Can you check your antivirus to see if it might be getting in the way?

antivirus not running.

Have you checked the osquery logs?

@Kathy Satterlee using .msi package.

Anything I stressing in the osquery logs?

C:\Program Files\osquery\log

And is that the .msi created with

fleetctl package

, downloaded from the osquery site, or something else?

osquery is downloaded from osquery site.