Cloud Modernization Best Practices – Lessons from the Field (DevOps, Containers, and More)

Is your cloud infrastructure keeping up with your business needs? Outdated cloud architectures cost companies millions in lost opportunities and wasted resources. 

Most businesses started their digital transformation with simple “lift and shift” migrations. But those quick moves have created new problems: inflexible systems, security gaps, and bloated costs. The most successful companies now focus on true cloud modernization – rebuilding applications to fully use cloud capabilities, not just hosting them there.

At Multishoring, we’ve guided businesses through cloud modernization over our decade of Microsoft Azure consulting experience. We’ve seen what works, what fails, and how to avoid costly missteps. This article shares lessons from our experience – practical steps that help you modernize without disrupting your business.

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What is a Cloud Modernization Strategy?

Cloud modernization goes far beyond simply moving applications to the cloud. While migration focuses on relocating workloads, modernization transforms how applications work to fully utilize cloud capabilities.

Think of migration as moving your furniture to a new house. Modernization is redesigning that furniture to fit perfectly in each room of your new home. A cloud modernization strategy is your blueprint for this redesign process.

Why does this matter? Because companies that just migrate without modernizing miss the full potential of cloud benefits. They pay for cloud resources but don’t get the flexibility, speed, or cost savings they expected.

A proper cloud modernization strategy includes:

• Evaluating which applications need updates and when
• Choosing the right modernization approach for each application
• Planning how these changes affect your business operations
• Setting clear goals and measuring success

Key Parts of a Cloud Modernization Strategy

Application Assessment 

How well do you know your current applications? You need to understand each application’s:

• Technical architecture and dependencies
• Business value and criticality
• Current performance and limitations
• Security and compliance requirements

This assessment helps you prioritize which applications to modernize first and choose the right approach for each.

Modernization Approach Selection 

Based on your assessment, you’ll choose from several approaches.

• Rehosting: Moving applications with minimal changes
• Refactoring: Updating code to work better in the cloud
• Rearchitecting: Redesigning applications for cloud-native features
• Rebuilding: Creating new cloud-native applications from scratch

Technology Selection 

Which cloud services and tools will you use? This includes:

• Cloud platform choices (Azure services, containers, etc.)
• DevOps tooling for development and deployment
• Monitoring and management tools
• Security solutions

Implementation Planning 

How will you make these changes without disrupting business? This covers:

• Phased implementation timelines
• Testing strategies
• Team training needs
• Rollback plans for unexpected issues

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When to Start Modernizing Your Cloud Infrastructure

Is it time to modernize your cloud applications? Watch for these warning signs.

Rising Costs Without Added Value 

Are your cloud bills growing but you’re not seeing benefits? This often happens when applications weren’t designed for cloud efficiency. Many businesses find they’re paying 30-40% more than necessary because their applications waste cloud resources.

Performance Problems and Availability Issues 

Do users complain about slow response times? Do applications crash under heavy loads? Legacy applications often struggle to scale in cloud environments because they weren’t built for elastic resources.

Security and Compliance Challenges 

Finding it hard to meet security requirements with your current cloud setup? Applications not designed for the cloud often have security gaps that become harder to fix over time.

Slow Development and Deployment Cycles 

Does it take weeks or months to update your applications? Cloud-native applications can be updated in hours or days, giving your business a competitive edge.

Technical Debt Accumulation 

Are temporary fixes piling up? When your teams spend more time maintaining existing systems than building new features, it’s time to modernize.

Business Growth Limitations 

Is your current cloud infrastructure holding back new business initiatives? When technology limits your business goals rather than supporting them, modernization becomes crucial.

The best time to start modernizing is before these issues cause a significant business impact. Proactive modernization costs less and creates fewer disruptions than emergency updates.

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Business Benefits of Cloud App Modernization

How does cloud modernization actually impact your bottom line? Let’s skip the hype and look at real results companies achieve after modernizing their cloud applications.

