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Microsoft Azure VPN Gateway vs Tailscale comparison

 

Comparison Buyer's Guide

Executive Summary

Review summaries and opinions

We asked business professionals to review the solutions they use. Here are some excerpts of what they said:
 

Categories and Ranking

Microsoft Azure VPN Gateway
Ranking in Enterprise Infrastructure VPN
4th
Average Rating
8.4
Reviews Sentiment
6.4
Number of Reviews
28
Ranking in other categories
No ranking in other categories
Tailscale
Ranking in Enterprise Infrastructure VPN
14th
Average Rating
8.8
Reviews Sentiment
6.1
Number of Reviews
10
Ranking in other categories
ZTNA (5th)
 

Mindshare comparison

As of March 2026, in the Enterprise Infrastructure VPN category, the mindshare of Microsoft Azure VPN Gateway is 4.6%, down from 6.9% compared to the previous year. The mindshare of Tailscale is 4.8%, down from 6.8% compared to the previous year. It is calculated based on PeerSpot user engagement data.
Enterprise Infrastructure VPN Mindshare Distribution
ProductMindshare (%)
Microsoft Azure VPN Gateway4.6%
Tailscale4.8%
Other90.6%
Enterprise Infrastructure VPN
 

Featured Reviews

Srinivas A - PeerSpot reviewer
Director- Head of DevOps, security, and Complaince at Rightdata
Secure data links from on-premise sources have enabled private access to client databases
The best feature of Microsoft Azure VPN Gateway is its sophisticated security mechanism for transmitting data between on-premise to Azure or Azure to Azure. The process of building the VPN gateway is user-friendly, making it easy to configure. Additionally, it supports various options to establish connections between on-premise to Azure or other sources to targets. Using pfSense as a firewall and VPN at our on-premise allows us to establish connections between Microsoft Azure VPN Gateway and our on-premise pfSense VPN easily. This streamlined connection process occurs within a few steps. Microsoft Azure VPN Gateway has positively impacted our organization because it is core to our system and crucial for establishing private connections to our customer's data sources. Their databases lie in a private network with no communication with the outside world. Our customers trust Microsoft Azure VPN Gateway, and by extension, trust us because of this efficient networking establishment process.
reviewer2811270 - PeerSpot reviewer
DevOps Engineer at a consultancy with 1-10 employees
Secure access has simplified hybrid connectivity and has unified multi-cluster workflows
I would say that in terms of Tailscale, if I have so many tailnets I need to connect to, there are some issues in the login process that need a little bit of attention from the Tailscale team. Sometimes, you would probably need to restart your entire system for it to connect. As a DevOps as a Service engineer, I have so many clients that are using Tailscale, and I would need to connect to maybe five different tailnets because they are different clients. Client A might have a Tailscale, Client B, Client C, and so on. When changing between tailnets, sometimes it hangs. Sometimes you might need to restart your entire system. This is a bit of a headache in that aspect. However, I believe if you are just using a particular tailnet, just one, then it is quite easy and there won't be any headache. For me, I think it can be improved in the aspect of having multiple tailnets to connect to. A good refresh on the Tailscale side and the backend side to refresh the connection anytime there is a new connection to be made would be helpful. Instead of needing to restart the system, it should be able to refresh itself. The connection side and connecting to multiple Tailscale instances can be problematic, and sometimes you have to restart your system when switching between them. The ACL sometimes is like another language on its own entirely. It is fine, but they need to make it in a YAML format instead of the current format because it is quite new and something you have to go and study. If they can make it like a YAML format, that would be better. Aside from the switching which I mentioned and the fact that you have to relearn their ACL, if the ACL could be in a YAML format instead of JSON format, that would be beneficial. I don't think there is much they can do about the switching of tailnets, but if they can have a YAML format of the ACL, that would be good. Every other thing is a ten out of ten. The connection-wise is easy to set up and easy to install. It is good to have things connected all together from on-premises, from so many environments, and even exit nodes as well. It is good overall. The pricing, I think Tailscale can be a little bit on the higher side. It is not for teams with just small users. If you want to set it up for small users and a small startup, I don't think you can afford it and might need to go to other open-source alternatives. It is good for teams that have maybe fifty plus users or one hundred users. In terms of pricing, I would say it is on the higher side, but it is worth it. The price is worth the functionality. As a user, I would say it is more on the higher side, but based on its functionality, it is worth the price.

Quotes from Members

We asked business professionals to review the solutions they use. Here are some excerpts of what they said:
 

