- Microsoft Outlook is one of the most popular email clients in the world. However, several users have complained that it won't work over a VPN connection.
- If you're also experiencing VPN connectivity issues on Outlook, check out our simple guide below to troubleshoot this problem.
- Join our Outlook Troubleshooting Hub for more similar quick-fix guides.
- Visit our VPN section to learn everything about VPN services.

Microsoft Outlook is one of the most popular email clients worldwide.
Some of its users also turn to VPN services to secure their connections, bypass government censorship, and access blocked websites.
Unfortunately, many Outlook users have server connection issues right after establishing the VPN connection.
As a result, it’s impossible to use Microsoft’s email client to check the inbox, compose new messages, forward emails – anything that requires an Internet connection.
We’re showing you exactly what to do if Outlook won’t connect over VPN.
Check out our step-by-step guide below to troubleshoot this problem, whether you have PC experience or not.
BEST VPNS WE RECOMMENDHow can I make Outlook connect over VPN?
1. Update and restart Microsoft Outlook

Make sure you’re running the latest version of Microsoft Outlook. It could help resolve various compatibility issues with software, including VPNs.
You should be able to enable updates from your Office account after opening the main menu in Microsoft Outlook.
2. Check your Internet connection

If your Internet connection isn’t stable enough, it could be the reason why Outlook won’t connect over a VPN.
Perhaps there’s a problem with your router or your laptop’s Wi-Fi is too slow. To quickly test this, you can restart your router or switch to wired mode.
It’s also a good idea to run an Internet speed test in two parts: while staying connected to the VPN and without an active VPN connection.
3. Use a reliable VPN service
If you’re interested in a VPN service to secure your Internet connection, protect your online privacy, and unblock websites, then you need a reliable product like Private Internet Access.
PIA supports modern and secure protocols that create secure tunnels without sacrificing your connection speed: OpenVPN and WireGuard.
Plus, you can set up PIA on all popular platforms: Windows, Android, Linux, iOS, and Mac. It allows up to 10 simultaneous device connections.
It means that you can use Outlook over PIA on all your devices. And, if you ever stumble upon any problems, you can quickly get in touch with the support team through 24/7 live chat.
4. Add an exception to the Windows Firewall

If you follow these steps, you will fix firewall issues with VPN traffic. If Outlook connects over your VPN now, it means there was never a problem on the email client’s side, but with your firewall.
And, if you’re using a third-party firewall, make sure to adapt the instructions we provided for Windows Defender above.
A premium VPN service like Private Internet Access shouldn’t get blocked by your firewall because it automatically creates an exception for itself when you install it.
5. Disable the wireless network adapter

If you’re connected to the Internet in both Wi-Fi and Ethernet mode, it could result in conflict that causes the VPN connection error on Microsoft Outlook.
To easily fix this problem, simply deactivate your Wi-Fi connection and stick to wired mode.
It also indicates that you have Wi-Fi connectivity issues, which you should troubleshoot as soon as possible to continue using wireless mode.
6. Change your DNS settings

If your default DNS servers take too long to load pages, this could also cause VPN connection issues over Microsoft Outlook.
But you can solve this problem by changing the DNS servers. The servers we listed above are free, public, and belong to Google Public DNS. You can also try Cloudflare or OpenDNS.
However, if you have a reliable VPN service like Private Internet Access installed, you don’t have to worry about this issue.

PIA runs its private DNS servers to protect your DNS queries and speed up your Internet connection as soon as you connect to a VPN server.
7. Reset the network settings

ipconfig /flushdns ipconfig /registerdns ipconfig /release ipconfig /renew NETSH winsock reset catalog NETSH int ipv4 reset reset.log NETSH int ipv6 reset reset.log exit
Restart your computer to finish the modifications.
You can easily reset network connectivity settings on your Windows computer by flushing DNS servers and resetting Winsock.
A lot of VPN connection problems can be fixed this way.
8. Allow VPN traffic on your router or set up port forwarding
If your router doesn’t allow VPN traffic, you wouldn’t be able to connect to a remote VPN server or accept VPN connections. It doesn’t matter if you’re trying to use Microsoft Outlook or any other tool.
In this case, you must access your router’s admin panel, look for a NAT Passthrough option, and enable it for your VPN protocol. Out-of-the-box router firmware typically supports PPTP and L2TP.
If you intend to use a VPN protocol that’s not supported by your router’s firmware (like OpenVPN), here’s what you can do:
- Set up port forwarding at the router level* (not safe). But it only works with VPN server mode.
- Check if your router allows you to install third-party firmware. If so, you can set up DD-WRT, Tomato or OpenWRT (requires advanced skills). They support VPN client mode.
- If your router doesn’t support third-party firmware, you can purchase a router with VPN client capability and then set up bridge mode to avoid Double NAT.
*Private Internet Access is one of the few VPNs we know that support native port forwarding mode.

Instead of configuring router settings and risk messing up its functionality, you can just request port forwarding within the app.
Conclusion
To conclude, you can fix VPN connectivity issues with Office by updating and restarting MS Outlook, checking your Internet connection, and adding an exception to the Windows Firewall.
You can also disable the Wi-Fi network adapter, change your DNS servers, reset network settings, and allow VPN traffic on your router or set up port forwarding.
But one of the best ways to stay secure while using Microsoft Outlook is by turning to a reliable VPN service like Private Internet Access.
Your connection is not secure - websites you visit can find out your details:
- Your IP Address:
Companies can sell this information, alongside your location and internet provider name, and profit from it by serving targeted ads or monitoring your data usage.
We recommend Private Internet Access, a VPN with a no-log policy, open source code, ad blocking and much more; now 79% off.
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