This thread has been incredibly helpful! I just wanted to add one more perspective as someone who works in payroll - the issue you're describing is extremely common and often catches people off guard. For your in-laws' situation with $87k combined income, the mathematical reality is that their effective federal tax rate should be around 10-12%, which means they should expect to pay roughly $8,700-$10,400 annually in federal income taxes. The problem occurs because each employer's payroll system calculates withholding in isolation. Here's a simple way to think about it: if your father-in-law makes $50k and your mother-in-law makes $37k, his employer withholds as if he's single making $50k (putting him mostly in the 12% bracket), and her employer does the same for $37k (keeping her in the 10-12% brackets). But when you file jointly, that $87k combined pushes portions of their income into higher brackets than what was actually withheld. The quickest fix while you sort out the W4s: take whatever they owed last year, divide by their remaining pay periods this year, and add that as extra withholding immediately. This prevents another surprise while you implement the proper long-term solution using the IRS withholding estimator.

I've been helping people with similar withholding issues for years, and your in-laws' situation is unfortunately very common. For an $87k combined income with married filing jointly status, they should expect to pay around $9,000-$11,000 in federal taxes annually. The core problem is that when both spouses work, each employer calculates withholding as if that's the only income in the household. So if one makes $50k and the other $37k, each employer withholds at lower rates than what their true combined tax bracket requires. Here's my recommendation: First, use the IRS Tax Withholding Estimator tool immediately - it's free and designed exactly for this situation. Input both of their current pay stubs and it will give you precise numbers for additional withholding. As a temporary fix while you're sorting out the W4s, calculate last year's total tax owed, divide by their remaining paychecks this year, and have that amount withheld extra. This prevents another surprise bill while you implement the proper solution. For the new W4 forms, make sure they both complete Step 2 (the multiple jobs section) properly - either check the box or use the worksheet. This is crucial and often overlooked!

Just wanted to add another option for getting your old W2s - you can also call the IRS directly at 1-800-829-1040 and request a "wage and income transcript" over the phone. This saved me when I couldn't get the online account verification to work. When you call, have your Social Security number, date of birth, and current address ready. The agent will verify your identity and can immediately send you the wage and income transcripts for the years you need. They'll mail them to your address on file, which usually takes about 5-10 business days. The transcripts show all the W2 information that was reported to the IRS - your wages, federal tax withheld, Social Security wages, etc. It's basically everything you need to file your taxes except for state withholding (as others mentioned). I had to do this for 2016-2018 myself, and while the phone wait was long (about 2 hours), the actual process once I got through was really straightforward. The IRS agent was helpful and not judgmental at all about me being behind on my filings.

I went through this exact same situation last year - hadn't filed from 2016-2019 and was completely overwhelmed by where to start. Here's what worked for me: First, definitely get those wage and income transcripts from the IRS as others mentioned. I used the online method through IRS.gov which was instant once I got my account set up. The identity verification can be tricky - you need to answer questions about your credit history, but it's worth persisting through it. One thing I wish someone had told me earlier: don't panic about the penalties and interest. Yes, they add up, but the IRS has payment plan options and sometimes even penalty relief programs if you can show reasonable cause for not filing. I was so stressed about owing thousands in penalties, but once I actually filed everything and talked to them, we worked out a manageable payment plan. Also, file your returns in order (2016 first, then 2017, etc.) because sometimes the refunds from earlier years can offset what you owe in later years. I actually got refunds for two of the years that helped cover the penalties on the others. The whole process took me about 3 months from start to finish, but honestly the relief of finally being caught up was incredible. You've got this - taking the first step by asking for help here shows you're ready to tackle it!

I've been through this exact situation with my family restaurant LLC. What worked best for us was setting up clear independent contractor agreements with each family member based on their specific roles and level of involvement. For my mom who helps with bookkeeping twice a week, we created a 1099 arrangement with defined deliverables and hourly rates. For my brother who only helps during busy seasons, we structured it as project-based contractor work. The key things that helped us stay audit-proof: 1. Written contracts specifying exactly what work they'll do 2. Separate invoicing from them to the business (even though they're family) 3. Market-rate compensation - we researched what we'd pay non-family for the same work 4. Clear documentation that they control how/when the work gets done We've been doing this for 3 years now with no issues. The IRS agent I spoke with said family businesses get scrutinized more, so having everything documented properly from the start is crucial. One thing to avoid - don't try to disguise what are essentially wages as "consulting fees" if they're working regular hours under your direction. That's a red flag that can trigger an audit.

One thing I haven't seen mentioned yet is the self-employment tax implications for your family members. If you pay them as independent contractors (1099), they'll owe self-employment tax on those payments, which is about 15.3% on top of regular income tax. If you hire them as W-2 employees instead, you'd split the employment taxes with them (you pay half, they pay half through payroll withholding). Depending on how much you're planning to pay them, this could make a significant difference in their take-home amount. Also, make sure you're not inadvertently creating a "reasonable compensation" issue for yourself. The IRS expects single-member LLC owners who elect S-corp treatment to pay themselves reasonable wages before taking distributions. If you're paying family members but not taking a salary yourself, that could raise questions. Have you considered what election your LLC has made for tax purposes? That might influence the best approach for structuring these payments.

One important thing to keep in mind is that you need to receive Form 1098-T from your daughter's school to claim education credits. The school should send this by January 31st showing tuition and fees paid during the tax year. However, don't just rely on the 1098-T amounts - sometimes the form shows payments received by the school rather than what you actually paid. You should use your actual payment records (receipts, bank statements, etc.) to determine the correct amount of qualified expenses. Also, remember that room and board don't qualify for education credits, only tuition, fees, and required course materials like textbooks. Some people mistakenly try to include housing costs which can trigger IRS scrutiny later.

This is such a helpful thread! I'm in a similar situation with my son starting his sophomore year. One thing I learned the hard way is to keep detailed records throughout the year, not just wait until tax time. I created a simple spreadsheet tracking all education payments - tuition, fees, required textbooks, lab fees, etc. - along with dates and payment methods. This made it so much easier when I needed to verify amounts against the 1098-T form. Also, if your daughter buys textbooks from sources other than the school bookstore (like Amazon, used book sites, etc.), make sure those receipts clearly show they were required for her courses. The IRS can ask for documentation proving the books were actually required, not just recommended reading. One last tip: if you're paying tuition in December for spring semester, those payments count toward the current tax year's education credits, not the following year when the classes actually happen. The timing is based on when you pay, not when the education occurs.

mine always updated on fridays around 3am est but idk if thats the same for everyone

I feel you on the anxiety! I've been there checking every hour like it's going to magically change 😅 From what I've experienced, transcripts usually update overnight Thursday into Friday, but it's not set in stone. Sometimes they update mid-week or skip weeks entirely. The IRS systems are pretty unpredictable. My advice? Check once in the morning and try to resist the urge to refresh all day - easier said than done I know! The updates happen when you're sleeping anyway so you're not missing anything by checking constantly.