Microsoft's ecosystem, or your whole stack.
Outlook Copilot is Microsoft's most ambitious AI layer yet — cross-app automation within M365, task extraction to Planner, calendar management with rule-based RSVPs. If your team lives entirely inside Microsoft's world, it goes deep. this+that is built for teams whose stack doesn't.
Deep in one ecosystem vs. spanning all of them
Outlook Copilot's bet is that Microsoft has everything your team needs — and increasingly, that's a reasonable bet for enterprise organizations that have standardized on M365. The integration depth within that ecosystem is real. this+that's bet is that most teams aren't entirely in one ecosystem — Gmail and Outlook coexist, Slack runs alongside Teams, GitHub and Notion sit outside Microsoft's control. If your work happens across all of it, you need an agent that can reach all of it.
Feature by feature
How the two products compare across the things that matter most.
| Topic | Outlook Copilot | this+that |
|---|---|---|
| Core philosophy | AI across Microsoft 365. Deep cross-app integration within the Microsoft ecosystem — Outlook, Teams, Planner, Word, Excel, OneNote. | Delegate the work that follows messages. Extract tasks, run workflows, keep teams in sync — across whatever tools your team actually uses. |
| Task extraction | Copilot can extract tasks from email and add them to Microsoft Planner. Works well within M365. | Automatic. DoBox reads every conversation across email, Slack, and Teams and extracts requests, decisions, follow-ups, and deadlines as trackable, assignable tasks. |
| Workflow automation | Copilot Cowork (preview) chains actions across M365 apps. Promising, but still in limited preview — not generally available. | Full workflow builder, generally available. 32 action types. Plain-language creation. IF/ELSE branching, loops, and sub-agents across any connected tool. |
| Ecosystem dependency | Microsoft-only. If team members use Gmail, Slack, GitHub, or non-M365 tools, Copilot cannot reach them. | Provider-agnostic. Gmail and Outlook, Slack and Teams, Google Calendar and Outlook Calendar — all treated as one stream of incoming work. |
| Email provider support | Outlook only. | Gmail and Outlook. |
| Channels | Outlook email and Microsoft Teams. No Gmail or Slack. | Gmail, Outlook, Slack, Teams, Google Calendar, Outlook Calendar. |
| Calendar management | Rule-based RSVPs, scheduling suggestions, meeting preparation summaries from Outlook Calendar. | Calendar automation as workflow steps: RSVP, create events, reschedule, manage attendees across Google and Outlook Calendar. |
| External integrations | M365 apps. Copilot Studio supports custom connectors but requires developer configuration. | Open MCP standard. GitHub, Notion, Jira, Dropbox, HubSpot, and any tool with an API — no developer work required. |
| Pricing | $18–30/user/month for the AI layer alone, on top of existing M365 licenses. Can reach $50+/user/month combined. | Separate subscription. Free tier available. |
| Availability | Core features GA. Copilot Cowork (the agentic automation piece) still in limited preview. | All features generally available. |
| AI drafts | Draft with Copilot is strong — full message drafts, tone adjustments, meeting follow-up emails generated automatically. | AI draft replies and emails as workflow actions. Useful in automation context; not optimized as a standalone composition experience. |
- Deepest cross-app integration in the Microsoft ecosystem — Planner, Teams, Word, Excel, OneNote, and Outlook all connected.
- Task extraction to Planner works well for teams already using M365 project management.
- Copilot Cowork preview is the closest Big Tech has come to genuinely agentic workflow automation.
- Calendar management with rule-based RSVPs and automated meeting preparation is mature and polished.
- Draft with Copilot produces high-quality email drafts, including context from the broader conversation thread.
- For organizations that have standardized on M365, there is nothing to add — it is already in the tools.
- Works across the entire stack — Gmail AND Outlook, Slack AND Teams, Google Calendar AND Outlook Calendar.
- Task extraction from email, Slack, and Teams simultaneously — not just from Outlook.
- Full workflow automation is generally available now, not in preview.
- Open MCP: connect GitHub, Jira, Notion, Dropbox, or any tool with an API — no Microsoft dependency.
- Per-user pricing is not layered on top of existing licenses.
- Teams that are not fully standardized on M365 can still get agentic automation without switching ecosystems.
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