All classes Claude from Zero to Expert Syllabus · Episode 16 of 100

Claude from Zero to Expert Class #16: Uploading a PDF and Asking About Its Contents

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Learn to upload a PDF to Claude and ask about its contents: attaching the file, effective types of questions, asking for quotes and page numbers, turning a PDF module into practice questions as an Artifact, spotting hard-to-read PDFs, and safety rules for office documents. Episode 16 of 100, Session 4: Working with Files.

Software: Claude
Level: Beginner
Duration: ± 8 min
Series total: 15 h 1 min · 100 videos
Published: October 28, 2026

Episode 16 of 100 · view syllabus

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Claude from Zero to Expert Class #16: Uploading a PDF and Asking About Its Contents: Cover: Claude from Zero to Expert Class #16: Uploading a PDF and Asking About Its Contents

Claude from Zero to Expert Class #16: Uploading a PDF and Asking About Its Contents: Before you start, step list, and Step 1: Attaching a PDF to Claude

Claude from Zero to Expert Class #16: Uploading a PDF and Asking About Its Contents: Steps 2–3: Asking about a contract

Claude from Zero to Expert Class #16: Uploading a PDF and Asking About Its Contents: Steps 4–5: From a PDF module to practice questions

Claude from Zero to Expert Class #16: Uploading a PDF and Asking About Its Contents: Done: summary and further practice

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Transcript

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Introduction

Hi, and welcome to session four: working with files. In the previous session we pasted text into the chat box. Now we give files to Claude directly. In this episode we start with the file used most often at the office: the PDF. We'll learn to attach a PDF, ask about its contents, request page quotes, and turn it into ready-to-use material.

Step 1: Attaching a PDF to Claude

Pasting text is handy, but for a document a dozen pages long, copying it piece by piece is a real hassle. And tables and page numbers get jumbled along the way. The solution is to give Claude the document itself. With the whole file, Claude can read all of it, recognize its sections, and point to the page where a piece of information appears. This feature suits lots of work: reading contracts, comparing supplier catalogs, understanding new regulations, or preparing material from a lesson module. It all starts with one attachment button. It's simple. First, click the attachment button in the chat box. It's usually a paper clip or a plus icon. Second, if the file is on your desktop, you can also drag it straight into the Claude window. Third, wait until the upload finishes. The file name will appear above the message box. Fourth, write your question in the same message, then send it. The file and the question go together. There are limits on file size, page count, and number of attachments. They can differ by plan and change often, so check Anthropic's official documentation. The screens in this video are simulations, and button positions may differ slightly.

Step 2: Asking about a contract

Let's practice with Dewi. This morning she received an email from Nusantara Paper Ltd. with a draft partnership contract for next year. The attachment is a fourteen-page PDF, and Dewi has to respond before November twentieth. Reading a contract this long carefully could take hours. Dewi downloads the PDF. Because a contract is a company document, she first makes sure her office policy allows it to be read with Claude. Dewi attaches the contract PDF and asks for an explanation in five points, complete with page numbers. Claude reads all fourteen pages. This usually takes only a few seconds. The result is five points: the contract term, prices fixed for the first six months, payment in thirty days, a late delivery penalty, and termination. Each point has a page number, so it's easy to check. The penalty section matters most to Dewi. She asks a specific question and requests the original sentence and the clause number. Claude quotes Article seven, paragraph two, on page six: a one percent deduction per day after three working days, up to five percent. Dewi opens page six and matches it. Then Dewi tests Claude with a question about something that might not be in the contract: price increases for imported paper. Claude honestly answers that no such provision was found, and suggests asking the supplier. A not-found answer like this is just as valuable as a complete one. Within minutes, Dewi has an overview of the contract, a verified penalty figure, and one question to discuss with the supplier.

Step 3: The right questions for a PDF

From Dewi's practice, we can define five types of questions for a PDF. First, an overview with page numbers, as a map of the document. Second, find specific information, such as when the payment deadline is, or who is responsible for delivery. Third, ask for the original quote and the clause number for anything involving money, dates, or obligations. Fourth, ask about something that might not be there. This trains us to tell answers that come from the document apart from answers that are just guesses. Fifth, match it to your needs. For example: which parts of this contract are the riskiest for a small distributor like us? That fifth question is very helpful, but remember that Claude isn't a lawyer. For important legal decisions, take what you discussed with Claude to a legal expert or your manager. Those five question types can be wrapped into one template. The context block names your role and the type of document attached, such as a supplier contract or a lesson module. The task block holds one question. One question per message usually gets a more careful answer than five questions at once. The format block asks for a short answer, followed by the original sentence and its page or clause number, so it's easy to check. The limits block asks Claude to answer only from the document, and to say not found when the information really isn't there. Save this template in your prompt notes, together with the five writing templates from the previous session.

