TimeSentry is live · free plan, paid from $799/seat/yr · last verified 23 Oct 2026 · viability monitor
TimeSentry
AI time tracking that composes billable timesheets, invoices, and reports from the calls, mail, and documents you already handle.
If your firm bills hourly and leaks real money to unrecorded admin time, TimeSentry attacks a genuine problem, and the 2026 releases — Shared Catalogs, Integration Rules, Attio, Bill.com, vacation coverage — show it's built for multi-person firms, not solo users. The catch is the entry point: Amateur captures your day but withholds narrative AI and billing, and Professional runs $799 per seat per year, yearly billing only. Executive is invitation-only, so staffing and firm-wide analytics can't
Verdict generatedVerified 7d ago · liveness 68/100 · cite: rightaichoice.com/tools/timesentry
- Law firms billing by the hour that want timesheets composed instead of typed
- Consultancies and agencies tracking project time and utilization across staff
- Practices on Clio or MyCase that need bi-directional time sync
- Firms standardizing activity codes and billing guidelines across employees, contractors, and AI agents
- Freelancers wanting a free or low-cost time tracker — narrative AI and billing start at Professional
- Teams that want to keep entering time by hand without reviewing AI suggestions
- Non-billable operations like retail or manufacturing where hourly recovery isn't the metric
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Skip TimeSentry if you bill under a handful of hours a week or won't review AI-drafted entries before they hit a client invoice.
Professional is billed yearly per seat at $799, so a five-person practice commits roughly $4,000 up front rather than paying month to month.
At $799 per seat per year billed yearly, Professional sits above general trackers like Toggl or Harvest, which start near $10–$20 per user per month, and roughly level with practice-management suites such as Clio that bundle timekeeping with matter management. It fits a firm billing enough hourly work that recovering a few unrecorded hours a month pays the seat back; it does not fit small or non-billable teams.
In short
TimeSentry — AI time tracking that composes billable timesheets, invoices, and reports from the calls, mail, and documents you already handle. Best for Law firms billing by the hour that want timesheets composed instead of typed, Consultancies and agencies tracking project time and utilization across staff, Practices on Clio or MyCase that need bi-directional time sync. Free to start; paid plans from $799/seat/yr.
What is TimeSentry?
TimeSentry — AI time tracking that composes billable timesheets, invoices, and reports from the calls, mail, and documents you already handle. Best for Law firms billing by the hour that want timesheets composed instead of typed, Consultancies and agencies tracking project time and utilization across staff, Practices on Clio or MyCase that need bi-directional time sync. Free to start; paid plans from $799/seat/yr.
TimeSentry is AI time tracking built for firms that bill by the hour — law practices, agencies, and consultancies where every unrecorded minute is revenue gone. Instead of a start/stop timer, it watches the work already happening across your calls, mail, documents, and meetings, then classifies each moment by what it was, who it was for, and whether it's billable. The result lands as an editable entry with narrative, matter code, and duration to the minute, so you review and approve rather than rebuild your day from memory. Four stages carry the instrument: capture across connected sources, classification by frontier intelligence, crystallization into matter-coded entries, and billing. The AI Billing Assistant converts approved entries into invoices and fee statements, and the analytics layer reports utilization, profitability, and end-of-year projections for partner or committee review. Firm-wide tooling has shipped through 2026 — Shared Catalogs push activity codes and billing guidelines to employees, contractors, and AI agents with inheritance and revocation, while Integration Rules let you skip, mark as spam, assign a project, or auto-submit entries from email, calendar, chat, and phone lines on first-match-wins logic. The September 2026 releases widen the back office. The Attio CRM integration maps companies to clients, people to contacts, and deals or pipeline lists to projects — Attio stays the source of truth and TimeSentry never writes back. Bill.com sync sends invoices with the PDF attached and tracks status from sent to scheduled to paid as BILL clears payment. A Vacations tab under Staffing records time off and overlays it on coverage views, role budgets, and the staffing timeline. Security targets regulated work: CASA Tier II audited encryption in transit and at rest, a self-hosted LLM option, CSV export, and no data resale. The free Amateur tier covers automatic capture and personal timesheets, but narrative AI and the billing rails start at
Key features
- Automatic time capture from email, calendar, chat, and phone
- AI drafts a narrative for every time entry
- Classifies each moment as billable or non-billable
- Composes matter-coded entries with narrative and duration to the minute
- Integration Rules: skip, mark as spam, assign project, or auto-submit on first-match-wins logic
- Shared Catalogs distribute activity codes and guidelines with inheritance and revocation
