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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.

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The quietest week your engineering team has ever had might also be its best. No alarms going off. No escalations. No frantic Teams or Slack threads at 2 a.m. Everything humming along exactly as it should. And somewhere in a leadership meeting, someone looks at the metrics dashboard, sees a flat line of incidents and says: "Seems like things are pretty calm over there. Do we really need all those people?" ... I've spent many years in engineering, and this pattern keeps repeating ...

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If your best engineers spend their days sorting tickets and resetting access, you are wasting talent. New global data shows that employees in the IT sector rank among the least motivated across industries. They're under a lot of pressure from many angles. Pressure to upskill and uncertainty around what agentic AI means for job security is creating anxiety. Meanwhile, these roles often function like an on-call job and require many repetitive tasks ...

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

Enterprises are under pressure to scale AI quickly. Yet despite considerable investment, adoption continues to stall. One of the most overlooked reasons is vendor sprawl ... In reality, no organization deliberately sets out to create sprawling vendor ecosystems. More often, complexity accumulates over time through well-intentioned initiatives, such as enterprise-wide digital transformation efforts, point solutions, or decentralized sourcing strategies ...

Nearly every conversation about AI eventually circles back to compute. GPUs dominate the headlines while cloud platforms compete for workloads and model benchmarks drive investment decisions. But underneath that noise, a quieter infrastructure challenge is taking shape. The real bottleneck in enterprise AI is not processing power, it is the ability to store, manage and retrieve the relentless volumes of data that AI systems generate, consume and multiply ...

The 2026 Observability Survey from Grafana Labs paints a vivid picture of an industry maturing fast, where AI is welcomed with careful conditions, SaaS economics are reshaping spending decisions, complexity remains a defining challenge, and open standards continue to underpin it all ...

The observability industry has an evolving relationship with AI. We're not skeptics, but it's clear that trust in AI must be earned ... In Grafana Labs' annual Observability Survey, 92% said they see real value in AI surfacing anomalies before they cause downtime. Another 91% endorsed AI for forecasting and root cause analysis. So while the demand is there, customers need it to be trustworthy, as the survey also found that the practitioners most enthusiastic about AI are also the most insistent on explainability ...

In the modern enterprise, the conversation around AI has moved past skepticism toward a stage of active adoption. According to our 2026 State of IT Trends Report: The Human Side of Autonomous AI, nearly 90% of IT professionals view AI as a net positive, and this optimism is well-founded. We are seeing agentic AI move beyond simple automation to actively streamlining complex data insights and eliminating the manual toil that has long hindered innovation. However, as we integrate these autonomous agents into our ecosystems, the fundamental DNA of the IT role is evolving ...

AI workloads require an enormous amount of computing power ... What's also becoming abundantly clear is just how quickly AI's computing needs are leading to enterprise systems failure. According to Cockroach Labs' State of AI Infrastructure 2026 report, enterprise systems are much closer to failure than their organizations realize. The report ... suggests AI scale could cause widespread failures in as little as one year — making it a clear risk for business performance and reliability.

The quietest week your engineering team has ever had might also be its best. No alarms going off. No escalations. No frantic Teams or Slack threads at 2 a.m. Everything humming along exactly as it should. And somewhere in a leadership meeting, someone looks at the metrics dashboard, sees a flat line of incidents and says: "Seems like things are pretty calm over there. Do we really need all those people?" ... I've spent many years in engineering, and this pattern keeps repeating ...

The gap is widening between what teams spend on observability tools and the value they receive amid surging data volumes and budget pressures, according to The Breaking Point for Observability Leaders, a report from Imply ...

Seamless shopping is a basic demand of today's boundaryless consumer — one with little patience for friction, limited tolerance for disconnected experiences and minimal hesitation in switching brands. Customers expect intuitive, highly personalized experiences and the ability to move effortlessly across physical and digital channels within the same journey. Failure to deliver can cost dearly ...

If your best engineers spend their days sorting tickets and resetting access, you are wasting talent. New global data shows that employees in the IT sector rank among the least motivated across industries. They're under a lot of pressure from many angles. Pressure to upskill and uncertainty around what agentic AI means for job security is creating anxiety. Meanwhile, these roles often function like an on-call job and require many repetitive tasks ...