Does Cheerful work with Outlook?

Partly. Outlook is a connected app, so Cheerful’s agent can use your Outlook calendar and mail for meetings, searches and one-off emails. Campaign sending and inbox sync need Gmail or an SMTP/IMAP mailbox.

Can I send influencer outreach from Outlook with Cheerful?

Not through the Outlook connection. A Microsoft 365 mailbox can be connected for campaigns with SMTP and IMAP credentials if your administrator allows that access.

Connected app

Cheerful + Outlook integration

Connecting Outlook lets Cheerful’s agent work with your Microsoft 365 mail and calendar: it can find a free slot and put a creator call on your Outlook calendar, search your Outlook mailbox for an earlier conversation with a creator, and draft or send a one-off email from it.

Outlook is a connected app from the catalogue, and that distinction matters here. Campaign outreach, follow-ups and inbox sync run on Gmail or an SMTP/IMAP mailbox; Cheerful has no native Outlook sign-in for sending campaigns.

Connect Outlook in Cheerful Every integration, in writing

How influencer teams use Outlook with Cheerful

Book the call a creator asked for

When a creator asks to hop on a call, ask the agent to find a time that works on your Outlook calendar and create the event with the creator invited.

Find the thread from before Cheerful

Search your Outlook mailbox for past conversations with a creator or agency before re-pitching, so you do not open with a pitch they already declined.

One-off mail from your Microsoft address

For a contract or invoice that must come from your company Outlook address, the agent can draft it in Outlook for you to send or send it directly.

What Cheerful's agent can do in Outlook

Outlook exposes 287 actions to Cheerful’s agent. The ones used alongside creator campaigns:

Find meeting times across attendees
Create, update or cancel calendar events
Read your schedule and list events
Search and list messages
Create a draft or a draft reply
Send an email or a reply

How to connect Outlook to Cheerful

1
In Cheerful, open Settings, go to Integrations and search the catalogue for Outlook.
2
Sign in with your Microsoft account through Microsoft’s consent screen. Some organizations require an admin to approve the app first.
3
In the chat that opens, ask for what you need: a meeting, a search or a draft.

What the Outlook integration does not do

Outlook is not a campaign mailbox. Outreach, follow-ups and reply drafting run from Gmail or an SMTP/IMAP mailbox, and Microsoft mailboxes can only be added as SMTP/IMAP where your admin allows it.
Replies that arrive in Outlook are not synced into Cheerful’s inbox.
Your Microsoft 365 admin may block third-party app consent; if the sign-in fails, that setting is the usual cause.

Cheerful and Outlook: common questions

Does Cheerful work with Outlook?: Partly. Outlook is a connected app, so Cheerful’s agent can use your Outlook calendar and mail for meetings, searches and one-off emails. Campaign sending and inbox sync need Gmail or an SMTP/IMAP mailbox.
Can I send influencer outreach from Outlook with Cheerful?: Not through the Outlook connection. A Microsoft 365 mailbox can be connected for campaigns with SMTP and IMAP credentials if your administrator allows that access.