Step 4: From a PDF module to practice questions

Now another example. Mr. Hendra uploads a fractions module for fifth grade, then asks for four practice questions from pages twelve to eighteen, going from easy to medium. Claude reads the thirty-two-page module, then focuses on the pages requested. The right panel shows the practice questions as an Artifact. Each question has its source page, there's a word problem close to everyday life, and a button to show the answer key. The source pages make it easy for Mr. Hendra to check that the questions match the material. He still works through all four himself before sharing them, because the answer key needs checking too. You can use the same approach for other needs: an SOP becomes a checklist, a supplier catalog becomes a price table, or company rules become a Q&A for new employees.

Step 5: Difficult PDFs and safety rules

Not every PDF is equally easy. A PDF with regular text, like the contract earlier, is the easiest to read. Its risk of mistakes is the lowest. Scanned PDFs or photos are riskier. Letters and numbers can be misread, especially if the scan is crooked or blurry. Use a clear scan, and check the numbers. Complex tables are risky too, because columns or rows can get swapped. Ask Claude to turn it into a table, then match a few rows against the original. For very thick documents, small details can be missed. Ask questions chapter by chapter or section by section, not about the whole document at once. The principle is the same: the harder a document is to read, the more important it is to match Claude's answers against the original. Finally, the safety rules. First, follow your office policy on which documents may be read with AI. If there's no rule yet, ask your manager first. Second, mask personal data, salary data, and account numbers before uploading. Claude doesn't need them to answer most questions. Third, match important numbers and quotes against the original page, just as Dewi did with the penalty clause. Fourth, important legal and financial decisions still go through the experts. Claude helps you understand; it doesn't replace a lawyer or an accountant. Fifth, learn your account's privacy settings, including how to delete conversations. The details can change, so read them on Anthropic's official pages. With these five rules, PDFs become a very fast source of work, without sacrificing the security of office documents or your coworkers' trust.

Done!

We've learned to attach a PDF, ask about a contract with quotes and page numbers, use five types of questions for a PDF, turn a module into practice questions, and spot difficult PDFs and safety rules. In the next episode we move from documents to numbers: reading Excel and CSV data, starting with Sunset Coffee's sales data. See you there!

Practice exercises

Try these on your own after watching to lock in what you learned.

Upload one PDF and ask for a five-point overview with page numbers
Ask one specific question and request the original sentence as a quote
Turn one section of the PDF into a checklist, a summary, or practice questions as an Artifact

Ask the class material

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Memuat

Claude from Zero to Expert Class #16: Uploading a PDF and Asking About Its Contents

2 views

Software

Claude

Level

Beginner

Duration

± 8 min

Series total

15 h 1 min · 100 videos

Published

October 28, 2026

Episode 16 of 100 · view syllabus

Unlock All Premium Classes

▶ Watch the video lesson1 plays

Transcript

The full narration of this video. The current sentence is highlighted while the video plays; click any sentence to jump there.

Show transcript

Introduction

Step 1: Attaching a PDF to Claude

Step 2: Asking about a contract

Step 3: The right questions for a PDF

Step 4: From a PDF module to practice questions

Step 5: Difficult PDFs and safety rules

Done!

Your instructor

Cerdas Inovasi Digital Team

Software developers, BIM & 3D engineers, and AI practitioners

53 video classes1,296 episodes

See our clients →

▶ Video Lesson

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Transcript

0:03Introduction

0:26Step 1: Attaching a PDF to Claude

1:44Step 2: Asking about a contract

3:27Step 3: The right questions for a PDF

5:02Step 4: From a PDF module to practice questions

5:53Step 5: Difficult PDFs and safety rules

7:40Done!

Practice exercises

Ask the class material

My notes

Questions & answers

Your instructor

▶ Video Lesson

Recommended classes for you

Need more than a video?

Transcript

0:03Introduction

0:26Step 1: Attaching a PDF to Claude

1:44Step 2: Asking about a contract

3:27Step 3: The right questions for a PDF

5:02Step 4: From a PDF module to practice questions

5:53Step 5: Difficult PDFs and safety rules

7:40Done!

Practice exercises

Ask the class material

My notes

Questions & answers

Your instructor

Introduction

Step 1: Attaching a PDF to Claude

Step 2: Asking about a contract

Step 3: The right questions for a PDF

Step 4: From a PDF module to practice questions

Step 5: Difficult PDFs and safety rules

Done!

Introduction

Step 1: Attaching a PDF to Claude

Step 2: Asking about a contract

Step 3: The right questions for a PDF

Step 4: From a PDF module to practice questions

Step 5: Difficult PDFs and safety rules

Done!