My spouse hasn't filed taxes in over 5 years - could I face legal consequences?

What if they've been filing jointly in previous years? Would that make OP responsible for all his back taxes too? And is there any kind of "innocent spouse" protection or something if you didn't know your partner wasn't filing?

If they had filed jointly in previous years, that would indeed increase the risk. When you file jointly, both spouses are generally fully responsible for all the tax liability on that return - this is called "joint and several liability." There is indeed an "innocent spouse relief" program with the IRS, but it typically applies when a joint return was filed and one spouse didn't report income or claimed improper deductions/credits. It's harder to claim when the issue is completely unfiled returns, since both spouses should be aware of whether they filed or not. However, in situations where one spouse was genuinely unaware of unfiled returns, there are other types of relief that might apply, including separation of liability relief or equitable relief.

Does it actually help with unfiled taxes specifically? My brother is in a similar situation (his wife hasn't filed in like 3 years) and he's freaking out.

I'm skeptical about these AI tools for serious tax issues. How does it compare to just talking to a real CPA? This sounds like a situation where you'd want professional advice, not an algorithm.

It does address unfiled taxes specifically. It has a section that calculates potential penalties and interest for unfiled returns based on estimated income. It also clearly outlines the steps needed to get back into compliance, including options like streamlined filing procedures if applicable. It was super helpful for clarifying which years were highest priority to address. As for comparing to a CPA, I actually used both. I started with taxr.ai to understand my situation better and then took that information to a CPA. The CPA confirmed everything the tool had told me and was impressed I came in so prepared. The tool cost way less than what multiple CPA consultations would have, and it gave me 24/7 access to run different scenarios whenever I had new questions.

Wait I don't get it. How does this actually work? The IRS phone system is notoriously terrible - how does a third party service get you through faster?

This sounds like a scam. You're telling me you pay some random service and magically get through to the IRS when millions of people can't? Yeah right. The IRS phone system is broken by design - no way around it.

It's not magic - they use technology that continuously dials and navigates the IRS phone tree until they secure a place in line, then they call you and connect you. Think of it like having a digital assistant repeatedly calling until they get through, so you don't have to keep redialing yourself. I was skeptical too, that's why I watched their demo video first. But when you think about it, it's just automating the frustrating process of calling, getting disconnected, and calling again. You still talk directly to official IRS agents - the service just handles the nightmare of getting connected. I spent weeks trying on my own with no success, then got through in one afternoon with them. The IRS is indeed broken, but this is a legitimate workaround.

Thank you so much for this advice! I've been keeping all my filing separate but I'm still worried. Do you know if the IRS would come after our house if it's in both our names? And how bad would the penalties actually be after 5 years? I'm trying to calculate the worst-case scenario.

The IRS can potentially place a lien on jointly owned property like your house, but they typically use this as a last resort, especially for smaller tax debts. They prefer payment plans over seizing assets. Property seizure usually only happens in extreme cases with large tax debts where the taxpayer refuses to cooperate. Regarding penalties after 5 years, they can be substantial. There's the failure-to-file penalty (5% of unpaid taxes each month, capped at 25%), failure-to-pay penalty (0.5% per month, up to 25%), and interest on both the tax and penalties (currently around 7-8% annually, compounded daily). For example, a $10,000 tax debt could grow to $18,000+ after 5 years. However, the IRS does have programs like First Time Penalty Abatement that might help reduce these if your husband has previously been compliant.

The Fresh Start program is definitely still around. It's a collection of different options rather than one specific program. It includes installment agreements, offers in compromise (settling for less than you owe), and currently not collectible status. There are requirements for each option - usually based on your income, expenses, assets, and ability to pay. They did expand it a few years ago to help more people qualify.

Thanks for confirming! Do you know if there's a limit to how many years of unfiled taxes they'll accept under this program? My cousin mentioned something about a 6-year lookback period but wasn't sure if that's standard or if he just got lucky.

This is such practical advice! I hadn't thought about the possibility of refunds from those unfiled years - that's actually a really good point. If taxes were being withheld from his contract payments, he might have overpaid in some years. The separate account suggestion is brilliant too. I've been worried about our joint savings getting caught up in this mess, so having a clear "mine only" account makes total sense for peace of mind. I'm curious - when you were gathering documents for those unfiled years, how did you handle missing paperwork? My partner is pretty disorganized and I'm worried some of his 1099s or other tax documents from 2019-2020 might be long gone. Did you run into that issue, and if so, how did you work around it? Also, when you say the IRS was "surprisingly reasonable" - did you work directly with them or go through a tax professional? I'm trying to decide if we should handle this ourselves or get help from the start.