- AI Billing Assistant turns approved entries into invoices and fee statements
- Analytics for utilization, profitability, and end-of-year projections
- Document tracking alongside time entries
- Project aliasing to rename projects as matters or cases
- Staffing tab with vacation and time-off overlay for coverage planning
- Bi-directional sync with practice management systems like Clio and MyCase
- Attio CRM integration mapping companies to clients and deals to projects
- Bill.com invoice sync with automatic sent/scheduled/paid status
- Self-hosted LLM option for enterprise security
Behind the verdict
Most time-tracking tools ask you to become the sensor. TimeSentry flips that — it reads the day's calls, mail, documents, and meetings and hands you pre-drafted entries to approve. For a lawyer who loses 30 minutes a day to timer babysitting, that reversal is the whole product. Pick it when your revenue is hourly and your problem is recovery, not tracking. Firms already on Clio or MyCase get bi-directional time sync; the Attio mapping means a deal in your CRM becomes a project without manual setup, and Bill.com closes the loop from invoice sent to paid. The Integration Rules layer is underrated — skip, spam, assign, auto-submit on first match — because it's how you keep AI-drafted entries clean at scale instead of drowning in review. Pass if you're a freelancer hunting a cheap tracker. Amateur is free and captures your day, but narrative AI and the billing rails sit behind Professional at $799 per seat per year, and billing is annual — there's no monthly escape hatch at that tier. Executive, where staffing, team management, and firm-wide analytics live, is by invitation, so you can't self-serve into it. Two caveats worth naming. Professional is priced per seat per year, so a twenty-person firm is a real line item — model the recovered time before you sign. And CRM integration is read-only by design: Attio stays the source of truth and TimeSentry never writes back, which is fine until you want pipeline updates to flow the other way. Closest alternative depends on what you're missing. If you want timekeeping bolted to your practice management, Clio's native tools are already in your stack. If you want a horizontal tracker at a fraction of the cost, Harvest. TimeSentry earns its price only when recovered billables clear the seat fee — which, for most hourly firms,
Limitations
- TimeSentry is positioned for professional services — law practices, agencies, and consultancies — not consumers.
- The free Amateur plan captures time automatically but explicitly leaves narrative AI and the billing rails to the Professional tier.
- Professional is priced per seat at $799 per seat per year, billed yearly (the site advertises yearly as saving 30% versus monthly).
- The Executive tier is invitation-only, so staffing, firm-wide analytics, and bespoke integrations are not openly purchasable.
- TimeSentry admits new firms by invitation, so onboarding starts with a request rather than a self-serve account.
as of 2026-10-03
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Is TimeSentry still active?
TimeSentry is live · free plan, paid from $799/seat/yr · last verified 23 Oct 2026 · viability monitor.
Viability score
How well maintained and how widely used is TimeSentry? Built from what the vendor actually publishes (docs, changelog, tutorials, integrations, pricing), whether the site is live, and how much real users discuss it. How we calculate this
Last calculated: October 2026
How we score →What's new in TimeSentry
Checked 9 days agoAcross the latest 3 updates: 3 feature updates.
Your CRM Already Knows Who You Work For — Attio
Attio CRM integration maps companies to clients, people to contacts, and deals or pipeline lists to projects. Connect with one click or an API key; Attio stays the source of truth and TimeSentry never writes back.
One Invoice, Both Sides of the Table — Bill.com
Invoices can be sent through Bill.com with the PDF attached, moving from sent to scheduled to paid automatically as BILL clears payment, and round-tripped contractor bills avoid duplicate vendor creation in QuickBooks.
Staffed, but Away — Vacation Planning for Coverage
A Vacations tab under Staffing records time off and shows it as a hatched overlay on coverage views, role budgets, and the staffing timeline, so a filled-but-absent seat is visible weeks ahead.
What do users say about TimeSentry?
How we verified this
Every listed fact about TimeSentry— pricing, features, links, status — is re-read from the vendor's own pages by our verification pipeline and each change is logged with a date; the last pass ran on 23 Oct 2026. Pages mix model-assisted synthesis with human review; see how we verify.
Verification history
We have re-verified TimeSentry 11 times since . Each pass re-reads the vendor's own pages and re-checks every listed field against that evidence; passes where nothing had changed are marked as such.
- — changed pricing page
- — changed pricing tiers, who should skip it, our verdict, who it suits, description, summary, SSL certificate
- — changed who should skip it, setup time, hidden costs, pricing fit, integrations, limitations, switching in, switching out, use cases, summary, our verdict, description, features
- — changed limitations, pricing page
- — changed pricing tiers, who it suits, description, our verdict, features, who should skip it, summary
- — changed domain expiry
Showing the 6 most recent of 11 verification passes.
