In speaking with the Fidelity rep, he seemed to indicate that *any* conversion from a tIRA to a Roth IRA would *always* be a taxable event and based on the full amount in the tIRA. If what you say per point #2 is true, then I should only be taxed on whatever I contributed and whatever gains there were *after* the initial recharacterization from Nov 2014 to Feb 2015?
I was also reminded that recharacterization can only happen once a year. I went on to ask him, that assuming I do the deconversion back to a tIRA this year, if it's possible to recharacterize the tIRA to a Roth IRA in 2017 and thus avoid a taxable event but he mentioned that's not possible to do.
Not the date of the original recharacterization - the original contribution(s). The recharacterization makes it as if that was traditional all along.
Point #2 illustrated. Say I had 100K in a tIRA to start with. I then wanted to do a backdoor Roth IRA, so I contributed $5500, did not take the deduction, and converted $5500 to Roth. Everything is in cash, so no earnings to worry about. When I fill out my taxes, I am shocked to find that over $5200 of my conversion amount is subject to income tax, because the non-taxable $5500 is only about 5% of my account balance and the conversion is pro-rated.
A conversion is always a taxable event, but the tax is figured only on taxable amounts of the conversion. The well-documented Backdoor Roth IRA strategy is predicated on the fact that non-deductible contributions are not subject to tax on conversion to Roth, except to the extent there are earnings.
I'm not sure that recharacterization can only happen once. There are 2 types of recharacterizations - 1 changes the type of the contribution. The other undoes a Roth IRA conversion. Possible different rules for each type of recharacterization. I could see the first type of recharacterization working as many times as your broker is willing to do it, but the 2nd type can only happen once, I'm pretty sure. Not sure of the law on that
There is no such thing as a "deconversion". You can recharecterize the conversion back to traditional since it happened in 2015. That would fix your immediate tax problem, but you still have your money in a tIRA in that case, and the only way to get it out of the tIRA is to convert.
You are well beyond the deadline's to change the contribution type. Unless this tax bill (once figured correctly) is hugely problematic for you, I would not go with an "undo the conversion" recharacterization either. Get all the information, and do your taxes, pay any amount owed and be done with it.