Tag: Outlook Not Sending Emails on Wi-Fi or VPN? Troubleshooting Guide

Outlook Not Sending Emails? Your VPN Might Be the Problem

| December 18, 2025

Outlook Not Sending Emails? Your VPN Might Be the Problem

I’m not a VPN expert: But here’s my story today.

Many of my clients are calling in with oddball problems with Outlook and programs needing the internet. For the past few months, the #1 suspect is VPN and very strong firewalls. McAfee, Norton and Malwarebytes are the usual suspects but some clients have a VPN specific product. I get why they want to use a VPN but it can cause issues. With Outlook, VPN is not a friendly companion. If you’re having struggles with Outlook and using a VPN, you might need to contact the company and see if they can add an exclusion for Outlook. Or find another product that is Outlook friendly, or decide if you really need a VPN.

I have a feeling these companies found a hole to promote VPN to people via commercials. In all my years of IT support, only corporate people needed VPN to connect to their business networks. I guess “hiding behind a VPN” helps to some degree, but a VPN will not help if you give out your password online, or stop you from clicking on phishing links. Just my two cents on that today.

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