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Scheduled Transactions are marked as paid automatically when you download a transaction from your bank that matches a scheduled transaction in your register.
For example, suppose you have a scheduled transaction for your electricity bill. You scheduled it to be paid on the first Friday of every month. Then later you pay that bill at your bank's website. When Quicken downloads a transaction from your bank account that consists of a payment to your electricity company that took place around the beginning of the month with the same amount as the scheduled transaction, it automatically marks the scheduled transaction for your electricity bill for that month as paid.
If Quicken fails to recognize that a downloaded transaction matches a scheduled transaction, you can match them manually by dragging and dropping one onto the other. Matched transactions are represented by the icon 
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