Connect Your Outlook / Microsoft 365 Account

Most insurance carriers and TPAs run on Microsoft 365. When your booking confirmation arrives from a no-reply address on a domain the adjuster has never seen, it lands in a quarantine folder nobody checks, or it triggers the carrier mail filter that strips external links. You think you sent it, the adjuster never sees it, and your inspection slot quietly evaporates.

Connecting your Outlook or Microsoft 365 account routes every AwardLettr email through your real mailbox. Carriers see a domain they already whitelist, replies thread back into the Outlook conversation history your assistant is already monitoring, and your sent items reflect every booking, status update, and award notification AwardLettr fires on your behalf.

This matters most if you work carrier files, where the other side is almost always on Microsoft, or if your firm runs on Microsoft 365 and you need outbound mail to come from your own domain to stay professional.

Connect your Outlook or Microsoft 365 email account to AwardLettr so you can send emails directly from your own email address.

You will need to create an "app password" — this is a special password just for AwardLettr. It is NOT your regular Microsoft password.

Prerequisites

An Outlook.com, Hotmail, or Microsoft 365 email account
Two-step verification must be enabled on your Microsoft account

Step 1: Enable Two-Step Verification

If you already have two-step verification enabled, skip to Step 2.

Go to Microsoft Account Security

Open https://account.microsoft.com/security and sign in.

Click "Advanced security options"

Scroll down and click the link for advanced security options.

Enable Two-step verification

Find "Two-step verification" and click "Turn on". Follow the prompts to set it up.

Step 2: Generate an App Password

Go to Advanced Security Options

Visit https://account.microsoft.com/security and click "Advanced security options".

Find "App passwords"

Under "App passwords", click "Create a new app password".

Copy the password

Microsoft will generate a password. Copy it immediately — you'll need it in the next step.

Step 3: Connect in AwardLettr

Go to Settings → Integrations

In AwardLettr, navigate to Account Settings → Integrations.

Find "Email Connection"

The Email Connection card is at the top of the integrations page.

Select "Outlook / Microsoft 365"

Choose "Outlook / Microsoft 365" from the Email Provider dropdown.

Enter your email

Type your full Outlook/Microsoft email address.

Paste the app password

Paste the app password you generated in Step 2.

Click "Connect Email"

AwardLettr will verify your credentials. If successful, you'll see a green confirmation.

Troubleshooting

"Could not connect to email server" — Make sure you're using the app password, not your regular Microsoft password. Verify two-step verification is enabled.

"App passwords" option not available — Some Microsoft 365 organizations disable app passwords. Contact your IT administrator to enable them, or ask if they allow SMTP access.

Frequently Asked Questions

**Will recipients see my real email address?** Yes. Emails will show your Outlook/Microsoft address as the sender.

**Where do replies go?** Replies go to both your Outlook inbox and your AwardLettr Messages tab.

**Can I disconnect later?** Yes. Go to Settings → Integrations and click "Disconnect".