We’ve just come back from an inspiring wave of events - from the energy of the Tax Mob Conference, where we gathered minds across specialties, to our own Executive Touch Power Hours, where real-world strategies move from slide decks into practice.

These moments remind us that learning isn’t passive. We invest in conferences, seminars, and retreats not only to fill a CPE quota, but to refine judgment, build networks, and walk away sharper.

Yet too often, professionals (and clients) assume: “If it’s a business event, it must be deductible.” The truth is more complex - and understanding those nuances is what separates tax preparers from tax strategists.

This week, I want to explore how we qualify conventions and seminars for deductions - connecting what the IRS actually allows to what you likely saw in recent events, and why it’s not just about paperwork, but about telling a defensible story.

The Real Rules: When Conferences & Seminars Actually Qualify

The law recognizes three buckets for professional events:

1. North American Conventions

The easiest to deduct — provided your attendance benefits your trade or business. The IRS defines “North America” broadly, covering places you might not expect: Jamaica, Panama, Guam, Puerto Rico, and more.

The IRS’s test? Reasonableness:

• Does attending benefit your trade or business?

• Is it reasonable for the meeting to be held in North America (which includes U.S. territories and certain partner countries like Panama, Jamaica, Guam)?

When the answer is yes — and you document why — travel, lodging, and the event itself become deductible. The definition of “North America” is broader than most realize: yes, San Francisco and New York, but also Panama City or Montego Bay.

Planning insight: After some retreats, I saw tax pros wisely attach event schedules and speaker lists to their files — showing the IRS why this wasn’t a vacation, but active professional learning.

2. Foreign Conventions

If the event is outside the North American area — think Paris, Tokyo, or Buenos Aires — the hurdle rises:

• The event must directly relate to the active conduct of your trade or business.

• And it must be as reasonable to hold abroad as at home.

The IRS looks at factors like: who’s attending, who’s organizing, and historical locations.

Example: An international tax conference drawing speakers and attendees worldwide could qualify. But a purely U.S.-member group choosing Rome for scenery likely wouldn’t.

3. Cruise Ship Conventions

The least common — and least practical:

• The ship must be U.S.-registered (rare outside Hawaii or select river cruises).

• All ports must be in the U.S. or its possessions.

• Deduction is capped at $2,000 per year.

• Strict documentation required: daily agenda, hours spent, and a signed statement from the organizer.

Planning tip: Some niche professional groups have successfully hosted on U.S.-flagged riverboats - but only after careful compliance planning.

The Latest Rundown – News in Tax & Advisory 🗞️

1. Congress Set to End IRS Direct File Pilot 🏛️

A “Big Beautiful Bill” passed by the Senate and headed to the president includes elimination of the IRS’s free Direct File service within 30 days of enactment. The service, available to simple filers in 25 states, had low usage (311.5K users) despite positive reception. A proposed public–private replacement is being funded at $15 million to potentially serve up to 70% of taxpayers.

2. IRS Faces Major Implementation Challenges 👥

With 26% of its workforce cut—primarily impacting IT, taxpayer support, and small-business divisions—the IRS now must swiftly prepare for implementing sweeping 2026 tax changes under the new legislation. Agency leaders warn this could derail readiness for the next filing season.

3. New IRS Commissioner Confirmed 🔐

On June 12, Billy Long was confirmed (53–44) as the 51st IRS Commissioner and was sworn in June 16. His appointment comes as the agency confronts deep staffing cuts and begins efforts to modernize compliance processes—like integrating AI tools—amid political pressure and division

🔎 What Tax Professionals Should Do Now:

• Evaluate filing systems - If you're using Direct File, plan for migration or alternative software/processes as the pilot is likely ending.

• Prepare for service impacts - Alert clients to potential delays in service, refunds, and IT responsiveness in 2026.

• Plan for TAS Act changes - Keep an eye on legislative movement that could lead to faster refund resolutions.

• Update digital asset workflows - Incorporate Notice 2025‑33 relief into broker-preparation processes; revisit AICPA resources.

Documentation: The Difference Between Knowing & Proving

Whether you operate solo or through an entity, the substance is the same: the event must qualify. But corporations face an extra procedural layer:

• The corporation must book and pay directly (e.g., corporate card), or

• The owner-employee must submit an expense report; the corporation then reimburses the documented expense.

Without the expense report and proper documentation, the corporation loses the deduction, even if the expense itself was legitimate. It’s an avoidable compliance trap — but only if you design internal processes intentionally.

For solo proprietors, the deduction flows directly onto Schedule C, provided it’s documented and clearly related to the trade or business.

Imagine this:

Your client is invited to a “networking retreat” in an island location. They assume, “It’s business — fully deductible.” Most preparers would nod and move on.

Instead, you ask the right questions:

• Who’s organizing the event?

• Where are the members based?

• What’s the formal agenda?

• Is it in North America or abroad?

You discover the event is in Aruba (North American area). The organizer is a national trade association. There’s a published schedule. You advise the client to:

• Retain the schedule and promotional materials.

• Keep receipts.

• Note why attendance benefits their specific business.

They leave not just with deduction advice, but a sense that you protected them from risk and unlocked tax value they could have missed.

That’s how expertise becomes retention.

When a client asks, “Can I deduct that retreat?” the best answer isn’t yes or no — it’s, “Let’s see how we can make it qualify.”

Too many tax professionals rely on general rules they learned years ago — missing the nuance that transforms compliance into strategy.

Inside The Executive Touch, we:

• Dive deeper than “surface answers.”

• Share real case studies and live discussions.

• Offer a peer community that values precision over generality.

And your first 7 days? FREE — because we’d rather prove value than promise it.

If even one client question leads to a smarter answer, the ROI is clear.

🎯 Closing Thought

First, not all conventions and seminars are deductible. It’s not about geography alone — but about alignment with your trade or business, and the structure of the event itself.

Second, corporations must handle the process right: expense reports, reimbursements, and documentation. Skipping these formalities can undo otherwise valid deductions.

And finally, the role of the advisor isn’t just to say yes or no. 

It’s to explore why, document how, and show the client that tax strategy isn’t just about avoiding mistakes - it’s about building defensible positions that reduce taxes over years.

Hope you learned a lot from this edition, see you on the next one!

With appreciation for the complexity you navigate, and belief in what you bring to your clients,
– Angie Toney & The Executive Touch