I have installed a new Acer Chromebook and connected to an HP6500 printer via a USB cable. The computer recognizes the printer and does print one job after start up, but it queues all following jobs. It requires a computer re-start inorder to print another job.
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The print driver is not hearing back from the printer that the job was completed.
Try a different USB cable.
Try a different USB port.
Try an updated HP Printer Driver for your Chromebook.
Finally, hook up the printer to a different (possibly Windows) machine and ensure the printer is working.