Real Agent Cases

Send an email straight from ChatGPT through a connected Gmail account (attachments didn't work)

Posted
by Graham Barlow (TechRadar)
Last checked
Method:
How we verify

Evidence: Article or interviewA newsletter, journalist or interview account of what happened.

PartialThe source says it only partly worked, or had a significant problem a person had to deal with.

What went wrong: Sending worked, but the attachment failed.

Outcome

A TechRadar editor connected Gmail to ChatGPT and asked it to write and send an email with a story idea, background and a source link. ChatGPT showed the exact email and asked him to Allow or Deny; after he approved, it arrived seconds later. But it failed when he tried to add an attachment, and the feature only works on the web for paid plans. Gemini told him it couldn't send email directly.

Agent

ChatGPT

Prompt Recreated prompt

The source didn't share its exact prompt, so we wrote this from what it describes.

Run this task now, exactly as written below. Everything you need is here, so start straight away and only stop if something required is missing or a rule below tells you to.

Goal: Write and send a short email from my connected mail account, with my approval before it goes.

Fill in before running:
- Recipient: [EMAIL]
- What the email should say: [POINTS]
- Links to include: [LINKS]
- Tone: [e.g. brief, friendly]

Rules:
- Show me the full email (recipient, subject, body) and wait for my OK before sending.
- Use only the facts and links I give you.
- If I need an attachment, tell me up front if you can't add one, so I send it from my mail app instead.
- Confirm once it's sent.
- If a site asks for a login, a CAPTCHA or payment details, stop and hand control back to me.
- Ask for my OK before you pay, book, send, submit or cancel anything.
- Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify.

Output: The draft for approval, then a sent confirmation.

You'll know it worked when: the email arrives as approved, or I know to send it myself if it needs a file.
Optional stronger version

Our rewrite with extra checks. The poster didn't test it.

Run this task now, exactly as written below. Everything you need is here, so start straight away and only stop if something required is missing or a rule below tells you to.

Goal: Write and send a short email from my connected mail account, with my approval before it goes.

Fill in before running:
- Recipient: [EMAIL]
- What the email should say: [POINTS]
- Links to include: [LINKS]
- Tone: [e.g. brief, friendly]

Rules:
- Show me the full email (recipient, subject, body) and wait for my OK before sending.
- Use only the facts and links I give you.
- If I need an attachment, tell me up front if you can't add one, so I send it from my mail app instead.
- Confirm once it's sent.
- If a site asks for a login, a CAPTCHA or payment details, stop and hand control back to me.
- Ask for my OK before you pay, book, send, submit or cancel anything.
- Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify.
- If the task needs an attachment, stop and give me the finished text to paste into my email app.

Output: The draft for approval, then a sent confirmation.

You'll know it worked when: the email arrives as approved, or I know to send it myself if it needs a file.

Before you finish: re-read my goal and constraints, check your answer against each one, and list anything you assumed or couldn't confirm.

Source

https://www.techradar.com/ai-platforms-assistants/chatgpt/i-sent-an-email-without-opening-gmail-thanks-to-chatgpts-new-feature-then-i-found-the-catch

  • Planning her daughter's fourth birthday, a poster used ChatGPT to create the party's run of show for everyone helping, think through a rain backup plan comparing restaurants with covered space, and draft emails to those restaurants with what she needed and could spend. She reads every draft and approves what gets sent; a virtual assistant handled invitations and vendor coordination.

    ChatGPT · Personal · Source date:

  • TechRadar's Eric Hal Schwartz set an event-triggered ChatGPT task on his Gmail: alert him only when an email required him to do something or came from family, explain it in one sentence, draft a reply, and never reply without his input. Over an afternoon with Gmail closed he got just 3 alerts (his bank, a family member whose drafted reply he sent after small edits, and an event itinerary change); afterwards he found only two emails he might have wanted earlier, neither urgent.

    ChatGPT · Personal · Source date:

  • A poster connected his Gmail and calendar to ChatGPT, then asked it to list all his subscriptions from his emails, unsubscribe from all but the ones he wanted, create deletion rules for the rest, and delete Promotions, Updates, Social and Trash. He says he deleted over 23,000 emails and made his inbox usable again, and ChatGPT told him when it was finished.

    ChatGPT · Personal · Source date: