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Jamf Connect vs Tailscale comparison

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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

iboss
Sponsored
Average Rating
8.4
Reviews Sentiment
6.9
Number of Reviews
24
Ranking in other categories
Secure Web Gateways (SWG) (6th), Internet Security (3rd), Web Content Filtering (1st), Cloud Access Security Brokers (CASB) (6th), ZTNA as a Service (6th), Secure Access Service Edge (SASE) (7th)
Jamf Connect
Average Rating
9.0
Reviews Sentiment
6.1
Number of Reviews
18
Ranking in other categories
ZTNA as a Service (12th), AI Customer Experience Personalization (14th)
Tailscale
Average Rating
8.8
Reviews Sentiment
6.3
Number of Reviews
28
Ranking in other categories
Enterprise Infrastructure VPN (2nd), ZTNA (2nd)
 

Featured Reviews

Ashok Ananthula - PeerSpot reviewer
Senior Consultant Proxy Engineering at a financial services firm with 10,001+ employees
Cloud gateway has strengthened remote web security and now needs better Mac and ISP support
The problem our organization had is that iboss failed for the Mac devices. It is not able to give a successful agent for the Mac agents. That is where in 2025, we had to migrate to the Palo Alto-based platform. If your use case is for just Windows laptops,you can consider this platform as an option One issue is the data center resiliency part. In India especially, they are not tied up with the Tier 1 ISPs like Tata or Airtel; they were having Tier 2 ISPs and encountered many issues reaching few major sites that my organization depends on, and they were having problems that they could not fix quickly. They also lack a mechanism to route that traffic within their data center; rather, they ask customers to make a pac file change to route it to Singapore explicitly. It would be better if they route from their backend , i mean even if I send it to India DC, they should be able to route it internally to make that work; however, they fail to do that and ask the customer to route it in the pac file. Another suggestion is that in China, they do not have the proper setup; they used to have numerous problems with slowness and lack of premium circuits in China as well. That leads to multiple sites working slowly with latency-related issues. So the main issue is the ISP-related problems that need to be solved.
Robert Ojok - PeerSpot reviewer
Systems Engineer Iii Apple Devices (Jamf Engineering) at a retailer with 10,001+ employees
Unified sign-on has simplified password management and now secures our mobile workforce
The ability to have a single password for the local device and the same password for the IDP is part of our security requirements. Jamf Connect integrates with multi-factor authentication from any IDP and facilitates initial device enrollment. It ensures that when a new user sets up the device, they sign in with their IDP username and password, which then creates the profile on the device. Furthermore, Jamf Connect is now integrated into Jamf Self Service Plus, providing a single dashboard for user password management and allowing users to sync and change their passwords. Additionally, Jamf Connect enhances security by offering two-factor authentication and permitting users to manage or seek help through support features directly within the app.
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.

Quotes from Members

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

Pros

"Content filtering is the most useful feature of iboss."
"First of all, the security policies are essential. I do not have to rely solely on Active Directory for our users."
"From a use-case scenario, what I like the most is the plug-in. I like the fact that we can do the filtering of these devices offsite independent of the network they are connected to, and we do not have to have traffic coming back inside our network."
"It was a very easy product to install. It can be deployed very fast."
"From a corporate perspective, I understand that it's important to keep the company data safe."
"The console is cloud-based, which is something I really appreciate."
"iboss is among the few products providing inline filtering where no application is needed on the device. It operates on the network side and is not device-based. This feature was one of the main reasons why we stayed with them for so long."
"Because of iboss, I did not have to assign web filtering tasks to my techs on a daily basis."
"I would rate the product's scalability an eight out of ten."
"The tool supports different types of authentication. It also integrates seamlessly if you are using other Jamf products."
"It's connection with Azure is the most valuable. It is easy to deploy and connect."
"Jamf Connect is an identity provider, and once you log in, you will have all the device's access."
"It has definitely reduced the IT support burden, as 31% of Mac tickets are password-related, costing an average of 70 or 80 dollars for just one ticket, and that has been drastically reduced with the automation of these tasks through Jamf Connect."
"The most valuable feature of Jamf Connect is the dual login screen, which has simplified the login process and eliminated the need for users to enter their password multiple times."
"The most valuable feature is ease of access. It's convenient to do things like resetting passwords. Previously, users were bound to their domain. We had to bind the user to the domain and log them in through the AD. Now, using Jamf Connect, we don't face any of these challenges. Resetting passwords is hassle-free so we can regularly rotate passwords according to best practices."
"It is easy to integrate into any existing IT workflow."
"Tailscale has positively impacted my organization by making the previously unusable doorbell with the cloud solution fast and reliable for remote access."
"The best features Tailscale offers for me are how easily we can connect to different clusters and different systems."
"Tailscale definitely saves me a lot of time securing our server because I can just install Tailscale, close many ports, and then share them with my teammates while benefiting from its very generous free tier."
"I have been using it every day since June 2025, and it has never given me a problem."
"The biggest benefit of Tailscale is simplicity; it is quick to set up and provides a stable and secure connection."
"There is no better option than this."
"In my job, Tailscale has reduced the amount of work and headache of having a VPN between servers and cloud, so instead of following a longer and complex process of having a site-to-site VPN and a device with a fixed public IP to connect with the cloud and other spots in Morocco, especially in Tangier, Tailscale simplifies all of that."
"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."
 

