Trust & Will and When I Die Files sit on opposite sides of the same problem. Trust & Will creates the legal documents: your will, your trust, your power of attorney. When I Die Files handles everything those legal documents don't cover: the personal letters, the life stories, the passwords, the "where to find everything" information your family will need.

These aren't really competing products. They're two halves of a complete plan. But since people often evaluate them side by side, here's an honest comparison.

What each product does

Trust & Will is an online estate planning platform. You answer questions about your family, assets, and wishes, and it generates state-specific legal documents: a last will and testament, power of attorney, healthcare directive, and guardian nominations. The Trust Plan adds a revocable living trust and related documents. Attorney support is available as an add-on.

When I Die Files is a legacy platform that combines secure document storage, guided legacy letter writing, and story prompts. You store your important documents (including the ones Trust & Will creates), write personal messages to individual family members, record your life stories, and control who accesses what. It doesn't create legal documents -- it stores them alongside everything else your family needs.

Head-to-head comparison

Feature	Trust & Will	When I Die Files
Creates wills	Yes (state-specific)	No
Creates trusts	Yes ($499+)	No
Power of attorney	Yes	No
Healthcare directive	Yes	No
Document vault	No	Yes (end-to-end encrypted)
Legacy letters	No	Yes (to specific recipients)
Story prompts	No	Yes (guided writing)
Family sharing	Beneficiary designations	Controlled access per person
Attorney access	$299 add-on	No
Pricing	From $199 one-time	One-time purchase (TBA)
Annual renewal	$19-$39/year (for edits)	None

Where Trust & Will wins

Legal document creation. This is what Trust & Will does, and they do it well. The documents are state-specific, legally valid, and generated through a guided questionnaire that takes about 15 minutes. If you don't have a will, this is a direct solution. When I Die Files doesn't create legal documents at all.

Attorney access. For $299, Trust & Will connects you with a licensed estate planning attorney in your state (available in 43 states plus DC). That's significantly cheaper than the $1,000-$3,000 most attorneys charge for a full estate plan. If your situation has any complexity -- blended family, business ownership, property in multiple states -- professional review is worth it.

Guardian nominations. Trust & Will makes it straightforward to name guardians for minor children and pets, with backup designations built into the workflow. If you're a parent, this feature alone justifies the purchase.

Immediate legal validity. Once you sign and witness your Trust & Will documents, they're legally binding. There's no ambiguity about whether they'll hold up. When I Die Files stores important information and personal messages, but nothing it produces has legal weight on its own.

Where When I Die Files wins

Personal legacy. Trust & Will doesn't have any way to write a letter to your daughter. Or explain to your family why you made the decisions you made. Or record the story of how you met your spouse. Legal documents handle assets and authority. When I Die Files handles meaning.

Legacy letters are the core of the platform. You write to specific people, and your words reach them according to your instructions. Our guide on combining legacy letters with a digital will makes the case for why both sides matter.

Secure document storage. Trust & Will creates documents but doesn't give you a vault. Once you generate your will and trust, you need somewhere to store them where your family can find them. When I Die Files provides an end-to-end encrypted vault for exactly this purpose -- your legal documents, insurance policies, account information, and personal files all in one place.

Practical information. Where's the life insurance policy? What's the financial advisor's phone number? What are the passwords for the accounts that need to be closed? Trust & Will doesn't touch any of this. When I Die Files does. See our essential end-of-life planning checklist for the full scope of what your family will need.

No recurring cost. Trust & Will charges $19-$39/year to maintain editing access to your documents. The documents stay valid if you stop paying, but you can't update them without resubscribing. When I Die Files is a one-time purchase with no renewal fees.

Story preservation. Guided prompts help you write about your life, your values, your memories. Trust & Will, understandably, has no storytelling features. It's a legal tool. When I Die Files includes the writing alongside the vault.

Pricing comparison

	Trust & Will (Will)	Trust & Will (Trust)	When I Die Files
Initial cost	$199 individual	$499 individual	One-time (TBA)
Couples	$299	$599	TBA
Annual renewal	$19/year	$39/year	$0
Attorney add-on	$299	$299	N/A
5-year cost	$275-$375	$655-$755	One-time purchase

Who should choose which

Choose Trust & Will if:

You don't have a will and need to create one
You want state-specific legal documents with professional backing
You need a trust for complex estate planning
Attorney access matters to you
Guardian nominations for children are a priority

Choose When I Die Files if:

You already have legal documents (or plan to create them separately)
Legacy letters and personal messages matter to you
You need a secure vault for documents, passwords, and practical information
You want guided story writing as part of your legacy
You prefer a one-time purchase with no subscription

Use both together (recommended):

Honestly, the best setup is both. Use Trust & Will to create your legal documents. Use When I Die Files to store them, alongside your legacy letters, life stories, account credentials, and practical information. Trust & Will gives your family the legal framework. When I Die Files gives them everything else.

Your will says who gets the house. Your legacy letter says why you chose it, what it meant to you, and the memory of the afternoon you first walked through the front door. Both matter. Your family deserves both.

When I Die Files is currently in pre-launch. Join the waitlist to be the first to know when we go live.

More comparisons: Best Trust & Will Alternatives | When I Die Files vs. StoryWorth | When I Die Files vs. Everplans