A colleague posed an interesting hypothetical to me, I wasn't sure about the answer so figured I'd ask y'all :)

• Let's say someone made the statutory maximum contributions to a traditional IRA for the past three years ($18k)
• Let's also say these contributions have not been deductible
• Finally, let's say that since the market has performed poorly, the value of the account is now $16k

In this situation:

Question 1: would it be possible / advisable to convert the IRA to Roth?

Question 2: would they lose the benefit of the capital loss if they did so?

Question 3: assuming that they could backdoor Roth convert the full amount, what would they need to do in order to report the prior year contributions as non-deductible on their tax return?