Microsoft Windows Server 2003 customers have just 100 days to upgrade their last instances of the product before support is pulled.
On July 14 Microsoft will no longer provide patches or support for the product and customers risk leaving themselves open to vulnerabilities and expensive compliance violations.
More than 20 vulnerabilities were identified in Windows Server 2003 in 2014.
However, with 57 per cent of Australian organisations still running at least one instance of Windows Server 2003, it presents an opportunity for channel players to move customers to a more modern infrastructure (Azure, Office365, CRM Online).
Microsoft Australia Cloud and enterprise product Manager, Mike Heald, told ARN the main risk of not migrating was around compliance.
"If you have one server that isn't updated that can make the whole infrastructure non-compliant and that's a big risk. The point is to look at the opportunity for these customers," he said.
"In terms of the cost, if customers don't do anything, it could be more expensive in the long run than doing a migration up front."
Heald said the upgrade opened the way for new technology, but that every customer was different.
"Customers might want to stay on premise, they could go hybrid or they could go cloud, so we are providing choice along that way," he said.
"We are seeing great growth around Office365, they might want to look at moving their email system on premise or maybe to the cloud, they might want to work backup into Azure, or they might want to stay on premise - every customer is different.
He said Windows Sever 2003 was quite old technology.
"Back then virtualisation was not available," he said. "There's a lot you can do now in consolidation of servers into less infrastructure, so in terms of IT costs it will help there.
"We have also done a lot with Cloud as well, so making sure we have the plug in to help customers move to the cloud.
"We have the plugins right to the servers now, so they can actually easily manage their cloud workloads from servers."
There is an estimated 23.8 million instances of Windows Server 2003 running across 11.9 million physical servers worldwide.
According to Spiceworks, a global professional network of more than 5 million IT Professionals, 65 per cent of organisations which use its tools in Asia Pacific are still running at least one instance of Windows Server 2003.
Microsoft Australia director of partner business development, Phil Goldie, said, from a partner perspective, it was a great opportunity to to go back to customers and try to understand what it is they were doing with the technology.
"I think one of our points of view is that nobody buys Windows Server for the sake of it, it's always a technology that underpins either a piece of infrastructure within the company, or its the basis of a line of business application that's running on top of an SQL server or applications from ISVs that are written in .NET.
He urged partners to have a good look at what the technology was being used to do and what was a modern way of achieving that outcome.
"We think we have got a pretty good story in terms of choice," he said.
"Those on premise versions can be updated to the latest and greatest of Windows Server, but equally there could be a thought process around moving them to hosted services or public Cloud on Azure or Office365."
He said it was an opportunity to have a conversation.
"It should be a trigger for rethinking what these servers have been used for historically, because there are thousand different scenarios, because there are many thousands of these servers still being migrated, so there's a great opportunity for the channel there."
He said momentum around moving to Cloud was strong in the SMB space at the moment.
"We have got a lot of momentum on our platforms, particularly Office365, so we can see customers making that choice about moving to the cloud," he said.
"The challenge is providing that clarity for the customers.
"What is the choice available? What's the best way to tackle that business problem and making that really clear.
"Whether that's remaining on premise, or upgrading technology, whether it's moving to a host or a public Cloud or a SaaS platform.
With 100 days to go, this is the period when businesses will take deliberate action, according to Goldie.
"So I think getting helping customers reach a decision in a timely manner and of course help customers with he implementation and migration is going to be a key part of that.
"Helping simplify the decision so we can get customers off the platform is probably the key challenge."
Microsoft has also moved to address underlying profitability for channel partners as they moved to a recurring revenue model.
Goldie said that while customer sentiment was very high, partners were concerned about margins and profitability under the new model.
"That's a huge area of focus and we have been doing a huge amount of work with our channel, both digitally and through face to face workshops, to help them understand the profitability business models for the cloud," he said.
"Because, ultimately, the main success you can have in this transition isn't simply moving customers to the cloud, but is how do I grow recurring revenues from that move versus continually project based services in my approach.
"How do you use this trigger to drive cloud conversation and then how does that cloud conversation become a recurring revenue opportunity around managed services, an apps and IT that you have built, versus just another project based deployment."
Goldie said sentiment has shifted in favour of Cloud following the opening of datacentres of Australian soil.
"The devils is in the how do it, not whether I should or shouldn't do it," he said.
"That's going to be a journey we are very passionate about here at Microsoft in terms of really helping partners, and it's not a trivial one.
"But it's one we believe partners can make, and ultimately that's going to be a great foundation for their success in the long term if they can make that transition, as well as moving their customers to the cloud."