How To Avoid Taxation On Life Insurance Proceeds
Dale Tamburro • December 24, 2025

Wouldn't it be nice if you could pass on your entire estate free of taxation? While this scenario is highly unlikely, there are some smart decisions that you can make to avoid future tax consequences. One poor decision that investors seem to make frequently is the naming of "payable to my estate" as the beneficiary of a contractual agreement such as an IRA account, an annuity or a life insurance policy. However, when you name the estate as your beneficiary, you take away the contractual advantage of naming a real person and subject the financial product to the probate process. Leaving items to your estate increases the estate's value, and it could subject your heirs to exceptionally high estate taxes. Here we show you some of the ways that you can reduce the taxes on your estate and ensure that your heirs will benefit from it as much as possible.


Taxation of Life Insurance Death Benefits 
One of the benefits of owning
life insurance is the ability to generate a large sum of money payable to your heirs in the event of your death. An even greater advantage is the federal income-tax free benefit that life insurance proceeds receive when they are paid to your beneficiary. However, although the proceeds are income-tax free, they may still be included as part of your taxable estate for estate tax purposes. 


Section 2042 of the Internal Revenue Code states that the value of life insurance proceeds insuring your life are included in your gross estate if the proceeds are payable: (1) to your estate, either directly or indirectly; or (2) to named beneficiaries, if you possessed any incidents of ownership (we'll discuss this more below) in the policy at the time of your death. In Massachusetts if your gross estate is over $2.0Million you will be required to file an estate tax return, which could cost $5,000-$10,000 and if your net estate is over $2.0Million you will owe estate taxes. An insurance policy of $500,000 or more will get you to $2.0Million very quickly. 


Ownership Transfer 
For those estates that will owe taxes, whether life insurance proceeds are included as part of the taxable estate depends on the ownership of the policy at the time of the insured's death. If you want your life insurance proceeds to avoid federal taxation, you'll need to
transfer ownership of your policy to another person or entity. Here are a few guidelines to remember when considering an ownership transfer:

  1. Choose a competent adult/entity to be the new owner (it may be the policy beneficiary), then call your insurance company for the proper assignment, or transfer of ownership, forms.
  2. New owners must pay the premiums on the policy. However, you can gift up to $19,000 per person in 2025, so the recipient could use some of this gift to pay premiums.
  3. You will give up all rights to make changes to this policy in the future. However, if a child, family member or friend is named the new owner, changes can be made by the new owner at your request.
  4. Because ownership transfer is an irrevocable event, beware of divorce situations when planning to name the new owner.
  5. Obtain a written confirmation from your insurance company as proof of the ownership change.


Life Insurance Trusts 
A second way to remove life insurance proceeds from your taxable estate is to create an
irrevocable life insurance trust (ILIT). In order to complete an ownership transfer, you cannot be the trustee of the trust and you may not retain any rights to revoke the trust. In this case, the policy is held in trust and you will no longer be considered the owner. Therefore, the proceeds are not included as part of your estate. 

Why choose trust ownership rather than transferring ownership to another person? One reason might be that you still wish to maintain some legal control over the policy. Or perhaps you are afraid that an individual owner may fail to pay premiums, whereas in the trust you can ensure that all premiums are paid in a timely manner. If the beneficiaries of the proceeds are minor children or individuals you would prefer to receive their share over time, an ILIT will allow you to name a trusted family member as trustee to handle the money for those individuals. under the terms of the trust document.


IRS Regulations 
The IRS has developed rules that help to determine who owns a life insurance policy when an insured person dies. The primary regulation overseeing proper ownership is known in the financial world as the
three-year rule, which states that any gifts of life insurance policies made within three years of death are still subject to federal estate tax. This applies to both a transfer of ownership to another individual and the establishment of an ILIT. So, if you die within three years of the transfer, the full amount of the proceeds are included in your estate as though you still owned the policy.


Another IRS regulation will look for any incidents of ownership by the person who transfers the policy. In transferring the policy, the original owner must forfeit any legal rights to change beneficiaries, borrow against the policy, surrender or cancel the policy or select beneficiary payment options. Furthermore, he or she must not pay the premiums to keep the policy in force. These actions are considered to be a part of ownership of the assets and if any of them are carried out, they can negate the tax advantage of transferring them. However, even if a policy transfer meets all of the requirements, some of the transferred assets may still be subject to taxation. If the current cash value of the policy exceeds the $18,000 gift tax exclusion, gift taxes will be assessed and will be due at the time of the original policyholder's death.


