Chat with Documents

Attach PDFs, images, and other files to any chat message and ask the AI questions about their content.

Overview

Chat with Documents lets you bring your own files into a conversation. Attach a file to any message, and the AI reads it alongside your question — so you can ask for summaries, pull out specific information, translate content, or compare multiple documents side by side. It works within your regular AI Chat conversations, with no separate tool to open.

How to Access

Open any chat conversation
Click the paperclip (file upload) button in the message bar
Select the file you want to attach
Type your question and send

The AI will read the file and respond based on its content.

Step-by-Step Guide

Attach a File

Start a new chat or open an existing one
Click the paperclip icon in the message input bar
Choose a file from your device — PDFs, images (PNG, JPG, and similar formats), and plain text documents are all supported
The file appears as an attachment in your message draft

Ask Your Question

Type what you want the AI to do with the file — a question, an instruction, or a specific task
Hit Send
The AI reads the file and replies based on its content

You can keep asking follow-up questions in the same conversation and the AI will continue to reference the file.

Attach Multiple Files

You can attach more than one file to a single message. This is useful when you want to compare two documents or ask a question that spans multiple sources.

What to Ask

Here are some useful prompts to get you started:

“Summarize this document in three bullet points.”
“What are the main arguments being made?”
“Find every mention of [topic] in this file.”
“Translate this into Traditional Chinese.”
“Compare these two documents — what are the key differences?”
“Extract all the data from the table on page 4.”
“Rewrite this section in simpler language.”
“Does this contract mention a penalty clause? If so, what does it say?”

The AI can handle both the content of documents and the visual layout of images, so these prompts work whether you’re attaching a PDF report or a screenshot.

Who Can Use This

Chat with Documents is available on Pro, Ultra, and Teacher plans. It is not available on the Free plan.

If you’re analyzing a long audio or video recording rather than a document, Meeting Summarizer may be more suitable — it’s purpose-built for transcription and structured summaries of long recordings.

Common Questions

What file types are supported? PDFs, common image formats (PNG, JPG, WEBP, and others), and plain text files. If you’re unsure whether your file type works, try attaching it — the upload step will tell you if the format isn’t supported.

How many files can I attach at once? You can attach multiple files to a single message. If you have a large number of documents to analyze together, attach the most relevant ones and describe the others in your message text.

I’m on the Free plan — can I use this? This feature requires a Pro, Ultra, or Teacher plan. You can upgrade from your account settings.

AI Chat — The main chat interface where this feature lives
Meeting Summarizer — Transcribe and summarize long audio or video recordings