Microsoft has stated that it doesn’t “officially” support Outlook connections via a VPN.
This means that if Outlook isn’t working with your VPN, Microsoft doesn’t hold itself accountable for fixing the issues.
Fortunately, there are a number of fixes you can try to resolve Outlook not working with VPN.
This article will explain how you can perform these fixes and prevent issues you’re having with Outlook not working with VPN from occurring again in the future.
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Outlook not working with VPN: Fixes
Try these fixes in order. If one doesn’t work, move on to the next until you’ve fixed Outlook not working with VPN.
Ensure your internet connection is functioning correctly
A good place to start when Outlook not working with VPN is to check your internet connection with the VPN turned off.
Turn your VPN off and test your internet connection here.
If you’re experiencing slower than usual internet speeds, the issues arising with Outlook might have nothing to do with your VPN.
If you don’t think your internet is functioning correctly, contact your internet service provider, and they’ll inform you how you can fix it.
Make sure Outlook has been updated to the latest version.
Often Microsoft will release updates that contain hotfixes for common problems.
These hotfixes might contain fixes for VPN’s not working with Outlook.
To ensure you have installed all of Microsoft’s hotfixes, update Outlook to its latest version.
Change protocol on your VPN
VPNs are often compatible with different protocols.
These protocols are a set of rules that the VPN abides by. Some protocols prioritise security, and some prioritise speed.
Outlook not working with your VPN might be occurring because the protocol your VPN is using either isn’t fast enough to work with Outlook’s servers, or the security is too stringent, and Outlook is inadvertently being blocked.
Try changing between the protocols on your VPN and see if that fixes Outlook not working with VPN.
Upgrade to a VPN proven to work with Outlook
If the above fixes don’t resolve Outlook not working with VPN, unfortunately, your VPN isn’t good enough to comply with Outlook’s servers.
Because Microsoft has stated that Outlook doesn’t “officially” support VPN connections, so your VPN needs to make itself compatible with the email service constantly.
This requires a significant amount of infrastructure as the VPN needs to be on top of the changes Microsoft implements, and it needs to have the financial backing to update itself to ensure its consistently compatible with Outlook.
To fix Outlook not working with VPN, you need to upgrade to a better VPN.
It also has a split-tunnelling feature (more on this below) that will guarantee Outlook will work when you have your VPN turned on.
Why doesn’t Outlook work with my VPN?
Outlook isn’t working with your VPN because of security measures it has to ensure your email account doesn’t get hacked.
When you connect to a VPN, your IP address changes, and when this happens it looks like you’re connecting to the Outlook servers from a different location. For example if you live in Australia and you connect to a US server on your VPN, it looks like you’re connecting to Outlook from the US.
When this happens, Outlook’s security measures kick in as it thinks someone in the US has hacked your account.
These security measures will freeze your email address so it cannot be accessed. Even though it’s your Outlook account, you won’t be able to access it until you log in again.
Constantly turning your VPN on and off will repeatedly result in Outlook thinking you’ve been hacked and Outlook won’t work with your VPN.
Does Outlook block VPNs?
Although Microsoft has said Outlook doesn’t support VPN connections, it doesn’t attempt to block VPNs.
When your VPN stops working with Outlook, it isn’t being blocked by Microsoft. It’s simply a security measure initiating to ensure you’re not being hacked.
Unfortunately, there’s no way to change this security measure. The only thing you can do is upgrade to a VPN that has features in place to ensure it works with Outlook.
Which VPNs work with Outlook?
The best VPN for Outlook is ExpressVPN ($6.67/month). There are two reasons why it’s the best VPN for Outlook.
The first is ExpressVPN ($6.67/month) is a VPN that’s constantly being updated and upgraded to ensure it works with Outlook. ExpressVPN ($6.67/month) uses its own protocol, Lightway, that’s fast, lightweight and secure.
ExpressVPN ($6.67/month) can constantly update its protocol to ensure its functioning with familiar apps and streaming services, like Outlook.
The second reason ExpressVPN ($6.67/month) is the best VPN for Outlook is because of its split-tunnelling feature. Split-tunnelling allows you to select what apps or programs you want the VPN to affect. You can use the split-tunnelling feature if you don’t want the IP changes that occur when you use your VPN to affect Outlook.
When using a VPN to watch Netflix, I inadvertently had problems with Outlook as my emails would be frozen, requiring me to log in to all of my email addresses again.
This got frustrating quickly as it happened every time I wanted to watch Netflix. Using ExpressVPN ($6.67/month) split-tunnelling feature, I made it so the VPN wouldn’t affect Outlook, and I never had issues with Outlook again.
