Kesslernity · M365 Copilot Field Guide
Copilot Cowork
Research. Plan. Execute. With your approval.
Cowork is the agentic execution layer in M365 Copilot. You describe an outcome — Cowork searches your M365 data, breaks the task into steps, and takes action with your explicit approval before anything is sent, scheduled, or changed.
Requires before you start
Microsoft 365 Copilot add-on licence (requires M365 E3 or E5 base). The licence is the access gate; Cowork usage is billed separately on consumption (Copilot Credits — see the Billing section). As of June 16, 2026 Cowork is generally available worldwide — Frontier enrolment is no longer required.
EU / EFTA / UK tenants only: Anthropic is disabled by default. Admin must enable it at admin.microsoft.com → Copilot → Settings → AI providers before Cowork works for any user in the tenant.
What's new — June to August 2026
June 16 GA wave: Cowork reached general availability worldwide, billed on usage through Copilot Credits ($0.01/credit pay-as-you-go, off until an admin enables it), and the Work IQ APIs reached GA the same day.
Mid-August 2026: Microsoft Learn now documents the model picker in one place, and the list has moved since this guide last recorded it. Auto stays the default; the documented choices are now GPT 5.5 (Frontier), GPT 5.6 Sol, GPT 5.6 Terra, Opus 5, Claude Sonnet 5 and Claude Fable 5, with a separate effort control (Light, Medium, High, Extra High, Max) governing how hard the model works and how quickly a user's limits are consumed. Claude Fable 5 is the one that carries a governance condition: in preview, off until an admin turns it on, and it requires data retention, so prompts and responses for that model are kept by the model provider rather than following Cowork's default no-retention posture, with a persistent banner shown while it is selected. An admin can switch the Anthropic model family off outright. See the model picker section below for the full list, and for the two entries recorded here in early August that are absent from the new table.
At a glance
What it is
An AI agent that takes action inside M365 —
sends emails, posts to Teams, creates calendar blocks.
Key difference from Chat
Chat drafts — you implement.
Cowork executes — with your approval at each action.
Built on
Anthropic Claude agentic model,
wrapped in Microsoft enterprise governance.
| Use case | What you describe | For |
| Meeting follow-up | Find my Teams transcript, draft and send the follow-up email to all attendees | Anyone who runs meetings |
| Weekly status post | Every Friday, pull my project emails, draft the Teams update, post after I approve | Project manager · Team lead |
| Focus time protection | Find gaps in my next 5 days, propose 90-min focus blocks, create them after I confirm | Anyone in back-to-back meetings |
| Commitment tracking | Find every "I'll send / I'll follow up" in my emails from the last 14 days, flag overdue | Account manager · Consultant |
| Conflict resolution | Find calendar conflicts next 7 days, propose resolutions, reschedule after I approve each | Manager · Executive |
| Renewal outreach | Search my history with [contact], draft a brief personalised email, send after I approve | Account manager · Customer success |
Cowork vs Copilot Chat — the one distinction that matters
| Aspect |
Copilot Chat |
Copilot Cowork |
| Output |
A draft or answer — you decide what to do with it |
An action taken — email sent, event created, post published |
| Execution |
You read, copy, paste, act manually |
Cowork executes; pauses for your approval at each step |
| Time span |
Single response, immediate |
Multi-step, runs over minutes with checkpoints |
| Steering |
Static response; you decide next turn |
You can interrupt, redirect, pause, or cancel mid-task |
| Scheduled tasks |
Not available |
Up to 5 recurring prompts that run on a schedule |
| Custom skills |
Not available |
Up to 50 saved instruction sets, auto-loaded per conversation |
Billing — Cowork runs on usage, not a flat seat
Your M365 Copilot licence is the access gate. Cowork usage is billed separately on a consumption currency Microsoft calls Copilot Credits. Pay-as-you-go is $0.01 per credit; a commit-for-discount plan ("P3") is available for tenants that want a lower rate against a usage commitment. Usage billing is off by default — an admin must turn it on before any Cowork task will run. For a full breakdown of what Cowork consumption costs in Copilot Credits, see the cost model reference.
