Skip to main content
You can attach files to any chat message in ZeroTwo. There are two ways: click the paperclip icon in the prompt bar, or drag-and-drop files directly onto the chat input area. Both methods work the same way and support the same file types and limits.

​
Two Upload Methods

  1. Click the paperclip icon in the prompt bar at the bottom of the chat.
  2. Your file picker opens. Select one or more files (hold Cmd/Ctrl to select multiple on desktop).
  3. Selected files appear as attachment previews above the text input.
  4. Type your prompt — or leave it blank and ZeroTwo will infer what to do.
  5. Press Enter or click Send.

​
Step-by-Step Guide

1

Initiate the upload

Click the paperclip icon or drag files onto the chat input area.
2

Select your files

Choose the files you want to attach. Limits by plan:
  • Free plan: 1 file per message
  • Pro+: Up to 10 files per message
3

Review attachment previews

Each file appears as a preview above the input field, showing the filename and a thumbnail or file-type icon. To remove a file before sending, click the X on its preview.
4

Write your prompt

Add a question or instruction in the text field. For example:
  • “Summarize the key findings from this report.”
  • “What does this function do and how can I improve it?”
  • “Transcribe this audio and pull out the action items.”
  • “Compare the financial projections in these two documents.”
If you send the file without a message, ZeroTwo will infer what to do based on the file type — but a specific instruction produces better results.
5

Send

Press Enter or click the Send button. An upload progress indicator shows while files transfer to ZeroTwo’s servers.
6

Wait for analysis

ZeroTwo processes the file and responds. Processing time varies:
  • Small documents and images: near-instant
  • Large PDFs or code files: a few seconds
  • Audio transcription: roughly 1 second per minute of audio
  • Video analysis: depends on video length and resolution

​
Upload Limits

PropertyFree PlanPro+
Files per message1Up to 10
Max file size50 MB50 MB
Max video file size50 MB200 MB
Upload timeout60 seconds60 seconds
Max files per message110
If your file exceeds the size limit or the upload takes longer than 60 seconds, the upload will fail. Compress large files, use lower-resolution video, or split large documents into sections.

​
What ZeroTwo Does with Each File Type

File TypeWhat ZeroTwo Does
PDF, DOCX, PPTX, XLSXExtracts full text for Q&A, summarization, and translation
Code files (JS, PY, TS, GO, etc.)Reads full source for review, explanation, and refactoring
Data files (CSV, JSON, Parquet, etc.)Analyzes structure, statistics, and patterns
Images (PNG, JPG, GIF, WEBP, etc.)Vision analysis — description, OCR, visual questions
Audio (MP3, WAV, M4A, etc.)Whisper transcription + discussion
Video (MP4, MOV, WEBM, etc.)Frame extraction + vision analysis
Notebooks (IPYNB, Rmd)Full cell and output reading
See Supported File Types for the complete format list.

​
Writing Effective File Prompts

ZeroTwo responds to the file in context of your message. Specific instructions produce more useful output.
Instead of…Try…
(no message, just the file)“Summarize this PDF in 5 bullet points"
"What is this?""This is a quarterly sales report — what are the top 3 trends?"
"Fix this""Review this Python file for bugs and explain each issue with a suggested fix"
"Analyze the data""Which product category had the highest revenue growth from Q1 to Q3?"
"Transcribe this""Transcribe this meeting recording and list all action items with the person responsible”

​
Combining Multiple Files

When you attach multiple files (Pro+ only), you can reference them together in a single message: 
Here are two versions of the product spec. Compare them and highlight what changed between v1 and v2.

I've attached three quarterly reports. Summarize revenue trends across all three quarters.
ZeroTwo reads all attached files in context and can cross-reference information between them.

​
After Uploading

Progress indicator: While the file uploads, a progress bar or spinner appears on the attachment preview. Do not close the tab during upload. Upload complete: The progress indicator disappears and the preview shows the final file state. Removing an attachment before sending: Click the X on any file preview to remove it from the pending message. This does not delete the file from your Files Library if it was previously saved there. After sending: The file is attached to that specific chat message. It is also automatically saved to your Files Library for reuse in future chats.
All uploaded files are automatically saved to your Files Library at /files. You can re-attach them to any future chat without uploading again — no duplicate storage.

​
Related Pages

Supported File Types

Complete list of accepted formats and how each is processed.

Files Library

Browse and re-attach all your previously uploaded files.

Files Overview

How files work in ZeroTwo — uploading, storage, and use cases.

Troubleshooting

Fix upload failures, size errors, and missing analysis.