I actually just finished filing with Column Tax this past season and wanted to share my experience since you're considering it. I'm also a small business owner (marketing consultant) and was in the exact same boat - always used TurboTax but was curious about the banking integration. The good: The automatic transaction import really is as convenient as advertised. It pulled everything from my business account and the categorization was surprisingly accurate - probably saved me 3-4 hours of data entry. The interface is modern and intuitive, definitely less cluttered than TurboTax. The concerns: Since it's newer, there's less online documentation and community support compared to established players. I did run into one small issue with a foreign client payment that required some manual adjustment. Their support was helpful but took about 24 hours to respond, which made me a bit nervous close to the deadline. My advice: Given that it's free with your Novo account, maybe try running through the process early (like in February) to see how it handles your specific situation. You can always fall back to TurboTax if you're not comfortable. The Schedule C handling seemed solid for straightforward business expenses, but if you have complex deductions or unusual situations, definitely review everything carefully before filing. Overall, I'd cautiously recommend giving it a shot, especially since the price is right!

I've been using Column Tax for my freelance writing business for about 8 months now and it's been pretty solid overall. The integration with my business banking (I use Relay) has definitely streamlined my expense tracking compared to the manual entry nightmare I used to deal with. A few things I've learned that might help with your decision: **Pros:** - The automatic categorization really does work well for common business expenses (office supplies, software subscriptions, travel, etc.) - The Schedule C handling is comprehensive - it caught several deductions I had overlooked in previous years - The interface is much cleaner and less overwhelming than TurboTax's maze of screens - Customer support has been responsive when I've needed help (though I always contact them well before deadlines) **Things to watch out for:** - Double-check any unusual or large transactions - the AI sometimes miscategorizes things it hasn't seen before - Make sure to review the final tax summary carefully before filing - If you have complex situations (multiple business entities, significant equipment purchases, etc.), you might want to have a CPA review it the first year Since it's free with your Novo account, I'd say definitely try it out for a practice run early in tax season. You can always switch back to TurboTax if it doesn't feel right for your situation. The time savings alone on transaction entry has been worth it for me. Good luck with whatever you decide!

I'm going through the exact same situation right now! Reading through all these suggestions has been incredibly helpful - I had no idea there were so many different ways to track down old employment information. I wanted to add one more tip that helped me recently: if you remember any coworkers from those jobs (even just first names), try searching for them on LinkedIn or Facebook. Sometimes seeing their current profiles will show their employment history, which might help you remember the exact company names or even jog your memory about other places you worked around the same time. Also, if you have any old resume files saved anywhere, those obviously list your employment history with dates. I found a resume from 2019 in my Google Drive that I had completely forgotten about, and it filled in several gaps in my memory about where I worked. One question for the group - has anyone tried using the "Get Transcript Online" feature on the IRS website multiple times? I'm wondering if sometimes the masking is inconsistent, or if requesting transcripts for different date ranges might show different levels of detail. Just curious if anyone has experimented with this. Thanks again everyone for sharing your experiences. This thread is going to save me so much time and stress!

I've been reading through all these suggestions and they're incredibly thorough! I'm in a similar situation with missing W2s from several years, and this thread has given me so many new avenues to explore. One additional resource I wanted to mention that I don't think anyone has brought up yet - if you've ever applied for a mortgage, auto loan, or other major credit during those years, your lender likely has copies of your employment verification documents and pay stubs in their files. Banks and credit unions typically keep loan files for 7+ years, and these often contain detailed employment information that could help you identify missing employers. Also, if you worked any seasonal or temporary jobs through staffing agencies like Kelly Services, Manpower, or Adecco, those agencies often maintain worker records for many years even after assignments end. They can usually provide employment verification and sometimes even duplicate W2s. For anyone dealing with this issue, I'd also suggest creating a timeline document where you write down everything you DO remember - approximate dates, cities you lived in, major life events, etc. Sometimes organizing the information you have helps trigger memories about jobs you might have forgotten about completely. Even partial information can be helpful when cross-referencing with the other sources mentioned in this thread. Thanks to everyone for sharing their experiences - this community is incredibly helpful!

I had a very similar issue last year! Turned out my company was including several benefits I didn't even know I had - basic life insurance ($50k policy they automatically enroll everyone in), short-term disability coverage, and even our employee wellness program that includes things like flu shots and health screenings. The key thing is that Box 12 DD is just informational - it doesn't increase your taxable income or affect what you owe. But given that your accountant was recently fired for embezzlement, I'd definitely recommend getting a detailed breakdown from HR showing exactly what benefits are included in that $4,350. You can also compare this year's W-2 to previous years. If this is the first time you're seeing Box 12 DD with a value, ask HR why it's appearing now. Sometimes companies change their reporting practices or add new benefits that trigger the reporting requirement. Don't stress too much about filing your taxes - you can proceed with the W-2 as is, but definitely follow up with HR for your own peace of mind about what's included in that figure.