What you pay for
A task's cost = four inputs
Every Cowork task draws credits across four things combined: model use (the LLM tokens), context retrieval (searching your M365 data), tool calls (the actions it takes), and runtime (how long the task runs). A short "draft one email" task is cheap; a multi-step research-and-execute task that reads dozens of files costs more.
Model picker
Choose the model to manage cost
Cowork lets you pick the model per task. As of 14 August 2026 the Learn model page lists Auto (the default, Microsoft routes the task), GPT 5.5 (Frontier, hosted in Azure AI Foundry), GPT 5.6 Sol, GPT 5.6 Terra, Opus 5, Claude Sonnet 5 and Claude Fable 5. A separate effort control (Light, Medium, High, Extra High, Max) sets how hard the model works and how quickly it consumes a user's limits, which makes it a cost lever alongside the model itself. Use Sonnet for routine drafting and reserve the heavier models for complex multi-step reasoning to keep credit spend down. Governance flag: Fable 5 is in preview and stays off until an admin turns it on under Copilot settings in the admin center. It requires data retention, so prompts and responses for that model are kept by the model provider instead of following Cowork's default no-retention posture, and Cowork shows a persistent banner while it is selected. Treat it as a separate approval, not a dropdown choice. An admin can also switch the Anthropic model family off outright. Two entries recorded here on 5 August 2026, Claude Opus 4.8 and the paired Sonnet + Opus Advisor mode, are absent from the 14 August table; Microsoft publishes no diff and no retirement notice, so read that as the documentation changing rather than a confirmed removal. Model lists move monthly, so verify the live picker before writing it into a policy.
Off by default
No Cowork usage is billed until an admin explicitly enables usage-based billing for the tenant. Nothing runs up a bill silently.
Spend limits & alerts
Admins set spending limits and usage alerts at tenant, group, or individual user level — caps so a single user or team can't overspend.
Cost Management dashboard
A new Cost Management dashboard in the M365 admin center reports Copilot Credit consumption by user, group, and feature.
Frontier users — billing grace until July 1, 2026
Tenants that had a Cowork Frontier user during the preview window (Mar 30 – Jun 16, 2026) are not billed for Cowork usage until July 1, 2026. Use the grace window to set spending limits and alerts before the meter starts.
Setup — 4 steps
1
Verify your licence
Confirm you have the M365 Copilot add-on assigned (requires M365 E3 or E5 base). Check under portal.microsoft.com → Licences. Without this licence, Cowork is not accessible.
2
Confirm usage billing is set up
Cowork is metered in Copilot Credits and is off by default. An admin must turn on usage-based billing and set spending limits before tasks will run. Check with IT, or see the Billing section below for what each task costs and how limits work.
3
Open Cowork
Once your licence and usage billing are in place,
Cowork appears in the left sidebar at
m365.cloud.microsoft. Select it. The interface shows a chat input and a Tasks panel on the right.
4
Describe your first task
Type a task outcome in plain language — not a question, a delegation. "Find every unresponded email from this week and draft replies for each" is better than "Can you help me with emails?" See the Delegation Brief format below.
The Delegation Brief format
Structure every Cowork prompt with these 4 parts
How to write for Cowork — the 4-part structure
Part 1
Goal
The outcome you want — not the steps. State what done looks like, not how to get there. "Send a follow-up email to all attendees" is a goal. "Search Teams, then draft an email, then send it" is steps — Cowork works those out itself.
Part 2
Inputs
Which M365 sources to pull from. Name them explicitly: Outlook, Teams, Calendar, SharePoint folder, specific meeting transcript. Cowork can infer, but named sources produce fewer errors than "look at everything."
