According to a tweet posted by @MuscleNerd, a member of the iPhone Dev-Team, which has authored many jailbreak-related tools and tutorials, iOS 5′s new automatic over-the-air updates shouldn’t make jailbreaking harder.
The tweet, posted just a few hours ago, reads:

over-the-air delta updates of iOS should be fine for JBers (even if Apple didn’t let you disable them, the JB itself can)
Concerns arose, since automatic over-the-air updates, one of the flagship features of iOS 5, could possibly break jailbreaks whenever a new version of the firmware is released, essentially making a permanent and stable jailbreak unfeasible. While that might be true, a reliable jailbreak would also be able to disable automatic updating altogether.

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