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After upgrading to Ubuntu 11.10 I have found that my "open with gedit" right click menu in the file manager does not work unless I use it twice. Does anyone know why this might be?

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You should file this as a bug on LaunchPad by running ubuntu-bug nautilus –  Oli Oct 16 '11 at 20:37
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This is still present, and now it's Ubuntu 13.04. –  Shomz Apr 27 '13 at 1:16
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Yep! This is a bug. I've reported it quite a while ago.

https://bugs.launchpad.net/ubuntu/+source/gedit/+bug/827414 is the bug report. At the end of September they showed a fix committed, but it's still acting the same way for me. I need to test a little more and respond to the thread.

Check which versions of of unity, unity-lens-files, and unity-lens-applications you have installed. They should be newer than 4.20.0, 0.6.10, and 0.4.12, respectively.

paul@venus:~$ sudo dpkg -l unity unity-lens-files unity-lens-applications
Desired=Unknown/Install/Remove/Purge/Hold
| Status=Not/Inst/Conf-files/Unpacked/halF-conf/Half-inst/trig-aWait/Trig-pend
|/ Err?=(none)/Reinst-required (Status,Err: uppercase=bad)
||/ Name                             Version                          Description
+++-================================-================================-================================================================================
ii  unity                            4.22.0-0ubuntu3                  Interface designed for efficiency of space and interaction.
ii  unity-lens-applications          0.4.12-0ubuntu2                  Application lens for unity
ii  unity-lens-files                 0.6.12-0ubuntu1                  File lens for unity
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