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The examples I've seen in different dictionaries seen to imply very specific contexts the word is used in, many involving (verb)か分からない and かも知れない, but I haven't seen anything concrete about proper usage. Anyone know?

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いつなんどき or 何時{いつ}何時{なんどき}emphasizes that the when is unknown by repeating the expression of the same meanings.

Since its purpose is to emphasize that the when is unknown, it can be used in any context, whether negative or positive. (This point might be anecdotal) But because it easily hints the state of negative, for not knowing when, it's very common to find it in a negative context but it doesn't have to be. Some examples.

いつなんどき...

  1. 死ぬかわからない
  2. 夢{ゆめ}が叶{かな}うかもしれない
  3. 敵{てき}が来てもいい頃{ころ}だ
  4. 起{お}きてもおかしくは無い
  5. でも彼{かれ}と結婚{けっこん}できる
  6. でも電話{でんわ}してください
  7. でも行けます
  8. 見つかっても安全{あんぜん}
  9. 来るはずの電車を待つ
  10. 誰の挑戦{ちょうせん}でも受ける

As seen above, there is no real rule on its use. The closest in English might be whenever but it can also hint always, since you are just....not defining exactly when. And many great writers and figures have used it in varieties of contexts. #10 is an actual statement by the Japanese wrestling legend Antonio Inoki.

The use of "the" with Japanese wrestling legend was intended. I am biased.

いつなんどき、どんな挑戦が来ても俺は勝つ

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  • 「いつなんどき来るはずの電車を待つ」...???
    – chocolate
    Feb 1, 2023 at 4:49
  • Sorry i made it annoyingly too vague. Without はず you are just waiting for a train that you know will come. With はず it might not be so. Consider a situation where someone who's lost his mind, like dementia, or someone who's stuck in the moment he can't get out of. Maybe you know no more train will ever come to the station. But he looks up the clock, a min past the arrival time, and waits for a train that should be arriving any moment.
    – Kentaro
    Feb 2, 2023 at 2:59
  • Sorry I meant to say that the sentence sounds unnatural to my native ear.
    – chocolate
    Feb 2, 2023 at 3:00
  • 太宰治みたいな表現は控えることにしたほうが良さそうですね。
    – Kentaro
    Feb 2, 2023 at 3:03
  • 「いつなんどき敵が来てもいい頃だ」っていう例文も、不自然っていうか、変だと思うんですけど。。 太宰治みたいって、ちょっと古めとか、硬い感じの表現ってことですかね
    – chocolate
    Feb 2, 2023 at 3:05

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