DoubleDown has mentioned, there may be a need for you to hold your mouth partially agape, of fully agape.
This was what they did 12 years ago, and this was what I requested be done again, just 2 weeks ago, as I am again to trial the latest model Phonak Virto V90 when it arrives.
What I had found most recently, just doing a little “test”, was sticking my fingers into the outer canal, and then opening and closing my mouth to varying degrees, smiling, looking up, down, to the sides, etc.
I did note that when opening my mouth 1/2 open, to fully open, three was a difference in ear canal size seemingly, that the further I opened my mouth, the larger my outer ear canal became. (At the lower part of the outer ear canal)
I concluded in my own personal instance, that this difference could be a make or break fitting, that opening my mouth a bit too far just might cause a mold to be slightly too large. Yes, a tight-snug fit which might aid in reducing the seeming inherit feedback issues I commonly have, but also the worry of discomfort, perhaps such as you now experience in that when my mouth is closed, or smiling etc, that the molds would then be painful due to a too large mold.
I’m no fitting expert, but had also thought, that by being slightly too large, there could also be other downsides, in that when I close my mouth, the changing in size to a smaller ear canal shape could also cause the mold to begin to dislodge from the canal, thus with things like eating, speaking, etc the fit would then possibly become looser and looser, and here comes the feedback issues again, rearing their ugly head.
In your case, possible that the outer part of the mold is slightly too large in diameter, that the mold is not fitting further into the canal, is riding more to the outer portion of your canal, and causing rubbing or pressure issues there that are causing this pain.
I of course would first try some modification of the present molds, but do take time to see if all feels and works OK right then and there, and that if you believe such has not been rectified to your liking, then I would again try having new impressions again made, with some adjustments to the degree on lack of in which your mouth is open, or closed. To remember what you did last time, and possibly there needs to be a slight modification of such positioning of your mouth, or head.
In any case, another impression taken, might be an aid, in comparing this new impression, to the existing molds, that they can then both be examined, and perhaps the necessary fine tuning could be tried to the existing molds with some better success.
Hope this helps.