Chat & AI
Attaching files to a chat message
Add a file from your computer so the AI can read it: press the paperclip, drag it in, or paste it.
Step 1
Three ways in
Press the paperclip in the composer to open your normal file picker. Or drag a file from your desktop anywhere onto the chat; a Drop files to attach overlay appears. Or copy an image and paste it straight into the message box. All three do the same thing.
Press Enter to send, Shift+Enter for new line
Step 2
Any type, within limits
There is no file type restriction. Up to 20 files can go on one message, and each can be up to 150 MB, or 50 MB for spreadsheets and images. Large files upload in pieces on their own, and they count towards your storage. A file that is too big shows a red chip straight away and never uploads. Phone photos in HEIC are converted for you.
Press Enter to send, Shift+Enter for new line
Step 3
Watch it upload and get read
A chip appears above the box for each file. It says Uploading, then shows a short note while the server reads it, such as Reading 25 pages. Send stays grey until every file is ready. If a file cannot be read you see Could not read this file type; remove it and try another format.
Press Enter to send, Shift+Enter for new line
Step 4
Check it before you send
Press a chip to preview it: images and PDFs open large, Word renders as text, Excel shows its sheets, PowerPoint shows its slides, audio gets a player. Press the small cross on a chip to remove it. Nothing is sent until you press Enter.
Press Enter to send, Shift+Enter for new line
Step 5
Files from your library instead
The folder button next to the paperclip picks documents and folders already in Documents, without uploading anything. Folders arrive as amber chips. That flow, and the Depth setting that goes with it, is in Scoping a chat to specific documents or folders.
Press Enter to send, Shift+Enter for new line
Step 6
Afterwards
An upload lives only in this chat and is not searchable from Documents. Hover its chip in the sent message, or press the Session files button in the chat header, the file icon with a count, and choose Save to Documents to keep it in your library.
Q3 budget versus meeting notes
Try it in Secretary, or create an account to get started.
Related guides
Starting a new chat
The start screen, starter prompts, temporary chats, and what New chat does once you are already in a conversation.
Scoping a chat to specific documents or folders
Point the AI at exactly the files in your library it should answer from, and choose how deeply it reads them.
Selecting a model
Choose which AI model answers, read the speed, intelligence and price signals, and know why some models are greyed out.