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A. Do you know when he usually sends the money?
B. I can't tell when he usually returns.
Are these sentences natural? or do these sentences have incorrect grammar?
I'm not a native speaker so these sentences are natural in our language. But in native speakers' view, are these sentences awkward or wrong in grammar?
they are natural. In the question word clause we use normal word order: subject + verb.
Tell me who she is. (NOT Tell me who is she?) Could you please tell me what I should do now? (NOT Could you please tell me what should I do now?)
I can't tell when he usually returns.
This is fine unless you actually mean:
I can't tell you when he usually returns.
The first would be appropriate when someone is trying to determine (unsuccessfully) when this man usually comes back.
"I can see he leaves here every Sunday. I can't tell when he usually returns."
The second is an appropriate response from someone who can't or won't reveal when this man usually comes back.
"I'm sorry, I've been sworn to secrecy. I can't tell you when he usually returns."
A. Do you know when he usually sends the money?
B. I can't tell when he usually returns.
Are both fine. However there are some implications in the words which might not be clear to you.
A. Do you know when he usually sends the money?
"Sends" implies the transfer is being made indirectly, as perhaps through the mail. Money (actual currency) isn't typically sent indirectly. Rather you make a "payment." (eg check, money order or credit card authorization).
B. I can't tell when he usually returns.
The implication is that for some reason that you are restricted from telling. You just don't know, or there is a company policy that you can't divulge that information. If you say "I won't tell when he usually returns" then you know, but you will not tell.
