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How to upload files, photos, and screenshots

Attach the right file, confirm it arrived, and protect the information that should never leave your device.

5-minute read

THE REAL-LIFE PROBLEM

What this guide helps you do

You have a document, photo, or screenshot AI could help explain, but retyping or describing it can leave out the part that matters.

WHEN THIS HELPS

Use it when an AI tool needs to see a file directly so it can summarize, organize, compare, or help you prepare questions.

WHEN TO SKIP IT

Skip it when the file contains information you cannot safely share, when you lack permission, or when a qualified person must review the original.

What you need

A file already saved on your computer or phone. If it is on paper, take a clear photo first.
An AI tool you are signed into. This guide shows ChatGPT, but the basic process is similar in Perplexity, Claude, and Gemini.
One minute to open and inspect the file before you send it.

ONE MAIN PROMPT

Tell AI what the file is and what you need

ONE MAIN PROMPT FOR THE FILE

CONTEXT
I have attached [what it is]. I am trying to [your real goal].

ROLE
Act as a careful document or image reader. Use only what is visible in the attached file and do not guess about missing information.

INTERVIEW
Before analyzing it, ask me up to 3 short questions, one at a time, about what I need, which part matters most, and whether there are other pages or files you should expect.

TASK
1. Confirm the file name or visible subject so I know you received the right item.
2. Summarize what it actually says or shows in plain language.
3. List anything that would cost me money, create an obligation, involve a deadline, or require a decision.
4. Quote the exact wording or identify the visible area for anything important.
5. List what is unclear, missing, or impossible to confirm from this file.
6. Give me the questions I should ask the responsible person before I act.

The four steps, in nearly every tool

Find the plus sign

Look at the box where you type. The attachment control is usually a small plus sign inside or beside that box. ChatGPT and Perplexity currently label it with a plus. Claude and Gemini use the same general location.

You can also drag a file onto the chat box. Images can often be pasted with Ctrl+V on Windows or Command+V on a Mac.

Pick the file from the window that opens

Navigate to the folder where the file lives, then double-click it or select it and choose Open. Synced Google Drive, OneDrive, and iCloud folders can appear here like other computer folders.

Wait for it to finish attaching

The file appears near the message box, sometimes with a spinner. Large files and long PDFs can take longer. Wait until the spinner stops before continuing.

Type your question, then send

The attachment alone does not tell AI what outcome you need. Ask for the result, not merely a description of the file.

Confirm the right file actually went through

This step prevents the most common upload mistake. Check what the tool shows before you press Send.

The full ChatGPT process in 27 seconds with no sound. Waiting time is trimmed, and personal folder shortcuts are blurred. The video shows opening the attachment menu, choosing a file, waiting for its preview, and confirming the correct image before sending.

ChatGPT shows a preview

An image appears as a thumbnail in the message box.
The preview helps when several images look similar.
Use the small X to remove the wrong attachment.

Perplexity shows file details

The file appears as a labeled attachment above the search box.
The name and size help distinguish similar files.
Use the X to remove the wrong attachment.

BEFORE YOU ACT

Verify this before you send

Is this the correct file?
Is it the redacted copy rather than the original?
If you intended to attach several files, are they all visible?
Has the upload indicator stopped?

If anything is wrong, remove the attachment and start again. The file is not part of your message until you send it, although the provider may begin processing the upload before submission.

Size and file-type limits

These details change. Treat this as a current reference and check the official pages when a file is near a limit.

Limit	ChatGPT	Perplexity
Maximum size	512 MB per file, with 20 MB per image and about 50 MB for spreadsheets.	40 MB for all file types.
Common formats	Common text, document, spreadsheet, presentation, and image formats.	Text, code, PDFs, images, audio, and video.
Usage limits	Up to 80 files every 3 hours. Free users are currently limited to 3 uploads per day. Limits can be lowered during peak hours.	Daily allowances vary by plan. Check the current plan information in your account.
Long files	Text and document files are capped at 2 million tokens per file.	Long files may be processed by extracting the parts considered most relevant.

What AI can do with your file, and what you decide

What AI can do

Explain a document in plain language.
Pull dates, amounts, and deadlines into a list.
Compare several documents.
Read visible text from a screenshot.

What you decide

Whether the summary matches the source.
Whether to sign, pay, appeal, or wait.
What requires professional advice.
What was safe and permitted to upload.

When it does not work

What happened	What to try
The file is missing from the folder window.	Change the file-type view to All Files. If it still will not attach, convert it to a supported format.
The upload never finishes.	The file may be too large or the service may be having trouble. Use fewer pages or a focused screenshot, then check the service-status page if the problem continues.
AI cannot read the PDF.	It may be a scanned image without searchable text. Say that it is a scan and ask the tool to read the visible text.
AI answers about the wrong document.	Start a fresh chat with only the file you want.
The answer quotes something not in the file.	Stop and ask for the exact wording and page. If it cannot provide that, do not trust the summary.

Sources and details

OpenAI, File Uploads FAQ, for current ChatGPT file-size, rate, storage, retention, and training guidance.
Perplexity, File Uploads, for the current 40 MB limit, supported formats, drag-and-drop behavior, and long-file handling.

The interface steps were confirmed from the supplied ChatGPT recording made August 3, 2026. Interfaces change frequently and may look slightly different on another device or account.

Important: This guide provides general information, not legal, financial, medical, tax, privacy, or information-security advice. Do not upload employer, client, or third-party documents without permission.

Last checked: August 3, 2026

A considered reminder:

The upload button is easy. Deciding what is safe to put through it deserves your minute. Look at the file before you send it, every time.