Thank you for the replies yesterday about my drill. I think I’m going to get a cheap corded SDS drill and some big bits. This is what I need to feed through the wall and there is no way to detach the cable from the camera and feed it the other way. I know it needs to be weather shielded, but this is a mad amount of connectors!
Another option is to mount a junction box (like this) outside. Just run the ethernet cable through the wall, instead of the camera’s pigtail. This is a more future-proof method as you can change cameras without disrurbing the sealed wall penetration.
That’s a good call. I wasn’t sure on the cable seals and fitting all the wire through it and still being snug on the small cable.