Part 3
Output
What to produce and in what format. "A Teams post in bullet format" is different from "a formal email under 150 words." The more specific the output description, the less iteration you need on the draft.
Part 4
Boundaries
What Cowork must NOT do without your explicit approval. "Show me the draft before sending." "Do not create any calendar event until I confirm the full list." "Do not contact anyone outside my organisation." These are the lines that prevent surprises.
Example — meeting follow-up
Goal: Send a follow-up email after my last meeting.
Inputs: Find the Teams transcript or my notes from the last 2 hours.
Step 1: Extract action items (what, owner, deadline), decisions made, and open
questions. Show me this list and wait for my confirmation before proceeding.
Step 2: Draft a follow-up email to all attendees with the above structure.
Step 3: Show me the full draft and the complete recipient list. Wait for my
explicit approval.
Step 4: Send only after I approve.
Actions Cowork can take — by category
Email & messaging
- Draft and send emails
- Reply to and forward emails
- Post to Teams channels
- Send Teams direct messages
- Draft messages for your approval
Calendar & scheduling
- Create calendar events
- Add attendees to meetings
- Block focus time
- Reschedule events
- Find free slots across attendees
Documents & files
- Create Word, Excel, PowerPoint
- Generate reports and summaries
- Browse SharePoint and OneDrive
- Read and analyse file content
- Share documents with named users
Research & analysis
- Search across all M365 data
- Read meeting transcripts
- Synthesise from email threads
- Deep Research across enterprise
- Daily and weekly briefings
What it cannot do
- Delete files or folders
- Create Loop pages
- Upload files to Teams
- Access local device files
- Access systems outside M365
- Read encrypted files
- Process files over 200 MB
Plugins (May 2026)
- HubSpot
- Notion
- Miro
- monday.com
- Dynamics 365
- Power BI
- Custom plugins (org-built)
Scheduled prompts & custom skills
The two features that make Cowork a system, not a tool
Scheduled prompts — 5 slots, use them carefully
01
Monday week-start briefing
Calendar, email priorities, and commitments due this week — before the day starts.
Highest priority
02
Weekly commitment tracker
Every "I'll send / I'll follow up" from the last 14 days, sorted by age, flagged if overdue.
High priority
03
Daily inbox priority scan
Top 5 emails needing action today, with a one-line "why this matters" per email.
Medium priority
04
Project status digest
Weekly summary from a specific project's emails, Teams, and calendar — posted to Teams channel.
Medium priority
05
Friday end-of-week digest
What was completed, what is pending, what needs attention Monday.
Optional
How to create a scheduled prompt: Describe the task to Cowork and include a time — "every Monday at 7 AM" or "every Friday at 4 PM." Cowork will propose the schedule and ask you to activate it. Manage existing schedules under Tasks → Scheduled tab. Each scheduled run still requires your approval before Cowork acts.
Custom skills — save a workflow, reuse it without retyping
How skills work
A skill is a saved instruction set — a SKILL.md file stored in your OneDrive. Cowork reads all your skills at the start of every conversation and knows to use them when a matching task comes up.
Limit: Up to 50 skills per user.
Storage path:
/Documents/Cowork/skills/{skill-name}/SKILL.md
Create a subfolder per skill, then create SKILL.md inside it. You can also add up to 20 companion files per skill (templates, reference docs) — stored in the same folder.
Updating a skill: Open the SKILL.md file in OneDrive and edit it directly. Changes take effect at the next conversation. Or ask Cowork to update the skill during a conversation — it will modify the file if you confirm.
SKILL.md format
---
name: Weekly Project Update
description: Posts a structured weekly
update to a Teams channel from
the last 7 days of project emails
and Teams messages.
---
Every Friday at 4 PM, search emails
and Teams from the last 7 days for
[project name].
Draft a Teams post:
- ✅ Done this week
- 🔄 In progress
- 🚫 Blocked (with owner)
- 📅 Next week
Show me the draft. Wait for approval.
