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I have a script written in python 3 that is designed to send a file to our web server via HTTP POST. It's running on a Windows VM on my customer's infrastructure. I have compiled the python script into an .exe to make it easy on the customer (no virtual environments or dependencies to worry about). The exe is executed with Windows Task Scheduler. The code for the script isn't the problem because it works at a lot of other customer sites. But lately I've gotten a few customers where the script doesn't upload anything unless a human logs in and runs the program manually. Another clue: The human must have logged in within the last two hours. If they login at 8 AM and run the exe at 4:30, it fails in the same way until the user logs out and logs back in. I'm a coder, not a sysadmin, so I'm fairly clueless as to the cause. I'm not even sure what search terms to plug into google. What could cause this?

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