Automatic Time Capture from Microsoft 365 and Outlook
For most professional-services firms, a large share of billable work happens inside Microsoft 365. Client advice goes out as Outlook email. Matters are discussed in Teams meetings. Deadlines and calls sit in the calendar. Yet this is exactly the work that is hardest to bill accurately, because it is fragmented into dozens of small actions across the day — and none of them starts a timer.
This guide explains how to capture that time automatically from Microsoft 365, what a cloud connector sees that a desktop-activity logger does not, and how the captured activity becomes review-ready time entries.
Why Microsoft 365 time is the time firms lose
The billable work that flows through Microsoft 365 shares an awkward property: each action is short, and there are many of them. A two-minute reply to a client, a fifteen-minute Teams call, a calendar-blocked review — individually small, collectively a large part of the day.
Reconstructed from memory at 6 p.m., much of it simply disappears. You remember the long meeting; you forget the six emails around it. That gap is where billable time leaks, and it is the specific problem passive capture is meant to solve. We cover the mechanics in Why Law Firms Lose Billable Hours.
The goal, then, is to record this activity as it happens, with enough context to turn it into a defensible time entry — and to do it without asking anyone to start a timer.
Two ways to capture Microsoft 365 activity
There are two broad approaches, and the difference matters for billing quality.
Desktop-activity logging
A desktop agent watches which applications and windows are in focus. It can tell that Outlook was the active window for forty minutes. What it generally cannot tell you is which email, to whom, or about which matter — because it sees the application, not the content and metadata inside it.
For loose project billing that may be enough. For matter-based legal or accounting billing, "Outlook was open for 40 minutes" is not a billable line.
Cloud-connector capture
A cloud connector authenticates to Microsoft 365 through Microsoft's own APIs and reads the metadata of the work itself: an email's subject and recipient domain, a meeting's attendees and duration, a calendar event's title. That is far richer context, and it is captured from the source system rather than inferred from a window title.
Timentry uses this approach. Its cloud connectors for Microsoft 365, Google Workspace, Zoom, and telephony providers capture email, meeting, and call activity with the context needed to attribute and describe it — alongside a lightweight desktop agent for the work that happens outside those systems. Integration credentials are encrypted, and the connection supports SSO.
What automatic Microsoft 365 capture looks like in practice
Once a firm connects Microsoft 365, the flow removes the manual steps rather than adding them:
- Connect once. An administrator authorises the Microsoft 365 connection through Microsoft's consent flow. Credentials are stored encrypted; there is no password sharing.
- Activity is captured passively. Emails sent and received, Teams and other meetings, and calendar events are captured as they happen, with their metadata — no timer to start, no app to open.
- Attribution happens automatically. Timentry's deterministic attribution engine matches each item to the right matter using matter numbers, sender domains, and attendee names, with AI used only as a fallback where the rules can't resolve it. Most activity arrives pre-sorted to a matter.
- Narratives are drafted for you. The AI activity-clustering layer turns a matter's captured activity into a draft narrative time entry — a specific, review-ready description rather than a blank field.
- You review and approve. Every entry passes through a review and approval step with real-time updates. Nothing is submitted automatically; you stay the author of record.
Before entries leave the firm, Timentry also checks them against configured billing rules — outside-counsel guidelines, prohibited task codes, and increments — so predictable e-billing rejections are caught first. See Outside-Counsel Guidelines and E-Billing Rejections for why that check matters.
Privacy and control
Capturing activity from a firm's email and calendar raises a fair question about privacy, and it should. Timentry provides granular privacy controls, on-device filtering, and data-rights tooling for GDPR, so firms can decide what is captured and give individuals control over their own data. The aim is to capture billable context, not to surveil people — and the controls are there to keep that line clear.
This article describes Timentry's approach to Microsoft 365 capture for general information. Exact setup steps and available controls may change; check the current documentation or ask the team about your firm's configuration.
Getting started
If a large part of your billable day runs through Outlook, Teams, and the Microsoft 365 calendar, capturing it automatically is the single biggest step toward a timesheet that reflects the work you actually did. See how Timentry works, review the features, or talk to the team about connecting Microsoft 365 for your firm.