Insurance Trust Best Practices and Pitfalls

Date: Wednesday, November 11, 2020
Time: 8:30am - 9:30am
Location: Via Zoom
Speaker: Jessie A. Gilbert, Esq., Principal, Cummings & Lockwood LLC

We are pleased to announce that Jessie A. Gilbert, Esq., a Principal in Cummings & Lockwood’s Private Clients Group, will be our guest speaker on “Insurance Trust Best Practices and Pitfalls” at our virtual “breakfast” meeting on Wednesday, November 11, 8:00 a.m. to 9:00 a.m.

Jessie’s presentation will cover Administration, Audit Issues, Gift & GST Tax Reporting, and Fixing “Broken” Trusts.

She’ll also discuss how Insurance Trusts are an excellent tool to remove insurance from an estate for tax purposes, yet still have the funds available for family members. Poor trust administration can make this technique open to attack by the IRS on audit.  Learn best practices for administration, and gift and GST tax reporting. Find out what the IRS looks for on audit, and how to fix suboptimal trusts and trust administrations.

Jessie is a Principal in Cummings & Lockwood's Private Clients Group and is based in the Greenwich office. She advises high net worth individuals on estate and tax issues, helping them with succession, generation-skipping and asset protection planning. She also represents executors and trustees with respect to probate, estate and trust administration matters, as well as with estate and fiduciary income taxes. Jessie is a frequent writer and lecturer on estate planning and administration topics, including business succession planning, fiduciary income tax, and the Principal and Income Act. She is a graduate of Hamilton College, Case Western Reserve School of Law, and has a Masters of Tax Law from New York University.

Guest Attendees:

Due to the fact that we’ve had to move to all virtual programming, guests are welcome to attend our breakfast webinars at no charge. However, our guest policy remains essentially the same: guest attendance by a professional colleague is limited to two virtual events within a two-year period. Eligible guests and professionals that work or live in Fairfield County can apply for EPC-LFC membership by completing a membership application, accessible on our website ( Questions regarding membership or the application process can be addressed by Robin Sherwood, CFP®, our First Vice President, Membership, at 203-972-8262 or

Please click on the document link below for registration details for members and guests. Note, registration deadline is Monday, November 9.

Related Document(s):

See Upcoming Event Calendar