I called the CP line to ask about this. The agent said that I would not be upgraded b/c I have three people on my itinerary (me @ CP, wife @ gold, daughter @ silver). Then she said that was odd b/c all of us had been upgraded on the outbound. She went to a supe and came back and said it must be b/c there are three on the itin even though she couldn't understand why it went through on the outbound.

Perhaps they are closing that loophole whereby your co-itin's inherited your status if they had status.