We're currently running with php 5.2.5. We have now encountered a bug that creates a seg fault. Our first idea at the solution is upgrading to version 5.2.6 but are skeptical of problems that it will create. We are running Apache and host a dozen or so sites.
It's impossible for any of us to say definitely yes or no about your existing code breaking without performing an analysis on it first.
This is exactly what test environments are for. If you have a test environment set up, you can perform the upgrade, then do regression testing to see if anything breaks. Without this environment, you're making a gamble.
@Grant Wagner: Great point on virtualization. Setting up a good test environment doesn't have to be difficult.
With modern Virtual Machine options VMware Server, Microsft Virtual Server, Microsoft Virtual PC and others, why not set up a virtual environment running your existing platform, then upgrade and test that?
If you are willing to spend money, you can buy tools to do P2V (Physical-to-Virtual) that will take your existing setup and provide you with a virtualized copy of it (this could be valuable if you've done a lot of customization to the configuration that might be difficult to produce to a virtualized version that matches the original well enough to do proper testing).
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