Skip to main content

5 Terrible Things You Should Not Do with Your SaaS/Office 365 Networking

Jason Lieblich

The move to cloud-based solutions like Office 365, Google Apps and others is one of the biggest fundamental changes IT professionals will undertake in the history of computing. Microsoft Office 365 already has >70 million paid subscriptions with a goal to have annualized revenue reach $20 BILLION by 2018.


The cost savings and productivity enhancements available to organizations are huge. But these savings and benefits can't be reaped without careful planning, network assessment, change management and continuous monitoring. Read on for things that you shouldn't do with your network in preparation for a move to one of these cloud providers.

1. Don't expect to keep the network the same as when everything was on-premise

Networks will need to change with the adoption of massive cloud-based services like Office 365. When all the traffic was on-premise, internal routers and network paths may have been burdened. Now that the traffic is largely external, it will stress the network differently and have different IT infrastructure dependencies. We call it "Service Delivery Chain."


You probably thought when you adopted cloud-based services like Office 365 everything was going to be easy — just give the user a browser — but that's not the case. The Service Delivery Chain — including Single-Sign-In, Azure AD, proxies, firewalls, gateways, etc. — complicates SaaS application delivery. Especially at the branch office, for mobile and telecommuters too. End-to-end application response, uptime and availability for apps like Exchange Online, SharePoint Online and Skype for Business Online needs to be tested and measured.

2. Don't expect to keep all the firewalls and proxies just like before - they will need to change

This is a common initial desire for many mid-to-large enterprises — they want to proxy all the traffic between services such as Office 365, G-Suite and their end-users — no matter where they are. This is often seen at the beginning of migration to the cloud but it doesn't usually last or not in its initial form.

Proxying all your traffic for these services requires additional investment. It's more than likely your proxies will not be able to handle the additional load that the shift to cloud services places on them. You should synthesize and load-test the various Office 365 apps and workloads prior to and during a migration to Office 365. And you should make sure that your testing tools support proxies, single sign-on and the entire Service Delivery Chain.

3. Don't assume just because you route everything centrally, you don't need to measure end-to-end

Enterprise's may have had their own MPLS-routed networks in place for years. They put it in place back in the good old days of Exchange 2003 ;-). Then they go and believe that a decade-old network design will survive the shift to cloud/SaaS. Often, coincidental with this old network design, is their desire that they only monitor their central network because "everything just routes through to one place".

Talk about head meeting sand. If you're only monitoring from one location on the network, then you will have no idea what the experience is for end-users on the other side.

Additionally, routing everything centrally can be slow, expensive and less fault tolerant then if you sent secure, SSL-traffic directly over the Internet for branch offices and remote workers. Office 365 and wide-scale SaaS adoption for an organization places different demands on a network end-to-end.

4. Don't wait for direct data center connections like ExpressRoute for Office 365 or Azure

ExpressRoute is a new data center connection type that Microsoft has begun offering for fast connectivity from your own routed and VPN'd LAN to Office 365 and Azure tenants. Other SaaS providers often offer something similar.

Direct data center connections like ExpressRoute are still in their infancy and remain expensive. Customers still must backhaul their traffic from branch offices and other locations through their private WAN, into and out of the ExpressRoute colocation. While it sounds like it could make things simpler and faster, it does make the Service Delivery Chain longer and more complex where lots could go wrong that affects end-user experience.

5. Don't assume the problem is just going to be with the provider

The assumption that only providers like Microsoft, Google or Amazon are going to have problems is NOT a good way to start an organization's journey to wide-scale adoption of cloud services. You will have outages along the way and even post migration. The outages will occur within your own networks, your ISPs, your proxies, your Single Sign-On providers — everywhere. But with the right end-to-end monitoring and management you'll be able to quantify them and their consequences and hold each of the parties accountable for the Service Level Agreements they are signing up for.

Hot Topics

The Latest

According to Auvik's 2025 IT Trends Report, 60% of IT professionals feel at least moderately burned out on the job, with 43% stating that their workload is contributing to work stress. At the same time, many IT professionals are naming AI and machine learning as key areas they'd most like to upskill ...

Businesses that face downtime or outages risk financial and reputational damage, as well as reducing partner, shareholder, and customer trust. One of the major challenges that enterprises face is implementing a robust business continuity plan. What's the solution? The answer may lie in disaster recovery tactics such as truly immutable storage and regular disaster recovery testing ...

IT spending is expected to jump nearly 10% in 2025, and organizations are now facing pressure to manage costs without slowing down critical functions like observability. To meet the challenge, leaders are turning to smarter, more cost effective business strategies. Enter stage right: OpenTelemetry, the missing piece of the puzzle that is no longer just an option but rather a strategic advantage ...

