How to Upload Files and Images to DeepSeek (and Fix Failed Uploads)

The short version

Attach the file, then ask a precise question. “What does this say?” gets a vague summary. “List every deadline and penalty in this contract” gets something useful.

Step by step

1. Start a new chat for each document or set of related files. It keeps answers focused.
2. Attach the file from the message box, on the web or in the app.
3. Ask a specific question. Say what you want and in what format.
4. Ask for quotes. “Quote the sentence you’re relying on” makes it easy to check the answer against the file.
5. Follow up. “Now compare section 3 with section 7” or “Turn that into a table”.

If the upload fails

DeepSeek’s FAQ lists these causes:

• The format isn’t supported. Try saving as PDF, or copy the text in.
• The file is too big, or you added too many. Split it, or upload fewer at once.
• Your connection is unstable. Retry on a better connection.
• The file can’t be read, for example because it’s damaged. Re-export it.
• The content breaks DeepSeek’s terms.

If nothing happens after you pick a file, the FAQ suggests checking whether your local network (often an office network) blocks uploads. You can also check the File Upload Service line on status.deepseek.com.

Prompts to copy

A contract or policy:

From the attached document, list every date, deadline, fee and penalty.
For each one, quote the exact sentence and give the page or section.

A photo or screenshot:

This is a screenshot of an error on my website's checkout page.
Read the error text, explain what it probably means in plain English, and list what I should check first.

A spreadsheet export:

The attached file is our sales by month. Which three months were best and worst?
Show the numbers you used, and tell me if any rows look like errors.

Example

You upload: a 40-page insurance policy PDF and ask, “What isn’t covered for water damage? Quote each exclusion.”

A good result: a short list of exclusions, each with the quoted wording and section number, so you can find and read them yourself in seconds.

Mistakes to avoid

• Uploading confidential files. Contracts with client names, medical records, payroll or anything under an NDA don’t belong on DeepSeek’s servers. See keep your data private in DeepSeek.
• Trusting a summary of a document you’ll sign. Check the quoted parts in the original.
• Uploading a blurry phone photo. Text the model can’t read leads to guesses.
• Mixing unrelated files in one chat.

When not to use it

For sensitive documents, use a model that runs on your own computer. LM Studio says documents you chat with stay on your machine. See run DeepSeek in LM Studio.

Related: fact-check DeepSeek’s answers.