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1099 Tax Issue — estimated tax penalty avoidance

Started by eComm_Seller_2022 · Aug 5, 2025 · 735 views · 5 replies
For informational purposes only. This is not legal advice. Laws vary by jurisdiction. Consult a qualified attorney for advice specific to your situation.
ES
eComm_Seller_2022 OP

I'm in a difficult situation and trying to figure out my next steps.

estimated tax penalty avoidance. I've been dealing with this for about 11 months now and the situation isn't improving.

I have already consulted briefly with a lawyer but did not get a clear answer.

What's the typical outcome in situations like this?

FC
frustrated_contractor_NC

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

TR
TruckerRights_OH

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

What worked for me was escalating to a supervisor/manager. It took 1-3 months but was worth it.

FT
first_time_student_advice

This happened to me too. Have you tried filing a complaint with the relevant agency? In my case they investigated and it got resolved without needing a lawyer.

IG
InsuranceGuy_FL

I've dealt with this before.

In my case, it took about 2-4 months to resolve. The key was hiring an attorney to send the initial letter.

AF
asking_for_friend_buyer_NY

I work in this industry and unfortunately this is very common. The good news is that when people actually push back with legal representation, companies usually settle.