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How to connect your Microsoft Outlook or Office 365 email to Trail

Connect your Microsoft Outlook or Office 365 mailbox to Trail so you can send client emails from your own address and have client emails filed automatically.

Written by Jacob Watters

Use this article to connect your Microsoft Outlook or Office 365 mailbox to Trail, so you can send client emails from your own address and have copies of your client emails filed automatically against the right client profiles.

Trail connects to Outlook using OAuth2, Microsoft's recommended and most secure sign-in method. Any Trail user can connect their own Outlook or Office 365 mailbox.

Prefer to watch? Jump to the step-by-step video guide at the end of this article.
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What do I need before I connect my Outlook email to Trail?

Before you connect your Outlook or Office 365 mailbox to Trail, check that:

  • You are logged in to Trail

  • You can sign in with Microsoft

  • Pop-ups are allowed in your browser, because the Microsoft sign-in opens in a new window

How do I connect my Outlook or Office 365 email to Trail?

Follow these steps in Trail to connect your own Outlook or Office 365 mailbox.

  1. In Trail, click Settings, then select Email Integration

  2. Click Connect with Microsoft / Outlook

    The Email Integration page in Trail Settings, showing the Connect with Microsoft / Outlook button.

  3. Sign in with Microsoft in the login window that opens

    The Microsoft sign-in window that opens when connecting Outlook to Trail, asking for your email address.

  4. When Microsoft asks for permission to connect Trail to your email, click Yes. This permission is what allows Trail to send, receive, and log your emails securely

    The Microsoft permission screen asking you to allow Trail to access your email, with the Yes button to accept.

    If you see an error saying your organisation requires administrator approval instead of the permission screen, your organisation's Microsoft account blocks the connection until a Microsoft 365 Global Admin approves it. Follow Why does my Microsoft email keep disconnecting or asking for admin approval? to get that approval, then start again at step 1.

  5. Check that you have been redirected back to Trail and that the Email Integration page confirms your Outlook address is successfully connected

    The Email Integration page in Trail after connecting, confirming that the Outlook email address is successfully connected.

Once your Outlook email integration is connected, Trail scans your mailbox for new client emails about every 45 minutes and files them against matching client profiles. On the first connection, Trail also runs a 7-year historic scan of your mailbox, so existing client emails from the past 7 years are filed for record-keeping. For more on what Trail syncs and why, see How Trail's Email Integration Works.
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Is there a video guide for connecting Outlook to Trail?

The video below walks through the same steps as above, from opening Email Integration in Trail Settings to confirming that your Outlook mailbox is connected.

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