Thanks to Chirag Mistry and Kevin Shumbera to this workaround.
If you have a situation where a wall wraps correctly around the windows in the 1/8" plan but fails to wrap in a detail callout (a floor plan callout wraps correctly.) The bad news is that this is appears to be a bug in Revit. The good news is that you do not have to recreate all of your callouts.
The workaround for fixing this in your Detail Callout is to:
-Select the wall and explore its element properties.
-Choose Edit/New for “Type” parameters.
-Change the wrapping at ends parameter to “none” and hit apply.
-Now change it back to either “Exterior” or “Interior” and hit apply again.
Changing this setting to none and back again seems to make Revit reapply the wrap. * If you change the crop region of the Detail Callout… this condition will occur again and will require the same steps to fix. That being said, there may be other random actions that can cause the view to revert.