How to Remove Your IP from the Gmail Blacklist
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What's better than running htmlEncode? Running it seven times!
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Most people should probably just use a third-party email service provider so they don't have to worry about issues like this. Deliverability is a pain to manage if you don't have to.
I didn't know about the existence of Google Postmaster Tools[0] so that was a cool discovery :)
Most cloud providers (e.g. Google [1] and Amazon) as well as ISPs block outgoing traffic on TCP port 25 (SMTP) so it's actually fairly hard to run your own SMTP server to begin with.
[1]: https://cloud.google.com/compute/docs/tutorials/sending-mail...
True, but many people will try to do it anyway. Amazon will allow you to send email on request. They just have a form you need to fill out.
Given their concern for ranking of their IP space, they'll be watching you with fifty eyeballs after granting you access.