FIX: Outlook won’t connect over VPN (8 tested solutions)

Elena Constantinescu
by Elena Constantinescu
VPN Expert & Privacy Advocate
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  • 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.
fix Outlook wont connect VPN
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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.

How can I make Outlook connect over VPN?

Update and restart Microsoft Outlook

enable Microsoft Outlook update
  1. Disable the VPN connection
  2. Update Outlook to the latest version
  3. Exit Outlook
  4. Connect to a VPN server
  5. Launch 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.

Check your Internet connection

Netflix has encountered an error

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.

Use a reliable VPN service

PIA

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.

More about PIA:

  • Split tunneling and kill switch to maintain your anonymity
  • Exclusive DNS servers to speed up your Internet connection
  • A zero-logging privacy policy
  • 30-day money-back guarantee
  • No free trial
Private Internet Access

Private Internet Access

Use this reliable VPN to connect to a secure tunnel over Microsoft Outlook and other software applications.
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Add an exception to the Windows Firewall

  1. Press the Start button, type firewall, and select Firewall & network protection
  2. Click Allow an app through firewall
  3. Click Change settings (you need admin rights)
  4. Find your VPN service on this list
  5. Enable the Private and Public options for its entry
  6. If your VPN isn’t here, click Allow another app to locate it

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 (buy here) shouldn’t get blocked by your firewall because it automatically creates an exception for itself when you install it.

Disable the wireless network adapter

disable Wi-Fi in Windows
  1. Go to Control Panel
  2. Select Network and Internet
  3. Go to Network and Sharing Center
  4. Click Change adapter settings
  5. Right-click your Wi-Fi connection and Disable
  6. Connect to the Internet in Ethernet mode

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.

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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.

Change your DNS settings

A padding to disable MSIE & Chrome friendly error page
  1. Go to Network Connections > Change adapter options
  2. Right-click your Internet connection and select Properties
  3. Double-click Internet Protocol Version 6 (TCP/IPv6)
  4. Select Use the following DNS server addresses
  5. Set Preferred DNS server to 8.8.8.8
  6. Set Alternate DNS server to 8.8.4.4
  7. Click OK

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 (buy here), you don’t have to worry about this issue.

use PIA DNS

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.

Reset the network settings

flush DNS servers in Windows 10
  1. Run Command Prompt with elevated rights: press Ctrl + R, type cmd, hold Ctrl + Shift and press Enter
  2. Copy and paste the next lines (press Enter between each line)
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.

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 (buy here) is one of the few VPNs we know that support native port forwarding mode.

Private Internet Access port forwarding

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, changing 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 (buy here).

FAQ: Learn more about Outlook

  • How do I fix Outlook connectivity problems?

To fix Outlook connection errors, you can disable the AppData directory redirection, create a new Outlook profile, repair Office programs, and try other possible solutions.

  • How do I fix error 0x8004011d in Outlook?

To repair Outlook error 0x8004011d, flush your DNS servers, verify add-in issues, repair the Outlook installation package, and so on,

  • What is the most anonymous email?

ProtonMail is one of the best anonymous email clients.

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