Why cover letters can't say the company's name yet¶
This is a plan, not something the app does today. Ticket: WING-369.
What's wrong¶
Work Wingman has one rule it will not break: it never says anything about you that your profile doesn't back up. A checker reads every draft and throws it out if it spots a company, school, degree or date you never told us about.
The catch: the company you're applying to isn't in your profile. It can't be — you don't work there. So when the AI writes a perfectly normal sentence like
I'm excited about the Platform Engineer role at Kohler Group.
the checker sees "at Kohler Group", doesn't find Kohler Group in your history, and throws out the whole letter. You quietly get the plain version instead, even though the AI was working fine.
Cover letters mention the company constantly, so this happens on most of them. It's a good part of why the app looked like it "wasn't generating" anything.
Why we can't just make an exception for that company¶
Two obvious fixes were tried and both broke something worse.
"Ignore the company name everywhere." That also ignores it in "I worked at Kohler Group for three years" — which is exactly the kind of made-up claim the checker exists to catch, sent to the one company guaranteed to know it's false.
"Blank out the company name before checking." The company name and job title come from the job ad, which anyone can write. Blanking them out by name turned them into a way to hide things: put the right words in a job title, and whole sentences slipped past unchecked.
The rule we settled on: it's safe to use the company name to throw a draft out. It's not safe to use it to let one through.
The plan¶
Stop letting the AI write the sentence that mentions the company.
The AI writes the parts about you — your experience, why it fits. The app writes the parts that mention them — the greeting, the opening line, the sign-off — from wording we've already checked. If the AI mentions the company anywhere in its own text, that's a rejection, not an exception.
Later, a bigger version: instead of writing paragraphs, the AI picks which of your real facts to use and in what order, and the app turns those picks into sentences. The AI never types a sentence that could contain a claim we haven't verified. That also catches things today's checker misses entirely — like "I led the migration" or "I have ten years of experience", where no company name appears at all.
What we deliberately won't do¶
- Teach the checker to tell "applying to" from "worked at" by reading the grammar. English is too slippery for that to be a hard guarantee, and three separate reviews broke every version of it we sketched.
- Let the AI keep rewriting until the checker is happy. That just teaches it to write around the checker — the mistakes that survive are the ones we can't see.
Honest about the gaps¶
Even the recommended plan has holes we know about — for example, one sentence that both applies to a company and claims you worked there, or a follow-up sentence saying "I spent three years there" with no company name in it at all. These are written down in the technical version so they get designed against instead of discovered by a user.
Who worked on this¶
Three reviewers looked at the problem separately on 2026-08-06 and independently landed on the same answer: Cedric, Jenny, and Gronktayvius (whose job was to break the other two's ideas, and who broke several). Clahadore wrote up the result.
The technical write-up is in docs/technical/honesty-guard-target-company.md.