My $.002 here.
Going to that "tough" place and not bailing him out is not what we moms want to do but do it because we know we have to for the sake of our addict children. We only want to be in that tough place for the minimum amount of time and then go back to that nurturing, helping place which is where we really want to be.
You were able to leave that tough place and go to the nurturing, helping place (which is where you would rather be) when your son was asking for your help while in jail. When your gut said he was getting arrogant again, you were put in the position of possibly having to go back to that tough place and part of you is fighting that tooth and nail.
Your story reminds me that i have to be flexible with my addict son (whether in recovery or not) and that I have to trust my gut instinct (immediately!) on whether this or that situation calls for "toughness" or "helping" or whatever...
like i said, just my $.002.