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If you're filing with multiple Schedule Cs, make sure you're using different business codes for each business if they're in different industries! This is on line B of Schedule C. Using the correct business codes helps prevent unnecessary IRS scrutiny. You can find the full list of business codes in the Schedule C instructions. Also, don't forget you might need to file Schedule 2 to report your self-employment tax from Schedule SE, and then the deductible portion of SE tax goes on Schedule 1 as an adjustment to income. Free fillable forms don't automatically carry these numbers over like paid software does.
This is exactly the kind of confusion I had when I started filing my own taxes with multiple businesses! One key thing that helped me was creating a simple checklist: 1. Separate Schedule C for each business (with different business codes as StarSurfer mentioned) 2. ONE Schedule SE that combines the net profit/loss from both Schedule Cs 3. Both Schedule C net amounts should flow to Schedule 1, Line 3 (combined) 4. SE tax from Schedule SE goes to Schedule 2 5. Half of your SE tax becomes a deduction on Schedule 1 The IRS free fillable forms can be tricky because they don't auto-populate like paid software. I always double-check that my Schedule 1, Line 3 equals the sum of both my Schedule C profits/losses before submitting. Don't panic - you're asking the right questions! The fact that you're being careful about this now will save you headaches later. Take your time with each form and make sure the numbers flow correctly between them.
This checklist is incredibly helpful! I'm just starting out with my first year of self-employment and have been overwhelmed by all the different forms. One quick question - when you say "half of your SE tax becomes a deduction on Schedule 1," is that something the forms calculate automatically or do I need to figure that out myself? I want to make sure I'm not missing any deductions I'm entitled to.
I can relate to this frustration! Filed with TurboTax on February 12th and had a similar experience - federal refund came via direct deposit within 10 days, but my Missouri state refund arrived as a paper check last week despite selecting electronic deposit. When I called Missouri DOR, they explained that their system flags certain returns for "enhanced verification" which automatically switches the disbursement method to paper checks. The representative mentioned this happens more frequently during peak filing season when their fraud detection algorithms are more sensitive. Regarding the transcript issue, I'd recommend checking both your Account Transcript AND your Return Transcript on irs.gov - sometimes one updates before the other. Also, make sure you're looking at the 2023 tax year specifically. The IRS phone lines have been swamped, but if you call right at 7am Eastern, you'll have better luck getting through. Don't panic though - this seems to be a common issue this filing season based on what I'm seeing in various tax forums.
Thank you for mentioning the "enhanced verification" explanation from Missouri DOR - that makes so much more sense than the vague "security reasons" I kept hearing! I'm curious, when you called Missouri, did they give you any indication of what specific factors trigger their fraud detection algorithms? I'm wondering if it's something predictable like using a tax prep software for the first time, or if it's more random. Also, great tip about calling the IRS at 7am - I've been trying during lunch breaks and getting nowhere!
I just went through this exact scenario two weeks ago! Filed with H&R Block on February 8th, federal direct deposit worked perfectly, but Missouri sent me a paper check despite selecting electronic deposit. After reading through all these responses, I called Missouri DOR yesterday and got some additional clarity that might help others. The rep told me that their "enhanced verification" system has been particularly aggressive this year due to increased identity theft attempts. She mentioned that even something as simple as using a different browser or device to file compared to last year can trigger their paper check protocol. For the IRS transcript issue - mine took exactly 41 days to show up after filing. What helped me was creating an account on irs.gov and checking both the Account Transcript AND the Wage & Income Transcript. Sometimes the W&I transcript updates first and can give you confidence that they have your information. Also, if you have access to your H&R Block account, check the "Where's My Refund" section - it should show an acceptance confirmation from the IRS even if the transcript isn't updated yet.
11 Our tax attorney recommended we establish a detailed shareholder agreement that requires minimum distributions of a certain percentage of earnings each year. This has helped address potential AET issues by demonstrating we're not unreasonably accumulating earnings. Has anyone else implemented something similar or found other governance approaches that help with these tax issues?
18 We implemented a formal dividend policy that requires distributing at least 30% of annual net income unless the board specifically votes to retain additional earnings for documented business purposes. Our tax attorney suggested documenting the business justification for any retained earnings above that threshold in detailed board minutes. This approach has worked well for us because it creates a presumption that we're not hoarding cash without legitimate business needs. Our accountant said this kind of formal policy demonstrates good corporate governance and makes it easier to defend against potential AET challenges.
