cloud migration risks

Our organisation intends on migrating many of our servers to azure. I was wondering from a risk and best practices perspective, if there are any best practice guides to follow for ensuring the process goes smoothly, i.e. testing plans etc. Is there anything out there which could be provided so we can provide assurance that the process goes well. Or any specific horror stories of cloud migrations gone bad and the root causes for that (i.e. bad testing/processes for migration). what kinds of risk can organisations face if not properly managing and planning such a migration.
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pma111Asked:
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David Johnson, CD, MVPOwnerCommented:
There is less risk in Azure than most on-premise sites. The physical security is more than you'd be comfortable to pay for. On-premises doesn't come with a service level agreement.

 The problem being that if there is a network outage the virtual machines are not accessible. Express Route can be costly (if you need it then it works very well even with 10G throughput), check for availability and cost. Do it slow and in stages

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btanExec ConsultantCommented:
Migration is a worrying use case and involved legacy and any form of data and information including those of great sensitivity required maintaining high vigiliance and due care in areas of security, access control, operationalisation and availability of services. They have to be validated before and after as key success factors in such exercise that there is no short change to your org.

Microsoft has it to move into Azure and you can see their use case started with assessing their legacy DC infrastructure, their asset, applications and critical services and adopting a hybrid but not a full outsource cloud. May be one consideration to avoid a big bang and phase it out before it is a total cloud hosted DC to org - sequence of migration
•Examining business practices. If a business unit routinely experiences busy periods, such as at the end of the month or during specific seasons, customers should avoid those periods. In contrast, slow periods and non-production times for a business unit are excellent migration windows.
 •Planning resource availability. Resources, both human and technical, need to be available throughout the migration period. Microsoft IT ensures that all critical resources are available and that human resources are prepared to dedicate the required time to the migration process.
 •Assessing automation availability. Automation of the migration process can save considerable time and effort in the migration. However, automation also has a set of requirements that must be met in order for a migration to be successful.
Connectivity integrity
•Site-to-site virtual private network (VPN). Site-to-site VPN encrypts the data between the Microsoft Azure virtual network and the on-premises network. This method uses the public internet for connectivity, and can be subject to traffic bottlenecks.
 •ExpressRoute. ExpressRoute is a new technology that Microsoft developed in conjunction with telecommunications providers. In the ExpressRoute scenario, the Microsoft Azure customer works directly with their telecommunications provider to facilitate a connection to Microsoft Azure
Migration automation
high-level steps are the key components of the migration process:
 1.A business unit submits a migration request.
 2.SDO gathers the environment data for the migration assessment.
 3.SDO exports any on-premises virtual machines.◦Export from Microsoft System Center 2012 - Virtual Machine Manager.
◦Convert disks to fixed virtual hard disks.
 
4.SDO uploads virtual disks to Microsoft Azure.
 5.SDO creates an Azure virtual machine deployment using existing disks.
 6.SDO performs quality checks.
 7.SDO hands off to application owner.
Suitability for migration
for existing on-premises servers, in this order of preference:
 1.Microsoft Azure.
 2.Private cloud.
 3.Virtualization in a non-private cloud.
 4.A physical server.
Not forgetting "Business management processes"
communicated to business units
•Central Microsoft Azure registration and commitment management. These processes give Microsoft IT the ability to understand the scope of a business unit’s involvement
•Standards for cloud services and subscription placement. Microsoft IT has specific standards and processes set for Microsoft Azure migration.
Sum up of best practices and I extracted some key ones
Production Application Support and Networking-•Enable the core infrastructure services of cloud connectivity and manageability.
Security and Risk Management - •Provide appropriate security policies and oversight for both private and public clouds
Business Units - •Participate in self-testing programs to test new cloud features.
Enterprise Architecture - •Provide guidance for cloud innovation, deployments, shared components, and architectural designs.
https://msdn.microsoft.com/en-us/library/dn727097.aspx

For the specific implementing of migration, do check out this as well as it covers important issues when implementing the migration:
•Setting up for validation tests
•Synchronizing databases to minimize cut over time
•Backup and restore
•Cut over to Azure

https://msdn.microsoft.com/en-us/library/azure/jj156155.aspx
btanExec ConsultantCommented:
Another I will encourage is read on the "Migrating Applications to Public Cloud Services:
Roadmap for Success"
to ensure successful migration of existing applications to cloud computing:
1. Assess your Applications and Workloads
2. Build the Business Case
3. Develop the Technical Approach
4. Adopt a Flexible Integration Model
5. Address Security and Privacy Requirements
6. Manage the Migration
http://www.cloud-council.org/Migrating-Apps-to-the-Cloud-Final.pdf
Shalom CarmelCTOCommented:
Check your licensing for everything that will run on Azure.
* Can you scale up or scale out on demand?
* Are some licenses tied to specific servers? MAC addresses? Hardware dongles?

Have backup plans for ISP connectivity problems. When you are in the cloud, no internet=no business.

Get professional consulting. IaaS clouds like Azure have capabilities features far and beyond running virtual servers, which may assist you both in migration and in ongoing operations.
btanExec ConsultantCommented:
For licencing estimate, an useful resource looking at Windows Azure offering is using the Pricing Calculator. It allows you to model the services you require and see the cost of those services when you purchased through (as example) the Pay As You Go or the 6 or 12 month (monetary type) commitment offerings. http://www.windowsazure.com/en-us/pricing/calculator/ 

For supported Microsoft server software running in the Azure virtual machine environment, see this and note Microsoft does not support an upgrade of the operating system of a Microsoft Azure virtual machine.
All Microsoft software that is installed in the Microsoft Azure virtual machine environment must be licensed correctly. By default, Microsoft Azure virtual machines  include a license for using Windows Server in the Microsoft Azure environment. Certain Microsoft Azure virtual machine offerings may also include additional Microsoft software on a per-hour or evaluation basis. Licenses for other software must be obtained separately. For information about the Microsoft License Mobility program see Volume Licensing
https://support.microsoft.com/en-us/kb/2721672
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