More in Money, Bills & Taxes. Also fits: Health & Medical.

Pick open-enrollment benefits with Claude after an HSA hallucination

PartialEvidence: Described by posterPosted Oct 16, 2025Last checked Nov 5, 2026

Claude helped Christie Pitts aim for $14,766 in benefits savings but wrongly said a plan was HSA-ineligible until corrected.

Source checked Nov 5, 2026
Results shared
Limitations noted

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Tap Copy prompt.
Open Claude.
Paste it into the message box.
Send it, then read the answer before acting on it.

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Prompt

Original prompt

The prompt as the person shared it in the source.

What the prompt labels mean

These are the person's own words, as shared in the source.

Review the [attached health plan summaries] and [attached plan financial details] and help me choose new health benefits. There are [number] of dependents on the plan: [describe the dependents: age, health needs/conditions, etc]. I am currently on the [current plan name], and I [do or do not] like it, because [reason]. My financial situation is [description] and I anticipate the following in the next calendar year [job change, major medical event / expense, life change, etc]. Make a recommendation for which plan to choose. Provide reasoning and a comparative financial analysis of the different choices.

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Optional stronger version

Our rewrite with extra checks. The poster didn't test it.

Before you start, ask me 1–3 short questions about the details below and wait for my answers. Once I've answered, confirm the plan in one line and run the whole task start to finish.

Goal: Recommend open-enrollment benefits and savings-account amounts with a clear cost comparison I can verify.

Questions to ask me first:
- How many dependents, and any known medical needs this year?
- Which plans and financial PDFs can you attach?
- What life changes (job, baby, surgery) are likely next year?

Inputs (fill in or confirm):
- Plan PDFs: [ATTACHMENTS]
- Dependents: [AGES / NEEDS]
- Current plan likes/dislikes: [NOTES]
- Financial situation and upcoming changes: [NOTES]

Rules:
- Compare health, dental, vision and named supplemental options.
- Include HSA/FSA/dependent-care contribution recommendations with tax notes.
- Flag uncertainty instead of inventing eligibility rules.
- Show math for total estimated annual cost under common scenarios.

Checkpoint: Before the final pick, restate each plan's HSA eligibility from the PDF text and wait for my OK.

If you get stuck: If a PDF is unreadable, ask me to paste the HSA and deductible lines rather than guessing.

Verify before you finish: Re-check HSA eligibility and premium math against the attachments before recommending.

Output: A ranked recommendation with a comparison table and contribution amounts.

Done when: I can submit open enrollment with numbers I have double-checked.

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Plan PDFs

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Dependents

Current plan likes/dislikes

Financial situation and upcoming changes

Your prompt

Before you start, ask me 1–3 short questions about the details below and wait for my answers. Once I've answered, confirm the plan in one line and run the whole task start to finish.

Goal: Recommend open-enrollment benefits and savings-account amounts with a clear cost comparison I can verify.

Questions to ask me first:
- How many dependents, and any known medical needs this year?
- Which plans and financial PDFs can you attach?
- What life changes (job, baby, surgery) are likely next year?

Inputs (fill in or confirm):
- Plan PDFs: [ATTACHMENTS]
- Dependents: [AGES / NEEDS]
- Current plan likes/dislikes: [NOTES]
- Financial situation and upcoming changes: [NOTES]

Rules:
- Compare health, dental, vision and named supplemental options.
- Include HSA/FSA/dependent-care contribution recommendations with tax notes.
- Flag uncertainty instead of inventing eligibility rules.
- Show math for total estimated annual cost under common scenarios.

Checkpoint: Before the final pick, restate each plan's HSA eligibility from the PDF text and wait for my OK.

If you get stuck: If a PDF is unreadable, ask me to paste the HSA and deductible lines rather than guessing.

Verify before you finish: Re-check HSA eligibility and premium math against the attachments before recommending.

Output: A ranked recommendation with a comparison table and contribution amounts.

Done when: I can submit open enrollment with numbers I have double-checked.

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AI tool

Claude

Outcome

Christie Pitts used Claude during open enrollment to choose 2026 family health, dental, vision and supplemental benefits and to set healthcare and childcare spending-account contributions. Claude produced comparative financial analysis across options. One hallucination: Claude first said the recommended plan was ineligible for an HSA when it was eligible; Pitts corrected Claude with details already shared. Aside from that, Pitts did not find other errors, saved hours of tedious work, and estimated an additional $14,766 saved next year through the plan plus savings-account selection.

Evidence: Described by posterThe person describes what happened in words, without screenshots or video.

Known limitations

PartialThe source says it only partly worked, or had a significant problem a person had to deal with.

What went wrong: Claude mislabeled HSA eligibility on the recommended plan until corrected; Pitts still estimates $14,766 in plan-plus-savings gains.

Source

Posted: Oct 16, 2025 by Christie Pitts (LinkedIn)
Last checked: Nov 5, 2026
Method:: How we verify

https://www.linkedin.com/posts/christiepitts_i-made-14766-with-claude-today-heres-activity-7384731154978906113-YG_4

Context: Date estimated from the LinkedIn activity ID. $14,766 figure is the author's estimate, not a verified payout. Partial because of the HSA eligibility hallucination.