Imported from digital-estate-inventory/digital-estate-inventory (SKILL.md). Install upstream with npx skills add digital-estate-inventory/digital-estate-inventory. Copyright stays with the author.

Digital Estate Inventory

What this skill is: A structured interview and capture tool. It helps you produce an organized record of your accounts, assets, credentials, contacts, wishes, and access paths — the information your people will need if they suddenly have to act on your behalf. It also produces a short Break Glass Kit — the minimum they need in the first hours.

What this skill is NOT:

• Not a legal estate plan. A legal estate plan is a set of legally operative instruments (will, power of attorney, advance directive, trust, or their jurisdiction-appropriate equivalents) executed with the formalities your jurisdiction requires. Those documents are created with a qualified attorney. This skill does not produce them.
• Not legal advice. The outputs of this skill are reference material — they do not grant authority, transfer ownership, or legally bind anyone.
• Not financial or tax advice.
• Not a substitute for talking to your people. The documentation is only useful if the right people know it exists and can get to it.

How to think about the outputs: Everything this skill produces is inventory and orientation material meant to sit next to your legal documents — not replace them. Think of it the way a business continuity plan sits next to incorporation documents: the legal papers grant authority; the runbook tells people what to actually do with it.

Attribution

This skill was inspired by the work of the Death & The Digital Estate Community Group (DADE CG) at the OpenID Foundation — in particular:

• The Digital Estate Planning Guide (DADE CG, March 2026), which shaped the session structure and the categories this skill asks about.
• The companion whitepaper The Unfinished Digital Estate: Culture, Law, and Technology After Death (Flanagan, Kiser, Saxe; March 2026), which provides the research foundation for why digital estate planning matters — covering cultural perspectives, abuse threat models, delegation semantics, and the global regulatory landscape.

This skill is an independent work inspired by those documents; it is not a DADE CG or OpenID Foundation publication. For more on DADE CG, visit: https://openid.net/cg/death-and-the-digital-estate/

IMPORTANT DISCLAIMERS

THIS IS NOT LEGAL ADVICE.

This skill provides general guidance for digital estate inventory work, inspired by the OpenID Foundation's Digital Estate Planning Guide. It is not intended, and should not be construed, as legal advice regarding any matter or jurisdiction.

You SHOULD consult a qualified estate attorney for advice tailored to your circumstances and jurisdiction. Laws governing access to digital accounts after death vary by location. Accessing someone's account without proper authorization may violate laws or terms of service — even if done with the express wishes of the account owner.

You MUST verify that the instructions and suggestions provided by this skill are appropriate and secure for your specific situation. The skill cannot account for your unique legal, technical, or personal circumstances.

Neither this skill's author, the OpenID Foundation, nor the DADE CG makes any representations or warranties regarding the legal accuracy or implications of the guidance provided.

Laws governing digital assets after death vary dramatically by jurisdiction. Consult legal counsel in your jurisdiction for guidance on fiduciary access to digital assets, credit monitoring, government benefit notification, and estate administration.

How This Skill Works

Modes

Plan mode (default): Build your own digital estate plan. The skill walks you through sessions, each covering one domain of your digital life. Complete them in order or jump to what matters most.

Break Glass Kit mode: Don't want the full plan yet? Build just the minimum your family needs to access your accounts in an emergency. Sessions 1 (Keys) + 2 (Financial/Autopay) + a condensed executor quick reference. Can be done in one sitting. Incomplete answers are fine — document what you know, flag what's missing. Users can always upgrade from break glass to full plan later.

Quick Win mode: Don't have time for 13 sessions? Do three things in 30 minutes that prevent 80% of the damage. See "Minimum Viable Plan" below.

Reactive mode: You're managing someone else's digital estate after death or incapacitation. The skill provides a time-sensitive triage checklist focused on stabilizing the situation.

Test mode (harness-only — not an end-user mode): Takes a persona fixture (a YAML file describing pre-filled Session 0 facts, plugin selections, and any canned per-session answers) and runs the full skill non-interactively, producing the same session files and consolidated artifacts that Plan mode would. Used by the automated test harness in tests/ to verify plugin activation, layer / facet composition, and output structure. Not advertised to end users; never offered as a path on the "which mode?" prompt. See tests/README.md and the Test mode contract below for the persona format, output contract, and graceful-degradation behavior.

First question: which mode?

Before anything else, ask the user which mode they want:

"Two paths forward. Which do you want?

1. Break Glass Kit — the minimum your family needs to access your accounts in an emergency. ~1 hour. Start here if you want something useful today.
2. Full Digital Estate Plan — comprehensive inventory across 12 sessions. Multiple sittings. Start here if you want to do this thoroughly."

A partial plan with gaps flagged is infinitely better than no plan. Never block on missing information — always capture what's known and move on.

Session-Based Design

Digital estate planning is overwhelming if you try to do it all at once. This skill breaks it into focused sessions — each one takes 15–30 minutes and produces a concrete output document. You can stop after any session and pick up later.

Couples Planning

Couples planning is handled by the coupled facet (plugins/facet/coupled.md). The facet activates whenever the user is planning together with a partner — legally married, civil-union / registered partnership, cohabiting, engaged, or any other committed pair — and adapts the session structure to joint + individual sessions producing ONE plan with both partners' content clearly labeled by partner. The substantive guidance (joint-vs-individual session breakdown, authorized-user recommendations, family-plan continuity, partner cross-access) lives in the facet.

"Both of us" simultaneous-loss scenario: stays in core (this section). It applies to any multi-person planning structure, not only married couples — divorced co-parents with shared minor children, chosen-family co-trustees, business partners, and so on all have the same issue. The principle: if both lead actors in a plan are unavailable at once, the secondary executor and technical support person need access instructions, contact info for each other, and a clear playbook. Address explicitly in Session 10 and Session 12.