@Quinn Herbert really hit on something important with the missing documents issue! When we dealt with this, we were missing several 1099s from 2019-2021. Here s'what saved us: You can request wage and income transcripts directly from the IRS that show all the income reported to them by employers/clients for each year. This includes W-2s, 1099s, interest statements, etc. You can get these online through the IRS website or by calling them. These transcripts will show you exactly what income the IRS has on file for your husband for each year. For missing receipts/deductions, you can often reconstruct records from bank statements, credit card statements, or even photos if your partner took any pictures of receipts. The IRS accepts reasonable documentation for legitimate business expenses. Regarding working with the IRS directly vs. getting professional help - we started by trying to handle it ourselves, but honestly, having a tax professional for the actual filing made everything smoother. They knew exactly which forms to use for each situation and caught things we would have missed. However, for the initial assessment of what years needed to be filed and gathering documents, we did that part ourselves to save money. The IRS agents we spoke to were actually pretty helpful in explaining what we needed to do - much more patient than I expected!

@Natasha Romanova Great questions! For missing documents, you can request wage and income transcripts from the IRS that show what was reported to them by employers and clients. These transcripts will have all the 1099s, W-2s, and other income documents for any given year. You can get them online through the IRS website or by calling them. This is actually often more complete than what people have in their own records. We handled most of it ourselves initially - used the transcripts to reconstruct the income, then had a tax preparer do the actual returns for the more complicated years. The IRS was reasonable when we called them directly, but having a professional prepare the returns gave us confidence we weren t'missing deductions or making errors that could trigger additional scrutiny. One thing that really helped was calling the IRS early in the process just to let them know we were working on getting compliant. They made notes in our file, and I think it showed good faith when they eventually processed everything. The agents were actually pretty helpful in explaining our options once we demonstrated we were serious about resolving it. The whole process was way less scary than I d'built up in my head. The hardest part was just getting started!

@Natasha Romanova Great questions! For missing documents, I had to get creative. The IRS actually has transcripts of what income was reported to them by employers/clients, so you can request those to reconstruct missing 1099s. Also, many companies keep records for 7+ years, so your partner can contact previous clients directly to request copies of 1099s they issued. For bank records and receipts if (he had business expenses to deduct ,)most banks will provide statements going back several years for a small fee. Honestly, even if some documentation is missing, it s'better to file with what you have than to keep not filing at all. As for working with the IRS directly vs. getting professional help - I did both. I started by trying to understand the situation myself used (some of the tools mentioned earlier in this thread ,)then hired a tax preparer for the actual filing since multiple years of returns felt overwhelming. The preparer was worth every penny because they knew exactly which forms were needed and caught deductions I would have missed. Plus, having a professional handle the filings gave me confidence everything was done correctly. The IRS communication part I actually handled myself once the returns were filed - they were very straightforward about payment plan options over the phone.

@Natasha Romanova - Great questions! For missing documents, you can actually request wage and income transcripts from the IRS that show all the 1099s and W-2s that were reported to them for any given year. This was a lifesaver for us since my husband had lost several 1099s from 2020. You can get these online through the IRS website or by calling them though (as others mentioned, calling can be a nightmare without services like Claimyr .)For expenses and deductions he might have taken as a contractor, you ll'need to recreate those records as best you can - bank statements, credit card statements, receipts you can find, mileage logs, etc. The IRS accepts reasonable reconstructed records if you can show you made a good faith effort. As for handling it yourself vs getting professional help - I did a hybrid approach. I used one of those AI tools mentioned earlier taxr.ai (to) understand the scope of the problem and what forms we needed, then hired a CPA for the actual filing of the most complicated year. For the simpler years with just 1099s, we ended up doing those ourselves using the roadmap the tool provided. This saved us money while still getting professional help where we really needed it. The IRS agents I spoke with directly were actually very helpful and patient. Once you re'actively trying to resolve the situation, they really do want to help you get compliant rather than punish you.

