transactional emails going to spam outlook

Outlook and Hotmail Are Trashing Your Emails - Here’s the Real Fix

 

If you’re sending important emails like account confirmations, password resets, system alerts - and users on Outlook or Hotmail say, “I didn’t get anything,” they probably did.

Microsoft just quietly moved it to Junk.

This is a structural issue, not a temporary glitch

Outlook’s filters aren’t just scanning content. They’re evaluating your sending infrastructure, header consistency, domain reputation, and alignment across SPF, DKIM, and DMARC.

Miss on any of those, and your email gets treated like a phishing attempt.

And when it lands in the spam folder, you’re no longer seen as a legitimate sender. You’re seen as noise.

Outlook Isn’t Broken, It’s Just Overprotective

Microsoft’s filters are designed to be conservative. The goal is to protect users from fraud, but the side effect is aggressive filtering that penalizes even slightly misaligned messages.

Here’s the hard truth: you’re not going to “trick” Outlook into inboxing your email with minor tweaks. No subject line will fix a mismatched DKIM header. No HTML prettiness will compensate for an untrusted IP.

This isn’t a content problem. It’s a positioning problem.

Most ESPs weren’t built to meet Microsoft’s bar. They treat email as generic transport. That works until it doesn’t. And Outlook is where it stops working.

Lemon Email Gets You Treated Like the Real Thing

Lemon Email doesn’t try to beat the system. It works with it.

We set up dedicated infrastructure that’s actually aligned with Microsoft’s expectations. That means:

• Your emails come from your domain, with clean headers and zero “via otherdomain.com” surprises

• All DNS records are properly configured, not just technically passing but actually aligned

• Your sending IP has a sending history that Microsoft trusts - and isn’t shared with random marketing traffic

• We warm, segment, and maintain IPs the way Microsoft prefers - quiet, consistent, and low complaint

We don’t guess. We engineer for inbox placement.

Why It Matters

Think about where your emails are landing. If they show up in spam, even if the content is perfect - you’re being lumped in with scams. Your product starts off with a trust deficit. That’s not just deliverability. That’s positioning.

Lemon Email ensures you start every user interaction from a place of credibility. Inbox placement isn’t a bonus feature. It’s the baseline for being taken seriously.

If Outlook is dropping your emails in Junk, it’s not your copy. It’s your infrastructure. Lemon Email fixes that. Permanently.