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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
22
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 (7th), 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 (18th)
Tailscale
Average Rating
8.8
Reviews Sentiment
6.4
Number of Reviews
26
Ranking in other categories
Enterprise Infrastructure VPN (3rd), 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

"iboss is pretty scalable. They provide good support. The case managers you work with to coordinate what you need are pretty good."
"Technical support is pretty sharp and very responsive."
"This product is solid, fairly easy to use, and reliable."
"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."
"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."
"Content filtering is the most useful feature of iboss."
"We chose iboss for both zero trust and proxy (SWG) because their SWG was superior."
"The iboss solution gives me the ability to scan the traffic through all the ports, through all the 131,000 PCP and UDP ports, and with this ability, we have the granularity also for consults over social media and applications on mobile, and this is an advantage that the customers are looking for right now."
"Jamf Connect is a pretty simple and straightforward tool overall."
"The most valuable feature is the synchronization of passwords with a local password, which works well."
"It is easy to integrate into any existing IT workflow."
"Jamf Connect has quite a nice interface, and the password synchronization and SSO elements are particularly good."
"Jamf Connect is very simple for us to use, and it is oriented towards productivity."
"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."
"For those kinds of users, it is an awesome solution because it syncs their password across the devices they are using, which was not the case previously."
"Tailscale has positively impacted my organization and consulting work by making remote connections easy, significantly reducing the friction and making this very reliable, even behind difficult networks with CGNAT or other situations that make establishing connections difficult using other means."
"Tailscale has positively impacted my organization by allowing us to speed up development without worrying about GDPR restrictions."
"The best features Tailscale offers are the ease of use and the security it provides for data in transition."
"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."
"Tailscale has positively impacted my organization by making the previously unusable doorbell with the cloud solution fast and reliable for remote access."
"Tailscale has positively impacted my organization with shorter time for setting up connections and improved accessibility."
"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."
"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."
 

Cons

"For zero trust implementation, we encountered complexity issues, especially with a large infrastructure company ExxonMobil."
"I have heard they are doing DDoS filtering, but I am not certain if they are implementing it correctly."
"Its pricing could be better."
"The dashboards for local use could be better."
"Sometimes, obviously, there are bugs."
"Sometimes the agent stops working in iboss, and we have to reinstall the agent."
"The endpoint-type solution is an area that needs some improvement."
"The area I would like to see improvement in is the ability with in the reporter to navigate directly to the content the user is traversing. It is kind of there, but it's not perfect. Quite frequently, I receive links that lead me to pages with error messages."
"We've had some issues when users restart their devices because the device asks for credentials afterward. Jamf Connect asks for a username, password, and MFA."
"However, there is a concern about pricing because Jamf Connect is a separate application that requires additional payment."
"The main use case for Jamf Connect was to synchronize local accounts with the identity provider, like Entra. However, due to some limitations with the enrollment sequence and user limitations, we decided to discontinue using it."
"The solution needs to improve its licensing."
"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."
"I see a potential area of improvement for Jamf Connect from the commercial side, not from the technical side, because technically we do not have any issues."
"The logs are an area with a shortcoming."
"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."
"The only improvement I see for Tailscale is that I would love to check out Headscale to fully host it on my own infrastructure."
"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."
"However, I think improvements could be made in the support for UI clients, especially on Linux machines."
"Regarding how Tailscale can be improved, I think for free users, there are some limited options."
"I am currently testing the ability to expose to the WAN certain services that we select, which is in beta. I imagine it is still in development, but from the tests we have done, the connection outward is quite slow, which is a point of curiosity, and I hope that aspect can be improved."
"I choose a seven because it sells what it does honestly, but I believe some more flexibility might be needed."
"I feel the speed of the control servers are a bit too slow."
 

Pricing and Cost Advice

"We have not priced the solution recently, but they were competitive with other vendors in the past."
"The overall pricing for iboss is very competitive and transparent."
"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 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 expensive compared to one of its competitors."
"It is probably in line with other solutions, but I do not deal with the financial side."
"I rate the cost as three out of ten, with ten being the highest."
"The pricing is good."
"The solution's price is reasonable."
"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."
"It's relatively inexpensive."
"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 definitely on the higher side."
"Jamf Connect has a yearly licensing cost, which is expensive."
Information not available
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Top Industries

By visitors reading reviews
Financial Services Firm
11%
Manufacturing Company
9%
Computer Software Company
8%
Construction Company
7%
Financial Services Firm
15%
Construction Company
10%
Computer Software Company
10%
Manufacturing Company
7%
Comms Service Provider
14%
University
10%
Financial Services Firm
9%
Computer Software Company
8%
 

Company Size

By reviewers
Large Enterprise
Midsize Enterprise
Small Business
By reviewers
Company SizeCount
Small Business7
Midsize Enterprise7
Large Enterprise9
By reviewers
Company SizeCount
Small Business5
Midsize Enterprise3
Large Enterprise12
By reviewers
Company SizeCount
Small Business16
Midsize Enterprise4
Large Enterprise4
 

Questions from the Community

What needs improvement with iboss?
The problem our organization had is that iboss failed for the Mac devices. It is not able to give a successful agent ...
What is your primary use case for iboss?
We used iBoss mainly for Internet Access by having an Agent on Windows laptops Primarily because when we try to use i...
What is your experience regarding pricing and costs for iboss?
I am not involved in pricing, but as per the information I have, during that time, the Blue Coat proxies we were usin...
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 would love to see two specific improvements brought to the Tailscale Android client, both of which are standard in ...
What is your primary use case for Tailscale?
I use Tailscale to connect to my home server for various tasks, such as checking its status and streaming movies or s...
What advice do you have for others considering Tailscale?
I am currently utilizing Tailscale's free tier, and it has performed flawlessly. For any individual, hobbyist, or sma...
 

Also Known As

iBoss Cloud Platform
Wandera, Wandera Private Access
No data available
 

Overview

 

Sample Customers

More than 4,000 global enterprises trust the iboss Cloud Platform to support their modern workforces, including a large number of Fortune 50 companies.
Mastercard, Deloitte, PayPal, Toshiba, BNP Paribas, EY, Otis, Rollins, Eurostar, Frontier, Sealy, Rolex, VITAS Healthcare
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 Zscaler, Cisco, Okta and others in ZTNA as a Service. Updated: June 2026.
902,894 professionals have used our research since 2012.