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Troubleshooting your Microsoft email integration
Troubleshooting your Microsoft email integration

Here’s what to do if you encounter trouble integrating your Outlook / Microsoft 365 email!

Conor Ferigo avatar
Written by Conor Ferigo
Updated over a week ago

As you set up your Microsoft Email Integration with Trail, you may encounter some troubles. An error message such as the below may appear:

Here are some steps to narrow down and troubleshoot any issue you may have with email integration!

In this article you will learn:

  • Step by step troubleshooting for Microsoft accounts

  • Additional information for allowing SMTP AUTH for specific Mailboxes

1. Ensure you are using the correct email details

Your email address entered into Trail must match the current email address. As an example, if you’ve changed your email address from to, you will need to use the current verified address.

An email address is a unique identifier for an email account. Every email address has two main parts: a username and domain name. The username comes first, followed by an at (@) symbol, followed by the domain name.

2. Ensure you have IMAP and SMTP enabled for your Microsoft account

If you are experiencing the above error message, you may need to check the following details with your IT provider or the person who originally set up your organisation's emails.

To check if your IMAP/SMTP settings are enabled, you will need to sign in to the Microsoft 365 admin center with security administrator, Conditional Access administrator, or Global admin credentials and view the following from the Admin Center.

  • Exchange in the left pane of Microsoft 365 admin center to go to Exchange admin center, then click recipients > mailboxes and double click on your account. Then select Manage Settings for Email Apps.

  • Select Users in the left pane of Microsoft 365 admin center > Active Users > double click on your account > Mail > Manage Email Apps.

If the above are all correctly enabled there may be a 'Conditional Access Policy' that is overriding these settings, to check this please log into your Azure tenant and go to Azure Active Directory > Security > Conditional Access Policies.

This will show a list of all ‘Conditional Access Policies’ and their On/Off state. Select one of the policies to view its settings. Click Users and Groups to see who it applies to (probably all users). Click Exclude to add mailboxes to exclude them from said policy.

If you do not have the SMTP Authentication setting at all, this may be due to Microsoft Security Defaults being enabled. To disable your security default setting,

  1. Sign into your Azure Active Directory account.

  2. From the left menu of the Dashboard, in the Manage section, select Properties.

  3. At the bottom of the Properties page, select Manage Security defaults.

  4. In the right pane, you'll see the Enable Security defaults setting.

3. Ensure your email is not being serviced by a Third Party email provider

If your email is hosted by a third party (FreeParking, CrazyDomains, etc), you will need to connect via IMAP/SMTP in order to establish a solid connection between your email inbox and Trail, rather than the Microsoft connection option.

You will need to use your third party email provider’s details when you connect via IMAP/SMTP. Depending on the email provider you use, you may need to get in touch with their support team in order to successfully integrate your email in Trail.

For example, here are the details you would need for an email address hosted by FreeParking:


Incoming IMAP server host name:

Port number: 993


Outgoing SMTP server host name:

Port number: 465 or 587

Secure/Encrypted Connection: Enabled for SSL or SSL/TLS

In addition, you will need to have multi-factor Authentication either enabled or enforced. If multi-factor authentication is disabled, we will be unable to connect your email via IMAP/SMTP.

Additional Troubleshooting Steps

Enable SMTP AUTH for specific mailboxes

The per-mailbox setting to enable (or disable) SMTP AUTH is available in the Microsoft 365 admin center or Exchange Online PowerShell.

Use the Microsoft 365 admin center to enable or disable SMTP AUTH on specific mailboxes

  1. Open the Microsoft 365 admin center and go to Users > Active users.

  2. Select the user, and in the flyout that appears, click Mail.

  3. In the Email apps section, click Manage email apps.

  4. Verify the Authenticated SMTP setting: unchecked = disabled, checked = enabled.

  5. When you're finished, click Save changes.

Still experiencing issues?

If you are still experiencing issues with integrating your email, please get in touch with us at

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