Reread the jailbreak thread -- there is a "hotfix" linked from the OP, which you can use to resurrect an out-of-date jailbreak that was hit by the 5.6.x firmware updates.
As a general rule of thumb -- you will always need to reinstall a hack (e.g. screensavers) but you shouldn't need to reinstall the jailbreak itself.
firmware 5.6.x is an exception because we had a sudden and unexpected need to run as root instead of defaulting to framework. Hence the hotfix, which updates your jailbreak to include gandalf (your friendly neighborhood passwordless su binary).
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