Special Situations & Federal Problem Resolution

For the problems that don’t fit a single practice area — and require knowing how the agencies actually work.

Some of the most serious matters a family office faces do not arrive labeled. They do not fit neatly into “tax” or “immigration” or “regulatory.”

They arrive as a phone call: something has happened, it touches a federal agency, and we don’t know who to call.

A principal receives an IRS examination notice referencing offshore structures.

A family member’s immigration status becomes entangled with a complex source-of-funds question.

A family-office executive is named in a FINRA inquiry.

A regulatory matter requires understanding not just what the law says, but how a specific agency evaluates, prioritizes, and resolves cases like it.

These are special situations. They demand more than a single specialist.

They demand counsel who can see the whole problem, coordinate across every dimension it touches, and draw on professionals who understand the relevant agencies from the inside.

That is the work of this practice.

The advantage: inside knowledge of how agencies actually operate

The difference between a good outcome and a damaging one often comes down to a single factor: understanding how the agency on the other side actually thinks.

How does the IRS decide which examinations to escalate?

How does a FINRA inquiry move from informal to formal?

What does a USCIS officer actually look for when source-of-funds questions arise?

These are not questions answered in a statute.

They are answered by experience — by people who spent careers inside those agencies making exactly those decisions.

Dilendorf Law Firm coordinates a vetted network of attorneys and former federal professionals — including individuals with backgrounds at federal law-enforcement and regulatory agencies — who understand these processes from the inside.

When a matter touches a federal agency, we are positioned to assess not only the legal exposure, but the practical reality of how that agency is likely to proceed, and to shape our client’s response accordingly.

This is the same principle that defines our cybercrime practice, where former federal investigators help us understand how cases are evaluated.

We apply it across the full range of federal matters a family office may encounter.

What we handle

Special situations vary by definition. The matters we are most frequently asked to resolve include:

Federal examinations and inquiries touching complex structures. IRS examinations involving offshore trusts, cross-border holdings, or sophisticated planning — where the technical tax question and the procedural reality must be managed together.

Immigration matters intersecting wealth and source-of-funds questions. Where a family member’s residency, visa, or citizenship process becomes complicated by the complexity of family wealth, prior structures, or international holdings.

Regulatory inquiries involving family-office personnel or entities. Including matters before financial-industry regulators where a family-office executive, advisor, or operating entity faces scrutiny.

Multi-agency and cross-border matters. Problems that touch more than one agency, more than one jurisdiction, or more than one area of law at once — and require a single coordinating counsel to hold the whole picture.

Sensitive matters requiring discretion and privilege. Problems a family prefers to resolve quietly, correctly, and under the protection of the attorney-client relationship, before any matter escalates.

How we work

One coordinating counsel. Complex problems fail when they are handed to multiple specialists who never speak to one another. We serve as the single point of coordination — holding the entire matter, managing every professional involved, and ensuring the strategy is consistent across every dimension the problem touches.

Under privilege. Where appropriate, our work proceeds under the protection of the attorney-client relationship, which helps keep sensitive assessments and findings confidential.

Discreetly. We understand that for many family offices, the priority is not only resolving the matter but resolving it quietly. Our approach is built around confidentiality.

With the right people. We bring in the specific expertise each matter requires — drawing on our network of attorneys, tax professionals, former federal professionals, and international counsel — and we manage them as one coordinated team.

Who this is for

This practice serves single- and multi-family offices, ultra-high-net-worth individuals, founders, and family principals who face a problem that:

• Touches one or more federal agencies
• Crosses multiple areas of law or jurisdictions
• Requires discretion and confidentiality
• Demands not just legal knowledge, but practical understanding of how the relevant institutions actually operate

If you are facing a problem and you are not certain who to call — that is precisely the situation this practice exists to resolve.

Why Dilendorf Law Firm

Our founder, Max Dilendorf, is counsel of record in more than 130 cybercrime arbitration matters and has built a practice defined by complex, high-stakes problems that cross conventional boundaries. The firm coordinates a network of professionals — including those with federal-agency backgrounds — assembled precisely for the matters that do not fit elsewhere.

We are the firm families call when the problem is serious, the path is unclear, and the people involved need to understand not just the law, but how the system on the other side actually works.

Contact us at info@dilendorf.com or 212.457.9797 for a confidential consultation.