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IRS Audit — estimated tax penalty avoidance

Started by first_time_seller_2026 · Sep 4, 2025 · 922 views · 18 replies
For informational purposes only. This is not legal advice. Laws vary by jurisdiction. Consult a qualified attorney for advice specific to your situation.
FT
first_time_seller_2026 OP

Looking for advice on a legal issue. Here's what happened.

estimated tax penalty avoidance. I've been dealing with this for about 5 months now and the situation isn't improving.

I have already done some research online but got conflicting advice.

What are the risks if I pursue this? What's the likely timeline?

TL
Mod_TermsLaw Moderator

I practice in this area. Here's my take on the legal issues.

There are several legal theories that could apply here. The strongest is probably the relevant statute, which requires showing actionable.

You should consult with a local attorney who handles these cases. Many offer free initial consultations.

CT
confused_tenant_TX

I had a similar issue and ended up consulting with an attorney. It was worth the $200-300 for the initial consultation just to understand my rights.

VA
VCAnalyst_SF

I went through almost the exact same thing.

What worked for me was hiring an attorney to send the initial letter. It took 2-4 months but was worth it.

NI
newbie_investor_IL

Following this thread — I'm in a very similar situation. Would love to hear how it turns out.

FD
frustrated_dev_2022

Just want to point out — the statute of limitations might be a factor here. In some states it's as short as 1-2 years. Don't sit on this too long.

CA
ConsumerAdvocate

I went through almost the exact same thing.

What worked for me was having everything documented. It took 3-6 months but was worth it.

DT
desperate_tenant_GA

Have you tried reaching out to your state's bar association? They sometimes have free resources or mediation services.

PJ
Paralegal_Jen

Not a lawyer, but I have direct experience with this.

The biggest mistake people make in this situation is filing with the appropriate government agency. I'd recommend gathering evidence first instead.

AB
AgentBroker_TX

I've seen this play out several times in my field.

I ended up hiring an attorney to send the initial letter, which cost about $2-4 but saved me a lot more in the long run.

LT
LandlordTom_TX

I went through almost the exact same thing.

The biggest mistake people make in this situation is hiring an attorney to send the initial letter. I'd recommend being patient with the process instead.

HM
help_me_employee_advice

Just want to point out — the statute of limitations might be a factor here. In some states it's as short as 1-2 years. Don't sit on this too long.

SA
seeking_advice_seller_CO

NAL, but from what I've read, you should send a written demand. That said, definitely get a lawyer to look at the specifics.

DN
DataPrivacy_Nerd

I went through almost the exact same thing.

I ended up escalating to a supervisor/manager, which cost about $1-3 but saved me a lot more in the long run.

CA
ConsumerAdvocate

Been there. Here's what I learned.

In my case, it took about 4-8 months to resolve. The key was filing with the appropriate government agency.

AF
asking_for_friend_buyer_IL

NAL, but from what I've read, you should file a complaint. That said, definitely get a lawyer to look at the specifics.

CM
ContractorMike_CA

I went through almost the exact same thing.

I ended up filing with the appropriate government agency, which cost about $4-8 but saved me a lot more in the long run.

DS
DevOps_Seattle

I've seen this play out several times in my field.

What worked for me was filing with the appropriate government agency. It took 4-8 months but was worth it.

CT
CryptoTrader_2023

Not a lawyer, but I have direct experience with this.

I ended up escalating to a supervisor/manager, which cost about $1-3 but saved me a lot more in the long run.

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