I work in HR and can shed some light on this! Box 12 DD reporting has actually become more common in recent years as the IRS has been stricter about enforcement. Many companies that previously didn't report these values are now doing so to stay compliant. The $4,350 likely includes multiple benefits you might not think of as "health coverage" - basic life insurance (very common to auto-enroll), any wellness programs, employee assistance programs, and even some supplemental benefits like accident insurance if your company provides it. Given your situation with the fired accountant, I completely understand your concern. Here's what I'd recommend: Request a "benefits cost breakdown" from HR - they should be able to provide an itemized list showing exactly what benefits comprise that $4,350. This is standard information they track for W-2 reporting purposes. Also, ask HR when they started including Box 12 DD reporting and why. Some companies only recently began reporting these values due to IRS guidance changes, which might explain why you haven't seen it before. The good news is this amount isn't taxable to you - it's purely informational. But getting that breakdown will give you peace of mind about what's actually being reported.

This conversation has really opened my eyes to how deeply unfair our tax system is to single taxpayers. I never realized the extent of the discrimination until reading through everyone's experiences and calculations here. What strikes me most is how this isn't just about tax rates - it's a comprehensive system that penalizes singles at every level. Higher effective tax rates during our earning years, fewer deductions and credits available to us, Social Security benefits that favor married couples despite identical contributions, and as many of you pointed out, we're subsidizing public services we use less of. The lifetime cost calculations some of you shared are staggering. $75,000-$100,000 extra over a working career just for being single? That's not a minor policy quirk - that's systematic economic discrimination based on marital status. I'm particularly frustrated by the outdated assumptions built into this system. The tax code seems frozen in an era when being single was just a temporary phase before marriage and children. But millions of us are single by choice throughout our careers, and we deserve equal treatment under the law regardless of our personal decisions about marriage and family. It's time for Congress to acknowledge that nearly half of American adults are single and reform the tax code to reflect modern demographics rather than 1950s family structures. We're not asking for special treatment - just equal treatment as citizens and taxpayers.

Reading through this discussion really highlights how pervasive this issue is - it's validating to see so many others experiencing the same frustration with our tax system's bias against singles. What bothers me most is the philosophical inconsistency. We're supposed to live in a country that values individual liberty and personal choice, yet our tax code actively punishes people for exercising those freedoms. Whether someone chooses to marry, have children, or remain single should be a personal decision, not one influenced by government tax policy. I've been single for most of my career and always felt like something was off about my tax burden compared to married colleagues. Seeing the actual numbers people have shared here - paying 3-4 percentage points more in effective tax rates, lifetime costs of $75,000-$100,000 extra - really puts it in perspective. This isn't just an accounting quirk, it's systematic discrimination. The resource usage argument is particularly compelling. As a single person, I consume fewer government services across the board yet pay higher rates to fund them. I don't use public schools, generate less waste, put less wear on infrastructure, yet I'm effectively subsidizing families who use significantly more resources per tax dollar contributed. It's time for policymakers to recognize that single Americans aren't just young people waiting to get married anymore. We're a substantial and growing portion of the population who deserve equal treatment under our tax laws, not penalties for our lifestyle choices.

This is incredibly frustrating but unfortunately becoming more common. I went through the exact same thing earlier this year - got a 12C letter that was completely blank where it should have specified what they needed. After multiple calls and a visit to my local Taxpayer Assistance Center, I found out they were questioning my student loan interest deduction even though the letter gave zero indication of this. Here's what finally worked for me: I gathered EVERY single document related to my tax return (W-2s, 1099s, receipts for deductions, etc.) and sent copies via certified mail with a cover letter explaining I received a defective 12C letter. I also included a copy of the blank letter itself. Within 3 weeks my refund was processed. The IRS representative at the TAC told me this is a known issue with their letter generation system and they're working on it, but in the meantime we're stuck dealing with these useless letters. Definitely try to get to a TAC in person if possible - they can actually see your full file and tell you specifically what's being questioned, unlike the phone agents who seem to have limited access. Don't give up! Your refund is coming, it's just going to take some persistence to get through their broken system.

I'm dealing with this exact same nightmare right now! Got my blank 12C letter three weeks ago and have been going in circles with the IRS ever since. Based on what everyone's sharing here, it sounds like this is a widespread system glitch that's affecting tons of people. I'm going to try the approach several people mentioned - calling and specifically asking for the Income Verification department, and if that doesn't work, I'll make an appointment at my local Taxpayer Assistance Center. The idea of sending everything via certified mail with a cover letter explaining the defective letter also sounds like a solid backup plan. It's so frustrating that we have to become detectives just to figure out what our own government wants from us. Thanks to everyone who shared their experiences - it's oddly comforting to know I'm not alone in this mess, even though none of us should have to deal with it in the first place. Has anyone had success with checking their online transcript to find clues about what's being questioned? I'm wondering if that might give me a head start before I spend hours on hold again.