[jeremyw]

So, running calibre from the command line works. The device is recognized. Here's the text:

[jeremywjw-macbook ~]$ calibre
link  hasn't been detected!
link  hasn't been detected!
2008-12-18 14:04:04.628 python[6306:71f] No identifier for bundle at path '/Users/jeremyw/Library/Application Support/SIMBL/Plugins/OnePasswdCamino.bundle'
2008-12-18 14:04:04.629 python[6306:71f] No identifier for bundle at path '/Users/jeremyw/Library/Application Support/SIMBL/Plugins/OnePasswdDEVONagent.bundle'
2008-12-18 14:04:04.631 python[6306:71f] No identifier for bundle at path '/Users/jeremyw/Library/Application Support/SIMBL/Plugins/OnePasswdNNW.bundle'
2008-12-18 14:04:04.631 python[6306:71f] No identifier for bundle at path '/Users/jeremyw/Library/Application Support/SIMBL/Plugins/OnePasswdOmniWeb.bundle'
2008-12-18 14:04:04.632 python[6306:71f] No identifier for bundle at path '/Users/jeremyw/Library/Application Support/SIMBL/Plugins/OnePasswdSafari.bundle'

So, I thought maybe there's something missing from the PATH when I launch from the gui, but my environment.plist contains a PATH reference which resolves to:

/sw/sbin:/bin:/sbin:/usr/bin:/usr/local/bin:/Library/MySql/bin:/Users/jeremyw/bin:/Developer/Tools:/usr/X11R6/bin:/usr/local/oracle/product/10.2.0/client_1/bin

Various scripts in .bash_profile and .bashrc append the following values to the PATH:

/usr/sbin:/usr/X11/bin:/opt/local/bin:/opt/local/apache2/bin:/usr/local/bin:/usr/local/mysql/bin:/Users/jeremyw/bin:/Developer/Tools:/usr/X11R6/bin:/usr/local/instantclient:/usr/local/sbin

so I couldn't see any cause for the latter to be successful instead of the former. BUT, if I do this:

[jeremywjw-macbook ~]$ export PATH=/sw/sbin:/bin:/sbin:/usr/bin:/usr/local/bin:/Library/MySql/bin:/Users/jeremyw/bin:/Developer/Tools:/usr/X11R6/bin:/usr/local/oracle/product/10.2.0/client_1/bin
[jeremywjw-macbook ~]$ which calibre
/usr/bin/calibre
[jeremywjw-macbook ~]$ calibre
link  hasn't been detected!
link  hasn't been detected!
2008-12-18 14:10:22.668 python[6446:71f] No identifier for bundle at path '/Users/jeremyw/Library/Application Support/SIMBL/Plugins/OnePasswdCamino.bundle'
2008-12-18 14:10:22.669 python[6446:71f] No identifier for bundle at path '/Users/jeremyw/Library/Application Support/SIMBL/Plugins/OnePasswdDEVONagent.bundle'
2008-12-18 14:10:22.669 python[6446:71f] No identifier for bundle at path '/Users/jeremyw/Library/Application Support/SIMBL/Plugins/OnePasswdNNW.bundle'
2008-12-18 14:10:22.670 python[6446:71f] No identifier for bundle at path '/Users/jeremyw/Library/Application Support/SIMBL/Plugins/OnePasswdOmniWeb.bundle'
2008-12-18 14:10:22.670 python[6446:71f] No identifier for bundle at path '/Users/jeremyw/Library/Application Support/SIMBL/Plugins/OnePasswdSafari.bundle'
Unable to open device
Traceback (most recent call last):
  File "calibre/gui2/device.pyo", line 59, in detect_device
  File "calibre/devices/prs505/driver.pyo", line 271, in open
  File "calibre/devices/prs505/driver.pyo", line 134, in open_osx
  File "calibre/devices/prs505/driver.pyo", line 112, in get_osx_mountpoints
  File "subprocess.pyo", line 595, in __init__
  File "subprocess.pyo", line 1106, in _execute_child
OSError: [Errno 2] No such file or directory

It fails. So some experimentation revealed that appending /usr/sbin to my environment.plist fixes the problem. So, this is a nominal solution for non-recognized devices for users with customized environment.plist files, but I suspect get_osx_mountpoints should probably just reference the appropriate binary by specific path. (I suspect diskutil, but you know better than I).

Thanks for the pointer! Let me know if I can help your project any further; it's a fantastically useful app (especially now that I don't have to run a VM windows to play with it).