I've posted before about this, but to prevent from bumping old threads, the short version is that I'm after these things in this order: - Reliability (no silent filtering; things get delivered, or someone gets a nondelivery report) - Push and background updating on iOS devices (deleting a message in webmail removes it from my iOS unread badge, etc) - Solid IMAP or EAS - Secure - Private With Microsoft transitioning Outlook.com free accounts to Office 365's infrastructure (mine is already there), I'm unsure what to expect for #1 and #2. As a superficial thing, I'm not crazy about the domain name "fastmail.com" or any of their alternatives, but that's about all I've got against them. Would love to keep everything on one service, but iCloud mail leaves much to be desired. Would appreciate anyone's thoughts. Seems to me Fastmail is the better choice over Outlook and even Gmail.