If a title company tells us they will issue the 1099, do we allow them to do it or should we be the one issuing it? And should we issue a 1099 to the title company, the same as we do for attorney fees, since we don't always know who the beneficiary is?

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Unless you have some kind of documented agreement stating that the title company will take the responsibility to issue the 1099, you should issue the 1099. You do not need to issue a 1099 to the title company, even if the title company were to issue the 1099 to the seller.

As for attorney reporting, the IRS specifically requires reporting of payments to attorneys, even in the case of a settlement in which the attorney is not the beneficial owner. Attorney reporting is in its own separate category. The answer we provided was corroborated by Ms. Hord at the IRS (with whom we raised the same question about this being “like” an attorney payment).   

You might wish to speak to the IRS’s information reporting customer service center in Martinsburg, WV directly. You can reach them at (866) 455-7438.

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