Post only after I confirm.
What Cowork can read
Cowork reads from your M365 environment — email, Teams, calendar, files. It does not access systems outside M365, cannot read locally stored files, and cannot retrieve information from the internet.
Outlook email — inbox, sent, search
Outlook calendar — events, availability, invites
Teams channels & chats — read and post
Meeting transcripts — via Teams recording
SharePoint files — documents, folders
OneDrive files — personal and shared
Dynamics 365 — rolling out 2026
Power BI dashboards — coming soon
Local device files — not accessible
Internet / web search — not accessible
SAP · Primavera · external ERP — not accessible (custom plugins can bridge this)
Encrypted files — not readable even with access
The approval model — what Cowork shows you before acting
Low risk
Reading emails, searching Teams, browsing files, drafting content for review — no approval required.
Medium risk
Creating calendar events, creating documents, posting to Teams — shows approval dialog with preview.
High risk
Sending emails, modifying shared files, rescheduling others' meetings — shows approval dialog with prominent risk indicator.
- 01
Every sensitive action shows a full preview before executing. For emails: you see the full draft and recipient list. For calendar events: you see the proposed time and attendees. For Teams posts: you see the full message and the channel.
- 02
Cowork is not fully autonomous. There is no setting that removes approval requirements for sensitive actions. Human-in-the-loop is the design, not a limitation.
- 03
"Don't ask again" applies to the current conversation only. If you click the dropdown on an approval button and select "don't ask again," Cowork skips similar approvals for the rest of that conversation. It does not persist to future conversations.
- 04
You can pause or cancel mid-task at any point. If Cowork is mid-execution, you can interrupt, redirect, or stop it. Actions already approved and taken cannot be undone by Cowork — use normal M365 tools (e.g., Outlook recall) for those.
EU / EFTA / UK tenants — action required before Cowork works
Cowork is built on Anthropic's Claude model, which operates as a Microsoft subprocessor. In EU, EFTA, and UK tenants, Anthropic is disabled by default because data may be processed outside the EU Data Boundary.
To enable: admin.microsoft.com → Copilot → Settings → View All → AI providers operating as Microsoft subprocessors → Anthropic → Enable. This requires an admin to explicitly acknowledge that data will leave the EU Data Boundary. Users cannot enable this themselves — it requires tenant-level admin action.
Failure modes to expect
Cowork searches the wrong time window. Without a time boundary in your prompt, Cowork may pull from too broad a range (months of email instead of the last 7 days). Always state the window explicitly: "from the last 14 days," "since Monday," "from this week's meetings only."
The draft email includes the wrong recipients. Cowork infers recipients from context — which can produce unexpected results if a contact has multiple email addresses or if CC patterns from old threads are picked up. Always review the full recipient list before approving send.
A scheduled prompt fails silently. If a scheduled prompt encounters an error (no transcript found, a Teams channel permission changed), it may produce an empty or partial result without a visible error message. Check the Tasks panel for run history if a scheduled prompt seems to have not executed.
A custom skill is not applied to the task. Skills are matched by description at the start of the conversation. If the skill description is too vague, Cowork may not recognise that it applies. Write skill descriptions as specific outcome statements: "Generates the weekly HSE summary report for a named project from the last 7 days of incident data" rather than "weekly report."
Cowork cannot find the meeting transcript. Transcripts require Teams Meeting Recording to be enabled and the meeting to have ended. If the recording was off, or if the meeting was outside Teams, there is no transcript for Cowork to read. In that case, paste your own notes directly into the prompt.
After this guide
Every guide in this set is free, and stays free. What they do not cover is the rollout itself: the operating model, the 90-day plan with owners and decision gates, the governance checklist, and the ROI case for a finance team that has already said no once.
That is the M365 Copilot Deployment Kit. $97, one payment, no subscription.
See what is in the Deployment Kit →