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上手く立ち回って、退学にならないようにしてね。

ようにする: 1. (following a verb) to be sure to; 2. to do (something) so that; 3. to make sure to; 4. to try to. (according to nihongomaster.com)

I was just wondering is it proper to apply ようにする on 2 verbs?

If it was based on the above sentence, the translation will be like:

"Well, make sure to deal with it properly, and try not to drop out of school"

It sounds much better and clearer.

Thank you in advance for your guidance.

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    It's always hard without a context. But definitely, in this situation "try not to drop out" is incorrect. It sounds like you want them to fail. xD "make sure to not drop out of school" sounds and fits more. – Natsu Kage Jan 27 at 21:37
  • In short, the speaker was telling someone who was in danger of dropping out of school (almost definite) due to the conspiracy of his classmates, that's why I thought that "try not to drop out of school" might be fit. But I agree with your suggestion. It's just the front sentence has no suggestive words, such as "you should". That's why I was wondering whether ようにする is applicable on both verbs. – Amanda Zhang Jan 27 at 21:49
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    Normally, the ようにして doesn't apply to the rest of the sentence. Also, 立ち回る means to outmaneuver/play your cards ejje.weblio.jp/content/%E7%AB%8B%E3%81%A1%E5%9B%9E%E3%82%8B – Natsu Kage Jan 27 at 22:17
  • "Make sure to handle it properly and don't drop out of school." That's what I can think of, if ようにして can't be applied on both verbs. I have a hard time to find a better word to translate 立ち回る in english. – Amanda Zhang Jan 27 at 22:35
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退学にならないようにしてね means "Please make sure you aren't kicked out of school" (退学になる excludes voluntary dropping out). 上手く立ち回って here means "maneuvering right / playing your cards right" precedes this avoidance of being kicked out (it implies this would be the cause of not being kicked out).

So, taken together it means:

Play your cards right and avoid getting kicked out of school

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