Rookie mistake and lesson learned! I now know I should have had the contractor complete one prior to paying him.

What are my options now? I paid him about $800. He's been saying he'll complete a W9 for the past 2+ months with no action.

I did some research online and see different recommendations for what to tell him (i.e. telling him it's required by law, telling him I'll file a partially completed form stating he refused to complete it, telling him his info will be on my taxes anyway so the IRS will have it, etc.). I've also read that some folks advise to send contractors who won't complete a W9, a 1099 MISC. I don't know that form well yet, but if they won't complete a W9, why would they complete this form?

As Doogie says, this guy has more to lose than you do.

If he doesn't comply, all you have to do is report him to the taxing authority and they will probably see that as a red flag and go after him. He MUST claim his income.

You, on the other hand, are not obliged to claim an expense. If you simply decide not to take a deduction for the $800 paid, it's no skin off your teeth.

I'd try the carrot approach first. "Hey Bob, we need to get this W-9 form done today. We don't want the IRS causing you any problems for not reporting income. I've got a copy and can meet you today to get it done!"

Then if he fails to comply or gets horsey, you can always try, "Bob, I've got to claim this as an expense so I'll be sending it in under your name with my tax filings with or without your tax ID number. I sure don't want to cause you any problems so let's just take care of this today over a beer....my treat!"

He has already decided to be a thief and liar.

He does not care if you or your family suffers.

You are not going to change him.

If he has done this to you he does it to everyone.

You, me and the rest of the honest people have to pay more because he wants to steal from us.

He does not care!

He won't stop.

He will enjoy a better lifestyle while you have a poorer lifestyle.

Next contact: dear so and so I need your information so I can fill out your W9 for the 800,000.00 I paid you for the last job.

If no response-- send in 1099 for 800,000.00. Oops hate when that happens-- I made a mistake when I mailed this to IRS-- HOPE IT DOESN'T CAUSE U A PROBLEM?????

If you paid by check you can deduct the expense and worst case if audited the deduction will be disallowed.

I am not a tax professional, but I also had a contractor refuse to give me his tax ID for a 1099 form. I completed the 1099 as required and sent it in. In my records, I printed out and attached copies of my two emails to him requesting his tax ID.

May not work for you, but hang out a carrot something like "....if you do not complete the W-9 as requested, I will not be able to use your services in the future....". Also, try to get the W-9 up front; if that fails, I tell them I have a check ready for them (enclose a copy of the signed check) and I will release the check when I get their W-9 (and insurance certificate)! Works like a charm.

Take the $800 deduction and let the IRS decide to audit you and ask for receipt and find the missing 1099. Very low chance you'll be caught for a one time miss. The IRS agents need to recover $1,000 per day they audit you to make it worth their time. $1,000 recovered requires $8,000 to $10,000 worth of your screw up.

There is a lot of advice here that seems to be based not on the law, but on the idea that you should work around the law and/or just hope you don't get caught. If you want to go that route (and I actually agree that it sometimes makes sense), then go for it.

If you want to follow the law, my understanding is that you have to start backup withholding immediately.

Here is what I found (and have seen multiple times over the years when I looked into this before):

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If a payee refuses or neglects to provide a TIN when properly requested by a business, the business should immediately begin backup withholding, at the rate of 28 percent, on any reportable payments made to the payee (and remit this amount to the IRS).

The business should also make up to three solicitations to the payee for the payee’s TIN, in order to avoid a penalty for failing to include a TIN on the Form 1099 information return filed by the business.

Finally, if a contractor, vendor, or other payee refuses or fails to provide his taxpayer identification number, the business should still fill out and timely file its 1099 information return(s) with a notation that the payee failed or refused to provide his taxpayer identification number. Failure to file Form 1099 based on a person’s refusal or failure to provide his taxpayer identification number does not excuse the business from timely filing all required information returns.

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Of course, someone else will come and say that we never have do to 1099-MISC anyhow, so none of this matters. That has been an ongoing, multi-year debate that usually comes down to "no one can find any case law or IRS record where a landlord was fine for not filing them." So, that's your call too. Good luck!

- John...

Chris: The real problem is that you already paid him. So, the IRS sees it like this: BEFORE YOU PAY, you need to request a W-9 from them. If they fill it out, great -- you're all set. If they refuse to do so (and you ask at least 3 times), then you should pay them what you owe them MINUS 28% withholding and pay that to the IRS.

That is basically how they see it.

Of course, in your situation (which LOTS of us have probably be in before) is that you already paid them. So, it isn't like you can claw back that 28%.

In any case, I'd do like what RentsDue says. :)

- John...

Thanks everyone. What do you think of this message to the contractor?

I know you’ve been trying to get me the W9 for a number of months now. I wanted to give you a heads up that I'm about to start passing much of my 2018 rental info to my tax accountant so he can get started on things.

He needs to file a 1099 MISC for the service you provided (based off the receipt I have on file). Some of the info he needs comes from the W9. Unfortunately, if we don’t receive it, he’ll have to note on the 1099 that you refused to provide the information (along with copies of the emails and texts saying you'd provide it). Just don’t want the IRS causing you any problems which is why I’m sending you this final email. Anyway, if I don’t hear back from you by Sunday, please know this is the route we’ll be talking.