When working on mail flow issues, one of the first troubleshooting steps with any mail server is to try and telnet into port 25 of the server. Exchange has an error, 530, that says that the smtp connection wasn’t authenticated. If you’re trying to relay through an Exchange server, that’s a good thing, as you wouldn’t want an open relay. However, if you’re trying to relay to an Exchange server, that’s not such a good thing. So let’s look at what this symptom looks like. First we try and telnet into port 25 of the server: telnet exchange.krypted.com 25 Which shows the following: 220 exchange.krypted.com Then we say hi: Helo…