Why do my scheduled Transaction groups keep dropping transactions?

I keep fixing my transaction groups and yet every time I try to use them to auto enter routine transactions, several have zeroed out with no transactions in them. I do keep current with updates and I have validated my file several times (no repairs necessary). I have been a quicken user since the early 80's DOS version, so I am not a novice user. This problem has been going on for quite a while and yet I cannot 1) find a solution in the community or online, nor 2) see where the folks at intuit have tried to fix the problem. What gives?

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