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I was studying about Past Continuous tense and my book states:

We use the past continuous when the repeated actions or events provide a longer background to something else that happened.

It also gives the following example,

During the time I started to get chest pains, I was playing tennis a lot.

One sentence that I made myself germane to this rule was

When Pablo came on police's radar, he was organizing mass smuggling of contrabands.

I have two questions regarding this 1. Does the second sentence conform to the rule which the author wanted to describe?

  1. Would it seem normal to native speakers or would they prefer to say it in some other way?

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It's a perfectly correct sentence.

Whether it conforms to the rule you state is a bit dependent on context - either Pablo was organizing mass smuggling of contraband repeatedly (in which case your rule applies), or he happened to be in progress of organizing mass smuggling of contraband when he came on police's radar (in which case a more general rule applies which says to use Past Continuous for continuing actions which are unfinished when another, shorter action occurs).

The sentences are identical regardless of which rule you think fits better, though, so it doesn't really matter.

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