For those wondering – the issue was not with the timeline code but rather more with the persistent stores I was using for Core Data. There seems to be an issue when background tasks try to access properties without inverses. When I was adding back inverses to migrate to CloudKit, the issue seemed to be resolved so as a general rule of thumb make sure that all your core data relationships have inverses or random things will break I guess.

As a late reply to @levikline, I've been working on a similar app. Apple does state on their "Keeping a Widget Up to Date" documents that formatting a date as a Text.DateStyle is the only way to keep a widget up to date without timeline entries, but I've been playing with using ProgressView(timerInterval:countsDown:) with promising results. I'm having trouble using dates programmed in the entry, but if you use some code like the following, it seems to continuously update within one Timeline Entry ProgressView(timerInterval: Calendar.current.date(bySettingHour: 13, minute: 00, second: 00, of: .now)!...Calendar.current.date(bySettingHour: 14, minute: 07, second: 00, of: .now)!, countsDown: false)