Conclusion 
Today, it's not uncommon for individuals to be insured under a life insurance policy for $500,000 to $1 million in
death benefits. Once you add in the value of your home, your retirement accounts, savings and other belongings, you may be surprised by the size of your estate. If you factor in several more years of growth and the fact that the estate tax exclusion for Massachusetts is $2 million, it is clear that many of us are facing an estate tax issue. A viable solution to this is to maximize your gifting potential and to transfer policy ownership whenever possible at little or no gift-tax cost. As long as you live another three years after the transfer, your estate could save a significant amount of tax.


By Dale Tamburro July 10, 2026
Those of us who set up "Revocable Living Trusts" do so with at least one of these objectives in mind: 1. To avoid probate court supervision of your property in the event of your disability. 2. To avoid probate court supervision of your property at the time of your death and during the settlement of your estate. 3. To avoid probate court supervision of property which you wish to be managed in trust funds after your death. If your objective in establishing a Revocable Living Trust is solely to avoid probate court supervision of the trust(s) you establish for your family, and these trusts are not intended to come into existence until after your death, then there is no need to transfer title to your property into trust name while you are alive. You may continue to own all of your property in your own name, unless for tax or other reasons we have suggested that rearrangement of title be made as between yourself, your spouse, your children or other forms of trusts. Likewise, if your objective in establishing a Revocable Living Trust is to avoid probate court supervision of your property in the event of your disability, you need only give an appropriate "Durable Power of Attorney" to a family member, trusted friend or advisor. This Power of Attorney should authorize your attorney-in-fact to transfer your property to your Revocable Living Trust after you become disabled or incapacitated. No property need be placed in trust name prior to that time. Despite this, I often recommend funding the trust yourself, while you are alive because successor trustees often have better luck with financial institutions then being empowered under a Durable Power of Attorney. If your objective is to avoid probate of your property at the time of your death and the settlement of your estate, you will be successful only if and to the extent that your property is transferred into the name of the Trustee of your Revocable Living Trust before your death. This Memorandum is intended as a general guide for you to use in making the title transfers that are necessary if you wish to avoid probate of your estate by use of a Revocable Living Trust. Please keep clearly in mind that your Revocable Living Trust can still be an effective form of "Will" for you even if you do not place your property in the trust while you are alive, but you will not have the extra advantages of avoiding probate. Transferring property to a Revocable Living Trust while you are alive is best thought of as a means of avoiding the cost of probate after your death by doing the work yourself while you are still alive. You will not need legal help for most of the transfers, if you are willing to put in the time and effort. To the extent you do not wish to make this effort, we are perfectly willing to take care of these matters for you, but of course we will have to charge for our services at our usual hourly rates for attorneys and paralegals. I. Transferring Title to Property - The First and the Most Important Step It is unfortunate but true that there is no uniformity among the various banks, brokers and other institutions as to how title to property is properly transferred to a Revocable Living Trust. Until the time comes when there is such uniformity, each institution you deal with is apt to have its own requirements, assuming it is familiar at all with the concept of a "Revocable Living Trust." You will save yourself a great deal of time and trouble if the very first step in your program for transferring assets is to CALL THE INSTITUTION INVOLVED AND FIND OUT WHAT IT REQUIRES. When you call, you should say: " I would like to transfer my (description of property) into my Revocable Living Trust. Would you please tell me what I have to do and send me the necessary paperwork. " The institution may be perfectly familiar with this process, and have a quick answer for you. If so, follow its requirements to the letter. Do not attempt to argue with the institution as to whether its requirements are "right," you will most likely be dealing with someone at a relatively low level who has no decision-making capability and can only follow the instructions of his or her superiors. If the person you are calling doesn't seem to know what you are talking about, ask the person to refer you to someone else who might help you. If you still can't get any satisfaction, your best hope is to call us and ask for assistance. II. Completing the Papers Necessary to Transfer Title As we mentioned, each institution will have its own requirements for transferring title. You are