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Features FAQ

Can I upload files to AskAI.free?

Short answer: Yes, file uploads are a Pro / Max feature. Drop in PDFs, images, code files or text and the AI reads them as part of your question.

Yes. Pro and Max subscribers get the file-upload button in the chat composer. Drag files in or click the paperclip icon. Supported:

  • Images (jpg, png, webp, gif), the AI sees them via vision models. Ask "what's in this screenshot?" or "extract the text from this receipt".
  • PDFs and documents: text content is extracted and added to the prompt. Great for summarising contracts, reports or research papers.
  • Code files: drop in a whole file (or several) and ask the AI to refactor, explain or find bugs.
  • Plain text and CSVs: handy for data analysis questions.

Upload size is capped at 10 MB per file. The free tier doesn't include uploads, start a 7-day Pro trial to test it.

One sizing detail worth understanding: an uploaded document is converted to tokens and has to fit inside the model's context window along with your question and the answer. Claude Sonnet 4's 200,000-token window comfortably holds a 100-page contract or a mid-sized codebase; a 500-page book will need to be split or summarised chapter by chapter. Big uploads also draw down your monthly token allowance faster than typed questions.

To get better answers from uploads, ask something specific rather than just "summarise this". "List every obligation this contract places on the tenant, with clause numbers" or "find the three riskiest assumptions in this business plan" consistently beat generic summaries. And for scanned documents, image-based PDFs work too, the vision models read them, but clean text PDFs produce more accurate extraction.

How to get better results from uploads

Upload the smallest useful file, then ask a specific question about it. Instead of saying "summarise this PDF", ask for the decision points, risks, action items, contradictions, or a one-page executive brief. For code files, tell the AI what framework, runtime and goal you care about before asking for a refactor or bug hunt.

For privacy and accuracy, remove pages or sections that are not relevant. More context is not always better; irrelevant pages can distract the model and make the answer less precise.

How to apply this answer

Pick one real document from this week, a contract, a report, a long email thread saved as PDF, and upload it with a pointed question: "list the action items with owners" or "what should worry me in this agreement?". A specific question on a real document is the fastest way to judge whether uploads fit your workflow.

Related FAQ pages

Try it in a real chatYour first question is free, no signup needed. Ask with your real context, or compare ChatGPT 4o and Claude Sonnet 4 on the same prompt.

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