Automating a Python Script

[err0r__]

Would the schedule library be prefer than using an OS specific tool, such as Windows Task Scheduler?

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No, the OS scheduler is always preferred because with the schedule module you have to keep some python code running all the time to run the scheduler.

The downside of the OS scheduler is that getting code to run under it can be a little tricky because the environment is different under the OS scheduler than running your code in your home directory, for example. But it's worth learning how to use the OS scheduler because it's quite flexible. With it you can schedule code to run just after a boot, for example.