Modernized cloud applications deliver measurable business value – not just technical improvements. Organizations typically see ROI within the first year after completing their modernization projects. These aren’t just cost savings but true business advantages that help companies outperform competitors.

Cost Savings and Better Resource Use

Cloud bills often shock businesses that migrate without modernizing. Why? Because traditional applications waste cloud resources. They’re designed to run on static hardware, not dynamic cloud environments.

Modernized applications cut costs in several ways:

Automatic scaling significantly reduces infrastructure costs. Traditional applications run at full capacity 24/7, regardless of usage. Cloud-native apps scale down during quiet periods and up during busy times, so you only pay for what you use.

Many retailers see substantial monthly savings after modernizing their e-commerce platforms. These applications automatically scale down overnight and ramp up during peak shopping hours.

Pay-as-you-go pricing replaces large upfront investments. Instead of buying capacity for peak loads, you pay only for what you consume. This shifts spending from capital expenses (CapEx) to operational expenses (OpEx), freeing up cash for other business initiatives.

Better Security and Easier Compliance

Security breaches cost companies millions per incident on average. Cloud-native applications built with security in mind reduce these risks significantly.

How does modernization improve security?

Built-in security controls replace custom solutions. Cloud platforms offer sophisticated security features that modernized applications can use directly. This eliminates gaps and inconsistencies common in custom security implementations.

Automated security updates reduce vulnerabilities. Cloud-native services automatically update their security patches, unlike traditional applications that require manual updates. Healthcare organizations typically eliminate most of their security patching work after modernizing their patient-facing applications.

Centralized security monitoring improves threat detection. Modern cloud architectures allow unified security monitoring across all applications. This helps spot unusual patterns that might indicate a breach before damage occurs.

Scaling and Responding to Business Changes

Can your business seize opportunities when they appear? Modernized cloud applications make this possible.

Quick scaling meets unexpected demand. When a company experiences sudden publicity or seasonal spikes, modernized e-commerce systems scale automatically, handling surges without downtime. Before modernization, similar traffic spikes typically crash traditional websites.

Faster feature delivery keeps you competitive. Companies with modernized cloud applications deploy new features several times faster than competitors using traditional applications. Media companies often reduce their feature release cycles from months to days after modernizing their content platforms.

Geographic expansion becomes simpler. Need to serve customers in new regions? Modernized applications can deploy to multiple geographic locations with minimal configuration. Education and technology companies can expand to new countries in months rather than years after modernizing their platforms.

Business model changes happen faster. When market conditions shift, modernized applications adapt quickly. B2B service providers can add direct-to-consumer offerings in weeks by extending their modernized platforms, a process that typically takes many months with traditional architectures.

These benefits explain why most companies now rank application modernization as a top strategic priority. The question isn’t whether to modernize, but how quickly you can do it while minimizing risk.

Microsoft Azure Tools for Cloud Modernization

Microsoft Azure offers specific tools that make cloud modernization easier and more effective. These services help you transform legacy applications into modern cloud solutions without rebuilding everything from scratch.

Azure App Service and Azure Functions for Modern Applications

Azure App Service lets you modernize web applications without major code rewrites. Upload your existing .NET, Java, Node.js, Python, or PHP applications and get immediate benefits:

• Built-in load balancing and auto-scaling adjust to traffic demands
• Deployment slots allow testing before going live
• Managed certificates and security features protect your applications

Azure Functions takes modernization further by breaking applications into smaller, event-driven pieces. This serverless approach helps you:

• Convert monolithic processes into independent functions that scale separately
• Pay only when your code runs, reducing costs for intermittent workloads
• Connect easily to other Azure services through built-in triggers and bindings

Many companies start modernization by moving key processes to Functions while keeping their core application in App Service. This gradual approach reduces risk while delivering immediate benefits.

Azure Kubernetes Service (AKS) for Running Containers

AKS makes container management simple when modernizing complex applications. It handles the difficult parts of running Kubernetes:

• Automated health monitoring and repair keeps containers running
• Built-in scaling adds or removes containers as needed
• Simplified security with integrated Azure Active Directory

AKS works well for applications that need consistent deployment across development, testing, and production environments. It also helps applications that run across multiple clouds or on-premises systems.

