How to do it
Check which mailbox your follow-ups actually leave from
Do this before anything else. Microsoft's requirements are explicit: Copilot is only supported on primary mailboxes hosted on Exchange Online, and it is not available on archive mailboxes, group mailboxes, or shared and delegate mailboxes the user has access to. Small shops usually send follow-ups from a shared office address, which is exactly the case that is excluded.
Switch your compose format to HTML
Draft with Copilot does not support messages composed in plain text. If you or your IT setup default to plain text, the option will not work and there is no error explaining why. Go to Settings, then Mail, then Compose and reply, and select HTML from the dropdown.
Click the Copilot icon and choose Draft
The icon sits in the toolbar above the blank email. Choose Draft from the dropdown, type your prompt in the Copilot box, and select Generate. In chat you can use Help me write or Help me reply to do the same thing from the side panel.
Put the facts in the prompt, not the adjectives
The prompt that works names four things: what you did, what you found, what it costs, and what you want them to do next. 'Follow up with Dana Kessler on the estimate from Tuesday for a water heater replacement, $2,140, quote is good for 30 days, ask her to reply yes or no by Friday.' Asking for a professional follow-up email with no facts gets you a professional email with no facts.
Use the dropdown to shorten it instead of rewriting it
After it generates, the dropdown lets you change length, change tone, or run the same prompt again. Short is almost always the right choice for a follow-up. The first draft will be about twice the length anybody reads on a phone.
Use Coaching on the email you already wrote
This is the underused half. Instead of generating from nothing, write your own two sentences and ask Copilot to review them. You need to enter at least 100 characters before it can give useful feedback. Your version with the tone tightened beats a generated version that sounds like nobody.
Cut it once more before you send it
A follow-up that gets replies is usually four sentences: what we quoted, what it costs, what happens next, and one clear question. Every sentence beyond that lowers your reply rate. Delete the closing paragraph that thanks them for their time twice.
Where this goes wrong
The parts most guides skip, and the ones that actually cost you money:
- Shared and delegate mailboxes are excluded, and that is most small businesses. Microsoft's documentation is direct about it: primary mailboxes on Exchange Online only, not archive, not group, not shared or delegate. If your quotes go out of office@ and three people work that inbox, Copilot in Outlook is not the tool for those messages. Individual named mailboxes are fine.
- It is an add-on, not something already in your subscription. Copilot is licensed on top of a qualifying Microsoft 365 plan. Microsoft lists Business Basic, Business Standard, Business Premium and Apps for business among the base plans that Microsoft 365 Copilot Business can be added to. Check the current per-seat price on Microsoft's pricing page rather than trusting a number in a blog post, because it has moved more than once.
- Device-based licensing does not get Copilot. Copilot is not available when using device-based licensing for Microsoft 365 Apps for enterprise. If a shop laptop is licensed to the machine instead of a person, that machine will not have it, no matter what you bought.
- It does not know whether you actually did the thing. Copilot can see the thread. It cannot see your truck, your parts order, or whether the tech went back out on Thursday. It will happily write a smooth sentence saying the work is complete. Read for facts, not for tone, before you send.
- A great follow-up email does not fix a slow first response. If the estimate went out six days after the visit, no wording rescues it. Fix the gap between the visit and the quote first. Follow-up polish is the last 10% of the problem, not the first.
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Common questions
Can I use this on our shared info@ inbox?
No. Microsoft states Copilot is only supported on primary mailboxes hosted on Exchange Online and is not available on shared or delegate mailboxes. The workaround most shops land on is sending customer follow-ups from named individual addresses and keeping the shared inbox for intake.
Do I have to move to the new Outlook?
No. Microsoft says Copilot works with classic Outlook and new Outlook for both Windows and Mac, and the drafting feature is documented for Outlook for Microsoft 365, new Outlook for Windows, Outlook for Mac and the iOS and Android apps.
Why is the Copilot option missing for one of my people?
Common causes are a plain text compose default, a mailbox that is not a primary Exchange Online mailbox, no Copilot license assigned, or device-based licensing. Microsoft publishes a Copilot License Details diagnostic that checks whether a specific account meets the requirements.
Is this better than ChatGPT for follow-ups?
It is better at one specific thing: it can see the thread you are replying to, so it drafts in context without you pasting anything. For writing a follow-up template you will reuse a hundred times, the context does not matter and a general tool is fine and cheaper.
Sources
- Draft an email message with Copilot in Outlook — Microsoft SupportThe Copilot icon sits in the toolbar above the blank email with a Draft option; Generate creates the message; a dropdown modifies length and tone; coaching requires at least 100 characters; drafting does not support plain text messages and the fix is Settings, Mail, Compose and reply, HTML; the supported Outlook clients.
- App and network requirements for Microsoft 365 Copilot admins — Microsoft LearnCopilot is only supported on primary mailboxes hosted on Exchange Online and is not available on archive, group, shared or delegate mailboxes; it works with classic and new Outlook; it is not available with device-based licensing for Microsoft 365 Apps for enterprise; the Copilot License Details diagnostic verifies a user account.
- License options for Microsoft 365 Copilot — Microsoft LearnCopilot is an add-on requiring a qualifying base subscription, and Microsoft 365 Copilot Business lists Business Basic, Business Standard, Business Premium and Apps for Business as eligible base plans.
Related guides
- How to use ChatGPT for follow-up emails
- How to use ChatGPT for overdue invoices
- How to use ChatGPT for review requests
- Set up a shared inbox that never drops a lead
- How to use Claude for quotes and estimates
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