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The phrase "a discouraging challenge" is correct and usable in written English
It can be used to describe a task or situation that is difficult and likely to lead to feelings of discouragement or frustration. Example: "Despite the team's efforts, the project turned out to be a discouraging challenge that tested their resolve."
Exact(1)
I fully intended to go back to Northwestern and attend its graduate business school, but its location way across town presented a discouraging challenge.
Similar(57)
… Health system representatives Participants from all categories discussed the discouraging challenges ASHAs face while working in difficult field situations such as distant, hilly, scattered, inaccessible and insecure geographical locations; combined with illiteracy, myths and misconceptions, religious and cultural beliefs, and fear and distrust of community people on ASHAs and co-workers.
"You have to see that as an exciting challenge rather than a discouraging limitation".
Chocola said that Romney's apparent political opportunism was a discouraging sign for conservatives who want a nominee who is willing to take on tough challenges.
It was a discouraging setback.
It was a discouraging time.
It was a discouraging moment.
But it was a discouraging start.
And again, there is a discouraging precedent.
Their stories present a discouraging picture.
Put it all together, and it's a discouraging picture.
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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