Slightly different take - I've been a FreeTaxUSA user for years and they actually have a feature that lets you enter multiple 1099-INTs from the same institution but keeps them as separate line items on the final Schedule B. Look for the "Add Another Interest Payer" button after you enter the first one, and make sure to use the same payer name but fill in the amounts from each form separately.

Great discussion everyone! Just wanted to add that if you're using FreeTaxUSA and decide to enter them separately (which I agree is the safest approach), make sure to double-check that the software isn't automatically combining entries from the same payer. I've seen tax software sometimes consolidate entries behind the scenes, which could create the exact matching issue you're trying to avoid. Also, keep copies of all your 1099-INT forms even for small amounts. If you do get a notice later, having the original documents makes resolving any discrepancies much easier. The IRS automated matching system can sometimes flag things that look perfectly fine to a human reviewer. For $6 in interest, you're probably overthinking it, but your cautious approach will definitely save you potential headaches down the road!

Emma, I can definitely relate to feeling plateaued in government work! I made the switch from IRS Revenue Agent to a boutique tax consulting firm about 2 years ago and it's been one of the best decisions of my career. What really helped me was networking with other former IRS employees who had already made the transition. They gave me realistic expectations about the adjustment period and helped me understand which firms truly value our background versus those just looking for warm bodies during busy season. One thing I wish I'd known earlier - don't undersell your investigative and analytical skills. Private firms love that we know how to dig deep into complex financial situations and follow paper trails. That experience goes way beyond just knowing the tax code. My advice would be to start networking now, even before you're ready to leave. Attend local tax professional meetings, reach out to former colleagues who've left the IRS, and maybe even consider getting your CPA if you don't already have it. The transition takes time, but your experience is definitely valued in the private sector. Feel free to reach out if you want to discuss specific firms or have questions about the interview process. The government-to-private transition can feel overwhelming, but you've got skills that are in high demand right now!

Emma, as someone who recently made the transition from IRS Collections to private sector tax consulting, I can't emphasize enough how valuable your audit experience is! The knowledge you've gained about IRS procedures, examination techniques, and what really triggers compliance issues is incredibly marketable. One area that might be perfect for your background is working with high-net-worth individuals and family offices. These clients specifically seek tax professionals who understand audit risk from the IRS perspective. Your 7 years of experience means you can help them structure their affairs to minimize examination likelihood while staying fully compliant. I'd also suggest looking into roles with regional CPA firms that have dedicated tax controversy practices. They often pay premium salaries for former agents because your insider knowledge of IRS operations gives their clients confidence during difficult situations. The salary bump is real - I saw about a 55% increase from my government pay, plus performance bonuses that were never possible in federal service. The learning curve isn't too steep since you already understand the technical aspects; you're mainly adjusting to client service expectations and private sector pace. Start building your LinkedIn presence now and consider reaching out to recruiters who specialize in tax professionals. Many of them have specific searches for former IRS employees. Your timing is actually perfect - with all the recent tax law changes and increased IRS enforcement, firms are actively seeking people with your background. Best of luck with the transition!

This is a really important issue that affects local tax revenue and fairness. I've seen similar situations in my area where religious organizations were claiming exemptions on properties that clearly didn't qualify. One thing to keep in mind is that even if a church owns property, each individual property needs to meet the exemption criteria independently. Just because the organization has tax-exempt status doesn't automatically exempt every piece of real estate they own. The "primary use" test is critical - if these houses are primarily being used as rental income properties rather than for religious purposes, they should be on the tax rolls. I'd suggest starting with your county's online property records system (most counties have these now) to confirm the current exemption status and see what exemption code is being used. This will help you understand exactly what the church is claiming and give you specific information when you contact the assessor's office. Also, don't hesitate to reach out to your city council member or county commissioner if you don't get a satisfactory response from the assessor's office initially. Elected officials are often very responsive to property tax fairness issues since it directly impacts local budgets and services. Good luck with this - you're doing the right thing by looking into it!

