Are single owner delivery companies the same as a freight company when it comes to 1099s? Are they not to be reported?

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A. I spoke to information agent Mrs. Kerns (ID# 1002856258).

The issue is not whether the freight company is a single proprietorship or something else, but rather whether you are paying for freight or for deliveries. The difference is, according to Mrs. Kerns, that freight transport is paid by the pound, the mile, etc.; in other words, you're paying to transport goods from one place to another. Delivery charges are those in which you pay a driver directly for a service. 

As you know, in the case of freight, it's not reportable per the first page of Instructions for Form 1099-MISC (https://www.irs.gov/pub/irs-pdf/i1099msc.pdf). So if what you're paying for is freight transport, it doesn't matter whether it's a single person performing the services--you don't need to report it. If you're paying a delivery driver for his or her services, then you would report. 

However, it's worth noting that if in doubt, you're better off reporting when you don't need to than failing to report when you do. 

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