Anomalous Behavior of Spending by Category Report

@Quicken Alyssa , thank you for the follow-up and opportunity to provide additional information

Data File Location - My working data file is located only on my hard drive, in a location that is not synced to OneDrive or any 3rd party Cloud location, with a backup set to a folder in that same offline location every time I exit Quicken. As a failsafe in the event of a hardware failure, I do a weekly backup to OneDrive from within Quicken. I learned a while ago that keeping the working Data File in a location that is synced to OneDrive was a recipe for recurring misery.

Category List - Perusing through the Category List, all seems normal: Parent Categories appear in Bold, Sub-Categories are indented, and not Bold … see nothing unusual or different among the Cat/Sub-Cat groups that are acting badly.

Screenshots - I will send screenshots of the groups that match those I sent above.

From the two categories where there were ANOMALIES in the Report display

From the two categories where there the Report display was NORMAL

The entire Category List is too big to show up on one screenshot. I could send the entire Category List as a CSV file, if desired. Some of the categories I see are unfamiliar, that I don't recall creating, but there are no transactions tied to them anyway.

Building on what @Jim_Harman said, I was able to isolate a few transactions that fit the description of the "problem" case, involving transactions from an "Investing" account (in this case, Debit card purchases from a Brokerage account) with Categories assigned to the main (parent) Category, in some cases as part of a Split category. I was able to resolve and clear up the Auto and Insurance category / subcategory display and subtotaling anomalies with the editing of a few transactions. Another set with MANY more transactions to work through is Tax, and all the subcategories below it. That will take me some time, as they are spread across many years.

For what it's worth, from a >30 year customer, a critical Requirement for me is that Quicken Reporting should work correctly regardless of what type of Account the spending is coming from, or whether the categorization is at the subcategory level or the main (parent) category level. I can obviously spend from all of my Bank, Credit Card, Personal Cash, or other so-called "Banking" accounts. However, a growing portion of my spending is coming from one of my Brokerage accounts, and it is also the destination for any income I receive. I can do everything I need to do with this Brokerage account, except use Zelle, and the interest on Cash, at least in the current environment is superior. I think I am just now observing these kinds of problems because: 1) Some of my categories have evolved from initially being simple, main-only categories into more subdivided specific sub-categories, 2) Older transactions (prior to the existence of evolved subcategories) were obviously assigned to the main, since it was all that existed … and this is now causing this anomalous behavior in the Report software, 3) I am making a more concerted effort to access a deeper understanding of my spending, cashflow, and investment performance.

@Quicken Alyssa, or anyone else, your thoughts ? Is there a "Requirements" document for the Reports section of the software that suggests something contrary or unsupportive of the Requirement I expressed above ? Also, in one of the other recent discussions around Report issues, it was suggested or inferred that the use of the parent category for a transaction, when sub-categories existed below it was somehow illegitimate. Where is that written ? IMO, Category Lists should be free to evolve, from parent-only to parent+subcats, and that evolution should not render all previous transactions assigned to the parent as illegitimate, breaking the software, and forcing the user to recategorize past transactions to fix the situation. The software should be robust to such Category List evolution.

Update - I was able to isolate all the causes of the Tax category issues, and they were all due to Foreign tax transactions (paid out, or W/H) being swept into the parent Tax category. I'd tended to just accept the proposed category from Quicken, not knowing the consequences to the Report process. I will concede that it is better accounting practice to have all transactions within a defined subcategory. I have also now taken the extra steps (many) to eliminate all transactions that result in the dreaded "Other parent" subcategories in certain groups where that was being created by the existence of transactions assigned to the Parent. It's all cleaned up … for now.