@c3c812885916 Great question about missing documents! I definitely ran into this - my husband was missing several 1099s from 2019 and 2020. Here's what worked for us: First, you can request tax transcripts from the IRS that show what income was reported to them by employers/clients. This helped us identify which 1099s we were missing. You can also contact the companies directly if you remember who he worked for - many will reissue tax documents for previous years. For completely missing records, the IRS actually allows "reasonable estimates" in some cases, especially for business expenses. We worked with a CPA who helped us reconstruct what we could and properly estimate the rest. Regarding working directly with the IRS vs getting professional help - I'd honestly recommend starting with a tax professional, at least for the initial consultation. We tried to handle it ourselves first and made some mistakes that actually cost us more money in the long run. A good CPA or enrolled agent knows exactly which forms to file and can often get better outcomes with payment plans and penalty reductions. The peace of mind was worth the cost for us, especially since we were dealing with 4 years of unfiled returns. The professionals also know how to communicate with the IRS in a way that gets better results - they speak their language, basically.

Great questions! For missing documents, you can actually request wage and income transcripts from the IRS that show all the 1099s and W-2s that were filed under your husband's Social Security number for each year. You can get these online at irs.gov or by calling them. Most companies are also required to keep copies for several years, so you could contact previous clients or employers directly if needed. We started by trying to handle it ourselves using tax software for the back returns, but ended up getting help from an Enrolled Agent for the more complicated years. Honestly, if you're just dealing with W-2s and basic 1099s, you can probably handle the filing yourself. But if there were business expenses, multiple income sources, or you're worried about making mistakes that could trigger an audit, professional help is worth it. The IRS was reasonable when we worked with them directly - we set up a payment plan online through their website, which was surprisingly straightforward. The key is being proactive and communicating. They really do want to work with people who are making genuine efforts to get compliant. One more tip: if your husband qualifies as a "first-time penalty abatement" candidate (meaning he's been compliant in previous years), they'll often waive failure-to-file and failure-to-pay penalties for one tax year, which can save thousands of dollars.

@Natasha Romanova Great questions! For missing documents, we were able to get most of what we needed directly from the IRS and other sources. You can request wage "and income transcripts from" the IRS that show all the 1099s and W-2s that were reported to them for each year - this was a lifesaver for the missing paperwork. Most banks can also provide old statements if you need records of business expenses or other deductions. The IRS transcript request can be done online if you can verify your identity, or by mail if needed. It typically takes 5-10 business days to get them, and they show exactly what income was reported to the IRS for each year. This actually helped us catch some 1099s my husband had completely forgotten about. As for working directly with the IRS vs. getting professional help - we ended up doing both. I started by trying to understand our situation myself used (some of the tools others mentioned in this thread ,)then worked with a tax preparer to actually file the returns. For the payment arrangement, I handled that directly with the IRS since it was pretty straightforward once the returns were filed. The key is that you CAN do this yourself, but having professional help for the actual filing can save time and ensure everything is done correctly, especially if there are business deductions involved.

@Natasha Romanova Missing documents was definitely an issue for us! Here s'what we did: For 1099s and other income documents, you can request transcripts from the IRS that show what income was reported to them by employers/clients. Form 4506-T lets you request these for free. This actually gives you most of what you need to reconstruct the tax returns even if you don t'have the original paperwork. For expenses if (he was deducting business expenses ,)we had to do some detective work - bank statements, credit card statements, receipts we could find, etc. The good news is that for unfiled returns, you re'not usually under the same scrutiny as an audit, so reasonable estimates for standard business expenses are generally acceptable. We started by trying to handle it ourselves using the transcript approach, but ended up getting help from a tax pro after the second year because it got complicated with some of his contractor payments. The professional was worth it - they knew shortcuts for reconstructing records and helped us identify deductions we would have missed. Cost about $1,500 total but probably saved us more than that in penalties and missed deductions. If your partner s'situation is straightforward just (basic 1099 income without complex deductions ,)you might be able to handle it yourselves. But if there s'any complexity, I d'recommend getting professional help at least for the first year to see how it goes.

@Natasha Romanova Great question about missing documents! I definitely ran into this - my husband had lost several 1099s from 2019 and 2020. Here s'what worked for us: First, you can request wage and income transcripts from the IRS that show all the 1099s and W-2s that were reported to them for any given year. This is free and you can do it online at irs.gov. It won t'have every detail, but it ll'show the amounts and who paid him, which is usually enough to reconstruct the returns. For bank records and receipts for deductions, I contacted his banks directly. Most banks can provide statements going back 7 years for a small fee. We also reached out to some of his regular clients who were able to provide copies of the 1099s they had sent. As for handling it ourselves vs. getting help - we started by doing the document gathering ourselves, then hired a CPA for the actual filing. The CPA cost about $200 per year of returns, but it was worth it for the peace of mind and to make sure we didn t'miss anything. Plus, having a professional file the returns seemed to add credibility when we later set up our payment plan with the IRS. The IRS was reasonable in both contexts - they were helpful when we called directly for transcripts and procedural questions, and they were professional and accommodating when our CPA contacted them about the payment arrangement.

