My Delta plow anchor will also, on occasion, land upside down and not set. It seems to happen about 10% of the time. I am pretty sure it's more likely to happen if the boat is moving when the anchor is dropped and I always try to make sure the boat is stationary before I drop it. It's one of the limitations of that style anchor.
Rocna and Manson anchors have a roll bar that makes them self-right if they land upside down and may be worth looking into if you continuously struggle.
A Hanson anchor:
Make sure you have tons of scope before you try to set the bow anchor. Once it's set, you can reduce scope. I like to get at least 10:1 scope, deploy my stern anchor, then reduce the scope on the bow anchor to tighten up the rode (and increase the scope) on the stern anchor.
If you don't have a swivel between your chain and anchor, you should put one in. It may help with the anchor getting crossed up going into the bow roller. The machined stainless steel ones look nice, but the forged and galvanized ones are probably much stronger (and cheaper).
Machined stainless swivel:
Forged galvanized swivel:
