A Trustee-to-trustee transfer does not generate a 1099-R because the Traditional IRA is simply moved from one trustee to the other and remains a Traditional IRA at the destination - it cannot make any change to the IRA or it would not be a transfer.
You cannot do a Traditional IRA to Roth IRA conversion with a trustee-to trustee transfer.
Once transferred to the new trustee then you can have the new trustee convert the Traditional IRA to a Roth and that would generate a 1099-R from the new trustee showing the Traditional IRA distribution that you would enter as a conversion.
**Disclaimer: This post is for discussion purposes only and is NOT tax advice. The author takes no responsibility for the accuracy of any information in this post.**