The best VPNs for Outlook
The fastest and MOST reliable VPN of 2022Number of servers: 3,000+ | Speed: >80% | Bandwidth: Unlimited | IP locations: 160 in 94 countries | Devices supported: 5 | Live chat: Yes | 30-day money-back guarantee: Yes ExpressVPN is still the best VPN. And importantly, it ALWAYS has servers that are open with major streaming sites such as Netflix, Hulu, Disney+, HBO Max, Amazon Prime Video etc. ExpressVPN is usually very good at playing Cat and Mouse with online streaming sites (apart from BBC iPlayer). Meaning, whenever one of its servers is blacklisted it creates a new one – giving its users a constant stream of servers that aren’t blocked. Needless to say, this is a valuable attribute if you’re looking for a VPN to unblock streaming sites. Its app is easy-to-use and free to download on pretty much any device you can think of. Mac, Windows, iOS, Android, FireStick, Android TV, Roku, PS4, Xbox, Linux, even Apple TV (with a workaround). It’s got it all covered. The app is another main reason this VPN is so good at unblocking TV streaming sites (that claim they block VPNs) is that its software takes a pragmatic approach to user management. While other VPNs tempt customers by promising them access to hundreds/thousands of servers in multiple countries, ExpressVPN does things differently. With ExpressVPN you only have a handful of server locations to choose from. Once you select your location the app takes care of the rest. Assigning you to the fastest available server that’s not oversubscribed. This simple technique is so important, as it keeps ExpressVPN’s servers operating at lightning-fast speeds and prevent its IPs from getting blacklisted for “abnormal” usage in the first place.
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A very quick and trustworthy VPNNumber of servers: 5,000+ | Speeds: >80% | Bandwidth: Unlimited | IP locations: 62 countries | Devices supported: 6 | Live chat: Yes | 30-day money-back guarantee: Yes NordVPN is the most widely-used VPN in the world. And it’s easy to see why. It’s a polished app that delivers fast connections (more on this later) to a massive network of VPN servers. It’s the most reliable at unblocking popular streaming services too – US Netflix, Hulu, Disney+, BBC iPlayer, HBO Max, Amazon Prime Video, etc. This is because NordVPN hired a full-time technical team (that’s responsible for monitoring its servers’ connections with popular TV streaming services) and has been aggressively investing in its network of IP addresses in key locations. Another interesting thing to note is that NordVPN is an industry leader in its development of Nordlynx technology. Nordlynx is built using the WireGuard, a new VPN tunneling protocol designed to outperform current standards (OpenVPN and IPSec). The benefits, according to NordVPN, are dramatically faster transfer speeds while connected to a VPN. My tests – New Zealand to London – confirm that Nordlynx is currently the fastest VPN on the market. However, the difference isn’t dramatic, a few Mbps is all.
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The great budget VPN optionNumber of servers: 1,000+ | Speed: >65% | Bandwidth: Unlimited | IP locations: 275 in 100 countries | Devices supported: 5 | Live chat: Yes | 30-day money-back guarantee: Yes If you’re looking for an excellent VPN, with an even better price tag, Ivacy ($1.16/month) is a great option. This VPN has all the features you need to stream BBC iPlayer, in HD, from any country in the world. I’ve been testing the app recently on Mac, PC, Android, iOS and FireStick and the results have been impressive – unlocking BBC iPlayer, US Netflix, Hulu, Disney+, HBO Max, Amazon Prime Video, etc. with ease. The Ivacy app is a little different in regards to its UX (user experience). Instead of just selecting a UK server, you need to select the specific BBC iPlayer server. Don’t worry, this isn’t a bad thing – by connecting to a dedicated BBC iPlayer server, it simply means that you’re connecting to an IP address that Ivacy knows works with BBC iPlayer. For an extra $1.99/month (£1.74) you can add-on a dedicated IP. This will buy you sole access to an IP address in a country of your choice, meaning you won’t have to share your IP (and speeds) with any other use. I don’t recommend this though, using the regular Ivacy servers is enough 95 per cent of the time.
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5. CyberGhostNumber of servers: 6,000+ | Speeds: >65% | Bandwidth: Unlimited | IP locations: 200 in 90 countries | Devices supported: 7 | Live chat: Yes | 30-day money-back guarantee: Yes CyberGhost is one of the more established VPNs on the market. It has a well-established, and well-tested global network of servers that perform well. From my tests over the past several months, CyberGhost has no trouble at unblocking major streaming services – US Netflix, BBC iPlayer, Hulu, Disney+, Amazon Prime Video, HBO Max etc. This VPN performed well at maintaining download speeds, well above 65 per cent of my regular (non VPN) ISP speed. That said, there’s nothing really unique about the service. Which forces you to look at its price-point. And there’s nothing special here. Its short-term $12.99/month price tag puts is well above the industry average of $10.10/month. Similarly, its long-term $2.75/month for 3 years deal isn’t much of a “deal” either. Oddly, CyberGhost’s most unique feature is its a 1-day, no obligations, free trial. This is an appealing offer to customers who are new to VPNs. However, it’s important to remember that most reputable VPNs will offer customers a 30-day money-back guarantee, so try not to be too seduced by the offer.
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