AI assistants went from drafting email to sending it in about two years. This page lists, by date, the launches that let an agent send email, the platform rules and laws that apply to that email, and the rulings that say who answers for it. Every entry links to the company's, regulator's or court's own text.
We update this page as things change, and the date at the top shows the last update. Entries are newest first. The last check of every link was October 7, 2026.
Short version. By October 2026, ChatGPT, Claude, Gemini, Copilot and Grok could all send email from a connected Gmail or Outlook account, and AgentMail, Nylas and Microsoft offered agents mailboxes of their own. The EU's disclosure duty for AI that interacts with people has applied since August 2, 2026, and the European Commission says agents should disclose both that they are AI and on whose behalf they act. Courts keep reaching the same answer: what your software says or does is treated as yours.
2026
- September 30, 2026: Grok Bot can send without a draft. Version 0.64.0 of Grok Bot added "Disable drafts for this Bot, so that Bot sends messages directly", for both email and Slack. Bots send from the Gmail or Outlook account you connect. Grok Bot changelog. What it means for your signature: Grok Bot email.
- September 26, 2026: Grok Bot sends from Outlook. Version 0.60.0: "review a Bot's new email in chat, then choose Send email to send it from your Outlook account." Grok Bot changelog
- September 9, 2026: Gemini sends email from any Workspace app. Google announced that Gemini can "Compose detailed emails based on meeting notes or active documents, open as a draft in Gmail or send it directly from the Workspace app you are in", with a preview card to review and confirm first. Rollout began September 2. Google Workspace Updates
- August 22, 2026: AgentMail gives Grok Bots their own addresses. AgentMail, an independent company, published a plugin for the Grok Bot plugin browser that gives each Bot an address at
agentmail.to. AgentMail says the listing "is the extent of the xAI relationship." AgentMail - August 11, 2026: Grok Bot launches. xAI's always-on agents "sign into the tools you already use and work across apps, inboxes, and more." SpaceXAI
- August 4, 2026: Amazon v. Perplexity. The Ninth Circuit vacated a preliminary injunction against Perplexity's Comet browser agent under the Computer Fraud and Abuse Act, holding that the user, not Perplexity, accessed Amazon: "However advanced the Assistant currently is, it is a tool, not a person for statutory purposes." The court stressed that it was not setting "a new legal regime governing agentic AI." Opinion, No. 26-1444
- August 2, 2026: EU AI Act Article 50 applies. Providers of AI systems that interact directly with people must make sure those people are told they are dealing with an AI, unless it is obvious. Regulation (EU) 2024/1689, Articles 50 and 113. For email: EU AI Act Article 50 and email.
- July 27, 2026: The Digital Omnibus on AI takes effect. Regulation (EU) 2026/1744, published July 24, gives AI systems already on the market before August 2, 2026 until December 2, 2026 to comply with the Article 50(2) machine-readable marking duty. The duty to tell people they are dealing with an AI keeps its August 2 date. EUR-Lex
- July 21, 2026: Grok for Outlook. An Outlook add-in that summarizes threads and drafts replies inside Outlook's compose window. SpaceXAI
- July 20, 2026: The Commission's Article 50 guidelines name AI agents. The guidelines (C(2026) 5054) say agents that interact with people while "managing correspondence" are covered, and "must be designed and developed in such a way that they disclose both their artificial nature and the person on whose behalf they are acting." Their example of a visual disclosure is "an email generated by an AI agent sent to a natural person that features an AI label at the top." European Commission. How to word it: AI email disclosure.
- July 16, 2026: Grok Automations. Jobs that run on a schedule or when a matching email arrives: "Email triggers watch your inbox instead." SpaceXAI
- July 7, 2026: Claude sends Outlook email. Anthropic added write tools to Claude's Microsoft 365 connector, so Claude can "draft, send, and organize email". As of October 7, 2026, Claude's help center also lists sending, replying and forwarding from Gmail, with approval before each send by default. Claude release notes, Google Workspace connectors
- June 17, 2026: Nylas Agent Accounts become generally available. An AI agent gets a hosted email address and calendar from one API call. Nylas. Signatures for them: Nylas agent email signature.
