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Warning- This is a seven and a half minute explanation of how I enter into Deep Half Guard. For some of you this is going to be too long of a video, if talking and theory are not your cup of tea you may want to skip this video.
I use this entry a lot when people are entering for the underhook and I'm late with my repummel. It's very important that you make sure to knock that foot off the floor by straightening your leg. It is VERY important that your leg goes completely straight and stays as close to the floor as possible. Make sure to reference the video to see what I am talking about.
Once you have knocked their foot off the floor and your straighten your leg you want to continue keeping it close to the floor through a full extension. I tell my students to imagine that they have a leg cramp in the extension and then roll onto their far side.
You will see, and hear my opinion on that bottom hand in the video. A lot of people stress hiding that bottom arm so that you dont get caught in a Kimura grip. I prefer to keep it collapsed on top of the knee with my elbow TIGHT against the body. If you're all the way up on your side the way you should be then the kimura wont be a problem.
In the event that you can not get all the way on your side then of course hide that hand and/or keep it tight to your body. It is baaaaad news when you get caught with a kimura grip or an underhook.
Hand placement is very important in the Deep Half Guard. Your top hand, the hand that is through the legs and around the back, should have the pinky finger on top of the knee cap. Make sure to reference the video to see how I talk about the turning of this hand and how you should be applying pressure.
As with all people who play Deep Half the position is about making sure you keep your opponent's leg completely straight. The straighter the leg the more control you'll have and the easier it will be to check your opponent's base and ultimately sweep them.