Separation and Divorce

Lifecycle facets handle the substantive content:

• Separated but not yet divorced — see plugins/facet/separated-not-divorced.md. Activates when the user is legally married but practically separated and divorce is not yet final. Covers the high-risk interim period (the separated spouse is typically still the legal next of kin and default beneficiary), what to update unilaterally now (powers of attorney, beneficiary designations, disposition-of-remains directive, medical-records release authorization, platform legacy contacts), and the silent-access audit. The facet also carries the safety callout for separations involving domestic violence, coercive control, or stalking — change passwords and recovery methods before any visible change to shared accounts.
• Divorce finalized — see plugins/facet/divorced.md. Treats divorce as a trigger for a full plan audit, not an incremental update, and lists the categories of action: beneficiary-designation re-cascade across every plan administrator and institution, will and trust review, POA / healthcare-proxy / disposition / medical-records-release replacement, guardianship-nomination review where minor children are involved, password-manager and platform-legacy-contact cleanup, real-property retitling per the decree, decree-mandated insurance-maintenance constraints, and re-running the jurisdiction analysis if the divorce included a move.

The facets are jurisdiction-neutral. Specific revocation rules, statutory citations, and tax mechanics live in the jurisdiction plugin.

Death vs. Incapacity

These are DIFFERENT scenarios and the skill addresses both:

• Death: Executor gets legal authority through probate. Legacy contacts activate. Accounts can be memorialized or closed.
• Incapacity: Person is alive but cannot act. Power of attorney agent needs CURRENT access to pay bills, manage accounts, and maintain services. Legacy contacts DO NOT activate. You cannot memorialize a living person's accounts. Bills still need to be paid. Services must continue.

Every session should prompt the user to consider BOTH scenarios: "What happens if you die?" AND "What happens if you have a stroke tomorrow and can't act for 6 months?"

Session Priority by Situation

Not everyone needs the same session order. After Session 0, adapt:

What You'll Produce

Two categories of output — keep them distinct. The skill produces both.

1. The Break Glass Kit (break-glass-kit.md) — a short, urgent, stress-readable document (5-10 pages) for the person making decisions in the first hours and days. Written for someone who is tired, scared, and not technical. Answers: where do I start, how do I get into the password manager, what must not lapse this week, who do I call first.

The Break Glass Kit is a subset of the full inventory — the parts that matter at 3 a.m. It is not comprehensive. It points to the full inventory for anything beyond the immediate crisis.

2. The Comprehensive Inventory — the detailed, session-by-session record of the user's digital and non-digital estate. This is reference material for later weeks and months — working through accounts, claims, closures, transfers, and legal administration. Includes:

• Individual session documents covering each domain of your digital life and non-digital assets
• A consolidated Quick Reference for whoever administers the estate — under whatever that role is called in the user's jurisdiction
• A First 48 Hours Checklist — time-critical actions (this is what the Break Glass Kit distills from)
• An Attorney Brief — a one-pager to bring to the jurisdiction-appropriate legal professional
• A Jurisdictional Assumptions document — what jurisdiction(s) the plan assumes, what terminology is used, what was adapted or skipped
• An Action Items list — consolidated, deduplicated, categorized task list of what the planner still needs to do

Why the split matters: In a crisis, no one reads 100 pages. They read the short document that tells them what to do in the next hour. Everything else is reference material they'll consult over weeks and months. Writing these as one blob means the urgent stuff gets buried. Keep them separate.

UPDATE MODE

A plan only works if it's current. Use Update Mode when the user has an existing plan from a prior run and wants to refresh it — after a life change (move, job change, marriage, new child, separation, divorce, health event), after a large financial change, or on a routine annual review. For separation and divorce specifically, see the "Separation and Divorce" section above — separation is a high-risk interim period and divorce should trigger a full audit, not just a diff.

Update Mode is NOT "redo the interview." It's a targeted diff: what changed, what's gone, what's new.

Input

The user points the skill at their existing plan directory. This directory should contain the session files from a previous run (00-orientation.md, 00-jurisdictional-assumptions.md, 01-keys-to-everything.md, … 12-attorney-brief.md, break-glass-kit.md, action-items.md, etc.).

Ask: "Where is your existing plan? Give me the directory path." Verify the directory exists and contains recognizable session files before proceeding.

Workflow

Step 1 — Load the prior state. Read every session file. Extract a compact inventory for your own reference:

• Accounts (email, financial, digital property, subscriptions)
• People (executor/administrator, technical support person, attorney, financial advisor, insurance agent, secondary contacts)
• Assets (property, vehicles, equipment with registrations)
• Loans and liabilities
• Insurance policies
• Devices
• Digital services (including mobile money, platform legacy contacts configured)

Also note the last reviewed date on each file.

Step 2 — Walk the user through by category, not by session. For each of these buckets, show the user a short summary of what's on record and ask three questions:

Here's what's on record for [category]:

• [bulleted list]

Three quick questions:

1. Anything NEW to add?
2. Anything that no longer applies?
3. Anything that has CHANGED?

Process buckets in this order (most likely to have changes first):

1. Financial accounts and loans
2. Insurance and employer benefits
3. Subscriptions
4. People (contacts, roles)
5. Devices and infrastructure
6. Digital property and professional accounts
7. Legacy contacts and platform settings
8. Communication/wishes
9. Media and memories
10. Real property

Keep each bucket to one screenful. Don't dump the full plan.

Step 3 — Life-change triggers. Ask explicitly about changes the user might not associate with the plan:

• Have you moved, changed jobs, changed marital status, had a child, or had a significant health event since the last update?
• Have any of your named people (executor, attorney, financial advisor, technical support person, insurance agent) changed roles, moved, or passed away?
• Have any of your minor children turned 18 or otherwise aged into new legal status?
• Have you acquired or disposed of property, vehicles, or major assets?
• Have you added or closed any financial accounts, credit cards, or loans?
• Have you changed password managers or added new credential stores?