likely to be dealing with banks, brokerage firms, insurance companies, companies in which you own stock or bonds, and so on. Some of their requirements may include: A. Identification of the Trust We normally recommend that you use a fairly formal legal title for your Revocable Living Trust, which includes the name of the Trustee or Trustees followed by the word "Trustee," the name of the trust (usually your own name) and the date on which the trust was signed. It might look something like this: "John L. Jones, Trustee of the John L. Jones Revocable Trust under trust dated May 14, 2024." Almost any variation on this name is appropriate, particularly if your Revocable Living Trust itself includes a statement that the trust may be known by a simpler name, such as "The John L. Jones Revocable Trust." However, do not insist on using this name if the institution prefers its own method. Be sure, however, the name chosen at least contains the name of the trust, the Trustee's name, the word "Trustee," and the date of the trust, such as "John Jones, Trustee u/d/t3 dated 5/14/24." B. Tax Identification Number Most institutions will request the trust's taxpayer identification number. If you are a Trustee or a co-Trustee, the tax identification number will be your Social Security number. If you are not a Trustee or a co-Trustee, you will need a taxpayer identification number. You should ask the Law Office of Dale J. Tamburro to obtain a taxpayer identification number for your trust or your accountant. C. Signature Authority If there is more than one Trustee, as, for example, where you and your spouse are co­ Trustees, you may be asked to designate who has power to sign documents on behalf of the trust. It is most likely your trust contains a power to delegate signing authority, in which case, if you wish, you may choose between having either Trustee sign on behalf of the trust or having both Trustees sign. D. Copy of Trust Agreement Occasionally, an institution may request a copy of the Revocable Living Trust Agreement for its files. In general, it is recommended that you provide the institution with a photocopy of the Agreement rather than with an original. If you do not feel comfortable with furnishing the institution with the entire Trust Agreement, ask the institution whether it will accept the first and last pages of the Agreement, which should be sufficient to identify the parties to the Agreement and the date it was signed. III. Transferring Title - Some of the Requirements for Common Types of Property A. Brokerage Accounts; Bank Custody Accounts You probably will find that brokerage firms and banks, in particular, and often other organizations, will ask to have another set of contracts of agreements signed by the Trustees of your Revocable Living Trust. Presumably they will be the same contracts or agreements you signed previously in your individual capacity. B. Registered Stocks and Bonds If you own stocks or bonds in your personal name (i.e., they are not registered in the name of your bank or brokerage firm), they need to be transferred into the names of the Trustees of your Revocable Living Trust. Your broker may ask you to endorse the back of the stock or bond certificate, or to supply what is known as a stock or bond "power" authorizing the transfer agent for the company involved to make the transfer on its books. Occasionally, you may be asked to provide a formal Letter of Instruction requesting the transfer which must be signed by you and guaranteed by an authorized official. C. Unregistered (Bearer) Bonds To transfer bonds which are not registered in your name (i.e., bearer bonds) to your Revocable Living Trust, we suggest that you open a safe deposit box in the trust's name and place the bonds in the safe deposit box inside an envelope which is marked with the trust's name. D. Real Estate You will need the help of an attorney to change title to real estate. The Law Office of Dale J. Tamburro, P.C. would be glad to help, or you can contact the attorney who handled the original closing for you. There is a fair amount to do in transferring title to real estate, but in most cases the charges for residential real estate should not exceed several hundred dollars if you can supply copies of the existing deed and the most recent tax bill for the property. You will be asked to sign new deeds transferring title from yourself to a simple "nominee" trust (the beneficiary of which is your Revocable Living Trust), and those deeds will then be recorded in Registry of Deeds where the property is located. There will be an additional small filing fee by the Registry for recording these deeds. If there is any indebtedness on the property, it may be advisable to obtain the written consent of the lending institution prior to completing the transfer. E. Partnerships Many people have invested in real estate, oil and gas, or other partnerships. Some of those partnerships are publicly traded; others are private. Some partnership agreements require that the consent of other partners be obtained before transferring the property to a Revocable Living Trust; others don't. It is important for you to contact the Managing Partner of the partnership (or the financial advisor or brokerage firm which introduced you to the partnership) and ask for their particular