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The phrase "a challenge with a" is correct and usable in written English.
It can be used when discussing a specific challenge that involves or is associated with something else.
Example: "The project presented a challenge with a tight deadline that required us to work overtime."
Alternatives: "a difficulty involving a" or "an obstacle related to a".
Exact(41)
We met a challenge with a challenge.
That could be a challenge with a suspect offensive line.
It's a challenge, with a 75% pass mark and a long list of potential questions.
Unplugging the area to evacuate the mess is a challenge with a relevance that goes beyond St Giles CircusSt Giles Circus
I threw that question out to four distinguished New York bartenders, or rather asked them to participate in a challenge — with a twist.
In 1988 a New Zealand team, exploiting a loophole in the America's Cup rules, declared a challenge with a 90-foot boat that dwarfed those in the Cup's traditional 12-meter class.
Similar(17)
After Cash's death, Rubin was searching for a challenge with an even higher degree of difficulty, a greater test for his powers of listening.
8 P.M. (Fox) MASTERCHEF In a two-hour episode the remaining 13 contestants confront a challenge with an unexpected ingredient before Christine Ha, the Season 3 winner, shows up for the elimination round.
Development of treatments for acute and chronic pain conditions remains a challenge, with an unmet need for improved sensitivity and reproducibility in measuring pain in patients.
During this asymptomatic period, it is possible to demonstrate an abnormality in carbohydrate metabolism by measurement of plasma glucose in the fasting state or after a challenge with an oral glucose load or by A1C.
During this asymptomatic period, it is possible to demonstrate an abnormality in carbohydrate metabolism by measurement of plasma glucose in the fasting state or after a challenge with an oral glucose load.
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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