For any "yes," follow up to understand the specific change.

Step 4 — Apply the changes.

• New items: append to the relevant session file's inventory table or list.
• Removed items: do not delete. Mark as ~~struck through~~ or append [REMOVED YYYY-MM-DD — reason]. This preserves an audit trail and makes the change visible to anyone reviewing history.
• Changed items: edit in place; note the change date in a footnote or table cell if the change affects access, beneficiaries, or authority.

Step 5 — Propagate to the Break Glass Kit. Any change that touches the critical path — master key location, first-call contacts, critical bills, primary accounts — must flow into break-glass-kit.md. The kit being stale is worse than the full inventory being stale, because the kit is what gets read first in a crisis.

Step 6 — Regenerate action-items.md. Rebuild the consolidated action item list based on the current state of all session files. New gaps become new items; closed gaps come off the list.

Step 7 — Update metadata. Bump the Last verified or Last updated date on each modified file and on the Break Glass Kit. If the skill produced a Jurisdictional Assumptions document, re-check whether anything there needs updating (moved jurisdictions, new cross-border exposure).

Step 8 — Present a change summary. Before closing the session, show the user a compact summary:

• Added (N items)
• Removed (N items, marked in place)
• Changed (N items)
• Files touched
• New action items
• Items that have rolled off the action list

Ask: "Does this match what you intended? Anything missed?"

What Update Mode does NOT do

• Re-interview the user from scratch
• Re-generate session files that have no changes
• Silently delete historical content (always mark removals in place with a date)
• Skip the Break Glass Kit update — that's the whole point of keeping it current

When to recommend a full re-run instead

If more than ~30% of the plan is stale, or a major life event has restructured the user's situation (divorce, relocation to a new country, loss of a named executor), recommend a full Plan Mode re-run instead of an update. Say so explicitly: "There's enough change here that an update will miss things. I'd recommend running the full sessions again — you can reuse most of the existing content as starting material."

MINIMUM VIABLE PLAN (Quick Win Mode)

If the user is short on time or overwhelmed, offer this. Three actions, 30 minutes, prevents 80% of the worst outcomes:

Action 1: Document your master key (10 minutes)

Whatever unlocks everything else — password manager emergency kit, the notebook in the drawer, the memorized master password — write it down and put it where your executor can find it. If you use a password manager, print the emergency kit. If you don't, write down the password to your primary email account. Put it in an envelope, seal it, write "OPEN ONLY IN EMERGENCY" on it, and give it to your executor or put it in a safe.

Test it. Can your executor actually use what you gave them to get in? If you haven't tested it, it's not a plan — it's a hope.

Action 2: Configure legacy contacts (15 minutes)

• Apple: Settings → [Your Name] → Sign-In & Security → Legacy Contact. Add your executor.
• Google: myaccount.google.com → Data & privacy → Inactive Account Manager. Set notification contacts and inactivity timeout.
• Facebook: Settings → Memorialization Settings. Choose legacy contact or deletion.

These are the three platforms most likely to lock out your family permanently.

Action 3: Tell someone (5 minutes)

Call your executor. Say: "I have a digital estate plan. Here's where to find it: [location]. If something happens to me, start there." If you don't have an executor, tell the person you'd trust most.

Output: quick-win-plan.md

Then come back and do the full sessions when you're ready.

OPTIONAL: Email Discovery Scan

This step requires explicit user opt-in. Never access email without it.

Email is one of the richest sources of estate-relevant information — subscription receipts, insurance policy documents, loan statements, utility bills, and financial account notifications all flow through it. An email scan can surface accounts the user has forgotten about and fill gaps in sessions 2 (financial), 3 (insurance/property), and 9 (subscriptions).

Offering the scan

After Session 0 (or at the start of sessions 2, 3, or 9 where more data would help), offer it once:

"I can optionally scan your email to help discover subscriptions, bills, insurance policies, and financial accounts for your plan. I'll run targeted searches — I won't read personal conversations. This requires an email connection. Want to try it, or would you prefer to fill everything in manually? (You can also ask me to run the scan at any point.)"

If the user declines: Proceed without it. Don't re-offer proactively — but run it immediately if the user asks for it at any point during any session.

If the user agrees: Check whether an email connector is available by looking at your current tool list for Gmail, Outlook, or other email MCP integrations. If none is available, tell the user clearly: "I don't have an email connection available in this session. You can add one in your Claude settings and run this again, or continue manually."

Running the scan

Run searches in batches by category. For each result, surface it as a candidate — never add it to the plan automatically. The user confirms, corrects, or dismisses each one.

Present findings as a simple table per category:

Searches to run by session target:

Session 2 — Financial accounts and loans:

• "account statement" OR "your statement is ready"
• "payment confirmation" OR "payment received"
• "loan statement" OR "mortgage statement"
• "annual fee" OR "membership fee"

Session 3 — Insurance and property:

• "insurance policy" OR "policy renewal" OR "premium due"
• "homeowners" OR "auto insurance" OR "life insurance" OR "umbrella"
• "property tax" OR "HOA" OR "homeowners association"

Session 9 — Subscriptions and recurring charges:

• "subscription" OR "your subscription" OR "renewal reminder"
• "receipt" OR "invoice" OR "billing statement"
• "free trial" OR "trial ending"
• "cancel anytime" OR "manage your subscription"

For each search: retrieve recent results (past 12 months is a good window), extract sender, subject, and approximate amount where visible. Do not read full message bodies unless the user asks you to.

Privacy and scope boundaries

• Only run the searches listed above — don't explore beyond the stated categories
• Don't read, quote, or store personal message content
• If a search returns results that are clearly personal (family emails, medical, legal correspondence), skip them silently
• When done, tell the user what categories you searched and how many candidates you found
• The user controls what gets added — nothing is automatic

After the scan

Fold confirmed findings into the appropriate session documents. Flag any that need follow-up (e.g., a subscription found but credentials unknown, an insurance policy with no policy number visible). Unconfirmed candidates are discarded.

