TimeSentry
AI time tracking that composes your timesheet for you
TimeSentry delivers on its promise: AI time tracking that composes accurate, billable entries from your actual work. The integration rules (July 2026) and Shared Catalogs (August 2026) are genuinely useful for firms with recurring engagements and multi-party billing standards. But the Professional price at $799/seat/yr is steep for solo practitioners, and there's no monthly billing. Skip it if you need a free or offline option; otherwise, it's a strong contender for law firms and consultancies that value automated time capture.
Verified 8d ago · liveness 56/100 · cite: rightaichoice.com/tools/timesentry
- Law firms billing by the hour who want automated timesheets
- Consulting firms tracking project time and utilization
- Professional services firms with multiple billable staff
- Practices using Clio or MyCase needing bi-directional sync
- Freelancers needing a free or low-cost time tracker
- Enterprise teams requiring offline-first mobile apps
- Non-billable industries like retail or manufacturing
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Skip TimeSentry if you are a freelancer or small team needing a low-cost or free time tracker, prefer manual time entry, or require offline mobile apps—the yearly $799/seat Professional price and cloud-dependent capture won't fit.
The Professional plan is billed yearly only at $799 per seat per year—there's no monthly option, so you must commit a full year upfront.
TimeSentry's pricing fits established firms that bill enough hours to justify $799/seat/yr. Compared to Toggl (from $9/user/mo) or Harvest (from $12/user/mo), it's significantly more expensive, but those tools lack AI drafting, billing, and practice management sync. For solo practitioners, the yearly cost may be prohibitive; cheaper AI-assisted options exist, but they don't offer the same depth.
In short
TimeSentry — AI time tracking that composes your timesheet for you. Best for Law firms billing by the hour who want automated timesheets, Consulting firms tracking project time and utilization, Professional services firms with multiple billable staff. Free to start; paid plans from $799/mo.
What's new in TimeSentry
Checked 8 days agoAcross the latest 2 updates: 2 feature updates.
Your Standards, Everywhere Work Happens — Shared Catalogs
TimeSentry now lets firms share time-entry guidelines and activity categories as catalogs across employees, contractors, and clients. Access revokes automatically when relationships end, and guidelines resolve by specificity and upstream authority.
Not Everything Is Billable — Rules for Your Connected Sources
New integration rules let you filter and automate entries from email, calendar, chat, and phone sources. Options include skip, mark as spam, assign a project, or auto-save/submit entries, with first-match-wins logic and support for multiple conditions and exceptions.
What people actually say about TimeSentry — is it worth it?
We ran a structured research pass across product reviews, community discussions, and post-purchase forum threads to surface the patterns vendors won't publish themselves. Below: the recurring strengths, the hidden costs people mention most, and the cohort that consistently regrets adopting this tool.
- +Automates timesheet creation from emails, calendar, and chat.
- +Integrates with 20+ tools including Clio, QuickBooks, Slack.
- +Rule-based filtering reduces manual time entry.
- +Supports self-hosted LLM for enterprise data security.
- +Customizable project aliases and reporting.
- −No community reviews to validate reliability or support.
- −AI accuracy for billable detection is unsubstantiated.
- −Self-hosted LLM may require heavy IT overhead.
- −New tool with unknown roadmap and stability.
- −Potential over-reliance on integration uptime.
- • Self-hosted LLM may incur infrastructure costs
- • Potential per-seat pricing beyond base tier
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: August 2026
How we score →Key Features
- AI time entry suggestions from email, calendar, chat, phone
- Automatic timesheets composed to the minute
- Rule-based integration filtering (skip, spam, assign, auto-submit)
- Shared Catalogs for billing standards across firms and contractors
- Project aliasing to rename 'projects' to 'matters' or 'cases'
- AI billing assistant for invoices and fee statements
- Analytics on utilization, profitability, end-of-year projections
- 20+ integrations including Gmail, Outlook, Slack, Zoom, Clio
- Drag-and-drop time entry review workflow
- Bi-directional sync with practice management systems
- Self-hosted LLM option for enterprise security
- CASA Tier II audited encryption
- Data export in CSV format
- Team management with billing rates
- Custom integration building via API
About TimeSentry
TimeSentry is an AI time tracking and billing platform for professional services—law firms, agencies, and consultancies. It automatically captures your work from email, calendar, chat, and phone, then uses AI to classify each moment into a clean, editable entry with narrative, matter, and duration. No timers, no forms—just review and approve. Recent updates added rule-based integration rules to skip, mark as spam, assign projects, or auto-submit entries, and Shared Catalogs for distributing billing standards across firms, clients, and contractors. The platform also includes an AI billing assistant that turns approved entries into invoices and fee statements, plus analytics on utilization, profitability, and end-of-year projections. It integrates with 20+ tools, with bi-directional sync for practice management systems like Clio and MyCase. For security, you can self-host the LLM, and the platform is CASA Tier II audited. Data export is available anytime in CSV. Pricing starts with a free Amateur tier, a Professional tier at $799 per seat per year (yearly only, saving 30% vs. monthly), and an Executive tier by invitation. Compared to general trackers like Toggl or Harvest, TimeSentry doesn't just track time—it narrates and bills it.
