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I wonder about the drainage every time I drive that section. How was this not addressed at the same time as the resurfacing and widening?

https://westseattleblog.com/2020/01/heres-whats-being-done-about-those-west-seattle-bridge-potholes/

How can I interpret the part in bold? Does it mean "should this have been addressed"? Or is it a genuine question asking why this was not addressed?

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book mango 418 is it a genuine question asking why this was not addressed?

It is a semi-rhetorical question asking that. Think of it as "How did it come to pass that this (the drainage) was not addressed …?"

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book mango 418How was this not addressed ...?

= Why was this not addressed ...?

book mango 418Does it mean "should this have been addressed"?

When we use 'how' for 'why', it suggests that something should have been done, but it wasn't.

CJ