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Some companies depend on support contracts for the smooth running of the business. Others rely on them only for particular pieces of software or hardware — especially costly ones. And another group only uses them when absolutely necessary. Regardless of the camp your organisation falls into, expired support contracts are a good sign that your technology is out of date and in need of upgrading.
When was the last time you audited the organisation to find out what versions of various software products were deployed? When you conducted that exercise, did you see anything seriously out of date? You'd be surprised at what's still out there. On occasion, I see Windows 98 or NT machines, or Windows XP machines running Office 2000. Ancient software can cause far more issues than some people realise — especially when users are collaborating with other companies, which are unlikely to be running Microsoft Office 98 or StarOffice.
Depending on what is being targeted, if you keep getting hacked, ancient software could be your weak spot. Of course, the breaches could be either hardware or software related, and you may be suffering from poorly configured security hardware, buggy or outdated software, or lax security policies. But while one break-in is understandable, multiple hacks suggest it is time for a major overhaul.