How to upload & analyze Files

What you can upload

• Images: PNG, JPEG, GIF, WebP, and HEIC/HEIF. Photos straight from an iPhone or iPad work without conversion.
• PDFs: contracts, research papers, reports, manuals.
• Office documents: Word (.docx), Excel (.xlsx), and PowerPoint (.pptx), including the older .doc/.xls/.ppt formats.
• Text and data: plain text, Markdown, CSV/TSV, HTML, JSON, and XML.
• Code: source files in any common language (uploaded as text).

Limits

• Up to 5 files per message
• 20 MB per file
• 50 MB per batch (across all files in one message)
• Files stay with the conversation. You can keep asking about them in later turns without re-uploading.

How to upload

1. Click the paperclip icon in the chat input (or drag and drop files onto the chat).
2. Wait for the upload to finish. Small files are instant; large PDFs take a few seconds.
3. Type your question. Naming the file helps when you attach several: "Summarize the methodology section of paper.pdf."

What happens with PDFs

When you upload a PDF, Calanthe indexes it and pulls the most relevant passages into view to answer your question. This works on every plan, even for documents far larger than the context window.

On Calanthe Pro (Power plan), she goes further: the PDF is read natively, page by page, so she also understands layout, tables, charts, and figures, not just the text.

Images and vision

Attach screenshots, photos, charts, or diagrams and ask about them. Calanthe Pro offers the deepest image understanding and is the right choice for detailed visual work: reading dense screenshots, interpreting charts, or analyzing photos.

Looking to create images instead? See the image generation guide.

Good ways to use file uploads

• Contract review: upload a PDF, ask "What clauses should I be careful about?"
• Spreadsheet analysis: "Who are the top 5 customers by revenue this quarter?"
• Screenshot debugging: upload an error message, ask "What is wrong here and how do I fix it?"
• Cross-document compare: upload two contracts, ask "What is different between these?"
• Code review: upload a source file, ask for issues and improvements.

Privacy & retention

Files are encrypted in transit and at rest, and they are never used to train any AI model. They live with the conversation and are removed when you delete it. Files untouched for 90 days are deleted automatically. Full details in our Privacy Policy.

Things that will not work

• Files over 20 MB. Split or compress them first.
• Password-protected PDFs. Decrypt before uploading.
• Audio and video files. (To speak with Calanthe, use voice conversations instead.)
• Executables and other binaries (.exe, .dmg, .app). Blocked for security.