This happened in Operation Crimson Hammer Tier 3 and 2 actually. I brought my SS buck to T3 and it could tank a bullet and it turned yellow. But when I played T2 OCH a lumber completely broke the shield and still dealt damage to me. I know a lumber is T2 lumber is tougher than a T2 Gun puppy, but this is a whole tier difference. I have not tested this with other shields or depths but I do believe that this may need further testing (I won't be able to test this). I don't know if this can happen with different monsters from different tiers either (Perhaps an alpha wolver in T1 and a devilite in T2).
Nope. OCH has stronger enemies on purpose. That lumber you fought on T2 was actually a T3 lumber.
Also consider status. If the gun puppy was neutral and the lumber had fire, your shield will break even faster.
Read the notes on the wiki
http://wiki.spiralknights.com/Operation_Crimson_Hammer#Clear_the_Gatehouse