requirements. F. Bank Accounts To transfer a bank account to a Revocable Living Trust, call your bank officer for instructions. Usually all that will be required is to open a new account and have the Trustees sign a new signature card. It is generally not advisable to transfer a checking account into the name of a Revocable Living Trust unless the account consistently contains a large balance. It should also be noted that transferring a Certificate of Deposit to a Revocable Living Trust prior to its maturity may result in a forfeiture of interest. G. Motor Vehicles and Boats Generally, we advise against transferring title to motor vehicles and boats to Revocable Living Trusts, partly because of the time and difficulties involved in dealing with the Department of Motor Vehicles, and partly because of the reasonably quick changeover or properties as one buys and sells them. However, in the case of an antique car of considerable value, or a very substantial boat, it might be worth the effort. Again, you will need to call the Department of Motor Vehicles or other appropriate state or federal agency to find out the transfer requirements. They all differ, and you should be prepared for conflicting advice. H. Contents of Your Home There is a difference of opinion among attorneys as to whether it is practical to transfer the contents of your home (furniture, furnishings and the like) into your Revocable Living Trust. Obviously, the contents of your home are ever changing. It is uncertain whether a transfer of the contents you now own will be effective with respect to furniture and furnishings you acquire later. Some of our clients who are extremely concerned about entirely avoiding probate at all costs have taken the step of assigning their "tangible personal property" to their Revocable Living Trust, following the format shown on Exhibit A to this memorandum. The Law Office of Dale J. Tamburro, P.C. feel it is appropriate to sign such an assignment, so long as you recognize that it can lead to disputes later on as to who owns the property, what types of property are included on the assignment, when ownership is to be determined and similar issues. To minimize such disputes, if you own valuable tangible personal property such as artwork which you wish to transfer to your Revocable Living Trust, we suggest you sign a separate assignment form fully describing the property. I. Insurance Policies on Your Life As a broad general rule, there are greater tax advantages to placing insurance policies in a separate form of trust known as an Irrevocable Life Insurance Trust rather than in a Revocable Living Trust. However, even if you elect not to place the insurance policies in an Irrevocable Life Insurance Trust, the insurance proceeds will still not pass through probate as long as they are payable to a named beneficiary. Therefore, it is only advisable to name your Revocable Living Trust as the beneficiary of your life insurance if you wish to add the proceeds to trusts established for your family under your Revocable Living Trust which will continue after your death. It would be very rare to name your Revocable Living Trust as owner of the policies, as this arrangement lacks the often considerable tax advantages of an irrevocable insurance trust. If you do decide to designate your Revocable Living Trust as beneficiary of your life insurance, contact the insurance company and request a change of beneficiary form for the policy. On the form, identify the Revocable Living Trust as beneficiary of the policy in the manner described above. J. Pension Plans and IRAs In some cases, it may be desirable to designate a Revocable Living Trust as beneficiary of an IRA or pension plan, particularly if you would like the proceeds to be added to trusts established for family members under your Revocable Living Trust which will continue after your death. Since it may not always be beneficial from an income tax standpoint to make such a designation, particularly if there is a surviving spouse, it is important to consult the Law Office of Dale J. Tamburro, P.C. prior to doing so. If you decide to designate your Revocable Living Trust as beneficiary, you should obtain beneficiary designation forms from the plan administrator or bank, and the Revocable Living Trust should be correctly identified as the new beneficiary on these forms. For some pension plans, a married person must obtain the written consent of his or her spouse in order to designate a Revocable Living Trust as the primary beneficiary of the plan. IV. Other Details to Consider In addition to transferring title to your property into the name of the Trustee of your Revocable Living Trust, you should consider some or all of the following: A. Transferring Insurance Coverage If you transfer some types of property to your Revocable Living Trust, such as your home, household furniture and furnishings, or your automobile, there may be insurance policies associated with this property. Most of us own homeowner's or automobile policies, for example. You should call your insurance agent and ask whether your policies should be rewritten so that they show the legal owner to be the Trustee of the Revocable Living Trust. B. Requesting Confirmation of Transfers Within a few weeks of transferring property to your