As described in these recent posts
https://community.quicken.com/discussion/7864610/missing-transactions-in-report-tax-summary#latestand
https://community.quicken.com/discussion/7864607/traditional-to-roth-conversion-and-tax-schedule#latestand many others, the way Quicken handles taxable transactions in tax deferred accounts is convoluted and confusing, often causing incorrect tax reports and and incorrect data in the Tax Planner.
The increasingly popular Qualified Charitable Distributions (QCDs) also fall into this category.
Properly designed wizards or Macro transactions to handle these events would be a big help.