How to format an email that Hotmail / Outlook is happy with?

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The From header is invalid. It must have the w3coded outlook format following syntax:, w3coded outlook format Stack Overflow for Teams w3coded outlook format Where developers & w3coded outlook format technologists share private knowledge with w3coded outlook format coworkers w3coded outlook format ,Which you can omit if it's the same as w3coded outlook format the From header (like in your case).,Mail server w3coded outlook format has SPF record, reverse DNS, is not blacklisted w3coded outlook format and passes all checks at mxtoolbox.com.

The From header is invalid. It must have the following syntax:

From: "name" <email-address>

In your case:

From: "Testing Site" <admin@myserver.com>

The same goes for your Reply-To header:

Reply-To: "Testing Site" <admin@myserver.com>

PS: RFC 2822 doesn't state that the display-name in an address should be quoted. In other words: the following 3 headers should all work:

From: "Testing Site" <admin@myserver.com>
From: 'Testing Site' <admin@myserver.com>
From: Testing Site <admin@myserver.com>

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