It’s easy to blame Microsoft. You did everything right. SPF? Set. DKIM? Passed. DMARC? Aligned. Yet your emails still land in Outlook’s spam folder. It feels unfair. Broken. You start thinking Outlook is just the problem. But here’s t ...
MailerLite vs. Mailchimp: The Pricing Trap That's Crushing Small Businesses You're probably looking at these two platforms thinking Mailchimp is the "safe" choice because everyone knows the name. I thought the same thing three years ago. &nb ...
Why Outlook’s Spam Folder Is More About Your Readers Than Your Content When your emails land in Outlook/Hotmail’s spam folder, it’s tempting to blame your content. But the truth is, Outlook’s filtering heavily depends on h ...
Beehiiv vs. Substack - Pick the Wrong Platform (And Pay For It Later) If you're reading this, you're probably frustrated. You want to grow your audience, monetize your passion, and build a brand that lasts, but you're stuck choosing bet ...
When it comes to Outlook, your domain’s reputation isn’t just important — it is everything. Outlook looks beyond SPF and DKIM. It tracks how long your domain has been sending, how consistently, and whether your past emails caused compla ...
Substack vs. Ghost: Why Your Content Strategy Is Bleeding Money You're probably staring at these two platforms right now, wondering which one will finally get your newsletter off the ground. I get it. I was in the exact same spot 18 mo ...
Hotmail and Outlook spam filters are no longer primitive. They’re powered by neural networks—deep learning models that don’t just look at email structure, but also understand meaning. Microsoft’s spam detection stack now includes ...
Outlook’s spam filter isn’t a simple keyword blocker. Instead, it uses Bayesian filtering as a foundational technique combined with advanced machine learning and behavioral analysis. Bayesian filtering looks at the probability that certain wo ...
AI agents are evolving fast—from single-task automation to orchestrated, multi-step workflows that mimic human behavior. But while the brains of these systems keep getting smarter, their communication layer—the email API—remains stuck ...
You’ve done everything right. Your app sends transactional emails exactly when it should. You’ve verified they were sent. But users with Outlook or Hotmail addresses still miss them. Later they say, “Oh, I found it in spam.” And t ...
If your app sends account confirmations, password resets, or receipts, those emails are supposed to be sacred. They’re expected. They’re wanted. Yet somehow, Outlook and Hotmail keep burying them in spam folders. The easy explanation is deli ...
In the world of email deliverability, few inboxes are as notoriously difficult to land in as Outlook and Hotmail. The Microsoft ecosystem operates on a different frequency—one that many developers and senders underestimate until it's too late. Unli ...
Ghost vs. Kit: The Business Model Confusion That's Killing Your Growth You're standing at a crossroads that most creators never see coming. On one side, there's Ghost with its beautiful publishing tools. On the other, Kit with its powerfu ...
Many transactional email senders hit a wall with Outlook.com and Hotmail. Microsoft inboxes (Outlook/Hotmail/Live) make up only about 5% of all mailboxes – but far more (15–20%) for many e-commerce and tech. In practice, that means a large fr ...
Most teams focus on SPF, DKIM, and DMARC but forget about the email headers — the invisible signals Outlook watches closely. Headers like Precedence or List-Unsubscribe can mark your email as marketing or bulk mail even when it’s transactiona ...
You're sending transactional emails. Receipts, confirmations, password resets - and they're ending up in Outlook’s junk folder. That’s more than an inconvenience. It's a broken customer experience and lost revenue. Microsoft Outlook isn&rsq ...
Outlook’s filters don’t just rely on technical checks. They pay close attention to how recipients interact with your emails. If users frequently delete your messages without reading, move them to junk, or don’t reply, Outlook’s ma ...
The Hidden Cost: What Junk Folder Placement Says About Your Brand Let’s step back and look at this from your customer’s perspective. They sign up for your product. They're waiting for a confirmation or a password reset. Nothing shows ...
Outlook’s spam filtering isn’t just one system—it’s a layered, complex engine that combines machine learning, behavioral analysis, and heuristic rules to decide if your email deserves the inbox or the junk folder. At its core, Out ...
Outlook’s spam filters use many machine learning techniques, including Support Vector Machines (SVM). SVMs are powerful classifiers designed to handle high-dimensional data—perfect for analyzing complex text features in emails. What does this ...
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 any ...
Outlook/Hotmail’s spam filters rely heavily on Random Forest models—ensembles of decision trees that analyze hundreds of features about your email to decide if it’s spam. Each decision tree looks at different signals like: Sending ...
Beehiiv vs. Kit: The Creator Income Mistake I See Everyone Make If you're reading this, you're probably where I was two years ago. Looking at Kit and Beehiiv, trying to figure out which one will help you finally make real money from your audience. ...
Outlook’s spam filtering system is a sophisticated combination of multiple machine learning models, behavioral analytics, and strict authentication checks. To truly fix deliverability issues, you need to understand how these pieces fit together&mdas ...
Outlook and Hotmail’s spam filter uses a blend of machine learning models, and one of the most important is Logistic Regression. This model evaluates a wide range of features from your email—like sender history, content traits, and engagement ...
Outlook and Hotmail use aggressive, proprietary spam filters built on machine learning, not just keyword lists. These filters analyze: 1. Metadata & Headers: Mismatched "Reply-To" and "From" fields Missing or misconfigured SPF, DKIM, and D ...
If you're sending transactional emails and they keep landing in Outlook's spam folder, the issue likely isn't your content—it's your infrastructure and configuration. Microsoft Outlook, including Hotmail, Live, and MSN, uses AI-enhanced filters pow ...
Beehiiv vs. Ghost: The Email Newsletter Platform Choice That Defines Your Success If you're reading this, you're probably at a crossroads. You want to build something meaningful online, but you're stuck choosing between two platforms that seem to p ...
When you send transactional emails to Outlook or Hotmail users, less is more. Heavy HTML, too many images, tracking pixels, and excessive CSS raise red flags. Outlook’s filters prefer simple, clean emails with minimal external resources. Complex em ...
Most developers assume that if their email is transactional, it will land in the inbox. It makes sense. A user signs up, you send a welcome message. They reset a password, you confirm it. Nothing spammy about that. But if you're sending those from a syste ...
Why First Impressions Matter for Email Deliverability When sending email to Outlook or Hotmail, you get one shot. If your first batch lands in spam, Microsoft’s filters lock you into a reputation that’s nearly impossible to recov ...
Be honest - when’s the last time you actually liked an exit pop-up? Probably never. But here’s the thing: they work. And let’s just say they are annoying, so what? That visitor was about to bounce. You can either let them leave and forg ...
Outlook and Hotmail doesn’t just want SPF, DKIM, and DMARC to pass. It wants them perfectly aligned. What does alignment mean? It means the domain in your From address matches the domains authorized in SPF and DKIM records. If there’s a misma ...
How Lemon Email Stays Out of Outlook/Hotmail Spam Outlook and Hotmail spam filters don’t just rely on naive rules or blacklists—they’re powered by modern machine learning models like Gradient Boosting, specifically XGBoost, trained on m ...