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Thanks for the response!

Unfortunately, even after deleting and reimporting the 1099R, its still not triggering that checkbox for me.

I can verify Box 7 on the 1099R is 'G'.

 

And the following questions from Turbotax:

 

Did you move this money from a 401(k) to a Roth 401(k)?
This includes rollovers from a regular 401(k), 403(b) or 457(b) plan to a designated Roth 401(k), 403(b) or 457(b) plan.
-Yes, I moved the money to a Roth 401(k), Roth 403(b), or a 457(b) plan

 

Did you make after-tax contributions to a 401(k), 403(b), or 457(b) plan?
This isn’t common but this is money you put in the plan yourself, not from your company.
-Yes

 

After all this, it still leaves the 1040 5c box 1 (rollover) checkbox unset.  Quite a frustrating experience for a product I've already paid for.