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Discover Ludwig"when should" is a perfectly correct and usable phrase in written English.
You can use it when expressing a condition or asking a question about what would be the most appropriate or desirable time for something to occur. For example: "When should we start trying to figure out a solution for the problem?".
Exact(60)
When should I enroll?
"When should we begin?" "Soon".
"When should the punishment end?
When should management get involved?
When should that be disclosed?
When should it be pruned?
When should you plant lilies?
When should I arrive?
When should I incorporate?
When should investors sell Apple shares?
When should you stand?
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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