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The phrase "a complicated task when" is correct and usable in written English.
It can be used to introduce a situation or condition that makes a task more difficult or complex.
Example: "It becomes a complicated task when multiple stakeholders have conflicting interests."
Alternatives: "a challenging task when" or "a difficult task when".
Exact(1)
Nathoo ensures this money is wired to the proper bank accounts, which is a complicated task when you are dealing with 30, 40 or even 80 startups (and more founders).
Similar(59)
Sensemaking theories help designers understand the cognitive processes of a user when he/she performs a complicated task.
It was a complicated task to try to find solutions for groups and individuals, when the opportunities and possibilities were limited by the societal context, and when the goals and expectations among different actors differed.
But that is a complicated task.
It can be a complicated task.
This has proved to be a complicated task.
In a collaborative context, IS design is a complicated task.
Forest management planning is generally a complicated task.
The design of workflows is a complicated task.
Thus, this is a complicated task of system engineering.
Changing deeply ingrained cultural ideas about darkness is a complicated task.
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Since I tried Ludwig back in 2017, I have been constantly using it in both editing and translation. Ever since, I suggest it to my translators at ProSciEditing.

Justyna Jupowicz-Kozak
CEO of Professional Science Editing for Scientists @ prosciediting.com