Haven’t experienced that but the following comes to mind
Either the tool head groove is blocked by something- dirt, debris, even a spent primer- not allowing it to fully seat
Or
There is something blocking pin holes
Is this a stock Dillon toolhead or a new CNN billit type? Dillon is cast with cavities on the bottom side, I think the billit is solid (I don’t know I never used one)
Just as an outside chance....
I'm wondering if the die lock nuts are interfering with the tool head position ? When you use non-Dillon dies on a 550, you may need convert the dies over to the Dillon 1" lock nuts to get the necessary physical clearance. Some brands of lock nuts are simply too large. They can overhang the die position, and may keep the Tool Head from properly locating in the press.
When I first Got my 550 back in 1986, the pins were long, they are now shorter, by me!!
Adjusting Dies, I "Made" them shorter!!
I think the newer 550, come with shorter pins, than the ones I had.
My original ones still are working
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