I use a python script to send mails. The script runs a VBA macro.
I'm scheduling the python script to run at a particular time.
My trust settings in Outlook has all macros enabled. I'm running the task with highest priority too.
I am able to send mails if I run the script manually. However, when I try to run it via Windows Task Scheduler, mails are not being sent.
Try a different scheduler and see if this works.
For example Splinterware system scheduler.
Trying a different scheduler can help you figure out if the problem is