Azure Application Migration Challenges

By Ben Briggs on

In this article I’m going to be drawing your attention to some of the key challenges during the Azure application migration process. 

In general, we break down a cloud migration into 3 phases:

  • Assess 
  • Migrate 
  • Optimise & Manage 

Let’s have a look at some of the complications that may arise at each of these stages.


Information gathering 

The first challenge to address is how to gather the required information. If documentation is on the thin side, then a fresh assessment is normally required. This should be a multi-pronged attack targeting in-house and vendor knowledge, in addition to any assessment tools to help automate the process. It’s important not to rely on any one solution as each method comes with its own benefits. An assessment tool is not going to highlight the business uptime requirements for example. 

In your assessment you should look for; 

  • Compatibility issues 
  • Opportunities to retire legacy applications 
  • Business requirements 
  • Financial Cost/impact 

Highlighting Dependencies 

Integrations are a key technical blocker when migrating applications to the cloud. It can take extensive analysis to unearth the dependencies which can often be custom solutions put in place by in-house IT teams. Some common examples are:  

  • Messaging (email, notifications) 
  • Data transfer routines 
  • Web services 
  • Database references 
  • Custom automation  


Choosing your Strategy 

Rehost, refactor, rearchitect or rebuild? Choosing the wrong strategy could leave you fighting the same legacy problems in the cloud or battling a lack of skills with new technologies. Your strategy should meet your business needs but also offer a solution that doesn’t require a refresh in a year or two. Generally, it should; 

  • Optimise, by taking advantage of cloud services 
  • Remove legacy support issues 
  • Provide business benefit through cost saving oexpanded revenue streams. 

Working with Vendors 

If your application was created by a 3rd party, then you’d typically want them involved in the migration to provide expert technical knowledge. In fact, this can also be a requirement to ensure the existing support contract is valid. Whilst having input from vendor can be essential, it also slows the process down, with vendors often having to verify new technologies yet to be tested. In this case you’ll often join the vendor on a discovery process to make sure they meet the desired migration strategy. 

Planning downtime 

Allocating downtime for critical business applications is obviously a challenging task. The coordination of resources is critical, and every good migration requires a clear and concise approach planned in detail. Your chosen strategy will affect the downtime required so understanding the cost implications for any downtime is essential. 

Optimise & Manage 


The self-service nature of provisioning in the cloud should be concern for all organisations. This represents a shift in mindset from traditional security, as before a physical process would have had to take place (building a server)However, with software defined architectures, services can be deployed in minutes, potentially racking up huge costs. Controlling and monitoring cloud usage is common oversight after a migration has taken place. 

Adopting new security concepts 

A traditional firewall as a security gateway is no longer a requirement in the cloud. One to one public address mappings are common by default and it’s now up to security professionals to understand these changes and mitigate with modern security architectures. 

How can Silversands help? 

Making sure all the boxes are ticket in a migration can be a challenging taskWith inhouse development and consultancy teamsSilversands has a wealth of technical knowledge to ask the right questions and perform a smooth migration to Azure. Please get in touch by filling out the form below and join one of our regular workshops and webinars providing the latest updates and expert advice about Microsoft 365, Cloud and Hybrid IT, security, compliance and partner tools. We also post regular blogs so please do follow us.

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