Scan to email constantly not working with your MS365 or Google environment?

When businesses set up devices such as copiers, scanners, or applications to send email, the natural instinct is to point them directly at their company’s Microsoft 365 or Google Workspace environment. After all, that’s where the mailboxes live. But in practice, this often leads to frustration, inconsistent delivery, and sometimes complete failure of scan-to-email functions. That’s why many companies turn to third-party services like Mailgun, SendGrid, or other SMTP relay providers as their backbone for outbound application mail.

The Problem with Native MS365 & Google Relay

Microsoft 365 and Google Workspace were designed with end-user mailboxes in mind, not machines and applications. While they do offer SMTP relay features, several issues frequently come up:

  • Authentication headaches: Modern email requires secure connections with TLS and proper authentication. Many older copiers and applications can’t support the complex authentication methods enforced by Microsoft and Google.
  • Rate limits & throttling: These platforms place daily and per-minute sending limits to prevent abuse. Even small businesses can run into these when devices send multiple scans or reports.
  • Strict anti-spam protections: Messages sent without perfect headers, DKIM, or SPF alignment may get quarantined—even inside the same organization. This makes scan-to-email “work sometimes, fail sometimes.”
  • Ongoing changes: Microsoft and Google continually tighten their relay policies, often breaking previously functional setups overnight. A recent change in Microsoft 365, for instance, left many businesses suddenly unable to send scan-to-email at all.

Why Mailgun & Similar Services Solve the Problem

Third-party email relay services like Mailgun exist specifically to handle application-generated and transactional email. Here’s why IT teams prefer them:

  • Simplicity: They provide a straightforward SMTP endpoint with clear credentials—compatible with nearly any device or app, old or new.
  • Reliability: Built to handle large volumes of automated mail, they have far fewer restrictions than Microsoft or Google.
  • Deliverability: Services like Mailgun specialize in making sure messages don’t get flagged as spam. They manage IP reputations and provide reporting tools to track delivery.
  • Scalability: Businesses can grow without worrying about hitting hidden daily sending caps or being throttled by their productivity platform.
  • Separation of concerns: End-user email stays in Microsoft 365 or Google Workspace, while machine/app-generated email flows through Mailgun. This separation improves security and troubleshooting.

Real-World Example

A nonprofit office running Microsoft 365 may rely on its copier to send scanned documents directly to staff email. When Microsoft tightened authentication rules, the copier suddenly stopped sending. Rather than investing in a costly hardware upgrade or fighting through complex relay settings, the IT team pointed the copier to Mailgun’s SMTP relay. Within minutes, scan-to-email was reliable again—and remained so regardless of Microsoft’s future policy changes.

The Business Case

At its core, using Mailgun or similar providers is about reducing risk and increasing reliability. Businesses don’t want their operations interrupted because a copier can’t send a scanned contract or a line-of-business app fails to send invoices. By decoupling application-generated email from user email environments, IT gains:

  • Consistent performance
  • Easier compliance tracking
  • Predictable costs
  • Fewer end-user complaints

Don’t Let IT Headaches Hold You Back

If your IT provider hasn’t helped you navigate this very common headache, you might be stuck troubleshooting problems that shouldn’t be yours to own. This is exactly where proactive support makes all the difference.

At Ultrex IT, we don’t wait until things break—we help clients stay ahead of these pitfalls with proven solutions, whether it’s scan-to-email, cloud migrations, or compliance. If you’re tired of feeling like your IT is just “keeping the lights on,” it might be time to see what real proactive support looks like.