I can not seem to get the steering lock to engage. Is their a trick? I push and apply just a little pressure while slowly easing the handlebar but it just won't engage.
Turn bars all the way to the left, push key straight in and turn key counter clockwise maybe 1/4 turn
Assume you have no aftermarket device installed that prevent bars from full rest position ( wind shield brackets/holders that may rest against gas tank and obstructing desired bar position at full rest)...as a simple advice.

Just tried this on mine. Are you pushing the key down? The key needs to be pushed down about 1/4" and turned counter clockwise to engage the lock mechanism. The key won't turn until the bars are in the full left position.