Hi @Jason Linville,
Thank you for posting your question in the Microsoft Q&A forum.
I understand you’re using Classic Outlook for Windows and when you choose “Pop Out” for a reply, the new message window doesn’t show Copilot. In Classic Outlook, Copilot features are available, but where the Copilot entry points appear can depend on your build, channel, and a few settings, in some scenarios the pop‑out compose window may not load them even though Copilot works elsewhere.
You can see: Copilot is now available in classic Outlook for Windows.
Here are a few things you can check:
1/ Confirm your Copilot eligibility and sign‑in account:
Make sure the account you’re using in Outlook has a Copilot license (work/school or an Outlook.com account if applicable). If Copilot is missing, first verify licensing and sign‑in, then refresh the license in any Microsoft 365 app.
- You can check it by login to: https://portal.office.com/account/?ref=Harmony#subscriptions and look under Licenses.
- Your IT admin can also check by following this instruction.
2/ Update Classic Outlook and verify the update channel:
Copilot features in Classic Outlook rolled out on specific builds (e.g., Summarize is available starting 16.0.17028.10000, and Coaching/Draft starting 16.0.17231.20182) on Current Channel or Monthly Enterprise Channel. If you’re on Semi‑Annual Enterprise, Copilot won’t light up, switch to Current or Monthly Enterprise and update Outlook. Your IT admin can set channels via Intune or Cloud Update if needed.
3/ Turn on required privacy settings:
In any Microsoft 365 app, you can go to File Account > Account Privacy > Manage Settings and make sure “Experiences that analyze your content” and “All connected experiences” are enabled.
These settings control whether Copilot shows in the apps.
You can find detailed instructions for these 3 steps here: How to find and enable missing Copilot button in Microsoft 365 apps.
4/ Submit support ticket:
If you've checked the above things and the issue persists, I recommend reaching out to your IT admin and ask them to submit a support ticket directly to Microsoft Support and share your Outlook version/build and update channel so engineering can review tenant configuration and policy interactions affecting compose windows.
You can create a support ticket by sign in to the Microsoft 365 Admin Center following steps from this link: Get support - Microsoft 365 admin | Microsoft Learn to raise a support ticket from admin center or calling the phone support to contact Microsoft Support: Customer service phone numbers - Microsoft Support.
If you are not an admin, you can contact your admin to contact Microsoft support. You can look for the way to find your admin through this link: How do I find my Microsoft 365 admin? - Microsoft Support.
We appreciate your understanding regarding the scope of support available through this forum. As moderators, our role is to provide general guidance and assist with common troubleshooting steps. While we do not have access to internal systems or administrative tools required to resolve account-specific or backend-related issues but we’ll continue doing our best to support you within the scope of our responsibilities.
I hope the information provided proves useful. Please proceed with the outlined steps and let me know whether they resolve the issue. If not, I’ll be glad to continue working with you to find a solution.
Thank you for your patience and understanding throughout this process. Should you have any questions or need further assistance, feel free to reach out at any time.
I'm looking forward to hearing from you.
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