Great questions! For missing documents, we had to request wage and income transcripts from the IRS (Form 4506-T). This shows all the 1099s, W-2s, and other income documents that were reported to the IRS for each year. It takes about 10 business days to get them by mail, or you can sometimes get them immediately online through the IRS website if you can verify your identity. For documents the IRS doesn't have (like certain deductions or business expenses), we had to reconstruct what we could from bank statements, credit card records, and receipts we could find. The tax preparer we worked with said it's pretty common and the IRS understands that older records get lost - they're generally reasonable about accepting reasonable estimates for smaller expense items as long as you're not claiming anything outrageous. We started by trying to handle it ourselves, but honestly, after filing the first year and seeing how complicated it got with penalty calculations and figuring out payment options, we hired a tax professional for the remaining years. Best decision we made - they knew exactly which forms to file and how to present everything to minimize penalties. Cost us about $500 per year to have them prepared, but probably saved us thousands in avoided penalties and mistakes. The IRS was reasonable both ways, but having a pro made the conversations much smoother since they knew the right terminology and procedures.

Great question about missing documents! I definitely ran into this - my husband was missing several 1099s from 2019 and 2020. Here's what worked for us: First, you can request wage and income transcripts from the IRS for each tax year. These show all the income that was reported to the IRS by employers/clients, so you can see exactly what 1099s and W-2s should exist. You can get these online or by calling the IRS. For missing documents, most companies are required to provide copies if you contact them directly. I had to reach out to a couple of his old clients, and they were able to send copies of the 1099s they issued. Some had gone out of business, but the IRS transcripts showed the income amounts anyway. Regarding working with the IRS directly vs. getting help - I started by trying to handle it myself using the online resources and phone support (though getting through was a nightmare before I found that Claimyr service others mentioned). For the actual filing of back returns, I ended up using a tax professional because my husband's situation was a bit complex with multiple income sources. But for simpler situations with just W-2s or basic 1099 income, you can definitely handle the filing yourself. The key is just starting the process. Even if you're missing some documents initially, filing what you can and then amending later is better than continuing to wait.

Great questions! For missing documents, you can actually get most of what you need directly from the IRS and other sources. You can request "wage and income transcripts" from the IRS that show all the 1099s, W-2s, and other income documents that were reported to them for each tax year. There's a small fee, but it's way easier than trying to track down old employers or clients. For really old stuff, you can also contact the Social Security Administration for wage records, and many banks can provide old interest statements if needed. The key is that you don't necessarily need the original documents - you just need the information that was on them. As for working with the IRS directly vs. getting help - I started by trying to handle it myself, but honestly, a tax professional was worth every penny. They know exactly which forms to file, how to minimize penalties, and can often get things resolved faster because they know the system. Plus, having someone else deal with the IRS calls and paperwork reduced my stress level dramatically. If money's tight, at least get a consultation with a CPA or enrolled agent to understand your options before diving in alone. Many will do an initial review for a reasonable fee and then you can decide if you want their help with the actual filing.

@c3c812885916 Great questions! For missing documents, you can actually request transcripts and wage/income transcripts directly from the IRS that show what was reported to them by employers and clients. This covers most 1099s, W-2s, and other income documents. You can get these online at irs.gov or by calling them (though calling is a nightmare as others mentioned here). I handled most of it myself initially, but ended up getting a tax professional involved when I realized there were some complicated deductions my husband could claim that I wasn't comfortable figuring out on my own. If your situation is straightforward (just basic income reporting), you can probably handle the filing yourself. But if there are business expenses, depreciation, or other complex issues from his contract work, a professional is worth it. The IRS was reasonable in that once we filed everything and showed we were making a good faith effort, they were very willing to set up a payment plan. The key is being proactive - they get difficult when people ignore them, but they're actually helpful when you engage with the process. We ended up with a 5-year payment plan at a pretty reasonable monthly amount.

