1

How do I know if the meaning of つつ in a sentence is whether "while" or "although"? You infer it just because of the context? or is there any signals before/after that gives you the meaning of it?

2

I would say it is mainly because of the context. If we look at https://dictionary.goo.ne.jp/word/%E3%81%A4%E3%81%A4/#jn-147598 :

  1. 二つの動作・作用が同時に並行して行われることを表す。それぞれが…して。…ながら。「諸事情を考慮しつつ計画を立てる」「大声で叫びつつ走りだす」
  2. 二つの動作・作用が矛盾して行われることを表す。…にもかかわらず。…ていても。「早起きが健康にいいと知りつつ、つい寝すごしてしまう」→つつも

we might be tempted to conclude that つつも can only mean "although" and not "while", but we can see that is not necessarily the case if we look at https://dictionary.goo.ne.jp/word/%E3%81%A4%E3%81%A4%E3%82%82/#jn-147737, in which both "while" and "although" are listed:

  1. 「つつ」を強めた言い方。…しながら。「働きつつも学ぶ」
  2. …にもかかわらず。「努力しなければならないと知りつつもついなまけてしまう」

I would argue that, in case of つつも, the connotation is leaned slightly toward "although": to me, 働きつつも学ぶ seems to slightly suggest that the writer considers "studying while working" to be an unusual thing requiring extra effort.

I would also argue that "while" in the English language is also often used to contrast two opposing ideas or concepts that nevertheless happen at the same time.

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