2026-09-23 / Signal #5
Grammarly carpet-bombed an entire company’s users with unhinged cancellation emails
“The AI that fixes your emails just doxxed your IT guy to the whole company.”
The Story
When one company told Grammarly it would not renew, the writing-AI vendor sent unsolicited emails and in-app popups to every licensed user, even publishing the licensing manager’s direct email. The sysadmin called it “greasy and desperate”; leadership immediately ripped the product out.
Why It Matters
Even the politeness AI has a feral customer-retention department. Classic internet-culture artifact of SaaS desperation in the AI era.
Evidence
Reddit r/sysadmin PSA (now circulating on HN)
Sources
Daily scan: 2026-09-23