How to check subcontractor insurance with ChatGPT
What ChatGPT can and cannot tell you from a pasted certificate of insurance, prompts that work, and how a connected compliance app answers across all vendors.
Updated
You can upload a subcontractor's certificate of insurance to ChatGPT and ask it to pull out the policies, dates, limits, and checked boxes, then compare them with your requirements. That is a useful first read of one certificate. A chatbot cannot confirm that an endorsement exists, that a policy is still in force, or remind you when a policy expires, so check its answer against the document.
What ChatGPT can do with a certificate
ChatGPT accepts PDF and image uploads. Given an ACORD 25, it can usually:
- List each policy with its insurer, policy number, and effective and expiration dates.
- Read the general liability, auto, umbrella, and workers' compensation limits.
- Report the Y or N in the ADDL INSD and SUBR WVD columns.
- Quote the description of operations and the certificate holder box.
- Compare those values with requirements you paste in, and list the gaps.
OpenAI notes that on most plans it reads the text in a PDF rather than the page image, and that values in scanned files or image-based tables may not come out reliably. Many certificates are scans, so check every number it gives you.
What it cannot do
| Question | Can a chatbot answer it from the certificate? |
|---|---|
| What limits and dates does the certificate show? | Yes, if the text extracts cleanly |
| Is the insured the company I hired? | Only if you tell it who you hired |
| Does the additional insured endorsement exist and cover my project? | No. The certificate does not show endorsement wording |
| Is the policy in force today? | No. Only the agent or insurer can confirm that |
| Which of my vendors expire next month? | No, unless you upload every certificate each time |
| Did the vendor send the renewal I asked for? | No. It has no record of your vendors |
The ACORD 25 states that it is issued as a matter of information only and does not change the policies. See how to read an ACORD 25 and red flags when reviewing a certificate.
Prompts that help
Give the model your requirements and ask for a structured answer. Vague prompts get vague summaries.
- "Extract every policy on this ACORD 25 into a table: type, insurer letter, policy number, effective date, expiration date, and each limit. Write not shown for anything missing. Do not guess."
- "Here are our subcontract insurance requirements: [paste them]. Compare the certificate with each one and list only the items that fall short, with the value shown."
- "Quote the description of operations exactly. Does it mention additional insured, waiver of subrogation, or primary and non-contributory?"
- "Which policies expire within 60 days of [date]?" Give the date yourself.
- "Write a short email to the vendor's insurance agent asking for a corrected certificate and copies of the endorsements for these gaps."
Connect a compliance app instead of pasting
Those limits come from a chatbot working on one document with no record of your vendors. An MCP app changes that. MCP (Model Context Protocol) is an open standard that lets an assistant call tools in another service. ComplySub runs an MCP server, so once it is connected, ChatGPT or Claude answers from the certificates, requirements, and findings already in your ComplySub account.
Questions you can ask:
- "Which of my vendors have open findings, worst first?"
- "Which certificates expire in the next 30 days?"
- "Why is the plumbing vendor out of compliance?"
- "Show me the compliance picture for the electrician on the Maple Street project."
- "Draft an email asking the roofing vendor for an updated certificate."
Behind those, the assistant calls tools such as list_vendors, get_vendor_compliance, list_expiring, list_findings, and draft_update_request. The draft lists exactly what is missing from the vendor's open findings and sends nothing. A separate send_update_request tool emails the vendor and their agent, and only an owner or admin can use it. Subcontractors can connect too and ask whether their packet is ready and what is missing.
How to connect it
In ChatGPT, a custom MCP app is added through developer mode on the web. Which plans can use it, and whether it can take write actions, depends on your plan and workspace settings, and ChatGPT may ask you to confirm before a tool makes a change. In Claude, you add it as a custom connector. Menus change often, so the current steps for each assistant are on the ComplySub MCP page. Assistant access is part of the Pro and Business plans for general contractors and the Subs Pro plan for subcontractors; see pricing.
The assistant still works from certificate values that software read. It does not see the endorsements either, so ask for endorsement copies on large jobs. See additional insured endorsements.
Check this automatically
ComplySub reads each certificate a vendor uploads through a link, compares it with your requirements, flags gaps and expirations, and reminds the vendor and their agent. You can review the results in the dashboard or ask your assistant. It is not legal or insurance advice.
This guide is general information, not legal or insurance advice. Insurance and licensing rules vary by state, carrier, and contract; confirm what applies to you with your insurance professional, attorney, or licensing board.