Pros

"The Azure tool is useful and powerful and availability for clients. The updates are very good and reliable."
"It sends us a lot of detections when we have any anti-virus updates. It provides the extended time needed to update a set of time needs and notifications."
"What I like best about Microsoft Azure VPN Gateway is that it's a managed VPN, so it's one of the most powerful VPNs I've ever found. It also provides point-to-site VPNs configurable within a few minutes."
"The interoperability with various firewall and access gateway vendors is one of this solution's most valuable features"
"Microsoft Azure VPN Gateway has positively impacted our organization because it is core to our system and crucial for establishing private connections to our customer's data sources."
"The most valuable feature is the networking. I didn't have a good experience with the networking that Sophos has."
"It is scalable and depends on your chosen network bandwidth."
"The solution is user-friendly."
"This quick setup with Tailscale has saved me probably days of work that I would have spent learning how to configure traditional VPN solutions, more traditional solutions like WireGuard, where I would have had to learn their entire configuration process and it would have taken days just to set that up."
"Tailscale has positively impacted my organization by making the previously unusable doorbell with the cloud solution fast and reliable for remote access."
"I have been using it every day since June 2025, and it has never given me a problem."
"For my organization, we use Tailscale for our database as a secure way to access our VPC, and it is an easy, lightweight, and very useful way for everyone to connect and disconnect with a very nice UI."
"Tailscale is a very solid framework and is very useful for smaller companies if they want to start out or even bigger companies who want to have a robust network of devices that they want to manage."
"Tailscale has really helped in terms of security because users can be in another part of the world and, instead of them connecting to the company environment through the local network there, they can switch on their Tailscale and once they switch on their Tailscale, they don't have to connect over their internet; they just go through Tailscale to access company infrastructures."
"With Tailscale, I set it up and forget it because it just works, allowing me to avoid worrying about the whole VPN aspect of my home network architecture."
"Tailscale has been helping my organization a lot, primarily for security, as I do not have to open up any port in my router, which is really helpful."
 

Cons

"It isn't stabilized on the first day, and you need to set up the channels properly."
"The product must provide a single sign-on."
"Considering my past interactions with Microsoft's support team, it is difficult to get the right support unless you find the right person to speak with from the customer support team."
"In the next release, Microsoft should add an option to schedule upgrades."
"Regarding pricing for Microsoft Azure VPN Gateway, it could be more cost-effective."
"The monitoring part needs to be improved."
"The solution must provide metrics to monitor the inbound and outbound traffic easily."
"I would like for them to improve the troubleshooting features. We have some problems with traffic and I can't identify where the problem is coming from. I have to open a ticket with support until it gets resolved. Microsoft doesn't offer enough tools to resolve the issue."
"Sometimes you might need to restart your entire system for it to connect."
"I initially got introduced to Tailscale in high school when I needed access to services running on my server, but due to deep packet inspection being in place, I could not use Tailscale."
"However, I think improvements could be made in the support for UI clients, especially on Linux machines."
"One thing I want Tailscale to improve is their user interface for Arch Linux, which is one of the devices I have that I installed Tailscale on, but they do not have the native package with full features, a capability I really want them to develop."
"I think Tailscale can be improved by enhancing the free side of things."
"Currently, if Tailscale goes down, our services are not operable."
"Regarding how Tailscale can be improved, I think for free users, there are some limited options."
"I feel the speed of the control servers are a bit too slow."
 

Pricing and Cost Advice

"There is a monthly license and the price depends on how many users are using Microsoft Azure VPN Gateway. The price could be less expensive."
"It's saved us money compared to getting a third-party appliance."
"Microsoft Azure VPN Gateway is the cheapest way for us to connect to our cloud infrastructure. Other solutions, such as ExpressRoute are very expensive."
"The cost could be lower."
"The software has good pricing compared to other vendors."
"I pay the licensing charges associated with the tool on an hourly basis. The tool is affordable."
"The costs are quite high."
"Payment for licensing the solution is part of the operating model. So, one needs to keep on paying while consuming the solution. In short, the payment is based on the solution's capacity."
Information not available
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Top Industries

By visitors reading reviews
Computer Software Company
11%
Manufacturing Company
9%
Comms Service Provider
8%
Government
8%
Comms Service Provider
16%
Computer Software Company
9%
University
9%
Financial Services Firm
8%
 

Company Size

By reviewers
Large Enterprise
Midsize Enterprise
Small Business
By reviewers
Company SizeCount
Small Business14
Midsize Enterprise2
Large Enterprise14
By reviewers
Company SizeCount
Small Business8
Midsize Enterprise2
Large Enterprise1
 

Questions from the Community

What needs improvement with Microsoft Azure VPN Gateway?
The logging mechanism could use improvement. More detailed logging would help in troubleshooting any failures during connection establishment or monitoring Microsoft Azure VPN Gateway. Otherwise, e...
What advice do you have for others considering Microsoft Azure VPN Gateway?
For those considering using Microsoft Azure VPN Gateway, read the documentation thoroughly. Create an Excel sheet outlining tasks for both the source and target sides, especially when establishing ...
What needs improvement with Tailscale?
Regarding how Tailscale can be improved, I think for free users, there are some limited options. However, we have a paid policy, so we pay Tailscale every month. At some point, we may want to host ...
What is your primary use case for Tailscale?
We have been using Tailscale for about four or five months, and we have been using it from the beginning. For our main use case, we use Tailscale because it creates a peer-to-peer VPN mesh where we...
What advice do you have for others considering Tailscale?
My advice to others looking into using Tailscale is that if there is a use case where you want to secure your private EC2 instances, the workflows, your Git repositories, and sensitive data, Docker...
 

Also Known As

MS Azure VPN Gateway
No data available
 

Overview

 

Sample Customers

Information Not Available
Bamboo Health, Duolingo, Shiguredo, Instacart, Corelight, Machinify, Bolt, Mercari, Cobalt, Yugabyte, Jasper, VersaBank, Zego, Gini and Finter
Find out what your peers are saying about OpenVPN, Fortinet, Check Point Software Technologies and others in Enterprise Infrastructure VPN. Updated: February 2026.
884,873 professionals have used our research since 2012.