latest.log file does not write until opened or right-clicked

I'm trying to monitor the latest.log file as it updates. I have tried FileSystemWatcher (.NET C#), Powershell (Get-Content), and other open source projects, all with the same result. I found that latest.log does not update on any of my Windows server environments unless I either right-click the file or open it. I was originally running Java 7, and tried the latest (or last) version of both 6 and 8. I am also running MC server on Ubuntu Linux and do not have this issue there.