Free to cite with attribution — this page re-verifies continuously.
How much does TimeSentry cost in 2026?
TimeSentry: Free to start; paid plans from $799/seat/yr. Pricing last verified 23 Oct 2026.
Plans compared
Every published TimeSentry tier, its price as the vendor publishes it, who it fits, and what it adds over the tier below. The 12-month cost projection follows.
| Plan | Price | Billing | Who it's for |
|---|---|---|---|
| Amateur | Free | — | A professional testing automatic capture on their own time before committing a firm, or a small practice wanting personal timesheets to the minute.Adds: Starting tier and free entry point: automatic capture from connected sources, personal timesheets to the minute, and CSV export — narrative AI and billing rails are not included. |
| Professional | $799/seat/yr | yearly, per seat | A billable practice of one or several people that needs AI-drafted narratives and invoices, priced at $799 per seat per year billed yearly.Adds: Adds AI-drafted narratives on every entry, billing, invoicing, and money movement, all 20+ integrations ungated, the individual productivity suite, and time analytics. |
| Executive | By invitation | — | Multi-partner firms and larger agencies that need staffing, firm-wide analytics, and custom connections, admitted by invitation.Adds: Adds staffing and team management, firm-wide analytics, bespoke integrations, early access to features before launch, and invitations to exclusive events. |
12-month cost
Project the real annual outlay, including the implied monthly cost when only an annual tier is published.
Vendor list price only. Add-on usage, seat overages, and contract minimums are surfaced under Hidden costs & gotchas.
Where the pricing makes sense
The company stage and team size where TimeSentry's pricing actually pencils out — and where peers do it cheaper.
At $799 per seat per year billed yearly, Professional sits above general trackers like Toggl or Harvest, which start near $10–$20 per user per month, and roughly level with practice-management suites such as Clio that bundle timekeeping with matter management. It fits a firm billing enough hourly work that recovering a few unrecorded hours a month pays the seat back; it does not fit small or non-billable teams.
Has TimeSentry's pricing changed?
No plan price for TimeSentry has moved since we began logging in Aug 2026; the pricing page is re-read on every verification pass.
Who should pick TimeSentry?
Pick TimeSentry if you are Law firms billing by the hour that want timesheets composed instead of typed, Consultancies and agencies tracking project time and utilization across staff, Practices on Clio or MyCase that need bi-directional time sync, Firms standardizing activity codes and billing guidelines across employees, contractors, and AI agents.
Look elsewhere if you are Freelancers wanting a free or low-cost time tracker — narrative AI and billing start at Professional, Teams that want to keep entering time by hand without reviewing AI suggestions, Non-billable operations like retail or manufacturing where hourly recovery isn't the metric, Buyers who won't commit to annual billing, since Professional is priced yearly per seat.
Skip it if Skip TimeSentry if you bill under a handful of hours a week or won't review AI-drafted entries before they hit a client invoice.
GeneratedReal-world workflow fit
Concrete scenarios for the personas TimeSentry actually fits — and what changes day-one when you adopt it.
Connect Gmail, Google Calendar, and the firm's phone line, set an Integration Rule to skip internal meetings, and let TimeSentry draft entries against each matter while the day runs.
Outcome: End of day, the partner reviews narrative-drafted entries with matter and duration already filled in, approves them, and the Billing Assistant turns the batch into a client invoice.
Connect Attio so companies map to clients and a pipeline list maps to projects, then let won deals create the project with the right contacts attached before anyone logs time.
Outcome: New retainers appear in TimeSentry fully staffed and coded, so the first timesheet against the account is accurate without manual client setup.
Connect the firm's Bill.com account, map each client to a Bill.com customer, and use Sync to Bill.com on outgoing invoices while contractor invoices land in the payables tab.
Outcome: Invoices move from sent to scheduled to paid automatically, and a round-tripped contractor bill links back to the same record instead of creating a duplicate vendor in QuickBooks.
Use cases
- Automatically generate daily timesheets from email and calendar activity.
- Send invoices to clients based on approved time entries with a single click.
- Set up integration rules to skip internal meetings and auto-file recurring client calls.
- Map TimeSentry terminology to your firm's vocabulary (projects, matters, or cases).
- Monitor team utilization and profitability through analytics dashboards.
- Sync time entries bi-directionally with Clio or MyCase for unified practice management.
- Map Attio companies to clients and deals to projects so a won deal becomes a live project before any time is logged.
- Send invoices through Bill.com with the PDF attached and track payment status back in TimeSentry.
