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The Cricut Gypsy and Imagine updates are available that will allow communication and design functionality between the two machines!
2) Update Gypsy using Cricut Sync- see steps above. To get it started, all you need to do is connect it using the USB cord that came with the Gypsy.
3) Plug in Imagine and update that using Cricut Sync.
Here's a link to a thread on the Cricut message board where people have commented on the update and done some troubleshooting: Imagine Gypsy Update Thread Check it out!