---
title: "Discussion on \"Why Your AI Agent Loses Context After Three Email Replies\" | Hashnode"
description: "Discussion on \"Why Your AI Agent Loses Context After Three Email Replies\". After three replies, email thread context quietly breaks. Here is why RFC 2822 header chains cause it, how Gmail and Outlook handle it differently, and how client.messages.reply() fixes it for good."
url: "https://hashnode.com/posts/ai-agent-email-thread-context-loss/69c9549db4b5752b5ad4509b"
---

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# [Why Your AI Agent Loses Context After Three Email Replies](https://mailbot.hashnode.dev/ai-agent-email-thread-context-loss?utm_source=hashnode&utm_medium=feed)

After three replies, email thread context quietly breaks. Here is why RFC 2822 header chains cause it, how Gmail and Outlook handle it differently, and how client.messages.reply() fixes it for good.

Mar 29 · 7 min read · mailbot.hashnode.dev  
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-   [#rfc2822](https://hashnode.com/tag/rfc2822)
-   [#ai-agents](https://hashnode.com/tag/ai-agents)
-   [#email](https://hashnode.com/tag/email)
-   [#threading](https://hashnode.com/tag/threading)
-   [#typescript](https://hashnode.com/tag/typescript)

## Written by

[Yopie Suryadi](https://hashnode.com/@yopie)

@yopie · Jakarta, Indonesia

  
[View profile](https://hashnode.com/@yopie)

founer of Mailbot

founder of mailbot

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