Cons

"If they could implement an extra security layer preventing access to iboss from the open internet, it would be great."
"Fold that in with the risk intelligence they're getting from all of the different subscriptions they are a part of. Now, these security companies subscribe to things like emerging threats, databases, etc. You can fold all this intelligence to decide what's happening on an endpoint. I would love to see them start moving into that space. That would compete directly with Microsoft. Maybe that's why they haven't. Having that ability native within the solution would be great. The other area in which I would love to see improvement is more detailed descriptions of why they block websites."
"The reporting feature needs improvement."
"One thing I would like to see differently with their Zero Trust platform is that some of the AI aspects related to high-risk activities have more false positives."
"File integrity monitoring would be very advantageous as an additional feature."
"Sometimes the agent stops working in iboss, and we have to reinstall the agent."
"I'd like to see them accelerate development on the security side, particularly around data loss prevention."
"The dashboards for local use could be better."
"The configuration could be faster."
"What can be improved is the login banner resizing. Currently, it is not fully compatible and could benefit from being a full-screen size banner on the Mac device."
"When a Mac is joined to Azure, the generic Pro console in the MDM should accurately display the Mac as joined to Azure in the inventory section. Currently, it shows "no domain account found," which can be misleading."
"Overall, there is a lack of consistent experience sometimes with some of their features."
"Jamf Connect is beginning to implement Multi-Factor Authentication for offline authentication, but the setup documentation is insufficient."
"User training has room for improvement. This improvement would benefit from more documentation, and I would appreciate seeing more automation pieces as well."
"We have faced issues with the product's configuration. If we use the tool with other business manager solutions, then there is the issue of naming conventions. The tool needs to be careful with newer updates so that it doesn't break any of the existing configurations."
"One area of Jamf Connect that I think could be improved is the recent merger with Self Service Plus, which is a solution we did not want."
"Currently, if Tailscale goes down, our services are not operable."
"I feel the speed of the control servers are a bit too slow."
"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."
"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 am currently facing an issue where on my Mac, Tailscale does not allow me to log in to multiple accounts."
"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."
"The only improvement I see for Tailscale is that I would love to check out Headscale to fully host it on my own infrastructure."
"I think Tailscale can be improved by enhancing the free side of things."
 

Pricing and Cost Advice

"The overall pricing for iboss is very competitive and transparent."
"It is expensive compared to one of its competitors."
"It is not expensive, and it is also not cheap. iboss is priced right in the sweet spot for the number of features it offers."
"It is probably in line with other solutions, but I do not deal with the financial side."
"We have not priced the solution recently, but they were competitive with other vendors in the past."
"We had the cost of purchasing a new appliance along with the implementation and licensing costs. However, the following year, the cost of just licensing was similar to what was paid the previous year for a new appliance along with the implementation and licensing costs."
"It's relatively inexpensive."
"Jamf Connect has a yearly licensing cost, which is expensive."
"I rate the cost as three out of ten, with ten being the highest."
"The pricing model could be improved, especially considering the availability of alternative MDM solutions like Kandji, which offers similar features for free or at a lower cost."
"The solution's price is reasonable."
"We pay 2 dollars per device monthly. For the plus version, you have to pay 4 dollars per month. I think the product will give discounts based on the number of users and devices."
"The pricing is good."
"The pricing is definitely on the higher side."
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Top Industries

By visitors reading reviews
Financial Services Firm
11%
Manufacturing Company
10%
Comms Service Provider
8%
Construction Company
7%
Financial Services Firm
15%
Construction Company
10%
Comms Service Provider
9%
Outsourcing Company
8%
Comms Service Provider
15%
University
9%
Financial Services Firm
8%
Outsourcing Company
8%
 

Company Size

By reviewers
Large Enterprise
Midsize Enterprise
Small Business
By reviewers
Company SizeCount
Small Business13
Midsize Enterprise7
Large Enterprise11
By reviewers
Company SizeCount
Small Business5
Midsize Enterprise3
Large Enterprise12
By reviewers
Company SizeCount
Small Business19
Midsize Enterprise5
Large Enterprise4
 

Questions from the Community

What needs improvement with iboss?
I think iboss could be improved by making reporting and dashboard customization more flexible, and simplifying troubl...
What is your primary use case for iboss?
I use iboss as a cloud-based secure web gateway to provide secure internet access, web filtering, and protect remote ...
What is your experience regarding pricing and costs for iboss?
My experience with iboss's pricing structure, setup cost, and licensing model has been positive, straightforward, and...
What needs improvement with Jamf Connect?
Jamf Connect is pretty good software and well developed. I just wish it would also be available for Windows, but I am...
What is your primary use case for Jamf Connect?
Jamf Connect is used for logging in from the Mac to our Okta, or connecting to my organization network, which helps M...
What needs improvement with Tailscale?
I have a pretty basic use of Tailscale. I do not deploy it for a big organization, so I am generally happy with the p...
What is your primary use case for Tailscale?
My main use case for Tailscale is to access my home network remotely. In my home network, I have deployed a wide rang...
What advice do you have for others considering Tailscale?
I rate Tailscale overall a ten out of ten. I chose ten out of ten because the ease of installation, access to documen...
 

Comparisons

 

Also Known As

iBoss Cloud Platform
Wandera, Wandera Private Access
No data available
 

Overview

 

Sample Customers

Trusted by global enterprises and government agencies.
Mastercard, Deloitte, PayPal, Toshiba, BNP Paribas, EY, Otis, Rollins, Eurostar, Frontier, Sealy, Rolex, VITAS Healthcare
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Find out what your peers are saying about Zscaler, Cisco, Okta and others in ZTNA as a Service. Updated: September 2026.
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