The Tool Desk
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This guide explains how to draft, revise, personalize, and send emails with ChatGPT, including writing blocks, Canvas, uploaded documents, Custom Instructions, Temporary Chat, and connected email apps.
The fastest way to use ChatGPT for email
Open a new ChatGPT conversation and describe these eight details:
- Recipient: Who will receive it?
- Relationship: Are they a customer, manager, colleague, landlord, supplier, or friend?
- Purpose: What must the message accomplish?
- Facts: Which details must appear?
- Requested action: What should the recipient do?
- Tone: Professional, warm, concise, apologetic, firm, or another style.
- Length: For example, 120 words maximum.
- Constraints: A deadline, required subject line, words to avoid, or formatting preference.
Use this reusable prompt:
Write an email to [recipient].
Purpose: [what the email needs to accomplish]
Context: [relevant background]
Include: [facts or points to include]
Requested action: [what the recipient should do]
Tone: [professional, warm, concise, apologetic, firm, etc.]
Length: [for example, 120 words maximum]
Subject line: Provide three options.
Do not invent facts, dates, names, prices, or commitments. Return the subject options first, followed by the email.
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The instruction not to invent information matters: without it, ChatGPT may fill gaps with a plausible-sounding date, explanation, promise, or name.
Example: draft an email from scratch
Instead of asking ChatGPT to “write an email to my landlord,” provide the details that affect the message:
Draft a concise email asking my landlord to repair a leaking kitchen faucet.
Facts: The leak began on March 2, 2026; water is collecting under the sink; I have attached two photographs; I am available Tuesday or Wednesday after 5 p.m.
Tone: polite but direct. Length: under 150 words. Include a clear request for a repair appointment.
This gives ChatGPT enough information to write a specific request rather than a generic complaint. It also tells the model which facts are fixed and what outcome the email should produce.
How to draft a reply to an email
For a reply, paste the original message into the chat and explain your intended response. Ask ChatGPT to address every question and identify uncertainty rather than guessing.
Draft a reply to the email below. Answer every question, preserve the facts, and identify anything that is unclear instead of guessing.
Original email: [paste the email]
My intended response: [describe what you want to say]
For a long or complicated message, use a two-stage process:
- Ask ChatGPT to list every question, request, deadline, and commitment in the original email.
- Ask it to draft a reply that addresses each listed item.
This helps prevent a polished reply that answers only the easiest part of the message.
Improve a draft with targeted follow-up prompts
Once ChatGPT has produced a draft, give it one focused revision request at a time. Specific instructions preserve more of the original meaning than a vague request such as “make it better.”
| Goal | Prompt |
|---|---|
| Shorten it | Make it 30% shorter without removing the request or the dates. |
| Change the tone | Make the tone warmer, but do not sound apologetic. |
| Clarify the action | Rewrite the second paragraph so the requested action is unmistakable. |
| Compare styles | Give me three versions: formal, conversational, and firm. |
| Remove artificial wording | Remove corporate clichés, inflated claims, generic pleasantries, and phrases that do not sound like a real person. |
| Make a complaint firm | Make this firm but non-accusatory. Describe the problem, its impact, and the requested resolution without assigning motives. |
| Preserve meaning | Improve grammar and clarity only. Preserve the meaning, level of certainty, dates, numbers, and commitments exactly. |
You can also ask ChatGPT to find problems before it rewrites the message: “Check this draft for unsupported claims, missing information, vague wording, and accidental commitments. List the problems before revising it.”
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Ask for an editable writing block or Canvas
When ChatGPT creates text intended for editing, it may display the draft in a writing block. Depending on your account, device, model, workspace settings, and rollout status, you may be able to edit the draft directly, copy it, revise selected text, open it in a full-screen editor, undo or redo AI-assisted edits, or open it in an email application. Some supported email drafts may also offer a send action.
Writing blocks support common formatting, including bold, italics, headings, links, bulleted lists, numbered lists, and checklists. Edits to supported writing blocks are saved with the conversation after a short delay. Edits made in Temporary Chat may not persist after the conversation ends. See OpenAI’s writing blocks documentation.
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You can also ask: “Use canvas to draft and revise this email.” On supported web and desktop interfaces, Canvas can also be invoked from the composer’s tools menu by typing /canvas. Canvas is available on web, Windows, and macOS, although available actions vary by model and account. It is not available with pro-series models. See OpenAI’s Canvas guide.
