Illustrator cannot print message and bug

I am running CS5.5 trying to print big pages with multiple large eps files or hi res photos.
when going to print I get a message that Illustrator cannot print. I press the cancel button. but illustrator continues to send nthe image to the printer anyway, if it is printed it only has part of the image, like it ran out of memory.
So I guess I am running out of memory?
any ideas how to deal with this?

OK
I have a simple example of the problem.
A 28 mbyte JPEG file.
I am running illustrator on an I7 mini mac server with the latest lion. the board is configured for 2Gbyte ram and I have two 500K disks.
I am printing to a wide format epson stylus pro 9890 and trying to generate a 40 inch by 60 inch work. Illustrator comes back with "cant print" no further explanation, Now here comes the bugs in how the app behaves, in that it will continue to print a partial document if i do not kill the print process.
I assume I have a memory problem?
Thanks for the assistance
gilad
I have an i

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