Chroot jail breaks can be avoided, but significant care, consideration, maintenance, and diligent testing are required to ensure the environment functions as intended before it is placed into production and/or after it is modified due to periodic updates. The maintenance portion is often where the cycle fails, as there is a tendency to set up chrooted environments and leave them be. Given the rate at which vulnerabilities are identified and corresponding exploits created, this is a recipe for trouble.
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