Use a previous email as a style reference
If you want a new email to sound like you, provide a representative message and clearly separate its style from its facts. Do not ask ChatGPT to copy the original message wholesale.
Use the email below only as a style reference. Do not copy its facts, names, dates, or wording.
Match sentence length, level of formality, greeting and sign-off style, and use of contractions.
Now draft a new email about: [topic]
Style reference: [paste your email]
This works well when you prefer short paragraphs, a particular sign-off, or a conversational tone. Remove confidential information from the reference email unless it is necessary for the task.
Draft an email from an attached document
You can attach meeting notes, a proposal, spreadsheet, presentation, image, or other source material with the composer’s attachment or add button. Current upload limits include:
- 512 MB per file
- 2 million tokens for a text or document file
- Approximately 50 MB for CSV or spreadsheet files, depending on row size
- 20 MB per image
- Up to 80 files every three hours, although limits may be reduced at peak times
- Three file uploads per day for free users
Failed upload attempts can sometimes count toward the rolling limit. On non-Enterprise plans, document processing uses text-based retrieval. Images embedded inside a PDF, presentation, or other document may not be visually analyzed, so upload an important image separately if its information affects the email. Details can change; check OpenAI’s File Uploads FAQ for current limits.
A source-based prompt should tell ChatGPT what to preserve and what not to add: “Using the attached meeting notes, draft a follow-up email. Include every assigned action item; preserve names, dates, and deadlines exactly; do not add decisions that are not in the notes; put unresolved questions in a separate list after the draft; and keep the email under 180 words.”
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Set a consistent email style with Custom Instructions
If you regularly use ChatGPT for email, add general writing preferences to Custom Instructions.
Web and desktop
- Open Settings.
- Select Personalization.
- Turn on Enable customization.
- Enter your preferences under Custom Instructions.
iPhone and Android
- Open Settings.
- Select Customize ChatGPT.
- Turn on Enable customization.
- Enter your preferences in the Custom Instructions field.
For example: “For emails, write in a concise, professional, human tone. Prefer plain language and short paragraphs. Avoid hype, clichés, excessive exclamation marks, and unnecessary apologies. State the requested action clearly. Do not invent facts, dates, names, or commitments. If important information is missing, ask a question or mark the gap instead of guessing.”
Custom Instructions are available on web, desktop, iOS, and Android. Current limits are 1,500 characters for Free and Go users and 5,000 characters for Plus, Pro, Enterprise, Business, and Education users. They provide general guidance, not the specific facts for each email. Include the current message’s dates, names, context, and requested outcome in the prompt. See OpenAI’s Custom Instructions guide.
Use Memory and Temporary Chat carefully
Memory can personalize responses with saved memories and, depending on your settings, relevant past chats. Control it from Settings > Personalization > Memory.
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For a one-off email containing sensitive information, start a new chat and select the Temporary button. Temporary Chats:
- Do not appear in chat history.
- Do not create or use memories for personalization.
- Are not used to improve OpenAI’s models.
- May still be retained for up to 30 days for safety purposes.
- Still follow enabled Custom Instructions.
Do not paste more personal, medical, financial, legal, or confidential information than the recipient needs. If you use a GPT with actions, information sent to third parties is governed by the third party’s privacy policy and may be retained longer. See OpenAI’s Temporary Chat FAQ and Memory FAQ.
Use a connected email account
If ChatGPT is connected to an email service, it may be able to find an existing message and use it as context. For example, the Outlook Email app can support prompts such as: “Draft a reply that covers the three main points in the last email from [sender].” You can narrow an Outlook search with a query such as: “Find emails from:[name] subject:[keyword] after:2025-10-01.”
The Outlook Email app can search and retrieve messages, including metadata and plain-text bodies. Editing or sending an email is an important external action and may require your approval. Write actions depend on the app, permissions, workspace configuration, and account; they are not available through Outlook when it is used via Company Knowledge.
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Send the finished email
There are three possible workflows:
- Copy and paste: Select Copy in the response or writing block, then paste the result into Gmail, Outlook, or another email client. This is the most widely available method.
- Open in an email app: Some writing blocks offer an option to open the draft in a supported email application. The option may not appear in every conversation.
- Send through a connected app: A connected email app may send the message when write actions and permissions are enabled. ChatGPT may request confirmation before sending.
ChatGPT cannot automatically send email for every user or plan. Availability depends on the account, app, model, device, permissions, workspace controls, and feature rollout. Treat any send button as an external action and check the final recipients and message before approving it.
