Skip to main content

Documentation Index

Fetch the complete documentation index at: https://replyless.ai/docs/llms.txt

Use this file to discover all available pages before exploring further.

Connecting Outlook or Microsoft 365 lets Replyless sync your inbox in real time, display messages in the Replyless UI, and send AI-drafted replies from your email address. Both personal Microsoft accounts (outlook.com, hotmail.com, live.com) and work or school Microsoft 365 accounts are supported, with a few differences noted below.

​
Connect an Outlook or Microsoft 365 account

1

Open account settings

In Replyless, click your profile picture in the top-right corner and select Settings, then go to Connected accounts.
2

Add an Outlook account

Click Connect account and choose Outlook / Microsoft 365 from the list of providers.
3

Sign in with Microsoft

A Microsoft sign-in window opens. Enter the email address and password for the account you want to connect.
4

Review and grant permissions

Microsoft shows a consent screen listing the permissions Replyless is requesting. Review them and click Accept.
5

Confirm the connection

You are redirected back to Replyless. Your account appears under Connected accounts with a green status indicator. Replyless begins syncing your inbox immediately.

​
Permissions Replyless requests

When you connect Outlook or Microsoft 365, Replyless requests the following Microsoft Graph permissions:
PermissionWhy it’s needed
Mail.ReadReads and syncs messages from your inbox to the Replyless UI.
Mail.SendSends AI-drafted replies from your email address.
Mail.ReadWriteMarks messages as read, moves them, or updates their status after you act on them.
offline_accessKeeps the connection active without requiring you to sign in repeatedly.
Replyless does not request access to your calendar, contacts, files, or any other Microsoft service.

​
Personal vs. work or school accounts

Personal Microsoft accounts (outlook.com, hotmail.com, live.com) and work or school Microsoft 365 accounts both work with Replyless, but there are important differences. Work and school accounts are managed by your organization’s IT admin. If your admin has restricted third-party app consent, you may need admin approval before Replyless can connect. Personal accounts do not require any admin approval.
If you are using a work or school account and see a message that says “Need admin approval,” contact your Microsoft 365 admin and ask them to approve Replyless in the Azure admin portal under Azure Active Directory → Enterprise applications.

​
Connect multiple accounts

You can connect multiple Outlook and Microsoft 365 addresses to a single Replyless account — for example, a personal outlook.com inbox alongside a work Microsoft 365 inbox. Repeat the connection steps above for each address. Each account appears as a separate inbox in the Replyless sidebar, and you can switch between them or view a unified inbox.

​
Disconnect an account

1

Go to Connected accounts

In Replyless, open Settings and select Connected accounts.
2

Remove the account

Find the Outlook or Microsoft 365 address you want to remove and click Disconnect. Confirm when prompted.
3

Revoke access in Microsoft (optional)

To fully remove Replyless from your Microsoft account, visit myapps.microsoft.com, find Replyless, and remove its access. For personal accounts, go to account.microsoft.com/privacy/app-access.
Disconnecting stops all syncing for that address. Messages already loaded in Replyless are removed from the UI within a few minutes.

​
Troubleshooting

Your Microsoft 365 organization requires admin consent for third-party apps. Ask your IT admin to approve Replyless in the Azure portal under Enterprise applications → Admin consent. Once approved, try connecting again.
Initial sync can take up to five minutes for large inboxes. If messages still don’t appear, go to Settings → Connected accounts, disconnect the account, and reconnect it.
Microsoft tokens can expire if your organization enforces short session lifetimes or if you changed your password. Open Settings → Connected accounts and click Reconnect next to the affected address.
Replyless currently connects to commercial Microsoft 365 endpoints. GCC High and DoD tenants use separate endpoints that are not yet supported. Contact support if you need assistance with a government-cloud account.