@c3c812885916 Great questions! For missing documents, you can request wage and income transcripts directly from the IRS for any year - they show all the 1099s, W-2s, and other income documents that were reported to them. You can get these online at irs.gov or by calling them. Most tax preparers can also help you request these transcripts. I started by trying to work directly with the IRS myself, but honestly, after spending weeks on hold trying to get through to someone, I ended up hiring a tax professional for the actual filing part. The professional was worth it because they knew exactly which forms to use for back returns and could handle multiple years efficiently. However, I did a lot of the preliminary work myself - gathering what documents I could find, getting the transcripts, and understanding our situation using some of the tools others mentioned in this thread. That way when I met with the tax pro, I wasn't paying them for basic information gathering. One thing that really helped was that the IRS agent I eventually spoke to (through that Claimyr service someone mentioned) actually walked me through exactly what documents I needed and confirmed that refunds were likely for a couple years. Having that conversation first made the whole process much less scary.

@c3c812885916 Great questions! For missing documents, we actually had good luck requesting transcripts directly from the IRS - they have records of all 1099s and W-2s that were issued to your SSN, even if you lost the physical copies. You can get these online through their website or by calling (though calling is a nightmare as others have mentioned). Many of the companies that issued 1099s were also willing to send duplicate copies when we called and explained we were trying to get compliant with back taxes. We ended up doing a hybrid approach - gathered all the documents ourselves and used one of those AI tools someone mentioned earlier to understand our situation, then hired a CPA for the actual filing. The CPA said we came in much better prepared than most people, which saved us money on consultation time. If your partner's records are really messy, it might be worth starting with a professional from the beginning. They know all the shortcuts for reconstructing tax information and can often get the work done faster than you'd expect. Plus, having a professional handle the filing can give you more credibility with the IRS if any issues come up later. The main thing is just getting started - every day you wait makes the penalty calculations worse!

@c3c812885916 Great question about missing documents! I definitely ran into this issue. For missing 1099s and W-2s, you can request wage and income transcripts from the IRS that show what was reported to them by employers and clients. These transcripts are free and available online or by mail. They won't have all the details you'd need for complex returns, but they're usually sufficient for basic filings. For expenses and deductions, it gets trickier with missing records. The IRS allows "reasonable estimates" in some cases, especially for standard business expenses, but you need to be conservative and document your methodology. Bank statements can help reconstruct some expenses even if you don't have receipts. We started by trying to handle it ourselves using the transcripts and bank records, but ended up getting help from a tax preparer for the final filings. The prep work we did ourselves actually saved money because we came to the professional organized and with most of the information gathered. I'd recommend starting with the transcript requests and document gathering yourself, then deciding if you need professional help based on how complex the situation looks once you have all the information. The IRS was reasonable both when we worked with them directly and through the tax preparer. The key is just being proactive and honest about the situation.

@c3c812885916 Great question about missing documents! This was actually one of my biggest worries too. What I learned is that you can request wage and income transcripts directly from the IRS that show all the 1099s, W-2s, and other income documents that were reported to them for each tax year. You can get these online through the IRS website or by calling them. For documents that weren't reported to the IRS (like some cash payments or expenses), you might need to do some detective work - checking bank statements, emails, contracts, etc. But honestly, the IRS transcripts covered about 90% of what we needed. As for working with the IRS directly vs getting professional help - I started by trying to handle it myself using the transcripts and some of the tools people mentioned earlier in this thread. But after filing the first return, I realized the penalties and interest calculations were getting complex, so I ended up hiring a tax professional for the remaining years. If your partner's situation is straightforward (just regular contract work with 1099s), you might be able to handle it yourself. But if there are business expenses, multiple income sources, or significant amounts owed, getting professional help from the start can actually save money in the long run by ensuring everything is done correctly and taking advantage of any penalty abatement options.

@Natasha Romanova Great questions! Missing documents was definitely an issue for us. The good news is that you can request wage and income transcripts directly from the IRS for free - they show all the 1099s, W-2s, and other income documents that were reported to them for each year. You can get these online at irs.gov or by calling. This actually gives you a complete picture of what income the IRS knows about, which is often more comprehensive than what people have saved. For other deductions or business expenses, you might need to recreate records from bank statements, credit card statements, or contact the companies that paid him to see if they can provide copies of old 1099s. As for working with the IRS directly vs. using a professional - we started by trying to handle it ourselves using the transcripts and online resources, but ended up hiring a CPA for the actual filing of 4 years of returns. The CPA fee was worth it because they knew exactly which forms to use and how to minimize penalties. But the initial information gathering and understanding our situation, we did ourselves. If your situation is relatively straightforward just (missing 1099 income, no major complications ,)you might be able to handle more of it yourselves and save money.

