Originally Posted by
MCO Flyer
This is incorrect. All award tickets are now available for comp UG for all status levels now, including companions.
Only when on same reservation, which in this case they won't be because he's booking his ticket through a company portal.
From Delta.dumb:
If you and your companion are in different paid ticket reservations that have been linked, upgrades to U.S. 50 domestic Delta One, First Class and Delta Comfort+ work a little differently