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If I could give 10 stars I would If I could give 10 stars I would Such an amazing service so needed during the times when EDD almost never picks up Claimyr gets me on the phone with EDD every time without fail faster. A much needed service without Claimyr I would have never received the payment I needed to support me during my postpartum recovery. Thank you so much Claimyr!
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Has anyone tried requesting a penalty abatement for first-time late filing? I heard the IRS has a First Time Penalty Abatement policy where they'll waive penalties for people with clean previous filing history.
Yes! I got my penalties waived using this last year. You have to call and specifically request "First Time Penalty Abatement" after you file and pay the original tax amount. They'll check if you've had any penalties in the past 3 tax years - if not, they usually approve it. Saved me about $800!
I'm going through something similar with my divorce proceedings - needed my 2021 return for financial disclosure and realized I never actually submitted it either! The stress is real when you need these documents for court. A few things that helped me: First, definitely file 2022 immediately as a separate return. The IRS systems are set up to handle each tax year individually, so there's no option to combine years anyway. For the court documentation, consider asking your attorney if they'll accept a copy of your prepared return along with proof that you've submitted it to the IRS (like a certified mail receipt if you file by paper, or the electronic confirmation if you e-file). Courts understand that IRS processing can take weeks, so they often accept evidence that you've filed rather than waiting for the processed return. Also, once you do file, you can request an Account Transcript from the IRS online at irs.gov which will show your filing status and any penalties/payments. This can serve as official documentation for court purposes while you wait for your actual return to be processed. The penalties will hurt, but getting this resolved quickly is more important than the extra money, especially with court deadlines looming. Good luck!
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Has anyone tried using one of those Certified Acceptance Agents instead of going directly through the IRS? The thought of sending my wife's original passport in the mail is making me really nervous...
I used a CAA for my husband's ITIN last year and it was SO much better than dealing with the IRS directly. They verified his original documents in person and then just submitted copies to the IRS with the application. Took about 8 weeks to get the ITIN back. Definitely worth the fee for peace of mind not sending original documents through mail.
Just to add some clarity for anyone else in this situation - you absolutely can apply for an ITIN after filing your return! I went through this exact process with my partner last year. The key things to remember: 1. Use Form W-7 and include a complete copy of your already-filed tax return as supporting documentation 2. If you're nervous about mailing original documents (totally understandable!), definitely look into using a Certified Acceptance Agent - they can verify originals in person and submit copies 3. The ITIN application won't affect your already-filed return for this year, but it will give you more filing options next year The whole process took about 10 weeks for us when we went through a CAA. Yes, there's a small fee, but the peace of mind was worth it. Don't stress too much - this is a pretty common situation and the IRS handles it regularly!
This is really helpful, thank you! I'm actually in a similar boat - filed separately and now realizing I should get an ITIN for my spouse. Quick question about the CAA route: how do you find a legitimate Certified Acceptance Agent? Is there a directory on the IRS website or something? I want to make sure I'm not getting scammed by someone claiming to be certified when they're not.
Yes, there's an official IRS directory! You can find authorized Certified Acceptance Agents on the IRS website - just search for "CAA directory" or "Certified Acceptance Agent locator." The IRS maintains a searchable database where you can filter by location and services offered. Make sure whoever you choose is actually listed in the official directory - there are unfortunately some sketchy services out there that claim to be CAAs when they're not. The legitimate ones will have their authorization displayed and you can verify their status directly with the IRS if you have any doubts. Most tax preparation offices like H&R Block or local CPAs can also be CAAs, so that might be another route to explore in your area.
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Keep in mind that the "best" incorporation state isn't just about taxes. I incorporated in Delaware, and while I do pay the annual franchise tax, the legal protection has been invaluable. Had a major contract dispute with a client, and Delaware's Court of Chancery handled it efficiently. Also, if you ever plan to seek venture capital, many investors prefer Delaware C-Corps because of the predictable legal framework. Even if you save a little on taxes elsewhere, you might face higher costs if you incorporate elsewhere then need to convert to a Delaware entity later.
100% agree on the Delaware point for fundraising. We incorporated in Wyoming initially to save on taxes, but when we went for our Series A, our investors basically required us to convert to a Delaware C-Corp. Cost us way more in legal fees for the conversion than we ever saved on taxes.
Great discussion here! As someone who went through this exact decision last year, I'd add that you should also consider the ongoing administrative burden of your choice. While Wyoming and Nevada are tax-friendly, Delaware has the most streamlined annual reporting process I've encountered. Their Division of Corporations website is actually user-friendly (shocking for a government site), and you can handle most filings online without needing to mail paperwork or deal with antiquated systems. Also, since you mentioned retaining earnings in the corporate structure - make sure to factor in potential accumulated earnings tax implications at the federal level if you're planning to hold onto significant cash without distributing it. This is a federal issue regardless of state, but some states have additional rules around unreasonable accumulation that could affect your strategy. Given your SaaS model and remote workforce, I'd seriously consider running the numbers on a Delaware C-Corp vs. the traditional tax haven states. The legal predictability and ease of administration might be worth the modest tax difference, especially as you scale.
