@petch: In the POL Console.
@Quentin: I believe you're correct. The reason I'm confused is because my SD Card has exec permissions in actual use, it just appears POL isn't recognizing it at launch (SD is sdb1):
(trusty)andrew@localhost:~$ mount | grep sda1
/dev/sda1 on / type ext4 (rw,relatime,commit=600,data=ordered)
(trusty)andrew@localhost:~$ mount | grep sdb1
/dev/sdb1 on /mnt/external type ext4 (rw,relatime,data=ordered)
Just for clarification, the .PlayOnLinux folder is located on sda1 and so are all of the other contents, except for the wineprefix folder (where Office is installed), which is a symlink to a folder on sdb1 as sda1 has limited storage.
Checking Office's logs, everything has been working perfectly and there have been no errors (in the logs, never noticed any during normal use outside of what was logged) after I ran sudo apt-get install libp11-kit-gnome-keyring:i386, something I didn't have it installed by default.
This is a fairly jury-rigged linux installation as is, being that it's through Crouton on a Chromebook. I'm just trying to disable the message to get rid of the minor annoyance of having to press OK every time I open a document. I was just seeing if there was an easy way to do it. If it's not possible, it's nothing to stress out about. It's been amazing to only carry around this little inexpensive laptop and still be able to do everything I normally do (Skype, even WoW on occasion) as I travel and work on my thesis.
So, I'm not sure where to go from here but thanks for your responses!