A typical semester is 4 months, so you could conceivably get away with just a $50 gift card (14.95 + 4.95 + 14.95 + 14.95 = $49.80). If you tell Chegg that you want to cancel before your first month is up, Chegg will offer you the second month at $4.95. If you use cash, there is no metadata collection. These gift cards are often purchased by people using stolen credit cards, so there is some metadata collection if you purchase a gift card with another card. I would suggest paying with CASH, as this will basically 100% anonymize your transaction. The best way around this is to simply purchase a Visa or Mastercard gift card at a local store. And the name on the card WILL be turned over to your school, if your school files a complaint with Chegg. Chegg does not store your card number, but they do store the name on the card. There have been multiple stories about how people got burned this way. Do not use your personal or parents' debit/credit card to pay for Chegg.
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Recently, I've been fascinated by Chegg and how Chegg will rat you out on the drop of a dime. As an exam proctor, I've actually aided a few students in cheating-telling them to ask to "go to the bathroom" during an exam at exactly 9:30 and I'd be out there, waiting, on my own "bathroom break." I had access to the side of Canvas that only instructors and teaching assistants can see for several years.
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I've been on "both sides" of the whole war-the one raging between professors and students.