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Migrating to AWS Method 1 - Repurchasing, aka Drop-and-Shop

Repurchasing can be the simplest, fastest and least-risk method of running applications in the cloud. An organization can eliminate a lot of migration effort and cloud set up by directly consuming applications via the AWS Marketplace. Unfortunately, Repurchasing is often ignored as a migration option by most technical IT staff, creating opportunity cost of the business they work for.

This is the second in a five-part series covering the practical realities of migrating applications to AWS:

  • Part 1 - A Practical Guide to Understanding the 6Rs for Migrating to AWS
  • Part 2 - Migrating to AWS Method 1 - Repurchasing, aka Drop-and-Shop
  • Part 3 - Migrating to AWS Method 2 - Rehosting, aka Lift-and-Shift
  • Part 4 - Migrating to AWS Method 3 - Replatforming, aka Lift-and-Shape
  • Part 5 - Migrating to AWS Method 4 - Refactoring, aka Cloud Native

In this post we explore the Repurchasing migration method in the same consistent manner as the other three methods using the following outline:

  1. Defining what Repurchasing is
  2. Drivers of Repurchasing
  3. Benefits of Repurchasing
  4. Risks of Repurchasing
  5. How to Repurchase
  6. What you need to Repurchase
  7. Repurchase Summary and Next Steps

If you want to access the whole series in one sitting, you can go get the Cloudsoft white paper:

Everything you need to know about Migrating Applications to AWS

1. Defining what Repurchasing is

Let's look at some examples of Repurchasing:

  • Swapping a self-run email system for an online email-as-a-service offering.
  • Swapping a self-built VPN server for a vendor-built appliance.
  • Instead of adopting the cloud service providers vanilla service, use a specialist third party appliance such as Web Application Firewalls.

Uncovering these opportunities to Repurchase will happen through a Discovery process for the organization’s current application landscape.

For example, it is becoming increasingly unusual for organizations to build and operate their own email systems. As part of the Discovery Assessment, if an email service is found to be run in-house then it is highly likely that a recommendation to Repurchase this as a Software-as-a-Service email offering is the best value.

The Repurchasing method is constantly evolving and is likely to see significant growth from the current 5% of migrations to AWS (source: AWS) because this evolution is opening a myriad of Repurchasing paths.

AWS Marketplace and Service Catalog have always been ways to avoid migrating fragile on-premises applications and instead Repurchase them in the form of an appliance in the AWS Marketplace. This is like an upgrade process where old configurations and data are migrated to the Repurchased platform.

The evolution of AWS Marketplace and Service Catalog means It is now possible to not only rent appliances but also rent SaaS products, bring your own licence and even negotiate complex Private Offers with AWS and the vendor.

2. Drivers of Repurchasing

There are a couple of important tailwinds behind the cloud computing revolution.

2.1 Move to a consumption-based procurement model

Consumers of technology wish to move to a more consumption-based procurement model, swapping lumpy three-year capital expenditure deals for monthly, no commitment pay-as-a-you-go models that efficiently ties their spend to their own income.

2.2 Retire legacy “enterprise” software

The “Enterprise” in enterprise software is no longer the “gold standard” of technology. With the rise of open source and the rapid pace of innovation in software, “enterprise software” is now perceived as legacy, old, outdated, ugly, difficult to use. Customers want to rotate their software stacks faster to remain competitive.

Repurchasing software through cloud procurement frameworks such as AWS Marketplace is how enterprises can refresh their application stack in a frictionless manner, which is a huge driver for enterprises. It eliminates long, complicated and expensive software procurement cycles like multi-stage RFI and RFP processes.

Trialling software via AWS Marketplace, and turning it off if it isn’t suitable, is a far more efficient method of software procurement.

In terms of application migration to AWS, organizations choose Repurchasing to prune down the applications they self- design, build and operate to eliminate costs and improve bottom line net income.

3. Benefits of Repurchasing

There are several benefits with Repurchasing.

3.1 Let go of the past, grab the future

Replace antiquated systems with modern appliances and SaaS.

3.2 Simplify procurement

Buy appliances, BYOL, SaaS and Private Offers through one procurement mechanism.

3.3 Reduce in-house skills requirements

The systems purchased are built by specialists you don’t need to hire. SaaS means it is also run by people you don’t need to hire.

3.4 Reduce effort/increase speed of migration

The less there is to migrate, the faster, cheaper and less risky the migration program will be.

4 The Risks of Repurchasing

There are a number of risks when Repurchasing. Failing to consider and manage these can lead to poor migration experience and mismatched outcomes when the new, shiny purchased system simply doesn’t work.

4.1 Integrations and Dependencies

Example: If you replace your on-premises Active Directory system with a cloud version: which clients and applications must you reconfigure to use the new cloud service?

4.2 Procurement friction

Your Procurement team and procedures may be incompatible with this new way of buying applications. There are four methods they need to learn: Appliance (rented licence), Bring Your Own Licence, SaaS and Private Offer.

4.3 Incompatible financial models, culture and processes

Does Finance know how to handle pay-as-you-go, unpredictable future costs?

4.3 Incompatible operational models, culture and processes

Can Operations “migrate” to administer the purchased system? Migrations are often as much about people and process as they are about applications and data.

5 How to Repurchase

The seven steps below represent a common pattern to approach Repurchasing. Of course, different applications will require modified approaches, but this is a standard approach using AWS Marketplace.

  1. Compare the list of discovered/known applications to those in the AWS Marketplace
  2. Understand current and future possible licensing and purchase options
  3. Plan how the Repurchased application will be paid for (with Finance) and operated (with Operations) and consumed (by Users).
  4. Plan the configuration and data migration to the new application, identify any blockers early.
  5. Repurchase the application using the best AWS Marketplace mechanism to a well-architected AWS account.
  6. Configure the application and migrate data
  7. Test and Transition

6 What you need to Repurchase

Repurchasing is quite different from Rehosting and Replatforming because you are dropping your current system and shopping for a new system. This reduces the number of actual migration activities to carrying forward configurations and migrating data. Data migrations should be easy on systems that have import features.

The key capabilities you need to make Repurchasing happen are:

  • Procurement, finance and operations “onside”.
  • If you are replacing an existing application, have the in-house application expert (or partner) be involved in the process.
  • An expert AWS Marketplace and AWS Service Catalog partner, or train someone up internally. This requires expertise to navigate and execute properly.
  • A well-managed migration program with Repurchasing as a Work Package in the program, which a supporting business case, allocated resources and timeline.

There is no standard timeline or budget for Repurchasing, it is highly variable according to the software but – in general – it is the fastest, simplest migration method.

7 Summary of Repurchase and Next Steps

Any migration program that is missing Repurchase has inherent opportunity cost measured in migrating applications via the wrong, more costly, slower, brittle and fragile method. Repurchasing is a huge opportunity to modernize applications and should be considered as the first step in any migration program, but it is rare that it is.

Our advice to everyone considering repurchasing is to get some education on the following resources and choose a partner like Cloudsoft to help you where needed.


  1. The AWS Marketplace homepage
  2. The AWS Service Catalog homepage

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