Can't print more than one job at a time.

I am trying to print to either a HP DesignJet 1055cm plotter or a HP LaserJet 5000N. I can't send more than one file at a time. If i don't wait until the current job starts printing, the next one won't print. For example if I sent five files one right after the other, I might get 1, 4 and 5. I don't think it's a printer problem because it happens on two different printers, and it doesn't happen when I print from my PC. Any idea what could cause this?

My work around is to put all the jobs "on hold" in the print settings or just "stop jobs" on the printer window.
Then I click on each print job in the que and let them print one at a time. This way I can at least quit the program and move onto the next thing.

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