PLAN MODE — Sessions

When the user invokes this skill, determine which mode they need:

• Full plan → start with Session 0
• Quick win → jump to Minimum Viable Plan above
• Reactive → jump to Reactive Mode below
• Resuming → pick up where they left off
• Email scan → offer after Session 0 or at the start of sessions 2, 3, or 9

Session 0: Orientation & Jurisdictional Context

Goal: Understand what a digital estate is, map the people, establish the legal and cultural context the plan will operate in, and adapt the rest of the skill accordingly.

This skill was originally authored in a US/individualist framing. Estate law, succession practice, cultural expectations around death, and the practical institutions involved differ dramatically across jurisdictions. Before proceeding, this session establishes context so the rest of the sessions can be adapted appropriately.

Step 0 — Expertise check and existing work

Before the jurisdictional interview, ask two calibration questions:

1. "How familiar are you with digital estate planning?" If the answer is "very" (security professional, attorney, standards author, someone who already teaches this), skip the orientation lecture in Step 4. Go straight to the substantive sessions. Offer to explain anything on request, but don't walk a domain expert through "what is a digital estate."

2. "Have you already started documenting this anywhere — a notes file, a spreadsheet, a GitHub repo, a document in your safe?" If yes, treat it as the foundation and fill gaps. Don't rebuild what exists. Ask to see it (or a summary) so the skill's output aligns with what's already there.

Ask these one at a time, waiting for each answer. The rest of Session 0 also follows the one-question-at-a-time rule — never fire 10 questions in a block. It's a conversation, not a form. Power users may bulk-answer; let them. But don't default to bulk-question format.

Step 1 — Jurisdictional discovery

Ask the user:

• Where do you live primarily? (Country and, where relevant, state/province/prefecture)
• Where are your assets located? (Property in other countries, foreign bank accounts, investments held abroad)
• Do you have multiple citizenships or long-term residency in more than one country?
• Do your likely heirs live in other countries?
• Is your marriage or partnership recognized the same way everywhere it matters? (Customary, civil, religious, common-law, same-sex, polygamous — recognition varies)
• Are there family or cultural traditions that shape how estates are handled in your community? (Extended-family decision-making, eldest-child succession, customary law, religious authority, communal property, oral-tradition succession)

Surface multi-jurisdictional exposure explicitly. A US citizen with German real estate, a Japanese national with a US brokerage, or a Ghanaian with family land and a London flat each have materially different situations that downstream sessions need to acknowledge.

Step 2 — Research the jurisdictional context

Use web search to research the user's primary jurisdiction (and any others with significant exposure) before continuing. Do not rely on your pretrained knowledge alone — succession law, registries, and common practice change, and the skill must not repeat the US defaults when they don't apply.

Search for:

• The succession/inheritance law framework (statutory scheme, any forced-heirship or reserved-portion rules, treatment of community/marital property)
• Terminology actually used in that jurisdiction for: the person who administers an estate, the legal instrument that grants them authority, the legal document expressing wishes at death, and the instrument for decision-making during incapacity
• Required formalities for wills and powers of attorney (notarization, witnesses, registration)
• Any national registries for wills, advance directives, or property (e.g., Germany's Zentrales Testamentsregister and Vorsorgeregister, land registries, beneficial ownership registries)
• Common digital services that matter locally but not globally (mobile money in much of sub-Saharan Africa and South Asia; LINE in Japan; Kakao in Korea; regional banks, insurers, and telecoms)
• Cultural norms around discussing death and succession

Cite what you find. When you surface information to the user, link to the source you used. Say "this is what my research indicates — correct me if it doesn't match your experience."

Step 3 — Produce the Jurisdictional Assumptions document

Write 00-jurisdictional-assumptions.md before starting the substantive sessions. It should contain:

• Primary jurisdiction and any secondary jurisdictions with exposure
• Key terminology this plan will use — the jurisdiction-appropriate terms for "executor," "probate/administration," "will," "POA," "incapacity agent." Default US terms are used only if the user's jurisdiction is US.
• Legal framework summary — 2–3 sentences summarizing how succession works in the primary jurisdiction, with sources
• Forced-heirship or reserved-portion rules — if they exist, state that they exist and that the user's attorney will advise on their effect. Do not attempt to interpret them.
• Formality requirements — does this jurisdiction require notarized wills? Registered POAs? Note this so later sessions don't assume markdown documents are legally operative.
• Registries to consider — any national or regional registries the user should be aware of (wills, advance directives, real estate, beneficial ownership)
• Locally significant services — mobile money, regional banks, dominant social/messaging platforms, telecoms
• Cultural and family-structure context — what the user told you about how their family handles these decisions
• Sections of this skill that are being adapted or skipped for this user — e.g., "Credit bureau freeze guidance is US-specific and does not apply here"; "Customary successor role will be documented alongside statutory administrator"

This document shapes every subsequent session. When a session has US-default content that doesn't apply, note the adaptation in the session output.

Step 4 — Walk the user through the basics

Once the jurisdictional context is set, walk the user through:

1. What a digital estate includes (it's more than passwords — photos, messages, financial accounts, subscriptions, domains, code, social media, devices, cloud storage, local data, smart home, loyalty programs, browsing history, and jurisdiction-specific services like mobile money or regional platforms)
2. The "personas" concept from the guide — personal, professional, parent, volunteer, community, religious, and family roles. Each may have different accounts with different handling instructions. Ask: "Do you manage any accounts on behalf of organizations, clubs, HOAs, volunteer groups, religious communities, or extended family?"
3. What happens without a plan (lost memories, ongoing charges, fraud exposure, legal barriers, family conflict — and in some jurisdictions, frozen accounts and administrative paralysis until formal authority is granted)
4. The 7-step roadmap from the guide, adapted to jurisdiction:
   1. Identify digital assets
   2. Document access details
   3. Choose a technical support person for whoever will administer the estate
   4. Communicate your wishes
   5. Store the information securely
   6. Review and update regularly
   7. Seek legal guidance from a professional qualified in your jurisdiction

Step 5 — Ask the context questions

Ask one at a time. Explain briefly why each question matters — users answer more completely when they understand the relevance.