Amidst the threat of cyberhacks and data breaches, companies install several security measures to keep their business safely afloat. These measures aim to protect businesses, employees, and crucial data. Yet, employees perceive them as burdensome. Frustrated with complex logins, slow access, and constant security checks, workers decide to completely bypass all security set-ups ...

Image
Cloudbrink's Personal SASE services provide last-mile acceleration and reduction in latency

In MEAN TIME TO INSIGHT Episode 13, Shamus McGillicuddy, VP of Research, Network Infrastructure and Operations, at EMA discusses hybrid multi-cloud networking strategy ... 

In high-traffic environments, the sheer volume and unpredictable nature of network incidents can quickly overwhelm even the most skilled teams, hindering their ability to react swiftly and effectively, potentially impacting service availability and overall business performance. This is where closed-loop remediation comes into the picture: an IT management concept designed to address the escalating complexity of modern networks ...

In 2025, enterprise workflows are undergoing a seismic shift. Propelled by breakthroughs in generative AI (GenAI), large language models (LLMs), and natural language processing (NLP), a new paradigm is emerging — agentic AI. This technology is not just automating tasks; it's reimagining how organizations make decisions, engage customers, and operate at scale ...

In the early days of the cloud revolution, business leaders perceived cloud services as a means of sidelining IT organizations. IT was too slow, too expensive, or incapable of supporting new technologies. With a team of developers, line of business managers could deploy new applications and services in the cloud. IT has been fighting to retake control ever since. Today, IT is back in the driver's seat, according to new research by Enterprise Management Associates (EMA) ...

In today's fast-paced and increasingly complex network environments, Network Operations Centers (NOCs) are the backbone of ensuring continuous uptime, smooth service delivery, and rapid issue resolution. However, the challenges faced by NOC teams are only growing. In a recent study, 78% state network complexity has grown significantly over the last few years while 84% regularly learn about network issues from users. It is imperative we adopt a new approach to managing today's network experiences ...

Image
Broadcom

From growing reliance on FinOps teams to the increasing attention on artificial intelligence (AI), and software licensing, the Flexera 2025 State of the Cloud Report digs into how organizations are improving cloud spend efficiency, while tackling the complexities of emerging technologies ...

5 Terrible Things You Should Not Do with Your SaaS/Office 365 Networking

Jason Lieblich

The move to cloud-based solutions like Office 365, Google Apps and others is one of the biggest fundamental changes IT professionals will undertake in the history of computing. Microsoft Office 365 already has >70 million paid subscriptions with a goal to have annualized revenue reach $20 BILLION by 2018.


The cost savings and productivity enhancements available to organizations are huge. But these savings and benefits can't be reaped without careful planning, network assessment, change management and continuous monitoring. Read on for things that you shouldn't do with your network in preparation for a move to one of these cloud providers.

1. Don't expect to keep the network the same as when everything was on-premise

Networks will need to change with the adoption of massive cloud-based services like Office 365. When all the traffic was on-premise, internal routers and network paths may have been burdened. Now that the traffic is largely external, it will stress the network differently and have different IT infrastructure dependencies. We call it "Service Delivery Chain."


You probably thought when you adopted cloud-based services like Office 365 everything was going to be easy — just give the user a browser — but that's not the case. The Service Delivery Chain — including Single-Sign-In, Azure AD, proxies, firewalls, gateways, etc. — complicates SaaS application delivery. Especially at the branch office, for mobile and telecommuters too. End-to-end application response, uptime and availability for apps like Exchange Online, SharePoint Online and Skype for Business Online needs to be tested and measured.

2. Don't expect to keep all the firewalls and proxies just like before - they will need to change

This is a common initial desire for many mid-to-large enterprises — they want to proxy all the traffic between services such as Office 365, G-Suite and their end-users — no matter where they are. This is often seen at the beginning of migration to the cloud but it doesn't usually last or not in its initial form.

Proxying all your traffic for these services requires additional investment. It's more than likely your proxies will not be able to handle the additional load that the shift to cloud services places on them. You should synthesize and load-test the various Office 365 apps and workloads prior to and during a migration to Office 365. And you should make sure that your testing tools support proxies, single sign-on and the entire Service Delivery Chain.

3. Don't assume just because you route everything centrally, you don't need to measure end-to-end

Enterprise's may have had their own MPLS-routed networks in place for years. They put it in place back in the good old days of Exchange 2003 ;-). Then they go and believe that a decade-old network design will survive the shift to cloud/SaaS. Often, coincidental with this old network design, is their desire that they only monitor their central network because "everything just routes through to one place".

