MacFixit reports a problem and solution regarding iTunes 4.2.
“We previously reported an issue where iTunes 4.2 crashes shortly after connecting an iPod (under Mac OS X 10.3.x) The crash generally results both in the iPod not getting updated and a force-quit required for iTunes.
Some users have had success disconnecting all other external peripherals – particularly FireWire devices other than the iPod (and USB components), but for others the problem persists under the same conditions.
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