Email

Email, past the connect button.

Connecting a mailbox is the easy half. These guides cover the shapes a mailbox comes in, the authentication each one needs, and how to tell a delivery problem from a rules problem.

Connecting a mailbox

The shapes a mailbox comes in — personal Gmail, Google Workspace, Outlook, Microsoft 365 — and the permission each one needs before it will connect.

01 What you need before an AI can answer your email A mailbox, an agent to answer it, and knowing which of seven shapes your mailbox is. The third one decides whether you need an administrator. 02 Connect Gmail to an AI that reads and answers your email Four screens and one checkbox that breaks everything if you miss it. Works for a personal @gmail.com and for a Google Workspace address. 03 Connect a Google Workspace shared inbox (and what your admin has to approve) A real Workspace user mailbox your team shares, authorised once by a super admin through Domain-Wide Delegation. Not a Google Group — that is a different setup. 04 Put an AI on a support@ or sales@ Google Group — no admin needed A group address is answered by watching one member's mailbox and filtering on the List-Id header. The member has to already be in the group; nothing else needs approving. 05 Send email as an alias: connect a Gmail "Send mail as" address The mailbox you sign into keeps receiving the mail; outbound replies go out as the alias. The alias has to be verified in Gmail before you start. 06 Connect Outlook or Microsoft 365 to an AI email assistant One consent screen, seven permissions, and no administrator. Covers a personal Outlook.com inbox and a single-user Microsoft 365 work address. 07 Connect a Microsoft 365 shared mailbox: Full Access and Send As explained A shared mailbox has no password to sign in with. You connect as yourself, an admin grants two permissions, and the wizard refuses to finish without both. 08 Connect a Microsoft 365 Group so an AI can answer its shared inbox A mail-enabled M365 Group, connected through a member. Two one-time grants in the Exchange admin center, and drafts that live on the dashboard rather than in Outlook. 09 Why your Gmail or Outlook connection isn't working Failures by stage — sign-in, consent, naming the mailbox, verification, and the ones that appear weeks later. Each has its own message, and the message is the diagnosis.

Answering mail

What happens to mail once it arrives: who writes the reply, who approves it before it sends, and the quiet reasons one never left.

01 Can AI answer my emails? Draft, autonomous and human-only, explained Yes, in one of three ways, set per mailbox and overridable per thread. The same three settings are worded differently in setup and in the inbox, which is worth knowing before you go looking. 02 Let AI draft your email replies and approve them before they send Draft mode writes the reply and stops. Where the draft waits, what it tells you about its own sources, and why it is also sitting in your Drafts folder. 03 Make the AI answer email from your website and your documents Grounding is what turns a plausible reply into a correct one. Add a website, upload files or paste text on the agent's knowledge base, and every draft tells you what it drew on. 04 Summarise a long email thread Ask Octo in chat — there is no Summarise button in the inbox. The summary is written in the background as the thread grows, so the answer comes back without waiting on a model. 05 What an AI email assistant can't do with your inbox The structural limits, not the faults — what this will never do, so you can plan around it instead of discovering it in week three. 06 Why the AI didn't reply to an email Eight reasons, in the order worth checking. Most of them are a rule doing its job and saying so on the message — not a delivery failure.