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I appreciate the advice everyone. I've asked for a sit down with my Director to go over some of these and come up with a good plan. This is a great community, you guys are awesome!

Thanks for the advice, common sense stuff but always a little paranoid when the word "hacking" comes out. I kept saying pen testing he kept telling the CEO hacking. Thanks again

I am the system admin at my organization and my director has asked me to conduct some penetration testing. Partly because he wants to make sure we are secure, and partly because I want to do it. Not sure if this is the right place to ask this, but are there any legal concerns around me doing any testing of our network and systems? Some testing would occur with internal access to the network, and some would be external attacks. I know not really a technical question, and if this goes somewhere else let me know. Thanks!