- June 10, 2026: EU Code of Practice on marking and labelling AI content. A voluntary code to help providers and deployers meet the Article 50 transparency duties. European Commission
- June 2026: ChatGPT sends email from a chat. "If you've connected Gmail or Outlook, you can now ask ChatGPT to draft and send emails directly from the same conversation." Web only, on Plus, Pro, Business and Enterprise. ChatGPT release notes
- May 19, 2026: Gemini Spark. Google's 24/7 agent is "designed to ask you first before performing high-stakes actions like spending money or sending emails." Google
- May 14, 2026: Colorado replaces its AI Act. SB 26-189 repeals and re-enacts the 2024 Colorado AI Act as rules on automated decision-making technology in consequential decisions, with obligations starting January 1, 2027. It covers consequential decisions such as hiring and lending. Colorado General Assembly
- May 6, 2026: Grok Connectors. Grok's Outlook connector "can draft and send emails". SpaceXAI
- March 16, 2026: Agentforce Sales prospecting agent. Salesforce's agent "handles high-volume research and initial outreach". Salesforce
- March 10, 2026: AgentMail raises a $6M seed round to build "email inboxes for AI agents", led by General Catalyst. AgentMail. Signatures for them: AgentMail email signature.
- March 9, 2026: Copilot sends email from chat. Microsoft said "send email from chat is rolling out with broad availability this spring" and that Agent 365 would be generally available on May 1. In Microsoft's Frontier preview, an agent can also get its own user account that "can hold licenses and Microsoft 365 resources such as a mailbox." Microsoft 365 Blog, Agent 365 identity
2025
- December 3, 2025: Google Workspace Studio. General availability of a place for anyone in a company to build AI agents for everyday Workspace work, email included. Google Workspace Blog
- November 2025: Gmail tightens enforcement. "Starting November 2025, Gmail is ramping up its enforcement on non-compliant traffic." Agents that send at volume from their own domains have to meet the same sender rules as anyone else. Gmail Help
- September 15, 2025: Anthropic's usage policy covers agents. "All consumer-facing chatbots, including any external-facing or interactive AI agent, must disclose to users that they are interacting with AI rather than a human." Anthropic Usage Policy
- July 17, 2025: ChatGPT agent. OpenAI's agent did tasks "using its own computer". OpenAI has since marked the launch post outdated. OpenAI
- May 7, 2025: Utah's AI disclosure amendments take effect. SB 226 requires a business using generative AI in a consumer transaction to disclose it when a person clearly asks, and requires up-front disclosure in high-risk interactions in regulated occupations. Utah Legislature, SB 226
- April 2, 2025: Outlook.com sets rules for high-volume senders. Domains sending over 5,000 emails a day to Outlook.com, Hotmail and Live addresses must pass SPF and DKIM and publish DMARC. Microsoft Community Hub
- January 14, 2025: The FTC's DoNotPay order specifies a signature line. The final order against the "robot lawyer" company requires a notice email to customers "from an authorized DoNotPay, Inc. email address" that must "contain a signature line that refers to DoNotPay, Inc., with the sender's full contact information." FTC decision and order
2024
- September 25, 2024: FTC Operation AI Comply. Five actions against deceptive AI claims; Chair Lina Khan said "there is no AI exemption from the laws on the books." FTC
- September 12, 2024: Salesforce unveils Agentforce, autonomous agents for service, sales and marketing, including qualifying sales leads. Salesforce
- July 12, 2024: The EU AI Act is published. Regulation (EU) 2024/1689 appears in the Official Journal, with Article 50 set to apply from August 2, 2026. EUR-Lex
- April 1, 2024: The FTC's impersonation rule takes effect. It bars falsely posing as a business or government agency, including through email. FTC
- February 14, 2024: Moffatt v. Air Canada. A British Columbia tribunal held Air Canada liable for its website chatbot's wrong answer and rejected the idea that the chatbot was "a separate legal entity that is responsible for its own actions", calling it "a remarkable submission." 2024 BCCRT 149
- February 2024: Gmail and Yahoo sender requirements. Senders of 5,000 or more messages a day to Gmail must authenticate their email, avoid unwanted mail and make unsubscribing easy; Yahoo set matching rules for bulk senders. Gmail Help, Yahoo Sender Hub
Current as of October 7, 2026
Some facts that matter for agent email have no launch date. These are true on the vendor's own pages as of October 7, 2026:
- Gmail's signature is a compose-window feature. Google describes it as "included in messages composed with this alias in the Gmail web UI", so mail an agent sends through the Gmail API carries no signature unless the agent adds one. Gmail API reference. Why this happens: AI agent email with no signature.