Behind the Verdict
TimeSentry is built for professionals who bill by the hour and hate admin. Its core value is in the AI drafting of entries from your existing tools—email, calendar, chat, phone—so you never touch a timer. The recent integration rules (July 2026) let you encode recurring patterns: skip promotions, mark internal standups as non-billable, auto-assign client calls to matters, and even auto-save entries you'd approve anyway. This reduces review time dramatically. Shared Catalogs (August 2026) solve a real pain point for firms that must comply with client outside-counsel guidelines or distribute activity codes across contractors and AI agents. The AI billing assistant then turns approved entries into invoices, and analytics track utilization and profitability. Strengths: deep automation, bi-directional sync with practice management systems (Clio, MyCase), enterprise-grade security (CASA Tier II, self-hosted LLM), and a fresh UI that speaks your vocabulary (project aliasing—rename 'projects' to 'matters' or 'cases'). Weaknesses: price is high for solo practitioners ($799/seat/yr, yearly only), the free tier lacks billing and narrative drafting, and AI suggestions depend on connected data sources, so setup requires connecting all your tools and tuning rules. Also, no offline mobile apps—a limitation for field workers. Where it fits: law firms, agencies, consultancies with billable staff. Where it doesn't: freelancers needing a cheap tracker, non-billable industries, teams that prefer manual time entry.
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Real-world workflow fit
Concrete scenarios for the personas TimeSentry actually fits — and what changes day-one when you adopt it.
You connect Gmail, Outlook Calendar, and Zoom. You set up integration rules to skip newsletters and auto-assign your weekly client call to the 'Rivera acquisition' matter. End of day, you review the AI-drafted entries, adjust a few, and approve.
Outcome: Your timesheet is ready in minutes, with accurate narratives and correct matters, saving you over an hour of admin daily.
You use TimeSentry's shared catalogs to push your firm's activity codes to all contractors. When a contractor logs time, their entries automatically use your codes, and your billing standards are enforced.
Outcome: Contractors' time is immediately billable, reducing errors and time spent reconciling timesheets.
You connect Asana and Slack. You set rules to auto-submit entries for projects you manage, and bi-directional sync with QuickBooks sends approved invoices to your accounting system.
Outcome: Invoices are generated and synced without manual data entry, cutting billing cycle time by half.
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.
- Share billing standards with contractors and clients via Shared Catalogs.
Models Under the Hood
as of 2026-08-19
Limitations
- TimeSentry is designed for law firms, agencies, and consultancies.
- Pricing is available in monthly or yearly billing (with yearly saving 30%).
- The free Amateur plan lacks AI narrative drafting and billing features, while the Professional plan costs $799 per seat per year.
- The Executive plan is by invitation and includes bespoke integrations and early access to features.
as of 2026-08-17
Verification history
We have re-verified TimeSentry 5 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.
- — re-verified summary, description, our verdict, our analysis, pricing model, pricing tiers, features, integrations, who it suits, who should skip it
- — re-verified summary, description, our verdict, our analysis, pricing model, pricing tiers, features, integrations, who it suits, who should skip it
- — re-verified summary, description, our verdict, our analysis, pricing model, pricing tiers, features, integrations, who it suits, who should skip it
- — re-verified summary, description, our verdict, our analysis, pricing model, pricing tiers, features, integrations, who it suits, who should skip it
- — re-verified summary, description, our verdict, our analysis, pricing model, pricing tiers, features, integrations, who it suits, who should skip it
Free to cite with attribution — this page re-verifies continuously.
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.
Plans compared
For each published TimeSentry tier: who it actually fits, and what it adds vs. the previous tier. Cross-reference the cost calculator above for projected annual outlay.
Amateur
$0
Ideal for
Solo professionals just starting with time tracking and wanting automatic capture without AI drafting or billing features.
What this tier adds
Free entry point; includes automatic time-keeping, personal timesheets to the minute, and CSV export, but no AI narrative or billing.
Professional
$799/seat/yr
Ideal for
Billable professionals and firms that need AI-drafted narratives, invoicing, and all 20+ integrations, including practice management sync.
What this tier adds
Adds AI narrative drafting, billing/invoicing, all integrations ungated, productivity suite, and time analytics for $799/seat/yr.
Executive
By invitation
Ideal for
Firms needing team management, firm-wide analytics, bespoke integrations, and early access—reserved for high-revenue professional services organizations.
What this tier adds
Adds staffing/team management, firm-wide analytics, bespoke integrations, early feature access, and exclusive event invitations.
Where the pricing makes sense
The company stage and team size where TimeSentry's pricing actually pencils out — and where peers do it cheaper.
TimeSentry's pricing fits established firms that bill enough hours to justify $799/seat/yr. Compared to Toggl (from $9/user/mo) or Harvest (from $12/user/mo), it's significantly more expensive, but those tools lack AI drafting, billing, and practice management sync. For solo practitioners, the yearly cost may be prohibitive; cheaper AI-assisted options exist, but they don't offer the same depth.
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 solo practitioner connecting Gmail, calendar, and phone, you can be capturing time within 15 minutes. For a firm with multiple staff, practice management sync (Clio/MyCase), and custom integration rules, expect 1-2 hours to set up mappings and rules. Executive features require onboarding with the team.
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: Export your time entries as CSV and import them into TimeSentry to maintain continuity, then connect your email and calendar to start automatic capture.
- →From Clio: Use TimeSentry's bi-directional sync to map existing matters and time entries, and enable project aliasing to speak in 'matters'.
- ↗To Toggl or Harvest: Export your time data as CSV from TimeSentry and import into your new tracker; you'll lose AI-drafted narratives and billing features.
- ↗To Clio: Use TimeSentry's bi-directional sync to push time entries to Clio, then continue using Clio's native time tracking if you cancel TimeSentry.
Integrations
Resources & Guides
Tutorials & Learning
Official links
Tools that pair well with TimeSentry
Common stack mates teams adopt alongside TimeSentry, with the specific reason each pairing earns its keep.
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Featured 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.
Timesentry 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.
Timesentry 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.
Alternatives to TimeSentry
View allDataSnipper
Agentic AI platform for audit and finance teams that automates testing and analysis inside Excel.
Glean (CFO AI)
AI-powered AP automation and spend intelligence for accounts payable and finance teams
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