When we’re looking at the technical details of email addresses there are two quite different contexts we talk about. One is an “821 address” or “5321 address”. This is the email address as it’s used by the SMTP protocol, as part of the “MAIL FROM: <>” or “RCPT TO: <>” commands sent to the mailserver. It’s defined in RFC 821...
It looks like Microsoft are getting pickier about email address syntax, rejecting mail that uses illegal address formats. That might be what’s causing that “550 5.6.0 CAT.InvalidContent.Exception: DataSourceOperationException, proxyAddress: prefix not supported – ; cannot handle content of message” rejection. Why do we care? It’s good to send syntactically valid...
Most of the time when we’re talking about email addresses, we’re talking about the actual user@domain format that’s used to send mail over the wire, but that’s not how we most often see them. When they’re used in a To: or From: header they’re usually associated with a display name – the “real name” of the user with the associated email address...
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