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AgentWeb connects Emma directly to your Outlook / Microsoft 365 mailbox. Once connected, Emma can send single emails, group campaigns, and drip sequences from your real inbox, search and read your Outlook / Microsoft 365 messages on request, and automatically stop emailing leads whose messages bounce.

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Before you connect

You connect by signing in with a Microsoft account. Either type works:
  • A work or school account (Microsoft 365) — from any company, not just AgentWeb’s own.
  • A personal Microsoft account (Outlook.com, Hotmail, Live).
You can grant AgentWeb’s permissions yourself during sign-in — no IT approval needed in most cases. That said, some companies restrict what outside apps their employees can connect. If yours does, you’ll see a permissions error even after approving everything on your end — see Troubleshooting below.

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Connect

1

Open Settings → Accounts

In the Customer Portal, go to Settings → Accounts and find the Outlook / Microsoft 365 card.
2

Click Connect

AgentWeb opens Microsoft’s sign-in and permissions screen in a popup.
3

Sign in to Microsoft

Sign in with the mailbox you want Emma to send from.
4

Approve the requested permissions

You’ll be asked to let AgentWeb send mail, read mail, and see your basic profile. Approve all of them. Sending won’t work at all without the send permission; skipping the read permission won’t stop the connection, but it quietly turns off inbox search and bounce protection for that mailbox — so approve everything.
5

Confirm

You’re returned to the Accounts tab and the Outlook / Microsoft 365 card flips to Connected, showing the mailbox address you signed in with.
You can connect more than one Outlook / Microsoft 365 mailbox by repeating the flow — for example, one per teammate doing outreach.

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What Emma can do once connected

Once connected, tell Emma what you want in Agent Mode or set it as the sender on a CRM send, campaign, or sequence — no separate configuration needed. “Send a follow-up to my Q2 list from my Outlook / Microsoft 365 address.” “Search my Outlook / Microsoft 365 inbox for emails from acme.com this week.”
A “reply” sent through Outlook / Microsoft 365 arrives as a new email to the same recipient, not as part of the original email thread — some other mailbox providers can keep the thread together, Outlook / Microsoft 365 currently can’t. Also, sequences can’t yet tell on their own that a lead replied to an Outlook / Microsoft 365 message and stop automatically — if a lead replies, you’ll want to pause or stop that sequence yourself.

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Bounce protection

If AgentWeb sends an email through your Outlook / Microsoft 365 mailbox and it bounces, that lead is automatically marked so AgentWeb won’t email them again. This runs quietly in the background with nothing to set up — it starts working as soon as the mailbox is connected. It checks periodically rather than instantly, so it can take a little while (up to about 15 minutes) to catch a bounce, and in rare cases an unusually worded bounce message might not be recognized.

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Sending limits

A campaign or group send from a connected Outlook / Microsoft 365 mailbox is limited to 50 recipients per send, to keep sends fast and reliable. If your list is bigger, split it into smaller sends, or use a different connected sender for that campaign. Single sends and replies have no such limit.

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Reference

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Team access

If your AgentWeb account is part of an organization, you can share a connected Outlook / Microsoft 365 mailbox with your teammates so they can send from it too, without each person connecting it separately. On the account’s card in Settings → Accounts, click Share with org. You can turn sharing back off with Stop sharing — once someone else on the team has shared it, only an org owner can turn it back off or disconnect it.

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Disconnect

Click the Outlook / Microsoft 365 card in Settings → Accounts and choose Disconnect. To fully revoke access on Microsoft’s side too: Disconnecting stops Emma from sending or reading mail through this mailbox. It doesn’t change anything inside Outlook / Microsoft 365 itself.

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Troubleshooting

This usually means the send permission wasn’t approved, or something went wrong granting lasting access to the account. Click Connect again and make sure to approve every permission requested. If it keeps failing on a work account, your company’s IT admin may be restricting outside apps — check with them.
You have about 10 minutes to complete sign-in and approval once you start. If you take longer, you’ll see a session-expired message — just click Connect again to restart.
This can happen if your Microsoft account’s access to AgentWeb gets revoked or needs to be re-approved (for example, after changing your Microsoft password). The Outlook / Microsoft 365 card will show as disconnected — reconnect from Settings → Accounts.
Mailbox sends are limited to 50 recipients per send. If your list is bigger, split it into smaller sends or use a different connected sender for that campaign.
Bounce checking runs periodically rather than instantly, so it can take up to about 15 minutes to catch one. In rare cases, an unusually worded bounce message from the recipient’s mail provider may not be recognized at all.
This is expected today — Outlook / Microsoft 365 replies send as a new message rather than joining the original conversation. There’s no way to change this on the Outlook / Microsoft 365 side right now.
Sequences can’t automatically detect a reply to an Outlook / Microsoft 365-sent message and stop themselves yet. If a lead replies, pause or stop that sequence manually.
Every send from a connected mailbox is saved to that mailbox’s own Sent Items automatically. If it’s missing, first confirm the send actually succeeded (check Agent Mode or the campaign’s send report) rather than assuming Sent Items didn’t sync.

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Next steps

  • Agent Mode — brief Emma on an outreach send.
  • CRM — pick Outlook / Microsoft 365 as the sender on a campaign or sequence.
  • Gmail — the equivalent integration for a Google Workspace/Gmail mailbox.