Not sure how flexible the elastomer actually is. But I agree if it is pretty squishy, then making the top ring taller would assure a solid seal.
I am not super clear on the "indented slot" suggestion.
My original design had two grooves, one for the trans tunnel, and one for the mounting plate, but we thought it might be too difficult to seat both grooves. So are you suggesting making the barb smaller so it is easier to insert, but adding a stop above, so it doesn;t get pushed too far in? That seems like an interesting idea. Here's a version like that.
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View attachment 222121