Processing Contraints with Validation Template on Orgs Not working

I am working on a Processing Constraint to Capture History on Update of SSD post Booking in Specific OU's.
STEPS
The issue can be reproduced at will with the following steps:
1) Create a validation template name as TEST with org = X and Org=Y, Type =TBL
2) Run Create validation package

3) Define the processing constraint on Operation = Update Attribute =Schedule Ship Date User Action: Require Reason and Require History

4) Define 2 AND Conditions 

A) Group=101 , Scope =Any Validation Entity = Order Header ,Record Set =Order, Validation Template =Booked and

Group=101 , Scope =Any Validation Entity = Order Line ,Record Set =Line, Validation Template =TEST

If I remove the Condition B , the constraint works fine but that would mean that it gets enabled in all OU's but we want it active only on specific OU's. Please advise what could be the issue here.