Revocable Living Trust, you should contact the appropriate institution and request written confirmation that the transfers have been properly completed. Where appropriate, you should request the new documents of title (i.e., newly issued stock or bond certificates, deeds, etc.) and forward them to the Trustees of your Revocable Living Trust. C. Contact This memorandum is intended to provide general guidance with respect to transferring assets to your Revocable Living Trust. If you should encounter any difficulties or questions during the transfer process, you should consult the Law Office of Dale J. Tamburro, P.C. to ensure that the transfers have been properly made so that your objective in avoiding probate court supervision of your property may be accomplished. EXHIBIT A ASSIGNMENT OF TANGIBLE PERSONAL PROPERTY STATE OF ) ) ss: COUNTY OF ) I, John L. Jones, individually, hereby assign any interest I may have in all of my tangible personal property to myself as Trustee (or any Successors in Trust) of the John L. Jones Revocable Trust under Agreement dated May 14, 2011. John L. Jones, Individually ___________________________________________ John L. Jones, Trustee ___________________________________________ Witness ___________________________________________ Address___________________________________________ Witness ___________________________________________ Address___________________________________________ STATE OF ) ) ss: COUNTY OF ) The foregoing instrument was hereby acknowledged before me this day of , 2011, by John L. Jones, Notary Public: My commission expires:
By Dale Tamburro July 10, 2026
Whether you are married with children or a single adult, you should have an Estate Plan to protect your assets, loved ones and personal care in the future. What legal documents do you need to have an appropriate Estate Plan? Everyone is different and estate planning is unique to everyone, so it is difficult to generalize. However, most of us need the first four of the fundamental legal documents referred to below. More and more of us need a Trust of some kind but the specifics of why you need a trust and what kind of trust requires more discussion: Durable Power of Attorney Health Care Proxy A Will HIPAA Release Living Trust Credit Shelter Trust Version if you are married and have a net worth in excess of $2,000,000 combined. Joint Marital Revocable Trust if net worth is less than $2,000,000 Individual Revocable Trust if not married. ( Primarily for Long-term Care Protection you would consider an Income Only Irrevocable Trust ) ( Another trust called an Irrevocable Life Insurance Trust(ILIT) is used solely so the death benefits are not included in your Estate for Estate Tax Purposes ) A Durable Power of Attorney The Durable Power of Attorney is a written document which allows you (the Principal) to designate someone you trust (the Attorney-in-Fact) to make Personal, Business and Financial decisions for you in the event of illness or incapacity. The Durable Power of Attorney allows you to name someone who could take over your personal finances, pay your bills, sign a deed or bill of sale, sign you in or out of a hospital or rehabilitation hospital, make gifts, deal with the IRS, deal with your insurance company or stockbroker, purchase an annuity or engage in Medicaid or long-term care planning on your behalf. A well-drafted Durable Power of Attorney will enable your Attorney-In-Fact to do anything you could as if you were personally present. A Durable Power of Attorney can be broadly defined, or it can be very specific. It depends upon what one wants or needs. A Durable Power of Attorney does not necessarily take effect at the time of signing. A Power of Attorney can "spring" into effect only upon the principal's incapacity or disability whether sudden (an accident or a stroke) or gradual (Alzheimer's disease or mental weakness/illness). A Durable Power of Attorney should be signed while one is in good health. It is preferable to have discussed the Durable Power of Attorney beforehand and make sure the Attorney-In-Fact named in the document agrees to serve and understands what he or she is expected to do. A Durable Power of Attorney needs to be witnessed and be signed in the presence of a Notary Public. A Durable Power of Attorney has its drawbacks. If it is too old a bank or investment company may not accept it. If it does not reference the particular use that you need it for, its intent may also fail. Even if you have a Durable Power of Attorney, you should have it reviewed every three years to see if it is still sufficient. Health Care Proxy A Health Care Proxy is a relatively straightforward legal document that one signs designating another person to make any and all care decision for him/her in the event of illness or incapacity. The person who is appointed is called a health care agent. The agent is authorized to act only if the attending physician determines in writing that you lack the capacity to make or communicate health care decisions. The decision-making authority includes the authority to make decisions about life sustaining treatment. Again, similar to the Durable Power of Attorney a properly drafted Health Care Proxy will have sufficient detail to cover most if not all consequences. A general announcement naming someone to