Yes, I do like a challenge, and I agree that the questions should be the same with regard to the taxpayer and spouse (and I believe that they are).
Please check one thing for me. You mentioned that both of the forms reporting the insurance cost in box 5 were CSA 1099-R. Doing a test case, if I entered two CSA 1099-R (one for taxpayer, one for spouse), the question about box 5 comes up for both. However, before any data is entered, there is a question about what type of form you have. The box showing it is a CSA 1099-R and not just 1099-R must be checked for both the taxpayer and spouse forms.
Would you give that a try and let me know if you get the question about box 5 for both taxpayer and spouse?
@Chuck C1
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