What they did
The author rarely checked their child's school portal and only looked once something had gone wrong. They made a Cowork project in the Claude desktop app, connected a folder where Claude could keep notes about the portal between runs, and authorised the Gmail connector to send mail. They logged into the portal themselves in the app's browser pane so the session would carry into later runs. Their prompt had Claude explore what the portal exposes (grades per course, assignment scores, category averages, unscored work, the calendar, alerts), draft a sample email from the real data for their approval, and then set itself up as a scheduled task that runs nightly at nine and compares against what it saw the night before.
How it went
The emails arrive with subject lines such as a low classwork score plus an exam tomorrow. On the first run it found something they would have missed: an 86 overall in Biology that sat on top of a 64 classwork average, with labs at 95. Quiet nights get a subject saying nothing is new, which they delete unread. They say the exploration step mattered most, since they had not known the portal tracked category averages or listed unscored work.
Worth knowing
Claude does not type the portal password; you log in yourself, and that browser session expires after about two weeks. Tell it to email you when it hits the sign-in page instead of sending a fake update, so a silent night is not mistaken for good news. The post is written as a shareable prompt, so the outcome is one parent's report.