I'm trying to understand a specific uses of で + は particle, and I would like a more detailed explanation of how it's used.

I referred to these 3 resources: デジタル大辞泉 Weblio コトバンク

Namely, there are 2 uses that I can't understand completely.

The first use:

From デジタル大辞泉

4 〔…だったら〕

今からでは遅過ぎる It's too late now.

From Weblio

4 〈…であっては, …であったら〉

これでは困ります. This won't do.

I assume these two sites refer to the same usage.

I'm not confident if this では can be a complete replacement for だったら,

In this case doesn't だったら mean "if" or "when"?

だったら、遊びに行くよ。If you're free let's go play.

では、遊びに行くよ。If you're free let's go play. (I'm not sure if this is grammatical)

I'd like more clarification on how to use では in this context.

The second use:

From デジタル大辞泉


あの顔付きでは失敗したらしいね Judging from the look on his face, I'm afraid he has failed.

From Weblio


彼の態度では, きっと仕事を辞めると思います. Judging from his behavior, I am quite sure that he will quit his job.

From コトバンク


Reading the definitions, it seems that から判断すると can replace では in this context.

But according to Japanese people I asked, it sounds unnatural in some sentences:

I am confused by this discrepancy when applying the rules, why is it natural in some sentences and unnatural in others, when the definition says it's the same as から判断すると?

  1. 彼の態度では、きっと仕事を辞めると思います。Unnatural
  2. 彼の態度から判断すると、きっと仕事を辞めると思います。Natural
Judging from his behavior, I am quite sure that he will quit his job.
  1. では中止になる Natural
  2. から判断すると中止になる Unnatural
Judging from the rain it (some activity) will be called off. (from the コトバンク example)
  1. 彼の、今のコンディションでは、優勝はできないかも知れないな。 Natural
  2. 彼の、今のコンディションから判断すると、優勝はできないかも知れないな。 Natural
Judging from his current condition, he will not win.

I can't seem to find much explanation for these uses online, if there are better resources that provide a more detailed explanation, please let me know.

  • Did you make a mistake saying 彼の態度では is unnatural? Sometimes things aren't 100% interchangeable, stuff like から判断すると is just there to give you an idea of what the word being defined means. It doesn't mean you can swap them with each other in every case. There's also the thing about some speech patterns sounding like they belong on the news/in literature and not everyday speech. Some phrases are preferred over others when talking about certain things. では is a very fun, useful phrase. I suggest you instead check out Wiktionary's explanations of the term. – Fireheart251 May 26 at 22:52

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