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Use this feature if your bank has it and it saves you time and stamps. Your bills are paid quicker and you can even set them to autopay. Of course, this means that your transactions are out there in space.
I have been using my bank's web billpay service for 5+ years and have never had an issue with a bill or payment. One time my past landlord's wife threw away a check and the money was back in my account in 24 hours and a new check sent to him. We bank with USAA and they have the best customer service.
I don't like paying at each individual utility/credit card because it is easier to have everything in one location.