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Reply with ChatGPT or Claude, without sending them the details.

thinkhard.si for Outlook is a free add-in. Open an email, press Reply with AI, say what you want to answer, and ChatGPT or Claude gets the email with names, email addresses, phone and account numbers swapped for placeholders. Paste back the draft it writes and a reply opens with the real details in place. When you write an email, Check draft reads it before you send. It all runs in Outlook and sends none of your text to thinkhard.si.

Download the add-in fileHow to add itComing to Microsoft AppSource. Until then it is added from this file, in a minute.

Reply with AI

  1. Open the email and press Reply with AI.
  2. Write what you want to say in a few words, such as "yes to Tuesday, but ask for the budget first", and pick a tone.
  3. Press ChatGPT or Claude. It opens with the request ready, and the email in it has every name, email address, phone and account number replaced by a placeholder such as [NAME_1], the way Safe Paste does it.
  4. Paste the draft it writes back into the pane and press Reply with this draft. Outlook opens a reply with the real names and numbers back in, for you to read and send.

Check a draft before you send it

In a new email or a reply, Check draft reads what you wrote, or only what you selected: phrases that sound machine-made, claims and numbers to check, blanks the AI left such as [insert date], and email addresses, phone and account numbers that may not be meant for this reader. Safe for AI and Prompt work as they do in the Word add-in, with the result put in the email where your cursor is.

How to add it

Until it is listed in Microsoft AppSource, Outlook adds it from a small file that tells Outlook where the add-in lives.

  1. Download the add-in file (manifest-outlook.xml).
  2. In Outlook on the web or the new Outlook for Windows, open Get Add-ins: on an email, choose Apps or the menu with three dots, then Get Add-ins.
  3. Choose My add-ins. Under Custom add-ins, choose Add a custom add-in, then Add from file, and pick the file. The wording can differ slightly between versions of Outlook.
  4. Reply with AI now shows on emails you read, and Check draft on emails you write. Outlook on Windows and Mac usually picks it up from the same account.

Some workplaces turn off custom add-ins. There, your IT team can add it for everyone from the Microsoft 365 admin center (Settings, Integrated apps, Upload custom apps) with the same file.

Private by design

Everything runs in the pane, inside Outlook. The add-in sends nothing you write or read to thinkhard.si or anyone else, and stores nothing. It reads the email you have open only when you press a button, and it changes a draft only when you ask it to put text in. An email goes to ChatGPT or Claude only when you press their button, with placeholders in place of the details. The full detail is in the privacy policy.

Questions

Does ChatGPT or Claude see who wrote to me?

Not from the add-in. The sender's name and address, and every name, email address, phone and account number it finds in the email, are replaced with placeholders before the text leaves the pane. Open See what the AI will get to read exactly what leaves the pane before you press the button.

Why does it ask to read and change the item?

To read the email you have open when you press a button, and to put text into a draft where your cursor is when you ask. It cannot read other emails or send anything.

Is there one for the other Office apps?

Yes. thinkhard.si for Word checks documents and sends text to an AI with the details swapped out. The add-ins for Excel and PowerPoint do the same on a sheet or a deck.

Where are the other thinkhard.si integrations?

On the integrations page: the browser extension, the Google Docs add-on, the WordPress plugin, the MCP server for Claude and ChatGPT and the REST API.