Hi @chaddlee1978 Chad you should also check and adjust your hand position. Look in the mirror or better yet video record yourself. You can always share that here for @BanjoBen to give advice.
Discuss the Banjo lesson: Banjo Hand Positions
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Any tips for preventing the inside of the pick on my middle finger from catching on the first string? I am so frustrated having experimented with slight variations in hand angles and pick curvature. I’ve watched Ben attack the strings and mimicked him and many others but no luck. I’ve searched all over the internet for any advice but no one else seems to have that problem. Am I the only one? Please help!
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Hi @prating2 Charles 
to @BanjoBen 's Forum.
Interesting that you should ask this question on your first post here on Ben’s Forum. As it happens I used to have this exact same issue as a beginner. I was forever getting my middle finger pick caught on the strings. But for the life of me I cant exactly remember how I fixed the issue. What I can tell you is. I cant remember the last time this happened. So there is hope that this problem can be resolved.
I know that back when I was a beginner I used to use Dunlop nickel steel picks that caused me so much pain and discomfort. The blades on those picks were longer than the picks I use now. Which are ProPiks Stainless Steel - 2 Ang (Angled Picks). I remember I trialed lots of different picks before I settled on the SS 2Ang.
The reason I went for the Angled Picks was after watching a video of Alan Munde explaining why he bent his picks at an angle.
Alan’s style of picking involves playing inside rolls Ben being a former student of Alan’s also uses inside rolls and I think this maybe where I had the most issues with my picks getting caught up in the strings.
I also had another issue. The ‘flying’ middle finger where my middle finger would flick out and come back to strike the first string making it play much louder than the other strings and having an adverse effect on my timing.
By studying Alan & Ben’s picking hands closely, over time I changed the angle of my hand position. Cupping my fingers under, the way Ben does, focusing on picking slowly and deliberately. Many many hours of slow deliberate roll practice.
I know how frustrating that can be when you want to play fast but as someone once told me. " You can’t play fast and accurately if you can’t play slow and accurately.
Not sure if this is helpful but at least you now know your not alone and this issue can be resolved. 
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Post a video! I’m traveling right now but a video and/or pics of your setup would really help me.