Why DIY or AI-Generated Wills and Trusts are Risky

 Posted on June 26, 2025 in Estate Planning

Estate planning is one of the most valuable steps to protect your assets, provide peace of mind, and secure your legacy. In today’s digital world, online services and DIY planning are more accessible and often offer a lower cost. DIY and AI-Generated documents offer a cheap starting point but result in high cost of cheap planning. Rather than taking risks with your most precious assets and your loved ones, talk to an experienced Illinois estate planning attorney who can help you build a customized plan. Here are just a few of the top reasons using DIY planning for your estate plan is a risky bet. 

Estate Planning is not a Template

Estate planning is not a "template" or "fill-in-the-blank" process. Mistakes occur through mistakes in the document execution and the failure to correctly implement the estate planning strategies results in unforeseen consequences. An undervalued aspect of an estate planning attorney is the counsel and advice. Effective estate planning is not about documents or their execution. Rather, a good estate planning lawyer will listen to your concerns and family dynamics and recommend a solution to your unique family circumstances.

DIY and AI-generated documents lead to confusion, court battles, and more importantly broken families from a failure to invest in proper planning. Do it yourself kits result in financial losses, which are the consequences of improper planning and mistakes made in the drafting of the documents (and execution of the plan).

Do-It-Yourself and AI-Generated Estate Planning often discount the importance of state-specific laws, family dynamics, taxes, or creditor protection. Complex assets and large estates also create difficulties that are a challenge to coordinate an effective plan. Many DIY wills and trusts are invalid because of improper witness and notary execution. These are the four major problems:

• Proper witnessing and notarization are missing

• Specific trustee or executor’s powers are ignored

• Failure to provide clear distribution instructions or anticipate foreseeable problems that an estate planning attorney would identify

• Improper planning to coordinate retirement accounts, life insurance, or real estate

Initial Cost of Planning is Cheap, But the Results Create High-Cost Administration

The initial planning was cost-effective, but the results of poor planning cost thousands of dollars in legal fees and costs. Furthermore, ineffective trust administration or planning results in high-cost estate and trust administration. If your documents are invalid or unclear, your family may be forced into court to resolve family disputes, which is the opposite of trust planning. 

AI-Generated and DIY estate planning tools often miss critical aspects of Illinois law such as the Illinois estate tax. Estate tax planning is difficult for an experienced lawyer. Estate tax laws constantly change and failure to update one’s documents could result in thousands of dollars in court costs and financial losses. 

Failed Execution of Alternative Estate Planning Strategies

Additionally, estate planning strategies employed may have been simple, but ineffective. Revocable living trusts can be simple, but they can also be very complex. A higher asset value will often result in a revocable living trust which employs sub-trust and creditor protection strategies that are absent in DIY plans. Lawyers inexperienced at handling complex assets and estate planning will also make critical mistakes. 

Mistakes create financial losses and family strife. Family strife and court battles are the opposite of legacy planning. Here are some examples of many of the missed opportunities of estate planning:

• Simplified Revocable Living Trust was created to avoid Probate, but fail to achieve other goals

• Powers of Attorneys for Finances and Healthcare

• HIPAA Release

• Advanced Healthcare Directives that are thorough and comprehensive

• Special Needs Trust

• Execution of LLCs 

• Use of Asset Protection and Creditor Protection Strategies

By skipping these planning tools, you may expose your family to unnecessary taxes, court involvement, or loss of government benefits for loved ones.

• Revocable living trusts (to avoid probate and protect privacy)

• Powers of attorney (for finances and healthcare)

• Advance healthcare directives

• Special needs trust

• Asset protection strategies

By skipping these tools, you may expose your estate to unnecessary taxes, court involvement, or loss of government benefits for loved ones.

Outdated or Generic Language

Many online-generated trusts and wills use boilerplate language that minimizes the state’s current laws or the IRS private letter rulings. In Illinois, there are specific statutes like 755 ILCS 5 that govern trust provisions, real estate transfers, tax clauses, and probate procedures. Even well-executed and good-looking documents that look "official" may result in unenforceable results or confusion. Ambiguity and poorly drafted documents result in litigation, probate court involvement, and loss of control over how assets are handled.

Lack of Coordination of Beneficiary Designations

The biggest mistake of DIY and AI-Generated Planning is the failure to coordinate beneficiary designations. Trust and estate planning strategies contradict especially with the ownership and beneficiary designations of retirement plans and life insurance. On the internet, one article will state that retirement accounts such as 401(k) and IRA assets shall never be directed to a trust. In contrast, a standalone retirement plan estate plan specializes in addressing the unique nature of retirement assets. Standalone retirement plan trust can be a powerful tool when exercised by a skilled and experienced estate planning attorney.

Poor coordination of beneficiary designations involving the following accounts will result in probate and court involvement:

• Life insurance policies and plans

• Retirement accounts such as 401(k) and IRAs

• Risks of Simple Planning using Transfer on Death or Payable on Death Accounts

Accounts that are distributed according to beneficiary designations are a complex area of estate planning law. An inexperienced estate planning lawyer will often fail to properly account and plan for beneficiary designations, especially the coordination with trusts and wills. Improper designations will result in your money going to the wrong persons or – worse – to your in-laws. 

These accounts pass according to the beneficiary designation, not your will or trust. If your legal documents and beneficiary forms aren’t coordinated properly, your plan may fail and your money may go to the wrong person.

Call Your Oswego, IL Estate Planning Lawyer 

Hiring an experienced and skilled estate planning lawyer is an investment in getting your estate plan right. An estate planning attorney is an investment in your family’s future, especially their peace of mind. You are not just buying documents, but implementing a complex, personalized plan that addresses your family dynamics. An effective estate plan should do the following:

• Protects your assets

• Honors for your goals and wishes

• Minimizes or eliminates court involvement

• Tax Planning minimizes or eliminates taxation

• A well-prepared financial and legal plan provides peace of mind and wealth preservation

Even a small mistake or error in your DIY-or AI-generated plan can result in huge financial losses and emotional damage. The emotional trauma results in broken families and legacy plans unfilled. Call your Aurora, IL estate planning attorney today at Gateville Law Firm by calling 630-780-1034 or via online form.