Insurance is confusing

I got an email that one of dh's medical insurance claims from his recent visits to urgent care and then the ER, processed. Just last week (before any of these new claims had processed) I had been looking at his totals for the year to see how close he was getting to meet his deductible. It said he was $167 away from meeting it. 

So this newest claim was just processed on 10/25. It was for the urgent care visit. The total was $508 and after the discount contract amount the total is $237.56 and the EOB from the insurance company says he owes the full $237.56, as it was all applied to deductible. I'm so confused! If he only had $167 left to meet his deductible, then why wasn't $167 of this latest charge of $237 applied to deductible and the remaining $70 should have been processed at 20% co-insurance and the rest now paid by insurance?

And his little graphs show deductible now met at 100%. He's also only a little over $600 away from meeting his YTD out of pocket max, so I'm sure with the other claims coming thru soon for the ER visit he will (should?) meet his OOP max.

And then looking closer at my claims and what they are saying has been applied to my deductible so far - I see that when I had to go back for a second blood draw to recheck my levels - that the EOB says it was not covered (I didn't catch that when I paid the $69 bill, I just assumed that was my share and it went to my deductible). Why would this not be covered and go towards my deductible. The doctor ordered this test done, as a follow up. None of it makes sense, so I guess I will have to call to get some explanations, tomorrow. Or maybe I just need to look at it all again, later, LOL. I keep looking at all his EOB's and the amounts they say applied to deductible don't match what they show on the graphs as his "total claims".  It's making my head spin, but stuff like this drives me nuts, until I figure it out.