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Check the email before sending
Fluent writing is not evidence that the details are correct. Compare the final draft with your source information and check:
- Names, titles, and email addresses
- Dates, times, time zones, prices, quantities, and deadlines
- Attachments and links
- Whether the requested action is clear
- Whether the tone suits the relationship
- Whether ChatGPT added an excuse, promise, discount, commitment, or claim you did not authorize
Use this final review prompt if useful: “Audit this email against the facts I provided. List any invented or unsupported details, missing requests, ambiguous wording, accidental commitments, incorrect numbers, and attachment references. Do not rewrite it until you list the issues.”
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ChatGPT invents details
Use only the supplied facts and require a visible placeholder for missing information: “Use only the facts provided. If information is missing, write [NEEDS CONFIRMATION] rather than guessing.” Look particularly for invented dates, assumed reasons, unapproved discounts, incorrect titles, claims that an attachment was included, and statements that another person agreed to something.
The email is generic
Try: “Rewrite this for a client who is busy and unfamiliar with the technical details. Keep the tone confident and helpful.”
The email is too long
Try: “Reduce this to 100 words. Keep the deadline, requested action, and consequence of inaction.”
The request is vague
Try: “Make the requested action explicit in the first paragraph. State who needs to do what and by when.”
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The draft is too harsh
Try: “Make this firm but non-accusatory. Describe the problem, its impact, and the requested resolution without assigning motives.”
The response contains an unwanted preamble
Try: “Return only three subject lines and the email body. Do not include an explanation, notes, or disclaimer.”
The reply answers only part of the original email
Ask ChatGPT to list every question, request, and commitment in the original message first, then draft a reply that addresses each item.
The draft changes the meaning
Ask: “Improve grammar and clarity only. Preserve the meaning, level of certainty, dates, numbers, and commitments exactly.”
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Other interface and upload issues
Since June 22, 2026, pastes exceeding 10,000 characters are automatically handled as attachments for Free and Go users; the same behavior was already available for Plus, Pro, and Business users. Select Show in text field to convert the attachment back into text.
If deleting a chat does not remove an uploaded file, check Library and delete the file separately. Files saved there can remain after the conversation is deleted. See OpenAI’s File storage and Library guide.
If you turn off Settings > Data Controls > Improve the model for everyone, conversations can still remain in chat history; the setting means they are not used to improve the models. The app directory moved to the Plugin directory on July 9, 2026; existing app connections remain unaffected, but current instructions may use Plugins, Apps, or workspace-specific settings depending on the workflow. The interface may also differ from older tutorials because app navigation and names change across accounts and workspaces.
FAQ
Can ChatGPT write an email from a short instruction?
Yes, but the result is more reliable when you provide the recipient, relationship, purpose, facts, requested action, tone, length, and constraints. A short request may produce a generic message or cause ChatGPT to guess missing details.
Can ChatGPT reply to an email?
Yes. Paste the original message, state your intended response, and ask ChatGPT to answer every question while identifying unclear points instead of guessing.
Can ChatGPT send the email for me?
Sometimes. A supported writing block or connected email app may offer an open or send action, but availability depends on your account, app, permissions, device, model, workspace settings, and rollout status. Copying and pasting remains the most universal option.
How do I stop ChatGPT from making up facts?
Tell it to use only the facts provided and write [NEEDS CONFIRMATION] for missing information. Then check names, dates, numbers, promises, deadlines, and attachment references yourself.
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Can I make ChatGPT use my usual email style?
Yes. Add general preferences under Settings > Personalization > Custom Instructions, or provide a representative email as a style reference. Still include the facts and purpose of each new email.
Is Temporary Chat completely private?
Temporary Chats do not appear in history, do not create or use memories, and are not used to improve OpenAI’s models. OpenAI may nevertheless retain a copy for up to 30 days for safety purposes.
Why did ChatGPT lose images from my uploaded document?
On non-Enterprise plans, document processing is text-based, so images embedded in PDFs, presentations, or other documents may not be analyzed. Upload important images separately.
Why can’t ChatGPT find a recent Outlook message?
Search results can be delayed by Microsoft Graph indexing. Narrow the sender, subject, or date range, or split a broad search into smaller requests.
The Bottom Line
Use ChatGPT as a drafting and editing assistant, not as the final authority on what your email says. Give it specific facts and a clear requested action, revise with targeted prompts, and verify every detail before sending. For sensitive material, limit the information you share and use Temporary Chat when appropriate.
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