Talk about head meeting sand. If you're only monitoring from one location on the network, then you will have no idea what the experience is for end-users on the other side.

Additionally, routing everything centrally can be slow, expensive and less fault tolerant then if you sent secure, SSL-traffic directly over the Internet for branch offices and remote workers. Office 365 and wide-scale SaaS adoption for an organization places different demands on a network end-to-end.

4. Don't wait for direct data center connections like ExpressRoute for Office 365 or Azure

ExpressRoute is a new data center connection type that Microsoft has begun offering for fast connectivity from your own routed and VPN'd LAN to Office 365 and Azure tenants. Other SaaS providers often offer something similar.

Direct data center connections like ExpressRoute are still in their infancy and remain expensive. Customers still must backhaul their traffic from branch offices and other locations through their private WAN, into and out of the ExpressRoute colocation. While it sounds like it could make things simpler and faster, it does make the Service Delivery Chain longer and more complex where lots could go wrong that affects end-user experience.

5. Don't assume the problem is just going to be with the provider

The assumption that only providers like Microsoft, Google or Amazon are going to have problems is NOT a good way to start an organization's journey to wide-scale adoption of cloud services. You will have outages along the way and even post migration. The outages will occur within your own networks, your ISPs, your proxies, your Single Sign-On providers — everywhere. But with the right end-to-end monitoring and management you'll be able to quantify them and their consequences and hold each of the parties accountable for the Service Level Agreements they are signing up for.

Hot Topics

The Latest

According to Auvik's 2025 IT Trends Report, 60% of IT professionals feel at least moderately burned out on the job, with 43% stating that their workload is contributing to work stress. At the same time, many IT professionals are naming AI and machine learning as key areas they'd most like to upskill ...

Businesses that face downtime or outages risk financial and reputational damage, as well as reducing partner, shareholder, and customer trust. One of the major challenges that enterprises face is implementing a robust business continuity plan. What's the solution? The answer may lie in disaster recovery tactics such as truly immutable storage and regular disaster recovery testing ...

IT spending is expected to jump nearly 10% in 2025, and organizations are now facing pressure to manage costs without slowing down critical functions like observability. To meet the challenge, leaders are turning to smarter, more cost effective business strategies. Enter stage right: OpenTelemetry, the missing piece of the puzzle that is no longer just an option but rather a strategic advantage ...

Amidst the threat of cyberhacks and data breaches, companies install several security measures to keep their business safely afloat. These measures aim to protect businesses, employees, and crucial data. Yet, employees perceive them as burdensome. Frustrated with complex logins, slow access, and constant security checks, workers decide to completely bypass all security set-ups ...

Image
Cloudbrink's Personal SASE services provide last-mile acceleration and reduction in latency

In MEAN TIME TO INSIGHT Episode 13, Shamus McGillicuddy, VP of Research, Network Infrastructure and Operations, at EMA discusses hybrid multi-cloud networking strategy ... 

In high-traffic environments, the sheer volume and unpredictable nature of network incidents can quickly overwhelm even the most skilled teams, hindering their ability to react swiftly and effectively, potentially impacting service availability and overall business performance. This is where closed-loop remediation comes into the picture: an IT management concept designed to address the escalating complexity of modern networks ...

In 2025, enterprise workflows are undergoing a seismic shift. Propelled by breakthroughs in generative AI (GenAI), large language models (LLMs), and natural language processing (NLP), a new paradigm is emerging — agentic AI. This technology is not just automating tasks; it's reimagining how organizations make decisions, engage customers, and operate at scale ...

In the early days of the cloud revolution, business leaders perceived cloud services as a means of sidelining IT organizations. IT was too slow, too expensive, or incapable of supporting new technologies. With a team of developers, line of business managers could deploy new applications and services in the cloud. IT has been fighting to retake control ever since. Today, IT is back in the driver's seat, according to new research by Enterprise Management Associates (EMA) ...

In today's fast-paced and increasingly complex network environments, Network Operations Centers (NOCs) are the backbone of ensuring continuous uptime, smooth service delivery, and rapid issue resolution. However, the challenges faced by NOC teams are only growing. In a recent study, 78% state network complexity has grown significantly over the last few years while 84% regularly learn about network issues from users. It is imperative we adopt a new approach to managing today's network experiences ...

Image
Broadcom

From growing reliance on FinOps teams to the increasing attention on artificial intelligence (AI), and software licensing, the Flexera 2025 State of the Cloud Report digs into how organizations are improving cloud spend efficiency, while tackling the complexities of emerging technologies ...