This is really helpful perspective on the administrative side! I hadn't thought much about the ongoing paperwork burden, but you're right that it could add up over time. Quick question - when you mention accumulated earnings tax, what's the threshold where that becomes a concern? Is it based on a dollar amount or percentage of revenue? Also, for someone just starting to think about this stuff, is there a good resource to understand the conversion process if I pick one state now but need to switch later? Sounds like it can get expensive based on what @QuantumQuasar mentioned about their Series A experience.
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Has anyone had experience with how long it actually takes for the IRS to process Form 8822? The instructions say 4-6 weeks, but when I did this last year it seemed to take forever and I still had mail going to my old address months later.
In my experience it takes about 8-10 weeks for the change to fully process through their system. I recommend setting up USPS mail forwarding for at least 6 months to catch anything that slips through during processing.
I went through this exact same situation when I moved from Texas to California last year. The key thing to remember is that the "most recent location" they're referring to in the instructions just means where you currently live now, not where you previously filed. Since you're now in Arizona, you'll use the Arizona mailing address for Form 8822. Like Molly mentioned, it goes to Kansas City, MO 64999-0023. The IRS has regionalized processing centers, so all Arizona residents send their address change forms to the same place regardless of where they previously lived or filed. One thing I learned the hard way - make sure you also update your address with any estimated tax payments if you make them quarterly. The IRS doesn't always connect these systems immediately, so you might get notices sent to your old address even after Form 8822 is processed. Also, since you mentioned e-filing for years, don't forget to update your address in whatever tax software you use for next year's filing. It'll save you from having to remember to manually enter your new address when tax season comes around.
This is really helpful! I'm actually in a similar situation - just moved from Florida to Nevada and was confused about the whole "most recent location" language too. So just to confirm, I would use Nevada's mailing address for Form 8822 even though I filed my last few tax returns while living in Florida? Also, thanks for the tip about updating the tax software address. I use TurboTax and totally would have forgotten to change that setting before next filing season.
@690466b7a0bc Exactly right! You would use Nevada's mailing address for Form 8822, not Florida's. The form goes based on where you currently live, not where you previously filed. For Nevada residents, you'll send Form 8822 to the Ogden, UT processing center. And yes, definitely update TurboTax (or whatever software you use) with your new address in your profile settings. I forgot to do this one year and it automatically populated my old address on the return, which caused confusion when the IRS had conflicting address information in their system. One more tip - if you're doing estimated quarterly payments, make sure to send those to Nevada's address too going forward. The estimated payment vouchers and annual returns don't always use the same processing centers, so it's worth double-checking that in the instructions.
QuantumQuasar
Has anyone used the "last-month rule" instead of prorating in situations like this? From what I understand, if you're eligible on December 1st, you can contribute the full annual amount (individual or family based on December status) as long as you remain eligible through the end of the following year. Would that work in the original poster's situation?
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Giovanni Colombo
•Yes, the last-month rule could potentially apply here, but with an important caveat. Since only the husband was HSA-eligible on December 1st (with individual HDHP coverage), he could use the last-month rule to contribute the full individual maximum ($3,850) for 2023 - not the family maximum. He would need to remain HSA-eligible through December 31, 2024, to avoid penalties and taxes on the "accelerated" portion of that contribution. If he fails the testing period, he'd owe taxes plus a 10% penalty on the portion he wouldn't normally be eligible for. In this case, the prorated calculation allowing $6,450 actually permits a larger contribution than the last-month rule would ($3,850), so prorating is more advantageous here.
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Layla Mendes
This is a great breakdown of how to handle HSA contributions with mid-year coverage changes! I wanted to add one important point about timing that might help others in similar situations. When making these prorated contributions, you have until the tax filing deadline (typically April 15th of the following year) to make HSA contributions for the previous tax year. So even though you're figuring this out now, you still have time to make the calculated $6,450 contribution for 2023 if you haven't already maxed it out. Also, make sure to keep detailed records of the coverage change dates and your calculations. The IRS may want documentation if they ever question your contribution amounts, especially with the complexity of mid-year switches between family and individual coverage. Your insurance company should be able to provide letters or statements showing exactly when coverage types changed. Congratulations on the pregnancy, by the way! Once your little one arrives, you'll likely be able to switch back to family HDHP coverage and family contribution limits if that makes sense for your situation.
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