Key takeaways
- Outlook is a native connection, added by each person as Microsoft Inbox, with the same mail tools as Gmail.
- Categories and rules take the place of labels and filters, and they apply without an approval card.
- With Gmail and Outlook both connected, the assistant asks which mailbox to use.
- Pebbles Ai is Microsoft 365 certified, and contacts can be imported from Microsoft into the CRM.
What does the Outlook integration give the assistants
The Outlook integration gives the assistants the same mail tools Gmail users get: search, read, threads, compose, reply, forward, send and BCC. Pebbles Ai keeps the two providers at parity, so a team split across Google and Microsoft does not get a weaker assistant on one side.
For a Microsoft 365 team, the mail and contacts can stay on Microsoft accounts: connect the Outlook inbox and import contacts from Microsoft into the Pebbles Ai CRM, which is labelled Beta.
How do Outlook categories and rules work with AI
The assistant can apply Outlook categories and create rules from a plain request, and neither waits for approval in any mode. Categories suit deal stages, because one message can carry several; rules suit routing, such as moving supplier newsletters out of the inbox you sell from.
Because these changes apply straight away, phrase them as exactly as you would set them up by hand. Some illustrative requests:
- Put the Proposal sent category on every thread with the three accounts we priced this week.
- Create a rule that moves mail from our events supplier's domain into a folder called Events.
- Show me every thread in the Negotiation category with no reply from us in five days.
Which mailbox does the assistant use when both are connected
When both Gmail and Outlook are connected, the assistant asks which mailbox to use before it searches, drafts or sends. That matters for consultants and founders who sell from a Microsoft 365 company address but keep an older Google account for one client.
You can also connect more than one Outlook inbox. Say which address a draft belongs in, and the draft lands in that mailbox's drafts, ready to open in Outlook on any device.
Is Microsoft 365 AI email in Pebbles Ai certified
Yes, Pebbles Ai is Microsoft 365 certified under the Microsoft 365 App Compliance Program, which covers the Outlook connection. GDPR shows as compliant; SOC 2 Type II and ISO 27001 are pending, not held.
Each business sits in its own tenant under Tenant-Isolated AI, the Pebbles Ai architecture for tenant isolation and data security, and no customer's data trains a model. Disconnecting Outlook removes the stored credentials in Pebbles Ai; remove the app's access in your Microsoft account as well if you want the grant gone there.
How to connect Outlook and set it up for selling
Each person connects their own Microsoft mailbox; an admin does not do it for the team.
- Open Settings, Connections and choose Microsoft Inbox under Email inboxes.
- Sign in with the Microsoft account you sell from and approve the access it requests.
- If you also connected Gmail, expect the assistant to ask which mailbox to use, and answer by address.
- Ask for a draft reply in a chat and open your Outlook drafts to check it arrived.
- Describe the categories and rules you want precisely, since they apply without waiting for approval.
Where Pebbles Ai fits
- CapabilitySmartboxSmartbox brings Outlook mail into Pebbles Ai with Write with AI; Outlook and Gmail tools are at parity, with categories and rules in place of labels and filters.
- CapabilityProspecting & customer recordsImport contacts from Microsoft into the CRM (in Beta), then send a template to a segment through Outlook; template send asks for approval in every execution mode.
Common questions
Does Pebbles Ai work with Microsoft 365 mailboxes?
Yes, through the Microsoft Inbox (Outlook) connection, which each person adds in Settings, Connections.
Do Outlook sends always need approval?
In Manual mode, yes, and in Plan they are queued rather than sent. In Auto they run without asking, except template send to a CRM segment, which asks in every execution mode.
Can the assistant read a shared team mailbox in Outlook?
Pebbles Ai records connections per person and offers no shared-inbox assignments, so treat it as a tool for the mailboxes you connect yourself.
About this page. Written by the Pebbles Ai team for people who run sales, marketing and growth. Last updated .
