the OAuth connector. When Outlook webhooks are available, Drip Drop creates or renews a Microsoft Graph inbox subscription for the connected mailbox and shows an Inbound Status row for that subscription.

  • Inbound Status can show the Outlook inbox subscription as: Active, Expired, or Not Configured.
  • If the subscription expires or is missing, admins can retry setup from the Provider form.
  • Reply matching is based on Drip Drop message threading headers first, with a fallback to recent outbound-message matching when needed.
Note
App Password Outlook setup is for sending only in this docs flow, it is not the same inbound subscription behavior as OAuth.

Outlook providers expose Drip Drop internal tracking settings where available. Keep the expectations narrow: these settings cover Drip Drop link and open tracking behavior, not ESP-style provider event webhooks for clicks, opens, or deliveries.

  • OAuth requires Microsoft authorization for the live Drip Drop mail scopes used for sending and reading mailbox content.
  • The current OAuth flow requests Microsoft Graph mail access plus basic identity scopes so Drip Drop can connect the mailbox and support the inbox subscription flow.
  • App passwords depend on Microsoft account security settings. Some accounts or tenants may not allow them.

Helpful Microsoft references: Microsoft account security, Microsoft identity platform authorization, Microsoft Graph mail permissions, and Microsoft Graph change notifications / subscriptions.

OAuth problems
  • If the popup closes early or authorization is denied, restart the OAuth flow and complete the Microsoft consent step again.
  • If the provider shows an expired authorization state, use Reconnect to refresh mailbox access.
  • If OAuth succeeds but inbound setup fails, check whether Microsoft Graph mailbox notifications are allowed for the account and whether the connected mailbox still has valid access.
App password problems
  • If save or send fails, confirm you used an app password rather than the normal account password.
  • If you cannot create an app password, verify that two-step verification is enabled and that your Microsoft account or tenant still permits app passwords.
  • If the mailbox address is wrong, update it to the exact Microsoft mailbox that should send from Drip Drop.
Inbound/reply problems
  • If replies do not appear, verify the provider was connected with OAuth and that the Outlook inbox subscription is active.
  • If the inbound status looks expired or not configured, retry setup from the provider form.
  • If a reply reaches the mailbox but is not linked to the expected outbound message, test again with a fresh Drip Drop send so the message threading headers are present.
  • See Integrations for the shared provider setup flow and provider management basics.
  • Compare Gmail if you need the same mailbox-style workflow on a Google account instead of a Microsoft mailbox.