As someone who's dealt with similar PHC and AET challenges, I'd recommend focusing on three key areas: documentation, diversification of income streams, and formal governance structures. First, create bulletproof documentation for everything. We maintain detailed investment committee minutes that show our decision-making process, market analysis, and business rationale for each major investment. This helps demonstrate that our activities constitute active business operations rather than passive investing. Second, consider diversifying your income sources beyond traditional investments. We've had success providing family office consulting services to other wealthy families, offering investment research to institutional investors, and even acquiring small operating businesses that complement our investment thesis. These activities help keep passive income below the 60% PHC threshold. Finally, implement formal corporate governance that demonstrates you're operating as a legitimate business entity. Regular board meetings, written policies, employment agreements for family members who work in the business, and documented compensation studies all strengthen your position. The key is being proactive rather than reactive - don't wait for the IRS to question your structure. Build defensible positions from the start.
This is excellent comprehensive advice! I'm particularly interested in your mention of providing family office consulting services to other families. How did you structure those arrangements to ensure they qualify as legitimate active business income? Did you need to establish separate fee structures or formal service agreements? Also, what's been your experience with the IRS's scrutiny of compensation for family members - any specific documentation they tend to focus on during audits?
Has anyone had experience with amending their return before setting up a payment plan? I realized I made a mistake on mine and it might reduce what I owe, but I'm not sure if I should wait for the amendment to process or set up the payment plan now based on what I currently owe.
I'd recommend setting up the payment plan for what you currently owe, then filing the amendment. If your amendment is accepted and reduces your balance, the IRS will adjust your payment plan automatically or you can contact them to modify it. Amendments can take 16+ weeks to process, and you don't want penalties and interest accruing while you wait.
Don't panic! I went through this exact same situation last year owing about $8,200 and it worked out fine. Here's what I learned: First, you absolutely can set this up online - go to irs.gov and look for "Online Payment Agreement" or "Apply for Payment Plan." It's much faster than calling and you'll avoid the crazy hold times during tax season. Since you owe $7,400, you'll definitely qualify for either a short-term plan (pay it off within 180 days with no setup fee) or a long-term monthly plan. If you can swing paying it off in 6 months or less, go with the short-term option to avoid setup fees. For the long-term plan, if you set up automatic bank withdrawals (direct debit), the setup fee is only $31 online versus $130 without direct debit. The monthly payment would be around $200-250 depending on how long you stretch it out. The key thing is to get SOMETHING set up before the deadline, even if you're still figuring out the details. You can always call later to modify the payment amount. The important thing is avoiding the higher failure-to-pay penalties by having an agreement in place. You've got this! It's way more common than you think.
Giovanni Conti
22 Has anyone tried just getting a wage and income transcript directly from the IRS? Sometimes they have your income info from other sources even if the W-2 wasn't properly filed.
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Giovanni Conti
ā¢9 I tried that in a similar situation. The transcript only shows what's been reported to the IRS, so if the employer didn't file anything, there won't be anything on the transcript for that job. That's probably why the IRS is giving extra scrutiny in this case - they can see from other sources (maybe bank deposits?) that there should be income reported.
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Micah Franklin
This is unfortunately becoming more common with larger employers. I had a similar situation with a retail chain a few years back. Here's what worked for me: 1. **Document everything** - Keep records of all your paystubs, any communication attempts with Walgreens, and when you contacted the IRS. This creates a paper trail. 2. **Try multiple channels with Walgreens** - Don't just call HR. Try emailing their corporate payroll department, and if that doesn't work, reach out through their corporate website contact form. Sometimes different departments are more responsive. 3. **Set a deadline** - Give Walgreens a reasonable timeframe (like 10 business days) to provide your W-2, then move to the next step if they don't respond. 4. **File Form SS-8** with the Social Security Administration if you believe you were misclassified as an independent contractor instead of an employee. This sometimes happens with employers trying to avoid their tax obligations. The key is being persistent but methodical. Large corporations like Walgreens have procedures for this, but sometimes you need to escalate to get someone who actually knows what they're doing. Don't let them brush you off with "we'll look into it" - ask for specific timelines and follow-up dates. Your refund will definitely be delayed, but the IRS understands this isn't your fault. Stay on top of it and you'll get it resolved!
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Cass Green
ā¢This is really helpful advice! I especially like the idea of setting a specific deadline for Walgreens to respond. I've been dealing with vague "we'll get back to you" responses for weeks now. Quick question about Form SS-8 - how do you know if you were misclassified? I'm pretty sure I was a regular employee since I had a set schedule, wore their uniform, used their equipment, etc. But is there anything specific I should look for on my paystubs to confirm this? Also, when you say "try multiple channels," did you find that one department was generally more helpful than others? I've only been dealing with the store-level HR so far.
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