It looks like I figured out the cause, and it only sort of had to do with the security prompts. Apparently, the second connection was occuring before update was completing in the access database. The only reason it would work when clicking the prompts was it allowed an extra second or so for the update to happen, then run the check to get the next number. I somewhat adjusted for this by putting a timeout in the code, which I dont really like, but even a delay of 500 milliseconds makes it work.