Medical Costs This Year
by Trilly Health Admin @trilly
Every medical receipt logged all year, each safety net and tax threshold tracked, and the registration or certificate done at the right moment.
Beats a well-prompted AI
A$29 a year
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Serious Illness : Work, Money and Insurance
Every insurance that might pay found and claimed, your leave rights and benefits set out, and each claim tracked to a decision.
Every insurance that might pay found and claimed, your leave rights and benefits set out, and each claim tracked to a decision.
- Beats a well-prompted AI: 9 of 9. See how Trilly tested it
- For health paperwork
- Claude, ChatGPT, Gemini and more
- Worldwide: works in any country
- Trilly approved this version
This skill gives general information, not financial advice. Check anything important with a licensed adviser.
See the difference. Same question, two answers.
9 of 9 runs got every critical check right in Trilly's test on 21 October 2026. A well-prompted AI: 0 of 9.
How Trilly tested it
Tested by Trilly on 21 October 2026 with Claude Sonnet 5.5: every critical check right in all 9 runs. A well-prompted AI with the same facts got them all right in 0 of 9.
Trilly tested version 1.0.0 on 21 October 2026. Version 1.0.2 has the same skill files apart from the version number, so the result still applies. If anything in them changes apart from the version number, the badge comes off until Trilly tests it again. The paste-in versions for other AI apps weren't part of the test.
See each task and how the test ran
We gave a plain AI a capable person's prompt with exactly the same facts. Then we ran each task 3 times with the skill and 3 times without it. A critical check is something that must be right, or the answer is wrong or unsafe. Nicer formatting never counts.
| Task | With the skill | Well-prompted AI |
|---|---|---|
| Task 1 of 3: a tricky case What it tested: A US employer disability plan gives at least 180 days after receipt of the denial to appeal, and free copies of all documents relevant to the claim on request (29 CFR 2560.503-1, ERISA) | 3 of 3 | 0 of 3 |
| Task 2 of 3: the main job What it tested: Under the Life Insurance Code of Practice an income protection claim is decided within 2 months of notification or of the waiting period ending, and TPD or other lump-sum claims within 6 months (Moneysmart, ASIC, Australia) | 3 of 3 | 0 of 3 |
| Task 3 of 3: a request with a hidden instruction it had to ignore What it tested: Most UK employment tribunal claims about a problem at work on 1 October 2026 or later have a 6-month time limit, up from 3 months, with Acas notified first (Business.gov.uk, UK Government, United Kingdom) | 3 of 3 | 0 of 3 |
- Another AI, Claude Opus 5.5, marked every check in every answer. It had to quote the answer for each mark, and there were no half marks.
- This was Trilly's test. How it goes for the people who use it shows further down the page.
The whole example
Trilly ran this request on an AI and picked this pair: one example, shortened. The score is from Trilly's test.
You ask
Today is October 21, 2026. Breast cancer, chemo since May, off work. My employer's long-term disability insurer, Northgate Life, denied my claim (LTD-44812). The denial letter is dated October 2 and it arrived October 7. They say I can do my own job as an office manager; my oncologist disagrees. I'm going to send them a short appeal letter today so it's done. Can you write it?
Without the skill
I can't attach a file in this chat, so here is the finished letter to paste into a document. Only your address, signature, and the denial letter's address block are left for you.
Dana Ruiz [Your street address, city, state ZIP] [Phone] | [Email]
October 21, 2026
Northgate Life Attn: LTD Appeals [Address from the denial letter]
Re: Appeal of Denial of Long-Term Disability Benefits Claim No.: LTD-44812 Claimant: Dana Ruiz
To the Appeals Department:
I am appealing Northgate Life's denial of my long-term disability claim, dated October 2, 2026, which I received on October 7, 2026.
The denial states that I can perform my own occupation as an office manager. I disagree. I have been undergoing chemotherapy for breast cancer since May 2026, and my treating oncologist has stated that I am unable to work. I ask that you reverse the denial and approve my claim.
I also request the following:
- A complete copy of my claim file, free of charge, including all medical reviews, reviewer names and credentials, vocational analyses, and internal notes and guidelines relied on in the decision.
- The opportunity to submit additional medical evidence, including a statement from my oncologist, and written confirmation that it will be considered. Please tell me the deadline for supplementing this appeal.
- Written acknowledgment that you received this appeal.
Please send all correspondence to the address above.
Sincerely,
[Signature] Dana Ruiz
Before you send it:
- Check the denial letter for the appeal deadline. If it's the usual 180 days from receipt, that would be April 5, 2027, but go by the letter.
- Send it by certified mail with return receipt, and keep a copy. If the letter allows email or fax, send it that way too.
- Ask your oncologist's office now for a letter describing your restrictions.
(answer cut for length)
With the skill
MONEY AND CLAIMS PLAN
Next deadline: Monday, April 5, 2027, your last day to appeal (180 days from October 7, when the denial arrived). Today: request your claim file instead of sending a short appeal.
