How to transfer a folder from Outlook to chatgpt?

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How to transfer a folder from Outlook to chatgpt?

margot gordon 60

I’d like to send a folder of emails to chatgpt if anyone knows?

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Answer 1

John Jefferson Doyon 86,980 Independent Advisor

Hi, @margot gordon

Outlook.com does not have a direct option to send an entire mail folder to ChatGPT.

For individual emails, you can open the message, select the three dots (...) > "Download" to save it to your computer.

If ChatGPT does not accept the downloaded email format, another option is to save/print the emails as PDF files and upload those instead. ChatGPT supports common document formats such as PDF, DOCX, and TXT.

To help narrow down the best method:

About how many emails are in the folder?
Do you need the attachments included as well, or only the email text?

Click "Add comment" to let me know.

Thanks!

margot gordon 60 Reputation points

2026-09-02T17:29:26.3333333+00:00

28 emails

no attachments
John Jefferson Doyon 86,980 Reputation points Independent Advisor

2026-09-02T19:31:41.78+00:00

Thanks.
Before going through all 28 emails individually, what are you trying to accomplish with them in ChatGPT?

For example, are you trying to summarize the emails, analyze a conversation, extract specific information, or create a response from them?

That will help determine the easiest way to get the emails into ChatGPT.

Thanks!
margot gordon 60 Reputation points

2026-09-02T19:59:38.0233333+00:00

I need them each as evidence for a legal matter
John Jefferson Doyon 86,980 Reputation points Independent Advisor

2026-09-03T15:22:24.1133333+00:00

Thanks for clarifying.

Since the emails may be used as evidence in a legal matter, keep the original emails and avoid relying only on PDF copies.

In Outlook.com, you can open each email and select the three dots (...) > "Download." This saves the message as an email file, such as EML, which preserves more of the original message information than simply printing it to PDF.

Keep those original downloaded files unchanged and also leave the original emails in Outlook.

If your goal is to have ChatGPT organize or summarize the emails, you can make separate PDF copies for that purpose. ChatGPT supports PDF and other common document formats.

Just to clarify, are you trying to use ChatGPT only to organize/analyze these 28 emails, or are you planning to use what ChatGPT produces as part of the evidence you submit?

Thanks!
margot gordon 60 Reputation points

2026-09-04T08:21:42.38+00:00

I'm using chatgpt to help me chronologize my evidence so chatgpt can see what my rights sre
John Jefferson Doyon 86,980 Reputation points Independent Advisor

2026-09-04T09:17:33.62+00:00

Thanks, that makes sense.

If you are using ChatGPT to put the 28 emails into chronological order and help you understand the situation, you can save each email as a PDF and upload the PDFs to ChatGPT.

Since this relates to a legal matter, also keep the original emails in Outlook and keep the downloaded original email files unchanged. Do not rely only on the PDFs or ChatGPT’s summary as your evidence.

ChatGPT can help organize the timeline and explain general information, but your actual legal rights can depend on your country/state and the specific facts.

Are all 28 emails already in one Outlook folder, and are they arranged by date?

Thanks!
margot gordon 60 Reputation points

2026-09-04T10:10:34.67+00:00

yes, they are and thanks for your advice
John Jefferson Doyon 86,980 Reputation points Independent Advisor

2026-09-04T13:46:51.8466667+00:00

Glad to assist. Thanks!