- n8n stamps its own line. n8n's Gmail and Send Email nodes append "This email was sent automatically with n8n" unless you turn the option off. n8n Docs. How to replace it: remove "sent automatically with n8n".
- HubSpot's Prospecting Agent can send unreviewed. HubSpot says you "can switch to fully autonomous mode, which sends emails without requiring review first." HubSpot
Before 2024: the email signature rulings agents inherit
The rules on who an email binds were settled before AI agents existed, and they apply to whatever sends in your name:
- 1999 and 2000, US. The Uniform Electronic Transactions Act lets "electronic agents" form contracts, and the federal E-SIGN Act says a contract cannot be denied effect just because an electronic agent was involved, "so long as the action of any such electronic agent is legally attributable to the person to be bound." 15 U.S.C. 7001(h)
- 2006, England. J Pereira Fernandes v Mehta: an email address added automatically to a header was not a signature, while a typed name would have been. EWHC 813 (Ch)
- 2008, New York. Stevens v Publicis: a name typed at the end of an email made it a signed writing. 50 AD3d 253
- 2012, England. Golden Ocean v Salgaocar: a broker's email signed "Guy" could sign a guarantee for his principal. EWCA Civ 265
- 2019, England. Neocleous v Rees: a solicitor's automatic Outlook signature block signed a contract for land. EWHC 2462 (Ch)
The full story of these cases, and what they mean for an agent's signature block, is in Can an email your AI agent sends bind you?
AI agents and email timeline questions
Which AI assistants can send email for you?
As of October 7, 2026: ChatGPT (from Gmail or Outlook, on paid plans, on the web), Claude (Gmail, and Outlook through the Microsoft 365 connector), Gemini (from Workspace apps, after a preview card), Copilot (send email from chat, which Microsoft said would roll out in spring 2026) and Grok Bot (through its Gmail and Outlook plugins). Most ask for approval before each send by default; Grok Bot can be set to send without a draft.
When did the EU AI Act's AI disclosure rule start to apply?
August 2, 2026. Article 50(1) requires providers of AI systems that interact directly with people to make sure those people are told they are dealing with an AI, unless it is obvious. The Digital Omnibus gave existing systems until December 2, 2026 only for the separate machine-readable marking duty in Article 50(2).
Do AI agents get their own email addresses?
Some do. AgentMail and Nylas Agent Accounts give agents hosted mailboxes, and Microsoft's Frontier preview lets an agent hold a user account with a mailbox. Agents from ChatGPT, Claude, Gemini, Copilot and Grok mostly send from the human's own connected account instead.
Who is responsible for an email an AI agent sends?
Generally, the person or company the agent acts for. US electronic-transactions law attributes an electronic agent's actions to the person to be bound, the Moffatt tribunal held Air Canada responsible for its chatbot, and the Ninth Circuit called a browser agent "a tool, not a person" for the purposes of a computer-access law. This is general information, not legal advice.
Sources
Every entry links to its primary source. Checked on October 7, 2026.