reply on email does not send a message

I have an user which when he try to reply all when he receive an email, email is not send to one of the recipients, saying that the message cannot be delivered. If he explicitly write her email in the new mail , email is successfully send. Any idea how to fix this problem?
dedriAsked:
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Rajkumar-MCITPCommented:
Clear the auto address cache for the failed recipient on the affected users outlook and check the status

If you want to confirm the issue with outlook auto cache, ask the user to reply all the same email from OWA, he wont get undelivered email
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arrorynCommented:
What is the specific delivery error for that one recipient?
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dedriAuthor Commented:
The message is deleted and he didn't send me.
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Rajitha ChimmaniCommented:
It could be a problem with the legacy email address. You need to add the address in delivery failure as X500 address on the mailbox
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