• What legal documents have you already put in place (will, POA, advance directive, or their jurisdiction-appropriate equivalents)? When were they last reviewed?
• Do you use a password manager? Which one?
• How would you describe your technical comfort level?
• What's driving you to plan now? Common motivators — any of these resonate?
  • A death in the family or close circle
  • A health scare (yours or someone close)
  • A news story or someone else's disaster
  • A life event (new child, marriage, divorce, move)
  • Professional credibility — you're a security professional, attorney, standards author, or advisor in this space, and not having your own plan is an embarrassment. This is a distinct motivator worth naming. If the user is a professional in this field, the emotional hook throughout the skill should be: "You advise others on this. Does your own plan exist?"
• Do you have minor children? Do they have their own devices/accounts?
• Do you have adult children? If so: they may now be a resource in your plan (secondary executor, technical support person, contact) rather than just a dependent. Do they know they're in your plan? Have they been told what's in it? When minor children age into adulthood during the plan's lifetime, the plan should reflect the shift — but wills and POAs often don't.
• Are you more concerned about death or incapacity? (Both matter.)
• For couples: is your partner able to act independently on your behalf today if needed? What are the mechanics in your jurisdiction?

Step 6 — Note the legal foundation without interpreting it

• Will (or jurisdiction equivalent): Does one exist? Is it current? Does it meet the formality requirements you researched?
• Power of Attorney / incapacity instrument: Does one exist? Who is named? When was it executed?
• Healthcare / advance directive: Does one exist?
• Digital asset provisions: Older estate documents often predate explicit digital-asset fiduciary access laws in jurisdictions that have them. Ask the user to raise this with their attorney — don't characterize it as a gap yourself; whether it matters depends on the jurisdiction.
  • Age heuristic (not a rule): POAs and wills drafted before ~2018 rarely include digital asset provisions — this wasn't standard practice yet in most jurisdictions. If the user's documents are older than ~5 years, flag them proactively for attorney review. Don't interpret what's missing — just surface the age risk so the user doesn't have to know what they don't know.

Output: 00-orientation.md — summary of the user's starting point, people map, legal status, and plan outline. Plus 00-jurisdictional-assumptions.md from Step 3.

Session 1: The Keys to Everything

Goal: Document the foundational accounts that unlock everything else.

These are the highest-priority assets because they're the recovery path for every other account: email, phone, password manager, and primary device access.

Walk the user through documenting:

Priority order:

1. Password manager — this IS the master key. Document: which software, where is the master password / emergency kit, has the executor tested access?
2. Primary email — password resets flow here. Document: provider, 2FA method, recovery options.
3. Phone / mobile number — SMS codes for 2FA. Document: carrier, account credentials, transfer process. If the phone plan lapses, the number can be recycled and SMS-based 2FA dies with it.
4. Primary device access — phone PIN, computer password, biometric setup, disk encryption recovery keys.
5. Cloud account (iCloud, Google) — ties together devices, backups, photos, purchases.

Security guidance:

• Password manager emergency access is the single most important thing to document and store securely. If the executor has this, they can access almost everything else.
• Test the emergency access procedure. An untested backup is not a backup.
• Document where hardware security keys (YubiKeys, etc.) are physically located and which accounts they protect.
• Identify any accounts where a hardware key is the ONLY 2FA method with no backup codes — this is a single point of failure.

Passkey warning: Passkeys are becoming primary credentials for many services. If your passkeys are stored in a platform keychain (iCloud Keychain, Google Password Manager), understand the limitations:

• Apple Legacy Contact currently does NOT grant access to Keychain items including passkeys
• If an account uses passkey-only authentication with no password fallback, your executor may be permanently locked out
• Document which accounts use passkeys and whether a password fallback exists
• For critical accounts, maintain a password-based login option until platform legacy access catches up

Employer/workplace accounts:

• Work email, work laptop, employer-provided phone — these go back to the employer. Document what's on them that's personal (photos, personal files) and retrieve it NOW.
• Employer stock options, RSUs, ESPP — document vesting schedules and exercise windows. Some options expire 90 days after separation (including death).
• Employer life insurance, disability coverage, employer-sponsored retirement plan — document in Session 3.

Incapacity scenario:

• If incapacitated, your POA agent needs to pay bills, manage accounts, and maintain services. Can they access your email and phone TODAY without your help?
• Consider: 1Password Emergency Access or shared vault, authorized user on phone account, recovery contact on email.

Password manager emergency access features — check explicitly:

Many password managers offer a built-in emergency access or account-recovery feature that is separate from any printed emergency kit. Users often don't know it exists. Ask specifically:

• 1Password: Settings → Emergency Access. Designate a trusted contact who can request access after a waiting period.
• Bitwarden: Emergency Access (premium feature).
• LastPass, Dashlane, Keeper: All offer equivalent features under various names.

If the password manager supports this, configure it AND test it before relying on it. This is a second recovery path, independent of the printed emergency kit. Document which recovery paths exist and who is configured for each.

The "IN CASE OF EMERGENCY" shared vault:

Beyond individual credentials, ask: "Do you have a dedicated shared vault or document that consolidates emergency contacts — financial advisor, estate attorney, insurance agent, technical support person, secondary executor?"

