Small business owners need to prepare Form 1099s by the end of January of the month following the tax year. The IRS is watching this closely, though, and in many cases disallowing the expenses for contractors unless the Forms have been issued.
We continue to get a number of questions regarding what the rules on issuing Form 1099s is. If you have a question, here is a link to a blog entry from a few years ago. Please read the comments to see what others are asking.