Insights

Notes from the practice.

Reading of recent regulatory developments, patterns from active engagements, and the questions we routinely put to plan sponsors, brokers, and counsel. Written by the practitioners doing the work.

Practice Note · March 2026

The five Form 5500 errors we encounter most often on first review.

Patterns we see in third-party filings — and the corrective approach we take when remediation is preferable to amendment.

Field Note · 4 min read
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Audit · February 2026

Preparing for a DOL health-plan investigation: a 30-day operational checklist.

From the first letter through the on-site interview, the documentation an employer should already have assembled — and the documentation it almost certainly has not.

Field Note · 4 min read
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Practice Note · January 2026

Late filings: when DFVC is the right answer, and when it isn't.

The Delinquent Filer Voluntary Compliance Program is the cleanest path for most late returns — but not all. A short guide to when remediation looks different.

Field Note · 4 min read
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Practice Note · December 2025

The wrap-document trap: how acquired plans drift out of compliance.

Welfare plans inherited through acquisitions frequently outlive their original sponsor's documentation. Where the drift begins, and how to bring the plan back to the document.

Field Note · 4 min read
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Regulatory · November 2025

Reading a Form 5500 like a regulator: the questions our review starts with.

The first pass through a 5500 has a structure. We walk through ours — what we look for, what surfaces, and how the review informs the rest of an engagement.

By the Cherry Park Practice · 5 min read
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Audit · October 2025

The first letter from the DOL: what it asks, what it implies, and how fourteen days disappears.

A reading of the standard opening correspondence from a DOL health-plan investigation — and the operational moves that put an employer ahead, rather than behind, the response window.

Field Note · 4 min read
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