If not, prompt the user to create one (e.g., a shared 1Password vault titled "IN CASE OF EMERGENCY"). It should contain:

• Financial advisor — name, firm, phone, email
• Estate attorney — name, firm, phone, email
• Insurance agent — name, carrier, phone, all policy numbers
• Technical support person — name, phone, role, how they access the documentation
• Secondary executor — name, phone, role
• Critical account summary credentials (enough to get the executor started — not every login)
• Scanned PDFs of will, POA, healthcare directive, and insurance policy cover pages (see Session 7)
• Pointer to the full plan

Access model: The spouse/primary executor gets direct access as a family-vault member. Everyone else — secondary executor, technical support person, adult children — finds the vault via the break glass process (emergency kit → password manager → ICE vault). This reduces unnecessary credential exposure while keeping the vault reachable in a crisis.

The vault should be self-contained. Anyone who completes the break glass process should be able to act without needing anything else. Build it before sharing it — a half-populated emergency vault shared prematurely creates false confidence.

Password manager hygiene — two audiences:

A password manager only works as an estate planning tool if (a) it's used consistently so the vault is actually complete, and (b) the executor can navigate it cold. Both audiences need attention.

For the account holder, ask:

• Is the browser extension installed on all devices you use regularly?
• When you log into a new account, do you save it to the password manager?
• Do you use generated passwords, or do you reuse passwords across accounts?
• Is it set up on your spouse's / partner's devices too?
• Have you run the built-in security audit (1Password Watchtower, Bitwarden Reports) to check for reused, weak, or breached passwords?

If the answer to any is "no," briefly walk the user through fixing it. A vault with 50 entries and 200 missing credentials is not a complete estate planning record.

For the executor / survivor: assume they have never used 1Password (or equivalent) beyond browser autofill. The Break Glass Kit must include a short, plain-language "how to use the password manager" section covering:

• How to sign in on a new device
• How to search the vault
• How the browser extension autofills credentials
• How to handle a passkey entry
• How to view all vaults (family, shared, ICE)
• How to use a YubiKey if one is required
• What to do if they can't find something

Don't assume the executor is a power user.

Has the other person tested it?

Users often test emergency access themselves and feel confident. But they are not the one who will execute it — the executor / spouse is. The test that matters is whether that person can do it, alone, without help, using only what's stored in the emergency location. These are two different tests. Both need to pass before the plan is considered working.

"Have you told them?"

After the user names any person in a role — executor, technical support person, secondary executor, legacy contact, emergency vault viewer — immediately ask: "Does [name] know they have this role?" If no, it's an action item. The plan does not exist if the people in it don't know they're in it. Apply this rule consistently across every session.

Output: 01-keys-to-everything.md

Session 2: Financial Accounts & Autopay

Goal: Document all financial accounts, ensure beneficiaries are designated, and map the autopay chain.

Walk the user through:

• Bank accounts (checking, savings) — institution, account type

• Credit cards — issuer, primary cardholder

• Investment/brokerage accounts

• Retirement accounts (401k, IRA, Roth)

• Cryptocurrency wallets or exchanges — special attention: without the private key or seed phrase, crypto is permanently lost

• Mobile money and peer-to-peer payment services — in many regions this is the primary digital financial service, not a secondary one. Ask about whatever is dominant in the user's jurisdiction and any regions where they hold assets or have family. Examples by region (not exhaustive — research what's relevant):

  • Sub-Saharan Africa: M-Pesa, MTN Mobile Money, Vodafone Cash, AirtelTigo Money, Airtel Money, Wave, Orange Money
  • South Asia: Paytm, PhonePe, Google Pay India, bKash (Bangladesh), Nagad, JazzCash (Pakistan), easypaisa
  • Southeast Asia: GCash (Philippines), Maya, GrabPay, DANA, OVO (Indonesia), TrueMoney (Thailand), MoMo (Vietnam)
  • East Asia: WeChat Pay, Alipay, LINE Pay, Kakao Pay
  • Latin America: Mercado Pago, Nubank, Pix (Brazil), Yape (Peru), Nequi (Colombia)
  • Middle East & North Africa: STC Pay, Fawry, Benefit Pay
  • Europe: Revolut, Wise, Bunq, Bizum (Spain), Swish (Sweden), MobilePay (Denmark)
  • North America / Oceania: PayPal, Venmo, Zelle, Cash App, Interac e-Transfer (Canada), Beem It (Australia)

  Mobile money accounts are often tied to the SIM/phone number. If the number is deactivated, the account can become inaccessible — document both the account credentials and the SIM/carrier details. Succession processes vary significantly by provider and country; note the carrier's documented process where available.

• Tax preparation software/accounts

• Financial tracking apps (YNAB, Mint, Monarch, Copilot, spreadsheets) — if the user tracks finances in one place, document it here and note what it covers and what it doesn't. Confirm credentials are in the password manager.

• For each account: are credentials in the password manager? Are beneficiaries designated?

Tax records — where they live:

The executor often needs the last several years of tax returns and supporting documents to (a) file the decedent's final return, (b) calculate basis for inherited assets, (c) respond to any audit notice that arrives after death, and (d) value the estate. Document the location of:

• Filed returns — current year and at least the prior 3–7 years (retention recommendations vary by jurisdiction). For each year, where is the return stored? Examples: tax software cloud account, accountant's portal, paper folder in a filing cabinet, encrypted PDF in cloud storage, scanned in the password manager attachments.
• Source documents for unfiled or current-year returns — W-2s, 1099s, K-1s, brokerage 1099-B / 1099-DIV / 1099-INT, mortgage interest statements, charitable giving receipts, business expense records, HSA contributions, foreign income statements. Where are these collected through the year (e.g., a "tax 2026" folder in cloud storage, a physical inbox)?
• Basis records for assets — original purchase confirmations for stocks, real-estate closing documents, capital improvements to real property (which adjust basis on sale or inheritance), records of inherited property valuations. These are routinely lost; recovering them after the fact can be impossible.
• Tax preparer or accountant — name, firm, contact, what years they prepared, and whether they retain copies of past returns.
• IRS / state tax authority online accounts — confirm credentials are in the password manager. The executor may need these to retrieve transcripts or respond to notices.