Teams modernizing with AKS typically see deployment times drop from days to minutes and achieve more reliable operations with less maintenance work.

Azure DevOps and GitHub for Better Development Workflows

Modern applications need modern development practices. Azure DevOps and GitHub provide the tools teams need:

• Code repositories with version control track all changes
• CI/CD pipelines automate testing and deployment
• Work item tracking connects code changes to business requirements

These tools help development teams move faster while maintaining quality. Code changes automatically trigger tests, and approved changes deploy to production without manual steps.

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DevOps – The Backbone of Cloud Modernization

Cloud modernization fails without DevOps practices. Why? Because modernized applications need a different approach to development and operations.

DevOps bridges the gap between writing code and running applications. It combines culture changes, practices, and tools:

• Teams take responsibility for both building and running applications
• Automation replaces manual processes wherever possible
• Feedback loops help teams learn and improve continuously

Companies that adopt DevOps practices deploy code 24 times more frequently with 3 times lower failure rates. This speed and reliability become essential when running modern cloud applications.

Using Infrastructure as Code (IaC) in Cloud Modernization

Infrastructure as Code treats servers, networks, and other infrastructure as software. Instead of manually setting up servers, you create code files that define your entire environment.

This approach brings major benefits to modernization:

• Consistency across environments – Development, testing, and production environments match exactly
• Version control for infrastructure – Track all changes and roll back when needed
• Repeated deployments without errors – Eliminate manual mistakes

Azure offers multiple IaC tools:

• ARM templates – JSON files that define Azure resources
• Bicep – A simplified language that generates ARM templates
• Terraform – Works across multiple cloud providers

Start with simple resources like storage accounts, then gradually expand to define your entire environment in code.

Monitoring Your Modern Cloud Environment

Traditional monitoring tools fall short in modern cloud environments. Applications now span multiple services, making it harder to track performance and issues.

Modern monitoring solutions provide:

• End-to-end visibility across all application components
• Automated alerting when metrics fall outside normal ranges
• AI-powered analysis to spot problems before users notice

Azure Monitor with Application Insights tracks both infrastructure and application performance. It helps you understand how users experience your application and where bottlenecks occur.

Containers – Ways To Speed Up Your Cloud Modernization

Containers package applications with everything they need to run. This solves common modernization problems:

• Consistency issues between development and production environments
• Dependency conflicts between applications
• Portability challenges across different cloud platforms

Containers make applications more portable and predictable. They start faster than virtual machines and use resources more efficiently.

Most companies start with a few containers for new services, then gradually expand their use across more applications.

How to Move Legacy Applications to Containers

Moving legacy applications to containers requires a step-by-step approach:

1. Start with assessment – Not all applications work well in containers
2. Create a containerization plan – Identify components to containerize first
3. Prepare your application – Remove hard-coded paths and local storage dependencies
4. Build your container images – Package each component with its dependencies
5. Test thoroughly – Verify functionality in the containerized environment

Common pitfalls to avoid:

• Making containers too large or complex
• Storing data inside containers instead of external storage
• Ignoring security in container configuration

Start with simpler, stateless applications before moving to more complex ones with database dependencies.

Microservices – When to Break Up Large Applications

Not every application should become microservices. This architecture works best when:

• Different parts of your application need to scale independently
• Teams need to work on separate components without affecting others
• You need to update components frequently without downtime

The process of breaking up applications requires careful planning:

1. Identify logical boundaries in your application
2. Create APIs between components
3. Extract one service at a time, starting with less critical ones
4. Refactor gradually rather than rewriting everything at once

Warning signs that indicate you’re not ready for microservices:

• Unclear boundaries between application components
• Insufficient automation and DevOps practices
• Lack of experience with distributed systems

Many successful modernization projects use a hybrid approach, keeping some components as a monolith while extracting others as microservices.

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Planning Your Cloud Modernization – How To Approach This?

