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Migrating from On-prem Proxies to the Cloud

Sep 01 2020

Recently, a Fortune 500 customer asked us to migrate 5 million lines of URL policies into our cloud solution. This configuration included frequently used websites like,, and as well as hundreds of other URLs and domains that were no longer reachable or registered anymore. 

Our first question to the customer was, “Help us understand why you would want to do that?”, in the context of migrating their entire configuration. The reality is that enterprises are not always aware of the latest capabilities of technology, especially when it comes to a fast-paced environment like cloud. After all, you are running a business, not building computer security systems. 

Chances are you still have a massive stack of security equipment in your HQ, data centers, and branch offices. Have you paused to ask yourself why? Our internal research has shown large enterprises use and support security equipment from an average of 35 different vendors across the Global 2000. Taking into consideration that the majority of your workforce is now remote (and will be for a while to come), have you wondered why you are still maintaining a legacy VPN technology that backhauls traffic to your offices and consumes additional bandwidth? In your security stack, there is a high probability that you have one or many proxy servers, in some cases, this is the only way to the internet for your employees. Is this architecture still relevant for your business today? Or, are you trying to fit legacy technology into a cloud world? 

In today’s organizations, large enterprises have more than 2000 applications and 85% of them are in the cloud. The move to cloud computing has been driven by global accessibility, higher availability, predictable costs, and better performance. Your applications from email (O365/G Suite) to sales (SFDC) to HR (Workday) to helpdesk (ServiceNow/Zendesk/Jira) and collaboration (Slack, Teams, Confluence) are all now hosted in the cloud. Users are accessing these applications in “direct-to-net” and “direct-to-cloud” fashion. Legacy, on-premises solutions like proxy servers have no visibility to any of these applications. Next generation firewalls are also completely blind to this traffic and provide no security which ironically now makes them a legacy solution, despite the “next generation” moniker.

This leads to the next couple of questions we asked: 

  • Do your security controls follow your users at home, at coffee shops, at airports, at shared office spaces? 
  • Have you dramatically changed the technology you use to secure your business and your employees in the age of cloud?

While the global pandemic will eventually subside, the cloud is here to stay. The pandemic has accelerated the adoption of cloud for even the most conservative of enterprises.

It’s time to focus on the way forward.

The migration from on-premises proxy servers to a true cloud solution

For today’s discussion, let’s focus on proxy servers. We could talk about the entire security stack that large enterprises have, but that is a very broad topic and one that is best broken into pieces to make it easier to digest. 

Why are we focusing on the proxy? Because companies have been relying on proxy servers for years to provide visibility, reporting, and control over their users’ web activities. But in the era of cloud applications, they simply cannot provide what organizations need. Proxies were designed and built in a pre-cloud era. They were not built for users who are remote and accessing applications hosted in the cloud directly. Also, proxies were not designed to understand the language of the cloud applications (API/JSON/tenants/instances). Applications are written in new ways, using new programming languages and new threats and vulnerabilities are out there to try and exploit these changes. Simply put, the proxy servers you have on-premises were not designed for the modern workforce in the cloud era, and maintaining, upgrading, and paying for support on this hardware is incredibly expensive and time-consuming.

Executive management teams are always trying to reduce costs without sacrificing capabilities or putting their businesses at risk. It has become clear to business and technology leaders in today’s world, that buying hardware, upgrading hardware, and hiring employees to support that hardware is not the way of the future. Human capital is extremely expensive and employees are constantly in search of new challenges, promotions, and pay raises. In addition to all of that, the issues with scale and availability are well outside of most organizations’ capabilities and focus. If you know this, but still have proxy servers deployed, the question to ask yourself again is “why?”

The reason is that proxy servers have evolved over the last 10-20 years. They started as simple web filtering to block “bad” websites and allow “good” websites. As time went on, proxies evolved. Some added threat, some added firewalling, and so on. Remember the battle of proxy-based firewalls versus stateful-based firewalls? Neither does anyone else. The end of the story was that proxies lost. But even today, most organizations still use the proxy as a simple URL/website filter which is tightly integrated into their user store/directory. Why is this?

The answer is because migrating from a proxy that has years of effort put into it can seem overwhelming. It can also be a sense of job security to the teams maintaining that legacy technology. It might also be as simple as people being hesitant to change. Whatever the reason, proxy servers do not migrate 1:1 to the cloud and their “allow/deny” logic is not suited for a cloud environment where the rich context of users, devices, apps, app rating, instance, activity, threat, and action is so critical.

The enterprise evolution:

We have helped hundreds of customers migrate to the cloud from proxy servers. Companies continually ask if we can migrate their entire config to our cloud solution. Can we do this? Yes. Should you do this? Absolutely not.

Why? As stated above, migrating a legacy configuration that is based on “allow/deny” logic is not relevant in the era of cloud. Modern cloud security systems speak the language of the cloud. They understand concepts like tenants, instances, JSON, and APIs. This is what the cloud is built on and runs on. Legacy proxy solutions were built for on-premises authentication like Active Directory. In today’s world, customers have moved to new cloud-based identity solutions like Okta, AzureAD, G Suite, and others. 

So, when a customer comes to us and asks for help migrating, we understand the background and architecture you are coming from and we take the hard work off of you and your team. We go over everything from your security policies to the authentication systems to the applications in use. We help customers map out what their employees are doing and update your current security policies into a cloud world. This is what we do every day, we migrate customers to the cloud and safely enable cloud applications. 

We take the time to articulate, in detail, the multiple deployment and configuration options customers have when moving to Netskope. Everything from deploying our lightweight Netskope client to proxy chaining. We present multiple options with virtually no impact and reconfiguration required on your network. 

We have also built specialized tools to show customers how their configuration maps to Netskope, how their URL lists (thousands to millions of lines of code) will behave with Netskope, and what will and will not be inspected (e.g., personal banking over SSL/TLS to trusted sites is generally bypassed). Additionally, we show them the sites and domains they are “allowing” that don’t even exist anymore. The security ramifications of allowing traffic to these domains and URLs are massive. We can help with this problem and explain why this is so dangerous.

These tools, the data we present, and the conversations we have with customers allow us to effectively migrate a customer from their legacy, on-premises technology into a full-featured cloud solution that provides significantly enhanced security for their business while reducing risk and providing broad visibility. We take the hard and complex work off of you and your team and provide a smooth transition to the cloud. 

Let us know how Netskope can help you.

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