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Anyways, this is going to be a common issue popping up for sure, 2 days in and I already have seen a bunch of users with this problem. It is simply a bad design and it is quite easy to ruin your 50$ s-pen with this problem. There is no reason they should have designed it in the matter. The button tip should be bigger than the hole and there should be an area in the casing machined out slightly bigger to allow it to sit flush. It will be an easy revision if they choose to do it, otherwise I foresee some social media anger in the not too distant future, if the Note 5 Active doesn't quickly overshadow this model.
This major problem is that the S-pen clicker gets stuck in the holster port after you extract it after putting it in backwards. Inside the holster port is little catches that normally keep the s-pen in place, when the clicker button engages this it becomes stuck to the point where it can pop off the s-pen when extracting it. The good news is that the button can be extracted, you have to build a tool to do so.
The tool you need a long, thin rod with a small barb on the end of it. You insert this tool into the space between the button body and the holster port walls, you twist it in so the barbed hook engages the button body then you pull. Eventually you can work the button out.
You can build this tool from a relatively thick paper clip. Straighten the paper clip out, bend one side into a handle and the other side into a small hook. Use a pair of wire cutters to cut the hook into a small sharp point. When using this extraction tool you make need to utilize a small pair of pliers on the handle to get enough force both when twisting and when pulling out.
Let me be clear, I have no idea if this make cause damage to the internals of the holster port, but it beats sending it out for warranty with a button stuck inside it. Once replacement Note-5 S-pens are out I'll test to see if there is any damage. I may try to repair my s-pen with a small bit of epoxy on the button mating nib. But I'll do some testing before I try to stick it back inside (in the correct orientation).
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Finally, here is that little bugger extracted. Like I said, I'm going to see if I can reuse it.
Thank you guys, hope this helps some of you.