https://www.delta.com/us/en/skymiles...llion-upgrades
under "Complimentary Upgrades with Companions", the example scenario actually matches OP's exactly
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:
- For domestic Delta One and First Class, your upgrades will clear based on your individual Member Status and confirmation windows, if available. For example, if Platinum and Silver Medallion Members are traveling together, the Platinum Medallion Member will clear at the Platinum window and the Silver Medallion Member will clear at the Silver window. If your companion is a General Member who does not have Medallion Status, their upgrade will clear at the clearing time of the Medallion Member’s Tier. For example, if a Platinum Medallion Member and a General Member are traveling together, both will clear at the Platinum window.
- For Delta Comfort+, General SkyMiles Members are not eligible for Complimentary Upgrades. The Medallion Member will clear for their upgrade at their respective window.