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I have a macbook pro and planning to (finally) upgrade to Lion and currently have snow leopard. I am also planning to swap the hdd to something bigger. I wish to still be have the option of booting it from the current drive still.

Is there anything in particular I need to consider and whats the best of software to help me with this?

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Very easy : Push the option key at boot chime and select the external drive on which you want to boot.

You may want to use a FW enclosure for more speed (in comparaison with USB2)

  • I second Matthieu's recommendation about using a firewire external enclosure when you finally swap out the drives. – IconDaemon Oct 28 '12 at 2:58

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