Invoice reminders with pay links + trust retainer top-up alerts (Clio, Stripe, LawPay)

The problem

Work that is recorded but never collected is lost revenue. Clio's own benchmarks show how much of the day's billable time is never invoiced or collected.

• Clio's 2025 benchmarks: of about 3.0 hours recorded per 8-hour day, about 2.6 are invoiced and about 2.4 are collected. Source: Clio blog: How to find bottlenecks in your law firm (2025 Legal Trends benchmarks) (Vendor blog citing its own report data; read via search excerpt)
• ABA Model Rule 1.15(c): advance fees go into the client trust account and may be withdrawn only as earned. Your state's version governs. Source: ABA Model Rule 1.15: Safekeeping Property (Model rule text (your state's version governs))
• Connecticut Informal Opinion 2014-02: card processing fees must not be taken from client funds held in trust; the opinion suggests separate merchant accounts for trust and operating. Source: Connecticut Bar Association, Informal Opinion 2014-02 (credit card fees and trust accounts) (State bar ethics opinion; read via search excerpt)
• Clio's LawPay integration ended on August 31, 2026. LawPay still works on its own, but its payments no longer sync into Clio Manage and have to be recorded there by hand. Source: Clio Help Center: Activate Clio Payments (updated Sep 9, 2026) (Vendor help page)
• Clio runs two bill-reminder systems (automated bill reminders, and bill-reminder Workflows that need Clio Payments). Clio's own help warns that with both on, a client can get two reminders for the same bill. Source: Clio Help Center: Send Bill Reminders With Workflows (Vendor help page)

Who it's for

Solo and small US firms on Clio that bill hourly or take retainers and chase payments by hand.

Tools and monthly cost

Example month: Illustrative: 40 open invoices, 3 reminders each = 120 emails (Resend free). LawPay $19 a month for trust deposits. Stripe charges only when a client pays by link: a $1,000 card payment costs $29.30 in Stripe fees, paid from your operating account. Total fixed cost about $19 a month plus n8n; card fees depend on what clients pay.

Setup

1. Create a Clio API app with read access to Bills, Matters, Contacts and Trust (or Bank Accounts) and connect it in an n8n OAuth2 credential.
2. In LawPay, create a payment page that deposits into your trust (IOLTA) account and put its URL in LAWPAY_TRUST_URL. LawPay deposits trust payments in full and takes fees from your operating account; confirm that setting with LawPay. Clio's LawPay integration ended on Aug 31, 2026, so these payments no longer sync to Clio: record each trust deposit in Clio by hand.
3. Prefer trust payments inside Clio? Clio Payments is Clio's built-in option: it handles trust and operating payments and records them on the matter (Clio lists 2.95% for standard cards and 1% for ACH/eCheck). Put a Clio Payments trust payment link in LAWPAY_TRUST_URL instead; the variable is just a URL.
4. In Stripe, create a restricted key that can only write Prices and Payment Links and read Checkout Sessions, and store it in an n8n credential (never in the workflow). Use it only for earned fees paid into operating.
5. Set FIRM_FROM_EMAIL, ATTORNEY_EMAIL and BOOKKEEPER_EMAIL, and adjust the reminder days (default: 7, 14 and 21 days past due, then hand off at 30).
6. Run it once with the schedule off and read the attorney summary before letting it email clients.

Download

Download law-firm-invoice-retainer-reminders.zip

Contains the n8n workflow, the mock data, the test runner with its last results, and the mock server we tested against. All keys in .env.example are fake.

Test result

Every workflow was imported into n8n 2.45.4 and run end to end on our test machine. Clio Manage (API v4), Clio Grow, the email sender (Resend), Outlook (Microsoft Graph), Twilio and Stripe were replaced by a local mock server built from their official API docs: it checks the same request shapes and required fields, enforces Clio's rate limit (HTTP 429) and records every call. These recipes use no AI model; every decision is a written rule you can read. Matters, clients and invoices are invented. Nothing was sent to a real phone, client or account. The billing recipe was also run once against a real Stripe test-mode sandbox (no money moves).

Actual output from the test run

Emails sent in scenario B1 (mock run; payment link is a mock). Names and numbers are invented.

to maria.gonzalez@example.com
Subject: Invoice #1042 from Harbor Point Law - $1,850.00 open

Hi Maria,

This is a friendly reminder that invoice #1042 (00012-Gonzalez) has $1,850.00 open.

You can pay securely by card here: https://buy.stripe.com/test_60c0ec73e8f2

Already paid? Thank you - please ignore this. If you'd like to talk about payment options, just reply.

Harbor Point Law

---

to maria.gonzalez@example.com
Subject: Trust deposit #T-0007 from Harbor Point Law - $2,500.00 open

Hi Maria,

This is a friendly reminder that trust deposit request #T-0007 (00012-Gonzalez) has $2,500.00 open.

Please deposit to our client trust account here: https://secure.lawpay.com/pages/harborpointlaw-example/trust

Already paid? Thank you - please ignore this. If you'd like to talk about payment options, just reply.

Harbor Point Law

---

to dana@harborpointlaw.example, books@harborpointlaw.example
Subject: Billing follow-ups for Tue 27 Oct

- Invoice #1039 - Priya Natarajan - $640.00 open, 31 days past due (0 reminders sent). Automatic emails have stopped; follow up personally.

(Automatic summary from your billing workflow.)