When to dispose of check stubs

On tax records, many people would say just three years as that is the longest timeframe the IRS can generally go back and audit you. Three years would not be sufficient, however, as the IRS can go back much longer than this if you are suspected of subtantially under reporting your income or other tax fraud. This is a tough one, but I think five to seven years is a good guideline here.

The answer here will have a lot to do with how you pay your ongoing monthly obligations. If you use a checking account or online bill pay, you probably don't need to retain your bills or monthly statements after they are paid. Of course, if you are claiming a tax deduction for a particular item you would need to retain it as outlined in #1 above. Some would suggest holding on to statement for paid bills in a file for a few months, or even as long as a year (and I have no issue with this recommendation). I don't see any reason, however, for warehousing these statements for years and years. If you pay your bills in cash and have concerns about being able to prove you made a payment down the road, you would have a legitimate reason to keep your statements for maybe two to three years for this purpose (or at least your payment receipts).