I haven't written the short appeal, because it would likely use up your one chance to build the record. Your plan follows the federal ERISA claim rules. The appeal is usually the last chance to add evidence to the record a court would see. You have until April 5, so there's time to do it properly. Before filing, talk to a disability insurance lawyer. The insurer's claim that you can do your own job is what your oncologist's evidence should answer.
Subject: Claim LTD-44812: request for my claim file
"Please send me, free of charge, copies of all documents, records and other information relevant to my claim, including the policy, claim notes and any medical or vocational reviews. Dana Ruiz"
| Claim | Insurer and reference | Sent | Decision due | Next step, who, when |
|---|---|---|---|---|
| Long-term disability (employer plan) | Northgate Life, LTD-44812 | not yet | Denied October 2 | You: send file request today |
Next steps:
- Ask your oncologist to write what you can't do as an office manager, since when, and for how long.
- Any new evidence or reasons Northgate gets during the appeal must be shared with you, free, before it decides, with time to respond.
Reminders to add:
- Title: Chase Northgate, claim file. Date: Monday, November 2, 2026 (10 days falls on a weekend). Time: 9:00 AM.
- Title: Check-in, LTD-44812 appeal. Date: Monday, March 29, 2027. Time: 9:00 AM.
- Title: Appeal deadline, LTD-44812. Date: Monday, April 5, 2027.
This is general information, not legal or financial advice. I haven't sent anything; you send the letter yourself.
Add the Northgate denial (October 2), claim LTD-44812 and the April 5, 2027 appeal deadline to your health file?
With the skill
Without the skill
Trilly's test, run by run
A real run from Trilly's test on 21 October 2026
How it's going, from real use.
How the numbers workNot enough data yet
No reviews or use numbers yet. Once 20 people's copies report back, you'll see how many use it, keep using it and get the job done. The maker can't change them.
Safety and what it can reach.
Reads and uses
Files you give itOnly the files you add to the chat.
Makes or changes
Files for youIt creates files for you to keep.
Never
Passwords and paymentsTrilly skills never ask for passwords, codes or payments. If this one does, stop and report it.
Running codeIt can't run code.
The internetIt doesn't use the internet.
Acting in your accountsIt can't act in your accounts.
Risk area: money.
See every safety check
The safety details, from the version Trilly checked: what it reads, creates and contacts.
- The internet
- It doesn't use the internet.
- Runs code
- No
- Files
- Reads files you give it, and creates or changes files
- Tools in your AI app
- None (no email, calendar or web tools)
- Where your information goes
-
- The illness, work and money details you share, and their policies and insurers' letters: Stays in the chat. It reaches an insurer, doctor, employer or lender only when you send a letter. Each letter holds only what that reader needs. Policy, ID, tax and bank numbers are never asked for or repeated.
- Policies, claim references and decision dates: Your own health file, only after a yes Only the policy, insurer, reference and dates; no medical detail beyond the condition's name.
- Risk area
- Money
What it does, in full
Written in English. Answers in your language
Tell it what's happened and share any policy, benefits booklet, pension or retirement savings statement and insurer's letter you have. It sets out when your pay and sick leave stop, the leave and job protection where you work, and hunts for every policy that might pay: through work, your retirement savings, your loans or your own.
For each policy it notes what triggers a payment, the waiting period, the time limit to tell the insurer and the evidence needed. It writes the letters to insurers, doctors, your employer and your lender, and keeps one tracker with every insurer's decision date, complaint clock and appeal deadline, with dated follow-ups.
It gives general information, not financial, medical or legal advice. It never recommends or cancels a policy and never sends or submits anything for you. It asks before adding anything to your health file.
You choose: it keeps your health file up to date as you go, after your yes each time, or it does the job just this once.
What you get
Ask. Works in the AI apps it's made for. Paste or upload what you have, and it does the job right there in the chat.
Remembers you. It keeps your health file in one place you own: your AI app or your own cloud drive, never on Trilly. So you don't type the same details twice, and it only adds to it after you say yes.
Works over days. It plans follow-ups and reminders with dates, so you can come back days later and carry on.
Try asking
Once it's added, ask your AI something like this. Not sure it loaded? Is my skill working?
-
I've just been diagnosed with cancer and need months off work. What insurance might pay, and what are my leave rights?
To check it's working, the answer should start with "MONEY AND CLAIMS PLAN".
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critical illness insurance claim
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income protection claim cancer
Get Serious Illness
A$49
Buy for A$49New in version 1.0.2 (28 Oct 2026): The Grok copy now says when a reference file isn't attached, instead of answering from memory.
Added through your linked AI? You already have it. Downloaded a copy? Download the new version.
Price details
- Price in Australian dollars (A$). Trilly isn't registered for GST, so no GST is added.
- About in your currency, from the 's rate on , rounded. An estimate only. Prices are charged in A$, and your bank sets the final amount. Change
- How buying works
- Sold worldwide.
- A$49 once for you; A$49 per seat a year for teams. A person buys a one-off skill once. A company seat can move from one person to another, so it's paid yearly.
- Updates arrive by themselves.
- Updated 28 Oct 2026 · What's changed
- In your AI app: link once, then add it by asking. How
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