Hi @Gabriel_CSX ,
“I've enabled the option to show the From field in Outlook web, but when I try to send mail from the other mailbox, I receive the message "You don't have permission to send messages from this mailbox.", not a bounceback“
According to my tests, everything works fine when I click the “From” button in OWA and select “Other email address” to send mails from another account that I have the “send as” permission. I noticed that you mentioned that it works in the Outlook client, so the delegation permission should be fine.
My suggestions are that you can try to change the browsers or use another user account to give permission and try again.
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