I have virtually all my bills set up for autopay from my bank account and I have them synced to come out the day after we get paid. (As a general practice my wife and I always keep two months or so of expenses in our checking account in order to make sure we never have issues with unintentionally over drafting).
Our bank lets us set up automatic bill pay through the bank itself, but we elected to set up the autopay through each of the third parties themselves (cable company, power company, cell phone, student loans, even retirement accounts). My thought was that the utility or other third party themselves would be in a better position than the bank to resolve any issues that might come up if there was some sort of payment glitch.
As far as drawbacks, one of the main concerns I have heard with automatic bill pay is that a third party has access to your bank account, theoretically enabling it to withdraw at will and potentially cause you to be overdrawn and get you hit with overdraft fees. I have not actually heard of anyone I know having issues with this but have read horror on several personal finance blogs about people who paid off their student loans only to have the servicer continue withdrawing money from their account even after the loans were completely paid off. So, in my mind at least, the likelihood of this happening is fairly low. The specific concern about connecting the auto payments to your bank account versus a credit card is that once the money leaves your bank account it is gone whereas with a credit card your own money has not actually gone put the door. Having had to work to get some charges on my debit card reversed recently when it got stolen, I understand what a pain this can be.
I have some of my recurring bills auto paid to my credit card, including a charity I give to monthly, but there is no real rhyme or reason to this. I just set it up several years ago and never bothered to change it to auto pay from my bank account.
Auto paying your bills is a great method for reducing the hassle of paper bills and wasting postage on sending in checks. I would strongly urge you to consider it if you are not currently using it.
Do you pay all your bills automatically? What has your experience with this been?
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