Outstanding loans and liabilities — the executor needs to know these exist and have the information to act:

• Auto loans
• Personal loans or lines of credit
• Student loans
• Business loans
• Outstanding credit card balances

For each: document lender name and contact, account number, current balance, monthly payment, autopay source card, and whether credentials are in the password manager. How loans are handled at death varies by jurisdiction, loan type, and lender — the executor should consult an attorney. The goal here is making sure nothing is unknown or missing.

Beneficiary warning: Beneficiary designations on financial accounts may not align with your will. Verify every beneficiary is current and consistent with your wishes. Ask your attorney how beneficiary designations interact with your will in your jurisdiction.

Crypto special handling:

• Seed phrases and private keys must be stored securely AND accessibly
• Hardware wallet PINs must be documented
• Without the seed phrase, crypto is permanently and irrecoverably lost
• Exchange-held crypto (Coinbase, etc.) has account recovery processes but may require probate

Autopay chain analysis — CRITICAL: Map every recurring payment to the card/account that pays it. Then answer: "If this card is cancelled (because the cardholder died), which bills stop being paid?"

Always ask billing frequency — never assume monthly. Insurance premiums are often quarterly, semi-annual, or annual. Many subscriptions are annual. This matters because the executor needs to know which bills are coming due soon vs. which have months of runway. An annual insurance premium just paid is low urgency; a monthly phone bill is always one month away from lapsing. The urgency of redirecting each charge changes dramatically with frequency.

This is where families get blindsided. The deceased's credit card gets cancelled, and suddenly the mortgage autopay bounces, the utilities shut off, and the kids' phone plan lapses.

Family plan subscription continuity — flag explicitly:

If any subscription is a shared family / team plan paid for by one member (password manager family plan, Apple One family, Google One family, streaming family plans, cellular family plan), document it carefully. If that person dies and the subscription lapses, every family member loses access at once. The password manager family plan is the most dangerous — losing it can lock the whole family out of every vault at the worst possible moment. Flag these as bills that MUST NOT lapse, and ensure the surviving spouse / executor knows to keep them paid even before closing the deceased's accounts.

Incapacity scenario:

• Joint accounts: the healthy spouse can still pay bills. No issue.
• Sole accounts: the POA agent needs access NOW. Can they log in?
• If incapacitated, bills still need to be paid. Map which accounts are joint vs. sole.

Fraud prevention checklist for executor:

• Notify credit reporting agencies of the death and freeze credit reports (process varies by jurisdiction)
• Contact banks and credit card issuers
• Notify relevant government benefit agencies (process varies by jurisdiction)
• Monitor for fraudulent activity on open accounts
• Do NOT close joint accounts immediately — bills may autopay from them

Output: 02-financial-accounts.md

Session 3: Insurance, Benefits & Property

Goal: Document insurance policies, employer benefits, and real property that survivors need to claim, maintain, or manage.

[!important] Flag, don't advise Session 3 touches insurance, benefits, property, and titling — areas where it is easy to slip into legal, insurance, or financial advice. Do not. When you identify an issue — a title gap, a beneficiary inconsistency, a policy expiring, an unclear RSU scenario at death — name the issue, briefly explain why it matters for access or claims, and refer the user to the appropriate professional (attorney, insurance agent, financial advisor, plan administrator, HR). Do not explain how to resolve it. "Here are your options" is advice. "This is a gap; your attorney needs to advise on how to address it" is planning guidance.

This rule applies to every session — but Session 3 is where it's most tempting to cross the line.

Tell the user why you are asking each question. "I'm asking about your LTD policy because if you're incapacitated and can't work, your spouse needs to know it exists to file a claim — most people who have these policies forget to tell their spouse." The why creates engagement and produces more complete answers than a bare form.

Walk the user through:

• Life insurance — provider, policy number, beneficiary, agent contact

• Health, dental, and vision insurance — these are the most immediately relevant policies for incapacity, not death. A caregiver or POA agent needs this information on day one to authorize treatment and manage ongoing care.

  • For each: carrier name, plan name/type, member ID, group number, covered dependents
  • Where to find it: physical insurance cards (wallet, home), employer HR/benefits portal, carrier member portal, EOBs in email
  • Confirm credentials to the HR/benefits portal and each carrier's member portal are in the password manager
  • Add a summary (carrier, member ID, group number) to the emergency kit or ICE vault — this should be findable in minutes, not after a search
  • Note whether coverage is employer-provided or individually purchased; employer-provided coverage is contingent on employment status — the POA agent should know this and check with HR if employment status changes during incapacity

• Homeowner's/renter's insurance

• Auto insurance

• Disability insurance — especially important for incapacity scenarios

• Long-term care insurance — many families don't know this exists until it's too late

• Umbrella/liability insurance

• Employer benefits — life insurance through work, stock options, equity compensation, disability. Ask specifically about:

  • Pension or defined-benefit plan — is there one? Vesting status, plan administrator contact, survivor benefit options. Rules and portability vary by employer and jurisdiction.
  • Deferred compensation — any arrangement where earned pay has been set aside for future payment (sometimes called executive compensation, supplemental retirement, or similar). These don't always appear on a pay stub. Document the plan name, administrator, and account balance. What happens at death or separation is plan- and jurisdiction-specific — the executor should consult an attorney or the plan administrator.
  • Any other compensation that hasn't vested or been paid out yet

• Social insurance and government benefits — varies significantly by country and jurisdiction; ask explicitly rather than assuming. The jurisdiction plugin names the specific programs and procedures; the categories the inventory should capture are:

