How to Upload Multiple Files in Assist 2.0
Assist 2.0 makes it easy to upload more than one file at a time — whether you're attaching files in a chat conversation or adding them to your workspace's knowledge base. This guide walks you through both methods step by step.
Overview
Multi-file upload is available in two areas of Assist 2.0:
- In Chat — Attach multiple files to a conversation
- In Workspace Knowledge — Add multiple files to your workspace's knowledge base via the Library, so agents can reference them across projects
Method 1: Uploading Multiple Files in Chat
Use this method when you want to attach several files directly to a chat conversation.
Steps
1. Open a chat
Navigate to your workspace and open a chat — either a new one or an existing conversation.
2. Click the + icon
In the chat input bar, click the purple + icon to the right of the text field. A short menu will appear with the following options:
- Attach Files
- Use a Template

3. Select "Attach Files"
Click Attach Files. A system file browser will open.
4. Select multiple files
Navigate to the folder containing your files. Hold Ctrl (Windows) or Cmd (Mac) and click to select multiple files, then click Open.
5. Wait for upload to complete
Your selected files will appear as individual attachment tiles above the chat input box, ready to be sent with your next message.

Method 2: Uploading Multiple Files to Workspace Knowledge
Use this method when you want to add files to your workspace's knowledge base so agents can reference them across all projects and outputs in the workspace.
Steps
1. Open the Library
From the left-hand navigation, open the Library.
2. Go to the Knowledge tab
In the Library's sub-navigation, click Knowledge (alongside Marketplace, Agents, and Templates).

3. Click "+ Add Knowledge"
Click the purple + Add Knowledge button.
4. Choose "Upload File"
Select Upload File from the options that appear, then select your files from your device using Ctrl/Cmd + click to multi-select.
5. Add a title and save
Give the knowledge entry a descriptive title (e.g. "Brand Guidelines" or "Q1 Campaign Images"), add any optional agent instructions, and click Save Knowledge.
A confirmation will appear, and your files will be listed in the Knowledge tab. You may see a brief processing state before they're ready to use.

Tips
- Select multiple files at once by holding Ctrl (Windows) or Cmd (Mac) while clicking in the file browser
- Give your knowledge entries clear titles so they're easy to find later — e.g., "Brand Guidelines" or "Q1 Campaign Images"
- Workspace Knowledge is available across the whole workspace — once uploaded, agents and outputs throughout the workspace can reference it
- No need to upload one at a time — both chat and the knowledge base support batch uploads in a single action