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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:
 

ROI

Sentiment score
4.5
Microsoft Azure VPN Gateway offers cost-effective, scalable connectivity, enhancing security and efficiency while simplifying network setup for businesses.
Sentiment score
5.3
Tailscale increases productivity and efficiency by simplifying connectivity, reducing infrastructure needs, and minimizing configuration and troubleshooting efforts.
The solution provides significant cost savings, transitioning expenses from CapEx to OpEx.
Infrastructure Architect at a maritime company with 10,001+ employees
Time savings have notably increased because establishing the connection with Microsoft Azure VPN Gateway was straightforward.
Director- Head of DevOps, security, and Complaince at Rightdata
Previously, networks with FortiGate were used, and that forced us to spend on hardware. With Tailscale, that type of investment is not necessary.
Devops Engineer at Allenta
We have seen clear return on investment since implementing Tailscale by eliminating VPN server infrastructure costs.
System Engineer at a healthcare company with 11-50 employees
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.
Application Security Engineer at a tech vendor with 501-1,000 employees
 

Customer Service

Sentiment score
4.6
Microsoft Azure VPN Gateway support varies; premium praised for quick help, free criticized for delays; documentation gaps impact satisfaction.
Sentiment score
6.3
Tailscale's customer service is praised for responsiveness, but most find platform reliable and rarely need direct assistance.
Prioritization of tasks can also be challenging, impacting the timely resolution of problems.
Infrastructure Architect at a maritime company with 10,001+ employees
In a recent incident, I had an issue with the SharePoint API. It relates to documentation, specifically the lack of up-to-date documentation because Microsoft is moving away from the traditional SharePoint REST API to Microsoft Graph.
Head of Digital Engineering, Management Consultant at Stax Inc.
We received the required support whenever we encountered challenges.
Director- Head of DevOps, security, and Complaince at Rightdata
Tailscale is that reliable, and their documentation answers any questions I have.
Application Security Engineer at a tech vendor with 501-1,000 employees
The user interface, documentation, and support for Tailscale are fabulous.
IT Support / Sysadmin
I would give it a ten out of ten.
DevOps Engineer at CloudKite.io
 

Scalability Issues

Sentiment score
6.1
Microsoft Azure VPN Gateway is scalable and cost-effective, supporting various configurations and user requirements with high availability.
Sentiment score
6.7
Tailscale scales effectively across platforms, handling hundreds of devices, maintaining seamless performance and minimal speed impact without issues.
The process was very efficient to scale the solution, which supports a high level of scalability.
Senior Solutions Architect at EQ2 Technology
It is auto-scalable, and I do not see any issues regarding scalability.
Director- Head of DevOps, security, and Complaince at Rightdata
I would say it is really scalable, and I do not think I have ever experienced any downtime with Tailscale.
Software Engineer at Psycontech
As a free-tier user, I have tested my limits, connecting the maximum amount of devices, and everything performed great.
Application Security Engineer at a tech vendor with 501-1,000 employees
We have over 300 to 400 devices that use Tailscale that we connect with and utilize on a daily basis.
IT Support Engineer at a security firm with 11-50 employees
 

Stability Issues

Sentiment score
7.0
Microsoft Azure VPN Gateway is stable with minimal downtimes, though configuration and CI/CD integration improvements are needed for optimal performance.
Sentiment score
8.3
Tailscale is reliable with minimal downtime, easy setup, and high stability, though iOS updates may cause temporary issues.
Azure VPN Gateway is very stable due to reliance on Microsoft's own network.
Senior Solutions Architect at EQ2 Technology
Tailscale is a SaaS platform, so Tailscale scales it themselves.
DevOps Engineer at CloudKite.io
Tailscale is stable; it has never given me downtime on their side.
Infrastructure Lead & Student Developer (also Head of Ops - FOSSCET) at College of Engineering Trivandrum
For what we use it for—interconnection and networks—it is very stable.
Devops Engineer at Allenta
 

Room For Improvement

Microsoft Azure VPN Gateway needs better troubleshooting, support, threat protection, faster connectivity, easier deployment, affordability, and enhanced documentation.
Tailscale seeks better login processes, enhanced UI, improved network visibility, YAML ACLs, advanced options, and free-user features.
More detailed logging would help in troubleshooting any failures during connection establishment or monitoring Microsoft Azure VPN Gateway.
Director- Head of DevOps, security, and Complaince at Rightdata
The instructions on how to integrate P2N and P2S type networks into Azure VPN Gateway could be improved, though it is a constantly evolving process.
Senior Solutions Architect at EQ2 Technology
Tailscale could be improved with more advanced network visibility and monitoring tools, cleaner pricing tiers for scaling teams, and enhanced built-in reporting for device posture and controls for enterprise environments.
System Engineer at a healthcare company with 11-50 employees
At my apartment, I can do 2-gig networking, but when I connect via the exit node, and I'm wired in somewhere else, and that place also has 2-gig networking, I'm at max getting half of my speed.
Software engineer
I would like Tailscale to provide more censorship-resistant options, such as Shadowsocks or VLESS, as fallback protocols.
IT Support / Sysadmin
 

