I suppose this is a timing issue - the moment the rule becomes valid there's already/still presented a modal view (the sheet), which prevents the tip from appearing. After that, there's no trigger (state change re: the rules) to bring up the tip. This is re-evaluated during the next view update or the app is restarted (rule status is persisted as far as I know).

Seems like popover tips are dismissed on any view update - at least that's what I experience using CloudKit and Combine in my app. The code above was just an example to show this, I suppose.

Same here, thought it was related to prohibiting web access to my iCloud account, so I turned that option back on. After a short time it worked for that evening but not it's the same issue again for three days now... Contacted the support team but did not get a helpful answer yet.