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It sounds like you may have, perhaps inadvertently, connected the line to the shape. Is the line snapping to the center of the image before it disappears? If OG thinks a line is a connector, it stops drawing it at the edge of a shape. If the connection is intentional, this thread might be useful:

http://forums.omnigroup.com/showthread.php?t=21168

If you didn't intend to connect the line to the image, try holding the option key while drawing or adjusting the line.

Last edited by john.gersh; 2012-01-27 at 04:56 AM..