Now that the holiday season has past, I get to prepare myself, as do millions of other US businesses, for the annual printing, mailing and filing of 1099 tax forms.  In prior years, I used a few perl scripts to generate my "Copy B" 1099s prior to the January 31st deadline.  If you are new to 1099s, wikipedia has a descent overview on the subject.

We used to mail "Copy A" 1099s to the IRS, but for the last three years I've been filing them electronically with the IRS's FIRE system.  I prefer their electronic method of processing over the paper one, even on cases when I'm under the mandatory 250 form mark.  One of the best benefits for filing electronically with the IRS is that the deadline for filling is extended a full month (last day of March) instead of the last day of February.  Everything you ever wanted to know about filing 1099 electronically with the IRS can be gleaned from Publication 1220.

This year I discovered that the IRS rolled out a new application called "TIN Matching" under their e-services menu, which allows one to verify taxpayer names to their corresponding taxpayer identification number "TIN".  I'm hoping that by using this service, we will be able to cut down on exceptions.

-Chris