Why do memorized payees have new, manual, transactions automatically set as cleared? This is asinine. Just because a previous transaction was cleared (or reconciled) doesn't mean every future transaction will be. And yes you can change this in the Memorized Payee List, but you have to do it for not just every Payee but every category and subcategory for that Payee. How much time do you think your users have?
Coming over to Quicken for Windows from Quick for Mac seems like such a downgrade, I'm really considering cancelling my subscription. Especially trying to use this support system. Searching for a topic, you can't even filter down to the platform you are using, just dates. And you can't even add Tags for things within the program itself, like "Cleared", the name of a field in the register. It is almost like Quicken wants people to leave.
Quicken for Windows version R59.18 (though it doesn't matter since I've found articles about this going back years)