Certificate of insurance tracking that catches expirations before work starts

Certificate of insurance tracking without a spreadsheet nobody updates. On the first Monday of each month Sai reads the certificates your vendors and subcontractors have sent, records each policy’s expiration date and limits in your COI log, compares them with your requirements and drafts a renewal request to every vendor whose certificate expires soon or falls short. You approve the requests before they go out.

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The routine

# Routine: Monthly certificate of insurance check

Schedule: Monthly, on the 1st at 8:30 AM
Runs on: Scout's computer
Ask me before acting: yes
Stop a run after: 1 hour

## Each run
1. Open the COI log (vendor, contact, policy types, limits, expiration dates, additional insured, status) and its Requirements tab.
2. Read any new certificates in the COI inbox and the COI folder since the last run.
3. For each certificate, record the insurer, policy types, limits, effective and expiration dates, and whether we are listed as additional insured.
4. Compare each vendor with the requirements for their type of work. Mark them Current, Expiring in 30 days, Expired or Doesn't meet requirements.
5. Draft a short request to each vendor that needs a new or corrected certificate, saying exactly what is missing.

## Rules
- Ask me before sending any message.
- Record what the certificate says; don't interpret coverage or decide whether a vendor is compliant beyond the Requirements tab.
- If a certificate is unreadable or the dates conflict, flag it instead of guessing.

## Send me
Vendors expired or expiring in 30 days, certificates that fall short and why, and the drafted requests waiting for approval.

What is certificate of insurance tracking?

A certificate of insurance (COI) is a one-page summary, issued by an insurer or broker, showing that a business holds certain policies, with their limits and dates. Certificate of insurance tracking is the ongoing work of collecting COIs from vendors, subcontractors and tenants, recording their expiration dates and limits, checking them against contract requirements and requesting new certificates before old ones lapse.

Contractors, property managers, facilities teams and event organizers do this for every vendor, every month. The check is the same each time, which makes it a routine.

How this routine tracks certificates of insurance

Once a month Sai works through your vendor list:

1. Collect new certificates. Sai reads COIs that arrived in the COI inbox or were saved to the COI folder since the last run.
2. Record the details. Policy types, limits, effective and expiration dates and the additional insured wording go into your COI log.
3. Compare with requirements. Each vendor is checked against the limits and policies required for their type of work.
4. Flag what needs action. Vendors are marked current, expiring within 30 days, expired or not meeting requirements.
5. Draft the requests. Each vendor that needs a new certificate gets a short, specific request, sent after you approve.

What you get every month

The routine records and compares; decisions about coverage and whether work can start stay with you and your insurance advisor.

• An up-to-date COI log with dates and limits for every vendor
• Vendors expired or expiring in the next 30 days
• Certificates that fall short of your requirements, with the reason
• Drafted renewal requests, ready to approve

Ways to track certificates of insurance, compared

Most teams use one of these.

Large portfolios with hundreds of vendors and strict audit needs are better served by dedicated COI tracking software. For teams with a few dozen vendors and an existing log, a routine keeps that log current without a new system.

How often should you check COIs?

Monthly is enough for most vendor lists, with a 30-day warning window so renewals arrive before policies lapse. Also check before a new vendor starts work. If many policies renew on the same date, such as January 1, add an extra run in the weeks before it.

Set up the routine in Sai

1. Copy the routine above and paste it into Sai, or click Start with Sai.
2. Set the schedule to Monthly at 8:30 AM.
3. Keep Ask me before acting on, so you approve every request to a vendor.
4. Share the COI log with a Requirements tab listing the policies and limits for each type of vendor, plus the COI inbox and folder.
5. Run it once and compare the log with a few certificates by hand.

Reading certificates is a document task; the invoice data extraction skill shows the same reading-and-recording approach for invoices, and the AI PDF form filler covers vendor onboarding forms.

Why use a computer use agent for COI tracking?

Certificates arrive as PDFs and scans by email, in slightly different layouts from every broker, and the log usually lives in a spreadsheet. A computer use agent reads each certificate the way an assistant does, writes into the log you already keep and drafts the follow-up, so the tracking happens even when nobody has time for it.

Sai ranks at the top of OSWorld, the open benchmark for computer use. Here that shows up as certificates read completely and conflicts flagged instead of guessed.

Skills this routine uses

• Invoice data extraction: Read invoices from email and vendor portals and log vendor, amount, due date and line items in a sheet, with totals checked.
• AI PDF form filler: Fill out PDF and web forms from your W-9, bank letter and past forms, then stop before anything is signed or sent.
• Excel automation: Clean, merge and update workbooks, refresh a model from new numbers, and build the weekly report in the real Excel app.

Related guides

• AI project manager: Vendors, status and follow-ups
• Routines in Sai: How schedules, approvals and run limits work
• AI chief of staff: Vendor and team admin