Setup Cost

Microsoft Azure VPN Gateway is seen as affordable by some, but costs can be high for smaller businesses.
Tailscale offers affordable VPN solutions with predictable costs for enterprises and cost-effectiveness for small teams and startups.
We are paying around $300 per month for a VPN gateway, which seems high.
Director- Head of DevOps, security, and Complaince at Rightdata
The pricing is somewhat high but acceptable, considering it replaces the need for physical network equipment, leading to cost savings.
Infrastructure Architect at a maritime company with 10,001+ employees
The price of Azure VPN Gateway should be rated five from a purely invoice aspect.
Senior Solutions Architect at EQ2 Technology
Tailscale has definitely made it so I don't have to incur additional costs.
Senior Technical Support Specialist at a tech vendor with 10,001+ employees
The setup has been straightforward and predictable with the per-user subscription model and no infrastructure or hardware setup cost, making the initial deployment inexpensive.
System Engineer at a healthcare company with 11-50 employees
I never used a license. I never purchased or bought anything more than the basic free license.
Field Service Engineer at a tech services company with 51-200 employees
 

Valuable Features

Microsoft Azure VPN Gateway excels with high availability, easy configuration, robust security, fast performance, and seamless Microsoft integration.
Tailscale offers quick setup, strong security, and efficient management, featuring access control, cross-platform support, and seamless connectivity.
It simplifies the process of deploying a VPN connection, replacing all the physical network elements with a software appliance.
Infrastructure Architect at a maritime company with 10,001+ employees
The primary function of Azure VPN Gateway allows for designing subnets from existing networks, whether they are physical or virtual networks within Azure or other cloud instances.
Senior Solutions Architect at EQ2 Technology
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.
Director- Head of DevOps, security, and Complaince at Rightdata
The security is valuable, as there are many providers available, but Tailscale fulfills the requirements that we had, allowing us to access and expose internal apps without exposing them to the general internet.
Software Engineer
The most valuable features are the Zero Trust architecture, peer-to-peer connectivity using WireGuard, easy deployment and setup, access control for granular permissions, single sign-on, subnet and routing, exit nodes, and cross-platform support.
System Engineer at a healthcare company with 11-50 employees
Tailscale's security is fabulous, especially the access control features and the ability to use existing OAuth accounts for access.
IT Support / Sysadmin
 

Categories and Ranking

Microsoft Azure VPN Gateway
Ranking in Enterprise Infrastructure VPN
5th
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
4th
Average Rating
8.8
Reviews Sentiment
6.3
Number of Reviews
22
Ranking in other categories
ZTNA (3rd)
 

Mindshare comparison

As of May 2026, in the Enterprise Infrastructure VPN category, the mindshare of Microsoft Azure VPN Gateway is 4.0%, down from 6.7% compared to the previous year. The mindshare of Tailscale is 4.3%, down from 6.7% compared to the previous year. It is calculated based on PeerSpot user engagement data.
Enterprise Infrastructure VPN Mindshare Distribution
ProductMindshare (%)
Tailscale4.3%
Microsoft Azure VPN Gateway4.0%
Other91.7%
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.
Adeniyi Stephen - PeerSpot reviewer
DevOps Engineer at CloudKite.io
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.
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Top Industries

By visitors reading reviews
Computer Software Company
11%
Comms Service Provider
9%
Manufacturing Company
9%
Construction Company
8%
Comms Service Provider
15%
Computer Software Company
10%
Financial Services Firm
9%
University
9%
 

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 Business16
Midsize Enterprise4
Large Enterprise4
 

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?
Tailscale could be improved in different ways. I have not really found any problem with it so far. It pretty much solved the problems of other VPN clients that we have been trying. If Tailscale pro...
What is your primary use case for Tailscale?
My main use case for Tailscale is connecting to company internal systems due to GDPR requirements. The company is located in Germany with private servers in Germany, and I stay in the UK, so I use ...
What advice do you have for others considering Tailscale?
My advice to others looking into using Tailscale is to definitely try it out because it is going to really abstract away a lot of network problems, especially when it comes to private networks, pri...
 

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 Microsoft Azure VPN Gateway vs. Tailscale and other solutions. Updated: April 2026.
893,244 professionals have used our research since 2012.