Export iMessages to ChatGPT

Steps

1. Press “Connect” beside Messages on Exporter’s home, then “Open Messages Folder”. The panel opens in ~/Library/Messages: press “Select This Folder”.
2. Choose where the files go, like ~/Documents/messages, and press “Use This Folder”.
3. Wait for the first pass over your history, then press “Sync Now”. Each conversation becomes one file, named after the people in it.
4. In ChatGPT, attach the conversation’s file with the + button, or add it to a project.
5. Ask about it: “What did we agree about the flat?” or “List every date Anna mentioned.”

What you get

One Markdown file per conversation: a heading per day, then each message with who sent it and when. A reply links to the message it answers, an edited message keeps its earlier versions as footnotes, and reactions sit under the message. Photos are copied into attachments/ beside the file.

Markdown is plain text, so ChatGPT, Claude or any other assistant reads the file as it is. Exporter rewrites the file as new messages arrive; ChatGPT keeps the copy you attached, so attach it again for the latest.

Pitfalls

• Attaching a file sends that file to OpenAI. The export folder itself stays on your Mac.
• For questions across every conversation, attaching files one by one gets slow. Messages in Claude lets Claude search them all through Exporter’s MCP server.
• Your 50 most recent conversations are free. Older ones need the one-time unlock.

The file, field by field, is in the Messages docs.