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.

Try this in:

This prompt has blanks to fill in, like [EMAIL]. We'll copy it instead of filling it in, so you can edit it before you send.

Opens in a new tab. We don't see what you send.

These links are only a shortcut. We're not affiliated with OpenAI, Google or xAI, and your results may not match the source.

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

  • Back from a week away, Abha Malpani Naismith had more than 9,400 unread Gmail messages. Claude couldn't act inside the connected inbox for them, so they switched to ChatGPT with Gmail connected. It analysed the inbox by sender, subject and category without opening emails, built a 'Safe List' of financial, legal, medical, school and travel mail never to touch without approval, and then helped archive, label, delete or unsubscribe in bulk. They archived or deleted more than 4,500 emails and reached inbox zero in about 30 minutes.

    ChatGPT · Personal · Source date:

  • Gokul N.'s blood test results from Superpower took 20 days. Gokul asked ChatGPT to check the refund policy, look at the dates and email the concierge. The email cited Section 14(a) of the membership agreement, set out the timeline with Superpower's own support replies, asked them to confirm when results had actually been available, and added a fallback asking for an exception if a different policy applied. Two days later Superpower confirmed a full $199 membership refund.

    ChatGPT · Personal · Source date:

  • Ary Aranguiz connected ChatGPT to Gmail and asked it to create four labels: ACTION/Reply, ACTION/Decision, ACTION/Review and STATUS/Waiting. ChatGPT then reviewed 204 unread emails from the past seven days and proposed which belonged under each label, separating people waiting for a reply, invitations needing a decision, information to review and routine mail needing no action. It noticed the original label set was incomplete and recommended adding ACTION/Review. Aranguiz approved the proposals, and only then did it create the label and apply the labels. It didn't send, delete, archive, forward or mark anything as read.

    ChatGPT · Personal · Source date: