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@jordanhb

But if I use one of the second-level subcategories (i.e. Vet or Grooming) then the expenses no longer show up in planned spend and instead are listed under other spend.

That is strange. I just tested this by creating a second-level subcategory (Dining Out | Coffee Shops | Ground Coffee) and assigning that category to a transaction that was previously in Groceries. The "Ground Coffee" transaction is showing up as expected in the transaction list for the "Dining Out" Planned Spend expense series.

To test this, I would first check the category definitions to ensure that Pets is a sub of Sinking Fund and Vet is a sub of Pets. Then check that there is an existing Vet transaction dated in the month you are looking at. If those things are all in place, and you still aren't seeing the transaction in Planned Spend, then there must be some kind of data corruption.

(Note: It is possible to have similarly named categories in different locations on the category tree.)