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As long as you have a holster that covers the safety you shouldn't have any issues. I have an owb and I find it engaged sometimes
This is a perfect example of why I'm a fan of training with the safety if you have a gun equipped with one. I had a similar thing with the safety on my SR9c catching on my holster occasionally, so rather than risk having it accidentally engage, I started engaging it all the time, and practiced sweeping it off on my draw. Since it had a down stroke to disengage similar to a 1911, it was easy to make muscle memory. Now whether it's on or off I have the same motion on the draw. Is the Shield safety setup in a similar fashion?