I actually work in property tax assessment, and this is exactly the kind of situation we see frequently. What you're describing sounds like a clear case of improper exemption use. Religious organizations can only claim property tax exemptions on properties that are used "exclusively for religious purposes" - and that specifically excludes income-producing rental properties. The fact that these houses are actively being advertised for rent and the church isn't even local makes this particularly egregious. In our jurisdiction, we've found that some organizations deliberately purchase rental properties in different cities to avoid scrutiny from their home congregation or local officials. Here's my advice: Before you contact anyone, gather solid documentation. Take screenshots of any rental listings with dates, print out the property records showing the church as owner, and note the exemption codes being used. Most county assessor websites will show you exactly what exemption is being claimed. When you call the assessor's office, ask specifically for the "Exemptions Review Department" and mention you want to report a "potential improper religious exemption on rental property." Use those exact words - it will get you to the right person faster. They take these reports seriously because improper exemptions directly impact county revenue and shift the tax burden to other property owners. Don't worry about seeming petty or anti-religious - you're helping ensure tax law is applied fairly to everyone.

One additional consideration that might help with your decision: if you're planning to reinvest the proceeds from your loss sales, think about the broader market timing aspect. Since you mentioned you're "cleaning up your portfolio," this could be a good opportunity to not just harvest losses but also rebalance toward investments you actually want to hold long-term. For the short-term vs long-term loss question specifically - if you're truly torn between which losses to realize and don't have gains to offset, I'd lean toward taking the short-term losses first. Here's why: those positions haven't had much time to potentially recover, and if you're already unhappy with them after less than a year, they might be the weaker investments anyway. Also, if any of those short-term losers are individual stocks (vs diversified funds), selling them removes company-specific risk from your portfolio. You can always reinvest the proceeds in broader market funds after waiting out the wash sale period. Just make sure to document everything well for tax time - keep records of your purchase dates, sale dates, and the specific tax lots you're selling, especially if you're doing any tax-loss harvesting across multiple positions.

Most major brokerages like Fidelity, Schwab, and Vanguard will provide you with a 1099-B form that has all your sales data, but I'd still recommend keeping your own spreadsheet as a backup and for planning purposes. Here's what I track in my own loss harvesting spreadsheet: purchase date, purchase price, sale date, sale price, holding period (ST/LT), and the specific reason I sold (tax loss harvesting vs portfolio rebalancing, etc.). This helps me stay organized during tax season and also helps me learn from my investment decisions. The brokerage 1099-B will have the legally required info, but having your own records helps you double-check their math and gives you better visibility into your overall tax strategy. Plus, if you're selling specific tax lots (like selling your highest-cost shares first), you want to make sure the brokerage processed those instructions correctly. One more tip since you mentioned individual stocks - consider setting up a "watchlist" of the stocks you're selling so you can monitor them during the 31-day wash sale period. Sometimes seeing how they perform after you sell them helps reinforce whether it was a good decision or teaches you something for next time. Just don't let FOMO trick you into buying back too early and triggering the wash sale rule!

This is such a valuable thread! I'm dealing with the exact same situation right now - been on F1 OPT for 8 months and my employer has been withholding about $250/month in FICA taxes despite me bringing it up multiple times. What's really frustrating is that my company's HR department keeps saying "we treat all employees the same" and doesn't seem to understand that this is actually a legal requirement, not just a preference. I've shown them my I-94 and EAD card, but they keep insisting their payroll system "doesn't have options" for tax exemptions. Reading through all these responses, it sounds like the key is really pushing back with official documentation and framing it as a compliance issue rather than just a student request. I'm definitely going to try the comprehensive packet approach that @ca96349f75f6 mentioned - seems like having everything in one official-looking package makes a huge difference. Has anyone had success with larger corporations (Fortune 500 type companies)? I'm wondering if bigger companies are more resistant to making these changes because they have more bureaucracy, or if they're actually easier to work with because they have more sophisticated payroll systems.

I've been following this thread closely as I'm dealing with the exact same FICA withholding issue on my F1 OPT! Just wanted to share what finally worked for me after months of back-and-forth with my employer. The breakthrough came when I stopped focusing on HR and went directly to our company's external payroll vendor (in our case, it was Paychex, not ADP). I called their customer support line and explained that my employer needed to set up a FICA exemption for a non-resident alien employee. The Paychex rep immediately knew what I was talking about and walked me through exactly which tax codes needed to be changed. They even offered to do a three-way call with my HR department to walk them through the system changes! Turns out there's literally a checkbox in their system for "NRA FICA Exempt" that my HR team had never noticed. The whole thing was resolved within one business day once we got the payroll vendor involved. I think sometimes company HR departments just don't know their own payroll systems well enough to handle these specialized situations. For anyone still struggling with this, I'd definitely recommend bypassing HR and going directly to whatever payroll service your company uses. Most of these vendors (ADP, Paychex, Gusto, etc.) have dealt with this exact situation thousands of times and can guide your employer through the process much more effectively than trying to figure it out internally.