Setup time & first value
How long it actually takes to get something useful out of TimeSentry — broken out by persona, not the marketing-page minute.
For a Clio or MyCase practice already comfortable with integrations, expect a few days: connect mail, calendar, chat, and phone sources, write Integration Rules, and load Shared Catalogs for staff. Solo users can see captured time within the first day on Amateur, but narrative billing value only starts after upgrading and completing that integration pass.
Switching to or from TimeSentry
How to bring data in from common predecessors and how to get it back out — written for the switcher, not the buyer.
- →From Toggl or Harvest: connect your mail, calendar, and chat sources and let capture replace manual timers; Import clients as matters during setup.
- →From Clio or MyCase timekeeping: enable bi-directional sync so approved TimeSentry entries flow into the practice management system rather than being re-keyed.
- →From spreadsheets: use Shared Catalogs to load your activity codes and billing guidelines once, then push them to employees and contractors.
- →From Attio-based client lists: connect Attio so companies become clients and deals or pipeline lists become projects without a manual rebuild.
- ↗To Clio or MyCase: bi-directional sync keeps entries in the practice management system, and CSV export captures everything else.
- ↗To a general tracker like Toggl or Harvest: export a full CSV of your time at any time before you stop the subscription.
- ↗To in-house or spreadsheet billing: the CSV export gives you entries with narrative, matter, and duration for re-import.
Integrations
Resources & guides
Tutorials & Learning
YouTube returned 6 videos for “TimeSentry”, and we withheld 6: 6 could not be judged, because “TimeSentry” is a single word that other videos use for other things. We are showing none, because we could not prove any of them are about TimeSentry.
Official links
What are the best TimeSentry alternatives?
The closest alternatives to TimeSentry we list are Receiptor AI, Tailride and Stockline. Ranked by direct product-type match, not category overlap.
| Alternative | Pricing | Starts at | Last verified |
|---|---|---|---|
| Receiptor AI | Paid | Pricing not published | — |
| Tailride | Freemium | Pricing not published | — |
| Stockline | Contact Sales | Custom pricing | — |
Alternatives to TimeSentry
View all
Receiptor AI
Receiptor AI captures receipts and invoices from email, WhatsApp and iMessage and files them into Xero or QuickBooks.
Tools that pair well with TimeSentry
Common stack mates teams adopt alongside TimeSentry, with the specific reason each pairing earns its keep.
Receiptor AI
Receiptor AI captures receipts and invoices from email, WhatsApp and iMessage and files them into Xero or QuickBooks.
Tailride
Tailride captures invoices directly from your Gmail, Outlook or IMAP inbox — no forwarding address required.
Stockline
AI order entry for food wholesalers — turns WhatsApp, email, SMS and calls into clean ERP lines.
TimeSentry vs its closest rival
TimeSentry's closest head-to-head is with Transfix — TimeSentry and Transfix are purpose-built for entirely different verticals. Choose TimeSentry if you run a law or consulting firm and want AI to auto-capture billable hours from your email, calendar, and calls — recent integration rules make filtering even smarter. Choose Transfix if you're a freight broker needing AI-powered pricing models with private data, now enhanced with accounting and exception management. There's no overlap; your industry decides. Verdict generated
Head-to-head comparisons
Timesentry vs Transfix
TimeSentry and Transfix are purpose-built for entirely different verticals. Choose TimeSentry if you run a law or consulting firm and want AI to auto-capture billable hours from your email, calendar, and calls — recent integration rules make filtering even smarter. Choose Transfix if you're a freight broker needing AI-powered pricing models with private data, now enhanced with accounting and exception management. There's no overlap; your industry decides.
GeneratedTimesentry vs Cryptohopper
TimeSentry and Cryptohopper serve entirely different domains: TimeSentry is purpose-built for professional services firms automating time tracking and billing, while Cryptohopper is a cloud crypto trading bot for automating trades. Choose TimeSentry if you bill by the hour and want to reduce manual entry; choose Cryptohopper if you trade cryptocurrencies and want algorithmic strategies or copy trading. They are not competitors but sector-specific tools.
GeneratedTimesentry vs Bitsgap
TimeSentry and Bitsgap serve completely different domains, so the choice depends entirely on your profession. If you're a lawyer or consultant needing to automate timesheets and billing, TimeSentry is the clear winner with deep integrations and AI that understands practice terminology. If you're a crypto trader wanting automated bots across exchanges, Bitsgap offers a robust freemium platform with advanced strategies like grid and DCA, but lacks TimeSentry's compliance-focused features.
GeneratedFrequently asked questions
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Best-of guides
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