Outgoing Emails (Git Patches) Blocked by Windows Live

Answer 1

It means that your machine isn't considered to be a "legit" mail server (personal PCs generally aren't - especially those on dynamic IP ranges). The account you set the "From:" to doesn't matter; the server is rejecting your computer trying to talk to them directly. Instead what you could do would be to change the --to field to a local address (yourusername@localhost, for example), and then grab the email from your local inbox and resend it using an IMAP client connected to your Gmail client or some such (see here for more info).

Answer 2

It sounds like your mail client is set up to connect directly to the recipient's email server. As you're seeing, many email service providers refuse to accept incoming mail from dynamically allocated IP space. The way to fix this is to set your email client to use your ISP's outgoing SMTP server. They (Charter) should have a tech support page explaining what hostname or IP address (and possibly which port number) to use. If you're lucky, they might even describe how to configure your email client with the necessary settings. (I don't have a Mac in front of me at the moment to help you with that...)

Charter's outgoing SMTP server will certainly be in statically allocated IP address space, so once you get that set up, you should have an easier time getting your email accepted by the major email providers.