Follow these best practices to ensure the server OS patch process runs smoothly and doesn't introduce new issues and possibly sour the client relationship.
Many IT consultancies develop managed services packages that ensure clients' servers are properly updated as part of a larger monthly maintenance contract. Other consultants are simply responsible for ensuring clients' servers remain current with the latest OS patches and updates. Either way, regularly downloading and installing Apple, Linux, and Microsoft security patches, performance updates, and other OS hotfixes doesn't sound like that big of a deal, but seasoned veterans know that installing the wrong OS updates at the wrong time can cost you a client. Here's how to keep OS patching from souring a client relationship.
Determine upfront how quickly server updates will be deployed
If a client demands that your IT consultancy download and install OS performance patches and updates immediately upon release, you should educate them that new patches and updates frequently introduce other issues. For example, a security patch could: create a conflict with critical financial management software (such as .NET Framework patches recently did for QuickBooks users), prompt antivirus software to fail or freeze (as my office suspects occurred recently on some machines), or adversely impact a server's performance. Consultants should ideally have time to test the patches in a non-production environment, or at least to learn what issues other business and organizations are experiencing.
If the consultancy isn't given proper time to monitor issues that arise for other first adopters, the client must understand incompatibilities, unplanned outages, and performance failures could occur. Unfortunately, those are the possible consequences for loading OS patches as soon as they're released.
Agree how OS patches will be tested
If a client requests that your consultancy test OS updates prior to installation, you need to ensure that both parties agree about what constitutes testing. If the client operates two Windows 2008 servers (one a domain controller with proprietary software, and a second providing terminal services functionality), the client must understand they must purchase and maintain a second redundant network if they intend for your office to fully test patch compatibility and performance prior to deployment within the production environment.
Due to cost, many clients will likely request that you delay installing the patch for a few weeks and review first adopters' experiences instead. Even within 10 days of the patch's release date, you can do some quick Google searches to see whether widespread or even isolated issues are occurring due to the update.
Specify when server reboots will occur
Operating systems frequently require rebooting after the installation of performance patches, security updates, and other OS hotfixes. I've been unlucky in guessing when clients would prefer for the server reboots to occur. Don't make the same mistake.
I've discovered that some clients work on Sunday afternoons, while others catch up after-hours (as late as two or three in the morning) on weekdays, so there's no hard and fast rule as to when it's safe to reboot a server. I recommend making sure the client understands that a specific day and time are fair game for regularly rebooting the server. With such an agreement in place, it shouldn't be necessary to work through complex calling trees, all-company emails, and other arcane methods of ensuring all users understand that a server will be rebooted every time it requires restarting. Whether it's the third Friday of every month at 6:00 P.M. or every Monday at 6:00 A.M., ensure clients understand servers need to be rebooted and that, to minimize communication and other issues, the same reboot windows can be set each month.
Nothing easy about it
The only individuals I hear saying it's no big deal to patch a server OS typically administer servers for a single business. Most IT consultants support dozens if not hundreds of servers for numerous organizations, each with different schedules, needs, and requirements. To ensure the server OS patch process runs smoothly and doesn't introduce its own incompatibilities, frustrations, or other issues, work through these steps with all clients.