what exactly does 괜찮아요 mean and how does it differ from 알아서?
I believe that 괜찮아요 is closer in meaning to the English "are you ok?" or "I'm feeling fine"

whereas 알아서 is more like "do you understand?" or "yeah, no problem".

Am I right?

please use cultural reference points because I am living in Korea now and so that would be helpful.

Question

what exactly does 괜찮아요 mean and how does it differ from 알아서?
I believe that 괜찮아요 is closer in meaning to the English "are you ok?" or "I'm feeling fine"

whereas 알아서 is more like "do you understand?" or "yeah, no problem".

Am I right?

please use cultural reference points because I am living in Korea now and so that would be helpful.

Answer

You may need to correct that phrase to 알았어/아라써/.

괜찮아요? Are you OK? 
괜찮아요. I'm fine.

알았어? Do you get it? Do you understand? 
알았어. I got it. Okay.

Roughly you are correct. ^^

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