Tax Strategy
Complex Tax Issues Strategy
The Audit Process Step by Step
Here’s what happens from the moment you receive an audit notice to resolution:
- Notice received — The IRS sends a letter explaining what they’re examining and what documentation they need
- Power of Attorney filed — We sign Form 2848, which means the IRS talks to us, not you
- Document review — We review every document before anything goes to the IRS. We provide exactly what’s needed — nothing more
- Examination — The IRS reviews your records. For office and field audits, we attend all meetings in your place
- Proposed adjustments — If the IRS wants to make changes, they issue a written proposal. We review it line by line
- Negotiation or appeal — We challenge anything we disagree with. If we can’t resolve it at the exam level, we take it to appeals
- Resolution — Case closed. We make sure you understand the outcome and what it means going forward
Why You Need Professional Representation
Here’s the reality: anything you say to the IRS can be used against you. Even an innocent statement can be misinterpreted, taken out of context, or used to expand the scope of your audit.
Your CPA probably filed your return. That’s great. But filing a return and defending one are two completely different skills. You wouldn’t send your dentist to perform heart surgery — the same logic applies.
A qualified tax attorney knows IRS procedures inside and out, understands the legal standards the IRS must meet, and knows exactly how to position your case for the best possible outcome.
Appeals & Next Steps
If you disagree with the audit results, you have the right to appeal. The IRS Office of Appeals is independent from the examination division, and they settle the majority of cases they hear.
We’ve won over 100 appeals by building cases that are thoroughly documented and legally sound. The key is presenting a clear, well-organized argument that makes it easier for the appeals officer to rule in your favor.
If appeals doesn’t resolve it, the next step is Tax Court. We’re prepared for that too, but in our experience, most cases settle well before they get to trial.
How to Prevent Future Audits
Once your audit is resolved, the last thing you want is another one. Here’s what we recommend to minimize your risk:
- Keep meticulous records — especially for deductions and business expenses
- Report all income — even if you didn’t receive a 1099
- File on time, every time
- Use actual calculated figures rather than round numbers — while not a major audit trigger on its own, it’s a best practice that signals accuracy in your records
- Work with a qualified tax professional who understands your situation
- Consider a proactive tax strategy engagement to optimize your structure and reduce risk
Want to make sure this doesn’t happen again? After resolving your audit, we can help restructure your taxes to minimize future risk. It’s the other side of what we do — and it’s just as important as the defense. Learn about our tax strategies →
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Frequently Asked Questions
Complex Tax Issues Strategy FAQs
What qualifies as a “complex” tax issue?
Complex tax issues involve situations where multiple areas of tax law intersect, where the facts don’t fit neatly into standard categories, or where the financial stakes require a higher level of analysis. Examples include business restructuring with tax implications, multi-entity ownership structures, cryptocurrency and digital asset taxation, cannabis tax compliance (Section 280E), exit planning and M&A transactions, and cases involving both federal and state controversy simultaneously.
When should I hire a tax attorney instead of a CPA?
A CPA is the right choice for tax preparation, bookkeeping, and straightforward compliance. A tax attorney is essential when you face potential legal exposure — audits, collections, penalties, criminal investigation, or any situation where attorney-client privilege matters. For complex planning (entity restructuring, exit transactions, international issues), the ideal approach is a tax attorney and CPA working together. We regularly collaborate with our clients’ CPAs to ensure both compliance accuracy and legal protection.
How does Section 280E affect cannabis businesses?
IRC Section 280E prohibits businesses trafficking in controlled substances from deducting ordinary business expenses — even if the business is legal under state law. This means cannabis businesses often face effective tax rates of 60-80%. The only deduction allowed is cost of goods sold (COGS). Proper structuring of cannabis operations, meticulous COGS documentation, and strategic entity planning can significantly reduce the 280E burden. We represent cannabis businesses in both planning and IRS defense.
What tax issues arise when selling a business?
The structure of a business sale — asset sale vs. stock sale, installment sale vs. lump sum, allocation of purchase price among asset classes — dramatically affects the tax consequences for both buyer and seller. Other considerations include depreciation recapture, state tax apportionment of the gain, potential Qualified Small Business Stock exclusions (Section 1202), and the timing of recognition. We work with business owners well before a sale to structure the transaction for optimal tax results.
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