When I deployed my email server with DigitalOcean five years back, it delivered at a competitive price and performance. A few years later, the same server has gotten a price hike but no upgrades or resource increases. Even so, hosting your email server is not for the faint of heart, and IP reputation is a big part of the game. Therefore, I stayed with DigitalOcean until the depletion of resources finally forced my hand.

I’ve been getting quite a few emails from people wanting to know if I’ve made any progress on the deliverability issues I was facing when delivering email to outlook.com. As good fortune would have it, Microsoft accepted my request to delist my mail server from outlook.com’s internal IP blocklist.

If you’re a geek like me then you probably enjoy spending your time hardening and optimizing your servers to support modern security standards and policies. If so, I’d like to share my favorite online resources and encourage you to take up the challenge of beating paranoidpenguin.net.

Recently, I was trying to respond to an email delivered to me from an outlook.com sender address. Unfortunately, my response immediately bounced back, and I was informed that my mail server’s IP address had been added to outlook.com’s internal blocklist.

I recently moved my self-hosted email service from Scaleway to DigitalOcean. After receiving a new IP address for my mail server, I’m effectively once again the new kid on the block. Let’s find out if the big kids are willing to talk with me if I play nice and put on my best behavior.