make all medical decisions for you is not sufficient. A Will A Will is a document which, among other things, directs how your property will be disposed of after your death. It is also used to name a Guardian for your minor children in the event of a simultaneous death. The Will also allows you to choose the person or persons who you want to manage your Estate. If you do not have a Will, your property will be distributed according to the Statutory Laws of the Commonwealth, which may or may not be in accord with your wishes. Additionally, virtually anyone, including your creditors, could petition the Probate Court for permission to administer your estate if you have not appointed an Executor through a Will. The use of a Will is part of the Probate Process it DOES NOT AVOID PROBATE. HIPAA Release A signed HIPAA release form must be obtained from a patient before their protected health information can be shared with other individuals or organizations, except in the case of routine disclosures for treatment, payment or healthcare operations permitted by the HIPAA Privacy Rule. A HIPAA Release would allow your spouse, children or whomever is named in it to converse with your doctors about your condition. It does not allow them to make any health decisions, those are left to the person named as your Health Care Proxy. A Living Trust (revocable) A Living Trust is a document by which a person legally transfers ownership of certain property to another party to be held and managed for his or her benefit or for the benefit of others. The person who establishes The Trust is the Donor. A Living Trust, so called, is a trust that is established and takes effect while one is alive as opposed to a Testamentary Trust which is established in a will and only comes into being upon death. A Living Trust is often times revocable - meaning - the person who created it can revoke it. It also can be amended from time to time as situations and circumstances change. By placing property in a Trust, a Trustee is legally responsible for management of the Trust property. A Trust serves to avoid Probate upon the death of the Donor, as the Trust Assets are not in one person's name at the time of death. Unlike a Will, a Living Trust need not be filed with the Registry of Probate. One similarity of a Will and Trust is that the Trust can provide to whom the Trust assets will go upon the death of the one who created the trust (the Donor). One of the differences between a Will and the Trust is that the Will takes effect when you die. The Living Trust, on the other hand, can be established while you are alive, and the Trustee will hold your assets and manage them during your lifetime. The Executor of your Will can only distribute your assets to your heirs at the time of death. The Trustee can manage the Trust in both instances - while you are alive and following your death. A Living Trust provides needed flexibility to deal with changes over the years. It provides, as does a Will, a means to provide protection for handicapped, disabled, or mentally challenged family members or loved ones. It can protect a financially irresponsible beneficiary. It allows one to make specific arrangements for children or grandchildren from a prior marriage. A Trust can also be used to avoid or reduce estate taxes. EXAMPLES: I am asked for generalities: I don’t like generalities because each person, each couple are unique in my mind and the difference between being a document drafter and someone who provides an estate plan is understanding the individuality of your clients. However, examples sometimes help make things easier to understand. Anyone over the age of 18 should have a Health Care Proxy. Anyone one who is married should have a Health Care Proxy and Last Will and Testament. Anyone who owns a house or has a retirement account should have a Durable Power of Attorney. It is that simple. A single person or a widow or widower who have never had a trust will not need a credit shelter trust. They may or may not need a revocable trust or an irrevocable trust or both. This is what having an hour discussion is all about. But…. If you want to have complete unfettered control of what is held in trust, you do NOT want an irrevocable trust, you want a revocable trust. If you want to protect the assets of the trust from creditors or to qualify for MassHealth/Medicaid you do NOT want a revocable trust, you want an irrevocable trust. If you want to control some assets and protect other assets you might want one of each kind of trust. Both kinds of trusts will aid you in the management of the assets if you were disabled and to avoid the probate process if you have passed away. Again, be careful to not assume what I just described is for you. What you might hear in a seminar or a class, whether with me or another speaker is not designed to define what you need. It is a guide. It is essential that have a one on one with an estate planning attorney to create a plan that is distinctive for you. For more information on drawing up a Will, Durable Power of Attorney, Health Care Proxy, or Living Trust, contact your local attorney. For more information on The Law Offices of Dale J Tamburro, please visit our web site at www.tamburrolaw.com, email us at Dale@Tamburrolaw.com or call us directly at 617.489.5919.