You called this one: the watcher was not running any more, and the reason was mine. It ran under set -euo pipefail, and two helpers ended in a pipeline to head -1; when head exits first sed takes a SIGPIPE, pipefail turns that into a failed assignment and -e turns that into an exit. So the script answered the first dialog or two and then vanished without a word, which is exactly what a run that stops after its first install looks like. It now runs without -e, the helper pipelines end in || true, and it prints a heartbeat every thirty seconds so is it still running can be answered from the log.
Measured after the fix: two consecutive uninstall/install cycles both succeeded, the script stayed alive through a 75 s watch, and in a full benchmark run it was still alive at the end with two dialogs answered. That run lasted 1m29s instead of the previous 35s and one test got as far as driving the app, so the installs do sometimes get through now. One was still refused, and the run still failed overall.
SoftwareApp
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