2026-0998
Tax-loss harvest
When the AI is wrong
Nine percent of drafts are rejected by an advisor. We read every one. The three reasons that come up most, and what we changed because of them.
Date
Time
07:58 ET
Account
Brokerage
Amount
—
Status
Declined
Checks passed
Wash-sale clear · Band rule · Liquidity floor · Tax bracket · Position cap · Trading window · Cost vs benefit
Signed by
Hannah Weiss
CFP®
About nine in every hundred drafts from the morning pass are rejected by an advisor. Every rejection has a written reason, and once a month the advisory team reads all of them together. Three reasons account for most of the list.
The first is information the data does not have yet. A household tells its advisor about a home sale, a divorce or a new job, and the custodian feed will not show it for weeks. That is why every advisor note on a call is now read by the pass the next morning, and why the second signing question asks what has changed.
The second is a rule the document set but the data did not. A trust that cannot sell a family company’s shares, an inherited IRA with a distribution date. Since March, every trust document is read by an advisor and entered as limits before the AI drafts anything for that account. Rejections of this kind fell from 31 a month to 4.
The third is a correct draft at the wrong time: a harvest proposed on the day a household said it wanted to wait until after a meeting with its accountant. We added a pause, set by the advisor, that the pass respects until its end date.
The AI will keep being wrong some of the time. The point of the signature is that someone who knows the household is there when it is.