@c3c812885916 Great question about missing documents! I definitely ran into this issue. For 1099s and other tax documents, you can actually request transcripts directly from the IRS that show what income was reported to them by employers/clients. You can get these online through the IRS website or by calling them (though calling is a nightmare as others have mentioned). For 1099s specifically, you can also contact the companies that paid your partner directly - most are required to keep records for several years. Some might charge a small fee to provide copies, but it's usually worth it. We ended up doing a hybrid approach - started gathering documents ourselves and filed the simpler years on our own, but brought in a tax professional for the more complicated years where he had multiple clients and some missing paperwork. The pro was able to help estimate income based on bank deposits and other records when we couldn't find everything. The IRS was reasonable even when we had to estimate some figures, as long as we made a good faith effort and were transparent about any uncertainties. They'd rather have an imperfect return filed than no return at all. You can always amend later if you find missing documents that change the numbers significantly. I'd recommend starting with document gathering yourself, then deciding if you need professional help based on how complex things look once you see what you're working with.

Great questions! For missing paperwork, we had to get creative. The IRS can actually provide you with "wage and income transcripts" that show what was reported to them by employers/clients - this covers most 1099s, W-2s, and other income documents. You can request these online or by phone for the specific tax years you need. It won't have everything (like receipts for deductions), but it gives you the basic income information needed to file. For business expenses and deductions from his contract work, we had to reconstruct what we could from bank statements, credit card records, and any emails or contracts he still had. The tax preparer we worked with said it's pretty common and the IRS understands that older records get lost. As for working directly with the IRS vs getting professional help - we started with a tax preparer for the actual filing of back returns (especially since there was self-employment income involved), but then handled the payment plan setup directly with the IRS ourselves. The preparer charged about $400 per year of returns, which felt worth it for the peace of mind and to make sure everything was done correctly. Once the returns were filed and we knew exactly what we owed, dealing directly with the IRS for payment arrangements was actually pretty straightforward. The whole process was way less scary than I anticipated, and like others have said, the worst part was really the anxiety of not knowing what we were facing.

For missing documents, you can actually request transcripts from the IRS that show what income was reported to them by employers/clients. Form 4506-T lets you get these for free, and it covers most of what you need to recreate the tax returns. I had to do this for 2019 when my husband lost his 1099s. Banks can also provide old statements if you need to document business expenses or estimated tax payments. Most keep records for 7 years, so you should be able to get 2019-2020 statements if needed. We started by trying to handle it ourselves using tax software for the back years, but ended up getting help from a CPA for the final two years because there were some business expense complications. If your partner's situation is straightforward (just regular 1099s without a lot of deductions), you can probably handle the filings yourself. But I'd recommend at least a consultation with a tax pro to review your situation and make sure you're not missing anything important. The IRS was reasonable when we called directly, but getting through to them was the hardest part. That's actually where services like the one @Amina Diallo mentioned earlier become valuable - not because the IRS agents are difficult to work with, but because reaching them in the first place is nearly impossible through normal channels.

@c3c812885916 Great question about missing documents! I definitely ran into this - my husband had lost several 1099s from 2019 and 2020. Here's what worked for us: 1. You can request wage and income transcripts from the IRS that show what income was reported to them by employers/clients. This covers most 1099s, W-2s, etc. It's free and you can get them online or by mail. 2. For business expenses (if he was deducting any), we had to reconstruct records using bank statements, credit card statements, and any receipts we could find. The IRS accepts reasonable estimates for small business expenses if you can show a good faith effort. 3. Some companies will reissue 1099s if you contact them directly, though this gets harder the older the tax year. Regarding working with the IRS directly vs. getting professional help - we did both. Started by calling the IRS ourselves to understand what years they thought we owed for, then hired a CPA to actually prepare and file the returns. The middle ground worked well because we saved money on consultation fees but still got professional help with the actual filing. One thing that surprised me: the IRS was actually more helpful on the phone than I expected once I got through to someone. They walked me through exactly which forms we needed and even suggested some strategies for minimizing penalties.