A quick tip that helped me with a similar issue - request your "Account Transcripts" directly from the IRS before filing any amendments. These will show how your business is classified in their system. You can get these online through the IRS website by creating an account at https://www.irs.gov/payments/view-your-tax-account. The transcript will show if you're on record as an S-corp or LLC, which helps confirm whether your election was properly processed. This saved me a ton of headache because I could prove to my new accountant that the S-corp election was in the IRS system even though my old preparer had been filing incorrectly.

Quick warning based on personal experience - when you amend from LLC to S-corp returns, make sure your new preparer correctly handles any state tax implications too. I fixed my federal returns but completely overlooked that my state returns also needed to be amended to match the corrected filing status. Ended up with a mess at the state level when they couldn't reconcile my federal and state filings. Some states also have different rules for S-corps vs LLCs, so you might have overpaid state taxes too that could be refundable.

Based on my experience settling my cousin's estate, you absolutely need a tax professional who specializes in estates with tax problems. I'd recommend looking for an Enrolled Agent rather than a CPA - they often charge less but have specific expertise in dealing with the IRS. You should find someone in the deceased's state since they'll be familiar with both the state tax laws and potentially have relationships with the local IRS office. Most work can be done remotely, but having someone who understands the local requirements is invaluable. One thing nobody mentioned - if the estate doesn't have enough liquid assets to pay the tax debt, you might qualify for an Offer in Compromise specifically for estates. An EA can help determine if that's feasible given your situation.

One warning from my own experience - do NOT file any tax returns yet until you get the transcripts and understand what the IRS already has on record! I made this mistake with my father's estate and created a huge mess. Get Form 56 filed first to establish your authority, then get the account transcripts which will show assessments and balances. Also request the wage and income transcripts which show all income reported to the IRS on forms like W-2, 1099, etc. If the IRS has already made assessments (called Substitute for Returns), filing returns without understanding what they've already processed can create duplicate assessments or conflicting information that takes forever to resolve. You mentioned liens - check the exact type of lien. If it's a "Notice of Federal Tax Lien," that's public and affects property sales. If it's just a "Notice of Intent to Lien," you might still have time to request a Collection Due Process hearing.

I went through this exact thing! What state are you in? In my case (NC), they wanted proof that I had made my quarterly payments because their system showed I claimed credit for them on my return but they had no record of receiving them. Turns out my accountant had mistyped my SSN on ONE of the quarterly payment vouchers so it got credited to someone else's account!

This might sound silly but are you sure it's a legitimate letter? Scammers are getting more sophisticated with tax-related cons. Check the phone number on the letter against the official state tax department number on their website (not the one in the letter). My brother got a very official looking "state tax" letter that turned out to be completely fake.

One thing nobody's mentioned yet is contacting your Congressional representative's office. I had a nightmare situation with the IRS last year that dragged on for 8 months with no resolution despite sending in documentation multiple times. I finally contacted my Congressman's office and explained the situation. They have staff specifically dedicated to helping constituents with federal agency issues. I filled out a privacy release form, and within THREE WEEKS, the IRS had processed my documentation and resolved the issue. Congressional offices have special channels to IRS Taxpayer Advocate offices that can cut through red tape. Don't underestimate how effective this approach can be when you've tried everything else!

Has anyone tried using the IRS's online account features to resolve these types of issues? I set up an online account on IRS.gov recently and was shocked to find I could see all my notices, tax records, and even upload documents directly through the portal rather than mailing them. I'm wondering if uploading documents this way is more reliable than sending them through the mail where they seem to get lost in the void.

One thing to watch out for with multiple jobs in the same year: Social Security tax withholding. Each employer will withhold 6.2% for Social Security up to the annual wage base limit ($147,000 in 2022), but they don't know what another employer already withheld. If your combined income from both jobs exceeds the wage base limit, you might have excess Social Security tax withheld. The good news is you'll get this back when you file your return. Just something to be aware of when looking at your YTD totals.

I recommend getting an account on the IRS website to track your withholding. You can see what each employer has reported for your quarterly tax payments. Super helpful when you've had multiple jobs!