If there is a File condition on a Job, any tasks for that job that you attempt to run manually via "Run Task" context menu will not start if the file does not exist and that Job condition is not met. However, if you set the same condition on the Task itself and and run via "Run Task" the condition is ignored and the task starts if no file exists.

Why does the task inherit Conditions from the Job when running one off Tasks for that job, but ignores the Condition if applied directly to the Task?

When you right click to run you can choose if you want to run with Conditions or not. By default it is ignoring Conditions.

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