It seems like I lose way more in-game challenges than I should...
“Get a hit with contact swing” - I used contact swing but squared it up and hit a dinger. FAILED
“Advance the runner” - I hit it into the gap and everyone scores. FAILED
These were the last two I can remember, but I often leave challenges with a fail that shouldn’t be there.
I've had this happen before too. For the first one it seems they don't count a home run as a hit during that challenge. I've failed it multiple times hitting home runs which is definitely something they need to fix, very annoying. The second one I have no explanation for.