Upside Down Door Locks?

[Nick J.]

Hey guys, I never post in this type of thread simply because I'm not an expert on some things.

I've changed my fair share of door locks in my time. This weekend, while a long time tenant vacated one of my props I picked up some new locks at Home Depot and went on my way change the locks. I bought a 4 pack(2 handles, 2 deadbolts) for the front/side door.

The front door went on just fine as expected. When it came to the side door, it just wouldn't work unless it was upside down...

I left it but its been consuming my thoughts all weekend. Any idea what I did wrong? I double, triple and quadruple checked, it just wasn't going to work right side up.

Thoughts?