Cloud modernization fails when companies try to do everything at once. Successful projects follow a phased approach with clear milestones and measurable results at each stage.

Planning starts with understanding your current state and defining your target state. What works best is breaking this journey into manageable steps:

1. Assessment Phase – Document your current applications, dependencies, and pain points
2. Strategy Development – Create a roadmap with clear priorities and success metrics
3. Pilot Implementation – Start with a small, important application to prove your approach
4. Scaled Rollout – Apply lessons from the pilot to modernize additional applications
5. Continuous Improvement – Refine your processes based on results

Set clear milestones for each phase. For example, in the pilot phase, define specific performance improvements or cost reductions you expect to achieve. These concrete goals help keep your project on track and demonstrate value to stakeholders.

Most successful modernization projects take 12-18 months for significant results. This timeline lets you make meaningful progress without overwhelming your teams or disrupting business operations.

Which Applications to Modernize First

Not all applications deserve immediate modernization. Use this framework to identify your top candidates.

Business Value Assessment

• Revenue impact – Applications directly tied to customer purchases or service delivery
• Customer experience – Systems that affect how customers interact with your business
• Operational efficiency – Applications that could significantly reduce costs if improved
• Strategic importance – Systems core to your future business plans

Technical Assessment

• Modernization complexity – How difficult will the update be?
• Technical debt – How much maintenance burden does the current version create?
• Integration requirements – How many other systems depend on this application?
• Skills availability – Does your team have the knowledge to modernize this application?

Avoid starting with:

• Mission-critical systems with zero tolerance for disruption
• Applications scheduled for replacement in the near future
• Systems with complex compliance requirements

Many organizations find that customer-facing applications often provide the best initial modernization targets due to their direct business impact.

Helping Your Team Adapt to Cloud Modernization

Cloud modernization is as much about people as technology. Your technical teams need new skills, and your business teams need to adapt to new ways of working.

Skills assessment comes first. Map your current team capabilities against what you’ll need for your modernized environment. This identifies training needs and potential skill gaps to fill with new hires or external partners.

Training should be practical and timely. The most effective approach is:

• Just-in-time training that aligns with your modernization phases
• Hands-on workshops rather than theoretical classes
• Pairing experienced and less experienced team members
• Creating internal centers of excellence to spread knowledge

Beyond technical skills, focus on cultural changes. Successful cloud modernization requires:

• Breaking down silos between development and operations teams
• Adopting more collaborative working methods
• Becoming comfortable with automation and self-service
• Embracing continuous learning as technologies evolve

Many organizations find that creating a dedicated cloud center of excellence helps spread new practices and standardize approaches across different teams.

Conclusion – Building a Future-Ready Business with Cloud Modernization

Cloud modernization is no longer optional for businesses that want to stay competitive. The gap between companies using modern cloud applications and those stuck with legacy systems grows wider each day.

The benefits are clear:

• Reduced costs through better resource utilization
• Improved security and simplified compliance
• Faster response to market changes and business opportunities
• Enhanced ability to innovate and deploy new features

Success requires both technical expertise and strategic planning. The most effective approach combines:

• A clear assessment of your current applications and future needs
• A phased implementation that delivers value at each stage
• The right Azure tools for your specific modernization goals
• DevOps practices that support your modernized applications
• Container technologies that simplify deployment and management
• A people strategy that helps your teams adapt to new ways of working

Ready to start your modernization journey? Here are your next steps.

1. Conduct an application portfolio assessment to identify modernization priorities
2. Define clear success metrics for your modernization initiative
3. Select a pilot application that can demonstrate quick wins
4. Build or acquire the skills your team will need
5. Partner with experienced modernization experts to reduce risk

At Multishoring, we’ve guided organizations through successful cloud modernizations. Our decade of Microsoft Azure experience helps you avoid common pitfalls and accelerate your transformation. We combine technical expertise with practical business advice to deliver modernization that drives real business results.

Don’t let outdated cloud applications hold your business back. The time to modernize is now.