This topic comes up constantly in dental offices, and for good reason. Email problems tied to Eaglesoft can get confusing fast, and much of the advice circulating online is either incomplete or simply wrong. To make sense of it, it helps to start with some real-world context.

I spent 12 years at Microsoft working specifically on Exchange and Outlook. Exchange is the backend system that actually sends, receives, and secures email. Outlook is just the application people use to read and send messages. After leaving Microsoft, I started an IT consulting firm that originally focused on email migrations and now supports many dental practices. My wife is our largest client. She operates three high-volume pediatric dental offices, all running Eaglesoft.

This is not theoretical. These are problems we solve in real offices every week.

Here is what actually matters.

First, Eaglesoft is not an email system.

Eaglesoft is a practice management system. It handles scheduling, charting, billing, and recalls. Email exists inside Eaglesoft as a convenience feature, not as a full, modern email platform. When offices rely on Eaglesoft to send patient emails directly, failures are common. Updates break things. Deliverability drops. Security settings fall behind. This is not user error. It is a mismatch between the tool and the job being asked of it.

Second, “Outlook isn’t supported” is an oversimplification.

Email works on standardized protocols that nearly all providers follow. One of the most important is TLS, which encrypts messages while they travel between servers. Over the past several years, Microsoft significantly tightened TLS and authentication requirements to reduce spam, phishing, and data leakage. Eaglesoft’s email integration did not fully modernize alongside those changes. When offices are told that Outlook is not supported, what that really means is that Eaglesoft’s internal email feature has not kept pace with modern email security standards. Outlook itself is not the problem.

Third, consumer or bundled email has no place in a dental practice.
Addresses like @yahoo.com, @aol.com, @gmail.com, or @outlook.com fall into this category, as does email that comes “free” with website hosting. These are consumer or lightweight services. They are not designed for healthcare compliance, business identity, reliability, or advanced security controls. When a dental office is using one of these, it is usually a sign that they are not on a true business-grade email platform.

Fourth, paid secure email add-ons are often unnecessary.
Third-party products such as Paubox or Datamotion do provide secure email delivery. What is often missed is that the core features they advertise already exist inside platforms like Microsoft 365 and Google Workspace. TLS encryption, transport rules, keyword-triggered secure delivery, and secure message portals are built in. In many cases, offices are paying monthly fees for tools that simply wrap features they already own. That is rarely buying more security. It is usually paying for convenience.

What we recommend and deploy.

Dental practices should use a true business email platform such as Microsoft 365 or Google Workspace, configured on the practice’s own domain. TLS-based encryption should be enabled so sensitive emails are automatically protected during delivery. This functionality is built in. In most cases, paying extra for a separate secure email service is simply burning money to solve a problem you already own the solution for.

Staff training matters just as much as technology. Teams need to understand when secure sending is required and how to trigger it correctly. No system is compliant if the people using it are not. For the rare patient who truly cannot receive encrypted email, both Microsoft and Google already provide secure message portal options as a fallback.

Finally, the most important rule: Do not send patient emails from Eaglesoft.
Export or save what you need from Eaglesoft, then send it from your actual email system using Outlook or the web interface. Let Eaglesoft do what it does best. Let a real email platform handle email.

Every time we see an office struggling with Eaglesoft-related email issues, the root cause is the same. Eaglesoft is being asked to behave like an email platform. Once that responsibility is moved to a proper business-grade email system, the problems largely disappear.

Ready to stop fighting Eaglesoft email issues?

If your office is struggling with Eaglesoft email or unsure whether your current setup is secure and compliant, contact Olive + Goose. We’ll review your environment and show you how to fix the root cause, not just the symptoms.