  • National retirement / disability program (where the jurisdiction has one): has the user created an account with the relevant agency? Do they know their projected benefit?
  • Disability benefits the user may qualify for during incapacity
  • Survivor benefits — what does a spouse or dependent receive from government programs at the user's death? The executor and surviving spouse need to know to file claims; most are not automatic
  • Veterans' benefits — if the user is a veteran, document the relevant agency's identifier(s), service-connected disability ratings, and survivor-benefit programs available in the jurisdiction
  • Any other government benefit the user currently receives or has a future claim to

• "Is there anything else we haven't covered?" — always ask this explicitly before closing Session 3. Prompt with examples: "Any other insurance policies — pet, travel, event, collectibles, umbrella, identity theft? Any employer perks with financial value — legal plans, financial counseling, employee stock purchase programs outside of what we covered? Any income sources we haven't documented — rental income, royalties, side business, trust distributions, alimony or support payments?" The goal is to surface anything that doesn't fit neatly into the categories above. Don't assume the list is complete without asking.

• Real property — ask explicitly about each type; don't assume the primary residence is the only property:

  • Primary residence — mortgage lender, deed status, property taxes, HOA (if applicable)
  • Second home or vacation property — mortgage, property taxes, insurance, HOA, property manager if rented out
  • Rental properties — property manager contact, tenants, leases, rental income accounts, insurance
  • Vacant land — location, tax parcel number, property taxes, any liens
  • Timeshares — contract terms, ongoing fees, managing company contact, account credentials
  • Family-owned or jointly-held property — property shared with siblings, parents, extended family, or other co-owners (e.g., inherited cabin, family farm, inherited land). Document all co-owners and how to reach them; the executor will need to coordinate with them. Note whether ownership is documented in a formal agreement.
  • Fractional ownership, co-ops, or other shared ownership structures — governing documents, co-owner contacts, management company For each property: document address, how title is held, all co-owners if any, mortgage or lien (if any), insurance carrier, how property taxes are paid, and any property managers or tenants who need to be notified. Consult your attorney on how each property transfers — title structure and co-ownership arrangements vary significantly.

  Property documents — where they live. The executor or surviving co-owner cannot transfer, sell, refinance, file an insurance claim, or maintain the property without the underlying documents. For each property, document the location of:

  • Title and deed: for owned property, where is the recorded deed copy or title abstract held? If there is a mortgage, the user typically does not possess the original deed of trust or mortgage instrument — the lender holds the security instrument and the recorded deed is on file with the county recorder. Note this explicitly; record the lender, the loan number, the recorder's office, and where any closing-package copy is kept.
  • Title insurance policy — usually issued at closing; useful if a future title dispute arises.
  • Mortgage or HELOC documents — note number, lender contact, where statements arrive (paper, lender portal, email).
  • Property tax records — where the bills arrive, where past payment receipts are filed, the assessor's parcel number.
  • Survey, plat, and any easement documents — often in the closing package; useful for any boundary or improvement decision.
  • HOA or condo documents — bylaws, CC&Rs, current assessments, board contacts.
  • Home maintenance and improvement records — service histories (HVAC, roof, plumbing, electrical, septic, well), warranty documents, receipts for capital improvements (which affect the cost basis at sale or inheritance), permit copies. These commonly live in a dedicated home folder, a box of receipts, a dedicated app, or a notes document.
  • Appliance manuals and warranties — paper folder, scanned to cloud, manufacturer accounts. The executor managing a vacant inherited property will need these.
  • Keys and access codes — for the home itself, garage, gates, outbuildings, mailbox. Note locations only; do not record codes in the inventory itself unless the inventory is in secure storage.

• Vehicles, boats, RVs, motorcycles, trailers, and other titled property — ask explicitly about each category; people commonly forget the boat or the camper. For each:

  • Year, make, model, VIN or HIN (Hull Identification Number for boats), and how title is held.
  • Loan or lien (lender name, account number, payoff status, lien-release document if paid off).
  • Insurance carrier, policy number, and what coverage applies (comprehensive, liability, on-water for boats, etc.).
  • Registration status and where the registration is renewed (state DMV, state Department of Natural Resources or equivalent for boats, US Coast Guard for documented vessels).
  • Connected accounts: telematics (Tesla, OnStar, FordPass, BMW ConnectedDrive, etc.), EV charging accounts, dashcam subscriptions, marine GPS / chartplotter subscriptions, RV park membership accounts, toll transponders.

  Vehicle / boat / RV documents — where they live. For each:

  • Title and registration — where the original is kept (commonly safe deposit box, fireproof safe, file cabinet). For paid-off vehicles, where is the lien-release letter? For boats, the title or US Coast Guard documentation paperwork lives separately from state registration.
  • Owner's manual — paper, glove box, manufacturer app, downloaded PDF. Useful to the executor managing or selling the asset.
  • Service and maintenance records — dealer service history, independent shop invoices, oil-change logs, marine service records (engine hours, winterization, hull surveys), RV chassis and house-side service records. May live in glove box, paper folder, manufacturer app, third-party service-tracker app, or a notes document. For boats and RVs especially, well-kept service records materially affect resale value — flag this so the executor knows to preserve them rather than discarding "old paperwork."
  • Marine-specific: hull survey reports (recent surveys substantiate insurance and resale value), USCG documentation papers if a documented vessel, slip / mooring agreement, marina contacts.
  • RV-specific: chassis manual (often a different manufacturer than the house-side), house-side appliance manuals, dealer paperwork, any extended warranty contract, campground membership accounts (Thousand Trails, KOA Rewards, Good Sam, Harvest

Truncated - read the full file at https://github.com/digital-estate-inventory/digital-estate-inventory/blob/c554c9277bfc67de5aa933f14dbf88df9246f972/SKILL.md.