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How to troubleshoot your Microsoft365 Calendar integration

Trouble connecting your Meeting Bot with Microsoft365? This guide is for you!

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Written by Farran Jonker
Updated over 3 weeks ago

As you set up your Microsoft Calendar integration with Trail, you may run into some issues. Don't worry, most of these are caused by settings on your organization's Microsoft account that can be fixed quickly.

This guide will walk you through the most common problems and how to solve them.

1. What to check first

Before diving into specific issues, run through this quick checklist:

  • Do you have a Microsoft account? Trail's calendar integration works with both Microsoft 365 business accounts (like yourname@yourcompany.com) and personal Microsoft accounts (like yourname@outlook.com).

  • Are you using the right email address? Make sure you're signing in with the same Microsoft account that has your calendar. If your company has multiple domains (e.g., @company.com and @company.co.nz), try the primary one.

  • Try a different browser or incognito/private window. Old browser data can sometimes interfere with the sign-in process. Opening an incognito window gives you a clean start.

  • Clear your browser cookies for microsoft.com and microsoftonline.com. If you're signed into multiple Microsoft accounts, old sessions can cause conflicts.

If none of the above helps, read on to find your specific issue below.

2. You see "Need admin approval" when connecting

What you see:

When you try to connect your Microsoft Calendar in Trail, instead of being asked to sign in, you see a screen that says something like:

Why this happens:

Your organization's Microsoft 365 administrator has not yet approved Trail to access calendar data. This is a security feature, Microsoft requires an admin to approve third-party apps before employees can use them.

Think of it like this: your company has a "front door" that only the IT admin can open for new apps.

What you need to do:

You'll need to ask your IT administrator (the person who manages your company's Microsoft 365 account) to approve Trail. Here's what to tell them:

"Hi, I'm trying to connect my Microsoft Calendar to Trail, but I'm getting a 'Need admin approval' message. Could you please grant admin consent for the Trail application in our Azure Portal? Here's how:

1. Go to the Azure Portal

2. Navigate to Microsoft Entra ID (it's under "Azure Active Directory" in older portals)

3. Click Enterprise applications in the left menu

4. Search for the Trail CRM application

5. Click on it, then go to Permissions (under Security)

6. Click Grant admin consent for [Our Organization Name]

That should allow me and other users to connect our calendars."

What the admin sees in Microsoft 365 admin center:

The admin navigates through:

  • Admin centers in the left sidebar → Azure
    ​

  • Then Microsoft Entra ID → Enterprise applications
    ​

  • Find the Trail CRM app → Permissions (under Security section)
    ​

  • The Admin consent tab will be empty if consent hasn't been granted yet
    ​

Once the admin grants consent, wait about 15–30 minutes before trying again. Microsoft needs a bit of time to apply the change across its systems.

3. Some users can connect but others cannot

What you see:

One person in your office connected their Microsoft Calendar to Trail without any issues. But when another person tries, they get an error or the "Need admin approval" screen.

Why this happens:

There are a few possible reasons:

The admin only approved it for themselves

When your admin approved Trail CRM, they may have approved it only for their own account instead of for the whole organization. This is the most common cause.

How to fix it:

Ask your admin to grant organization-wide consent (not just for their own account):

  1. Azure Portal → Microsoft Entra ID → Enterprise applications

  2. Find Trail → Permissions

  3. Click Grant admin consent for [Your Organization Name]

The user doesn't have a Microsoft 365 license

The user trying to connect may not have an active Microsoft 365 license with Exchange Online (which provides the calendar).

How to check:

  1. Go to the Microsoft 365 Admin Center

  2. Click Users → Active users

  3. Search for the affected user

  4. Check their Licenses, they should have a Microsoft 365 or Office 365 plan that includes Exchange Online

The user has an on-premises mailbox

If your company uses a hybrid setup (some mailboxes in the cloud, some on-premises), the affected user's mailbox might be on an on-premises Exchange server. Trail can only access cloud-based (Exchange Online) mailboxes.

How to check: Ask your IT admin to verify the user's mailbox location. If it's on-premises, the user's mailbox would need to be migrated to Exchange Online.

4. Still stuck? How to contact support

If you've tried the steps above and your calendar integration still isn't working, we're here to help.

Before you contact us, please gather:

  1. A screenshot of any error message you see

  2. The error code (if visible), it usually starts with "AADSTS"

  3. Your email address (the Microsoft account you're trying to connect)

  4. What step of the process fails (e.g., "after I enter my password" or "after I click Connect")

  5. Whether this is a new setup or was previously working

Contact Trail Support:

For IT Administrators escalating to Trail:

In addition to the above, please also provide:

  • Your organization's Tenant ID (Azure Portal → Entra ID → Overview → Tenant ID)

  • The Correlation ID from the error (visible in the error details or Entra ID sign-in logs)

  • Screenshot of the Enterprise application's Permissions page for Trail

  • Any relevant Conditional Access policies that may apply

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