How to send a contract for signature from ChatGPT
ChatGPT can't email a contract for signature on its own, but it can drive an e-signature app that does. With SignMaster connected, you tell ChatGPT who the contract is for, it fills in your template, and SignMaster sends it once you approve. The whole thing takes a couple of minutes after the one-time setup.
Updated November 9, 2026 · 3 min read
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What you need
- A SignMaster account. The Free plan works and includes 3 envelopes a month.
- A ChatGPT plan that lets you add a custom MCP server. Business, Enterprise and Edu workspaces have it, sometimes only after an admin turns it on.
- The contract as a SignMaster template, with the fields already placed. No template yet? See the section below.
Send it in five steps
- 1
Connect SignMaster once
Copy the address from Settings › Connect an AI and add it to ChatGPT as a custom MCP server with OAuth sign-in. The ChatGPT setup page has the details.
- 2
Ask for a draft
In a new chat, pick SignMaster and say who it's for: “Start a draft from my Kitchen remodel template for Ana Torres, ana@example.com, job address 18 Birch Lane, price 14,500.” ChatGPT fills the template's fields that you named and creates a draft. Nothing is emailed yet.
- 3
Check the draft
ChatGPT tells you what it filled in. If you want to see the document itself, open the draft in SignMaster; it's under Drafts on the web and in the app.
- 4
Ask ChatGPT to send it
Say “send it.” ChatGPT can only ask, so SignMaster records a send request listing exactly who gets an email, and ChatGPT tells you it's waiting.
- 5
Approve the send
Open Settings › Connect an AI on the web, or Settings › AI requests in the iPhone app (which also gets a notification), and choose Approve. Requests expire after 15 minutes. Then tell ChatGPT to carry on and it confirms the contract went out.
Why the extra tap?
An assistant can misread a name or pick the wrong template. Holding every email for your approval means a slip in the chat never reaches a customer's inbox.
No template yet?
You have two options. Ask ChatGPT to write the contract and save it to SignMaster as a template: SignMaster lays it out as a PDF with a field on every blank, ready to send. Getting a contract an AI wrote signed walks through it. Or, if the PDF already lives at a public web address, ChatGPT can start a draft from that link; you then place the signature fields in SignMaster before approving the send.
Follow it up from the same chat
- “Has Ana signed the Birch Lane contract?” ChatGPT reads the envelope's status and who's still to sign.
- “Remind her.” Another request for your approval, then a reminder email to whoever's turn it is.
- “Get me the signed copy.” Once everyone has signed, ChatGPT returns a download link to the finished PDF with its certificate.
Questions? Answers.
Can ChatGPT send a contract for signature by itself?
Not by itself. It needs an e-signature service connected to it. With SignMaster, ChatGPT prepares the envelope and asks to send it, and the email goes out only after you approve the request.
Does the person signing need ChatGPT or SignMaster?
No. They get an email with a signing link and sign in their browser on a phone or computer, without an account.
Is a contract sent this way legally binding?
The same as any e-signed contract. Using an AI to prepare and send it doesn't change that under the ESIGN Act and UETA; see can an AI agent sign a contract. What matters is the contract's terms, so read them before you approve.
My ChatGPT plan doesn't show custom MCP servers. What now?
OpenAI decides which plans can add them and has changed it over time. You can do the same thing from Claude, or send from SignMaster directly in a minute or two.