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One thing nobody mentioned yet - make sure you're addressing both federal AND state taxes. Each state has different rules about how far back you need to file and penalties for late filing. I was in a similar situation (4 years unfiled) and got federal sorted out only to get blindsided by my state tax authority, which was actually much more aggressive than the IRS. Check if your state has a voluntary disclosure program too - many do.
That's a really good point I hadn't even considered. I've lived in the same state this whole time, but I should definitely look into their policies. Is there an easy way to find out about state voluntary disclosure programs?
The easiest way is to just google "[your state] tax voluntary disclosure program." Most state tax department websites have a section for this. Some states are surprisingly forgiving if you come forward voluntarily. Be aware that some states have shorter lookback periods than the IRS. For instance, my state only required me to file 3 years back, even though federally I had to do 6 years. Some state programs will waive penalties but not interest on what you owe.
I went through this after 7 years of not filing. Here's what surprised me: for most of those years, I was actually owed refunds! I ended up getting money back for 3 of the 7 years, even after penalties. Since you mentioned having maximum withholding, you might be in a similar situation. I used TurboTax for the more recent years and a CPA for the older, more complicated ones. Cost me about $1200 total for professional help with 4 years, which was worth it for the peace of mind. Don't panic about criminal charges - those are extremely rare and typically only happen in cases of deliberate fraud or extremely high dollar amounts. The IRS mainly wants compliance and their money.
Did you file all 7 years at once or space them out? I heard you should do the most recent ones first.
Don't feel bad! I've been in tax for 7 years and international issues still trip me up sometimes. What helped me was finding a mentor who specifically worked with expatriate tax issues. Have you tried asking if there's someone at your firm who would be willing to have brief pre-review sessions with you? Sometimes catching mistakes before formal submission can help you learn faster without the embarrassment of official review notes.
That's a good suggestion. There's a senior manager who seems approachable - maybe I could ask her if she'd be willing to do quick pre-reviews for me on the more complex returns. Did you find your mentor within your firm or through a professional organization?
I found my mentor within my firm initially, but I also connected with another experienced expatriate tax professional through our local CPA society's international tax committee. Professional organizations like that are goldmines for finding people who are willing to help. My in-firm mentor would spend 15 minutes with me before I submitted anything complex, which cut my review notes down dramatically. The external mentor was great for bigger-picture career advice. Don't underestimate how willing people are to help someone who shows genuine interest in improving!
Has anyone tried supplementing their knowledge with specialized training? I found that the general CPE courses don't really cover expatriate taxation in enough detail to be useful.
Filling out a W-9 is super easy! Just make sure you use your legal name that matches your social security card. And don't forget to sign and date it! One important thing: the company asking for your W-9 isn't actually sending any money to the IRS on your behalf - they're just reporting what they paid you. You'll be responsible for paying all your own taxes. If this is your first job, you might not realize how much you should set aside. I'd recommend saving about 25-30% of everything you earn for taxes if you're doing this kind of contract work. Trust me, you don't want to be shocked next April when you realize you owe a bunch of money!
Thanks for the tip about saving for taxes! Do you think I should open a separate savings account just for setting aside tax money? Also, do you know if I need to make quarterly payments or can I just pay everything when I file next year?
Opening a separate savings account for taxes is honestly one of the smartest moves you can make! I wish I had done that when I first started freelancing. It helps you mentally separate that money so you're not tempted to spend it. For quarterly payments, it depends on how much you'll earn this year. If you expect to owe more than $1,000 in taxes for the year, you should make quarterly estimated payments. Otherwise, you might get hit with an underpayment penalty. The IRS has a form called 1040-ES that helps you calculate these payments. As a new freelancer, it's definitely worth looking into since you don't have an employer withholding taxes from each paycheck.
Is there a difference between a W-9 and a W-4? My brother says I should be filling out a W-4 instead but the company specifically asked for a W-9.
They're totally different forms for different work relationships. A W-4 is for employees (people who get a regular paycheck with taxes already taken out). A W-9 is for independent contractors (people who get paid the full amount and have to handle their own taxes). If the company is asking for a W-9, that means they're treating you as an independent contractor, not an employee. This affects your taxes a lot - you'll pay more in self-employment taxes, but you can also deduct business expenses. Make sure this classification is correct for the type of work you're doing!
I went through this same identity verification nightmare last year! What finally worked for me was sending in Form 14039 (Identity Theft Affidavit) by certified mail with copies of my ID. Even though I hadn't actually had my identity stolen, this form triggers a manual review of your case and gets assigned to the Identity Theft department. About 3 weeks after sending it, I got a call from an IRS identity theft specialist who worked with me to verify my identity and release my refund. The whole process took about 6 weeks from mailing the form to getting my refund, but at least it worked!
Wouldn't filing an identity theft form when your identity wasn't actually stolen cause more problems? I'm worried that might flag my account in a bad way for future years.
That's a good question. When you can't verify your identity through normal channels, the IRS actually recommends filing Form 14039 with the box checked for "I received a notice from the IRS and believe someone may have used my SSN." Since you received notices about identity verification, this is technically accurate. It doesn't create problems for future years - actually, it creates an extra layer of protection. After resolving my case, they added additional security to my tax account and gave me a special PIN to use for future filings. Made me feel more secure, honestly!
Does anybody know if going to the appointment with a TAX PRO who prepared your return helps with these identity verification issues? My cousin said her accountant went with her and it made everything go smoother.
I'm a tax preparer and yes, this can definitely help! If we prepared your return, we can go with you to the appointment and bring our records which often helps verify everything more quickly. We can also contact the Practitioner Priority Service on your behalf, which is a special IRS hotline only for tax professionals that usually has much shorter wait times.
Micah Trail
7 Something similar happened to my father last year. It turned out to be a legitimate letter but the amount was incorrect due to a missed 1099 form. A couple things to check: 1) Did your grandmother have any unusual income last year - like selling investments, taking an early withdrawal from retirement, or receiving unemployment? 2) Is there any way she could have forgotten to report some income? The IRS computers automatically match reported income from employers/banks against what's on tax returns. 3) Did she receive any prior notices? The IRS usually sends several notices before demanding payment. Ask her to check her mail carefully - sometimes people miss the earlier notices or don't understand what they mean.
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Micah Trail
ā¢19 This is great advice. My mother got a letter because she forgot about a small stock sale that generated a capital gain. The brokerage reported it to the IRS but she forgot to include it on her return. Does your grandmother have any investments or retirement accounts?
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Micah Trail
ā¢7 Both great questions! For unusual income, she did sell some stocks last year after my grandfather passed away. She's not very financially savvy and has been relying on their longtime accountant who's getting up there in age himself. Regarding prior notices, that's actually very possible. She doesn't open all her mail right away and sometimes sets aside things she doesn't understand. I'm going to visit her tomorrow and go through her mail from the past few months to see if there were earlier notices. The investment angle seems most likely based on your experiences. I'll definitely check on that specifically when I see the letter. Thank you both for the helpful suggestions!
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Micah Trail
16 Be really careful about this - my grandfather almost fell for a similar scam last summer. The giveaway was that they wanted payment in gift cards (which the IRS NEVER does). What kind of payment method does the letter request?
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Micah Trail
ā¢6 Those gift card scams are terrible! My neighbor fell for one of those and lost $2000. Definitely check the payment methods requested. The real IRS offers multiple payment options and NEVER asks for gift cards, wire transfers, or cryptocurrency.
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