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I've been working on this for a few days now, and it's become quite a head-scratcher. I'm attempting to connect a SATO CL408e printer (it's a label printer) to it. Because the Pi lacks an LPT port, I used a parallel -> usb converter. The Pi sees the printer fine.

Now the weird part is that when I send a job (basically a text file containing instructions for the printer) using lpr it will not print unless I power-cycle the printer, then it prints instantly. Then the next job won't print. Always says "waiting for printer to become available."

Here's what happens when I have a job waiting in the queue:

pi@raspberrypi ~ $ lpstat -t

scheduler is running
system default destination: sato
device for sato: usb://SATO/CL408e
sato accepting requests since Fri 14 Jun 2013 17:05:35 UTC
printer sato now printing sato-20. enabled since Fri 14 Jun 2013 17:05:35 UTC
Waiting for printer to become available.
sato-20 pi 1024 Fri 14 Jun 2013 17:05:35 UTC

When when I power cycle it prints and shows:
pi@raspberrypi ~ $ lpstat -t

scheduler is running
system default destination: sato
device for sato: usb://SATO/CL408e
sato accepting requests since Fri 14 Jun 2013 17:05:55 UTC
printer sato is idle. enabled since Fri 14 Jun 2013 17:05:55 UTC
Sending data to printer.

Send another job and again it's stuck: pi@raspberrypi ~ $ lpr shiplabl.txt
pi@raspberrypi ~ $ lpstat -t

scheduler is running
system default destination: sato
device for sato: usb://SATO/CL408e
sato accepting requests since Fri 14 Jun 2013 17:06:04 UTC
printer sato now printing sato-21. enabled since Fri 14 Jun 2013 17:06:04 UTC
Waiting for printer to become available.
sato-21 pi 1024 Fri 14 Jun 2013 17:06:04 UTC

I'm using the generic text-only driver because it's the only driver it will accept other than the "raw" one (I've tried both). Running the latest (1.5.8) version of CUPS. No errors are shown in the log.

Anyone have any ideas?

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I'm going to guess something funky in the USB-to-LPT converter. Three things to try to help narrow it down: Use a USB printer with the Pi (any printer will do) and verify that it can print normally. Then try your label printer on a PC through the USB-to-LPT converter (with the same CUPS software & such if you can manage it). Optionally also try your label printer on that same PC via a parallel port to rule out the printer being funky. –  voretaq7 Jun 14 '13 at 18:27
    
CUPS isn't available for windows - it's the *nix printing interface, so I won't be able to test that. The cable does, however, work perfectly in Windows. The printer also works with a parallel connection. I think I'm going to try another cable and see what happens. That is, when I order it. –  Nathan C Jun 14 '13 at 18:39
    
@NathanC Windows since Vista/2008 speaks IPP directly, so it'll happily talk to your CUPS server. –  Michael Hampton Jun 14 '13 at 18:46
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