You can click the pillow installer over and over again it will not break anything. Can you post your pillow log (terminal output) after it installs? I have heard of someone having issues and they installed xcode command line tools then reinstalled pillow by clicking the button and it fixed their specific issue. Without any type of log after the pillow install I cannot debug it. There should be a list of supported dependencies that are installed upon successful installation in the log. There is a link here for command line tools:
https://forums.plex.tv/topic/108332-openplex-osx-app/page-8
I did the process again from the top and this is the Console log when I chose the theme and pressed Pillow
23/06/14 08:42:49,000 kernel[0]: Intego Uninstall (map: 0xffffff8036bb5b40) triggered DYLD shared region unnest for map: 0xffffff8036bb5b40, region 0x7fff92000000->0x7fff92200000. While not abnormal for debuggers, this increases system memory footprint until the target exits.
23/06/14 08:42:50,383 Intego Uninstaller[7801]: Activity on Intego folders ((
"/Applications/PlexConnect/.git/objects/pack/"
))- delaying uninstall detection.
23/06/14 08:42:52,453 Intego Uninstaller[7801]: No applications seem to have been manually uninstalled.
23/06/14 08:43:12,550 Intego Uninstaller[7809]: Activity on Intego folders ((
"/Applications/PlexConnect/assets/templates/plex/xml/Library/",
"/Applications/PlexConnect/assets/templates/plex/xml/",
"/Applications/PlexConnect/assets/templates/plex/xml/Movie/ByFolder/",
"/Applications/PlexConnect/assets/templates/plex/xml/Movie/"
))- delaying uninstall detection.
23/06/14 08:43:12,652 Intego Uninstaller[7809]: Activity on Intego folders ((
"/Applications/PlexConnect/assets/templates/plex/xml/Movie/Directory/",
"/Applications/PlexConnect/assets/templates/plex/xml/Movie/",
"/Applications/PlexConnect/assets/templates/plex/xml/Photo/",
"/Applications/PlexConnect/assets/templates/plex/xml/ScrobbleMenu/",
"/Applications/PlexConnect/assets/templates/plex/xml/SectionPreviews/",
"/Applications/PlexConnect/assets/templates/plex/xml/Settings/Template/",
"/Applications/PlexConnect/assets/templates/plex/xml/Settings/",
"/Applications/PlexConnect/assets/templates/plex/xml/",
"/Applications/PlexConnect/assets/templates/plex/xml/TVShow/Episode/",
"/Applications/PlexConnect/assets/templates/plex/xml/TVShow/Season/",
"/Applications/PlexConnect/assets/templates/plex/xml/TVShow/",
"/Applications/PlexConnect/assets/templates/",
"/Applications/PlexConnect/assets/templates/plexgrey/fonts/",
"/Applications/PlexConnect/assets/templates/plexgrey/fonts/OpenSans/",
"/Applications/PlexConnect/assets/templates/plexgrey/",
"/Applications/PlexConnect/assets/templates/plexgrey/images/"
))- delaying uninstall detection.
23/06/14 08:43:12,753 Intego Uninstaller[7809]: Activity on Intego folders ((
"/Applications/PlexConnect/assets/templates/plexgrey/images/backgrounds/",
"/Applications/PlexConnect/assets/templates/plexgrey/images/custom/",
"/Applications/PlexConnect/assets/templates/plexgrey/images/flow/",
"/Applications/PlexConnect/assets/templates/plexgrey/images/",
"/Applications/PlexConnect/assets/templates/plexgrey/images/icons/",
"/Applications/PlexConnect/assets/templates/plexgrey/",
"/Applications/PlexConnect/assets/templates/plexgrey/xml/Artwork/",
"/Applications/PlexConnect/assets/templates/plexgrey/xml/Channel/",
"/Applications/PlexConnect/assets/templates/plexgrey/xml/Directory/",
"/Applications/PlexConnect/assets/templates/plexgrey/xml/HomeVideo/ByFolder/",
"/Applications/PlexConnect/assets/templates/plexgrey/xml/HomeVideo/Directory/",
"/Applications/PlexConnect/assets/templates/plexgrey/xml/HomeVideo/",
"/Applications/PlexConnect/assets/templates/plexgrey/xml/Library/",
"/Applications/PlexConnect/assets/templates/plexgrey/xml/Movie/ByFolder/",
"/Applications/PlexConnect/assets/templates/plexgrey/xml/Movie/Directory/",
"/Applications/PlexConnect/assets/templates/plexgrey/xml/Movie/",
"/Applications/PlexConnect/assets/templates/plexgrey/xml/Photo/",
"/Applications/PlexConnect/assets/templates/plexgrey/xml/ScrobbleMenu/",
"/Applications/PlexConnect/assets/templates/plexgrey/xml/SectionPreviews/",
"/Applications/PlexConnect/assets/templates/plexgrey/xml/Settings/",
"/Applications/PlexConnect/assets/templates/plexgrey/xml/",
"/Applications/PlexConnect/assets/templates/plexgrey/xml/TVShow/Episode/",
"/Applications/PlexConnect/assets/templates/plexgrey/xml/TVShow/Season/",
"/Applications/PlexConnect/assets/templates/plexgrey/xml/TVShow/",
"/Applications/PlexConnect/assets/",
"/Applications/PlexConnect/assets/thumbnails/",
"/Applications/PlexConnect/",
"/Applications/PlexConnect/support/OSX/Pillow Installer/",
"/Applications/PlexConnect/support/OSX/",
"/Applications/PlexConnect/support/",
"/Applications/PlexConnect/support/Windows/",
"/Applications/PlexConnect/.git/"
))- delaying uninstall detection.
23/06/14 08:43:12,914 Intego Uninstaller[7809]: Activity on Intego folders ((
"/Applications/",
"/Applications/PlexConnect/",
"/Applications/PlexConnect/update/",
"/Applications/onlytemp/",
"/Applications/onlytemp/PlexConnect/",
"/Applications/onlytemp/PlexConnect/.git/refs/",
"/Applications/onlytemp/PlexConnect/.git/hooks/",
"/Applications/onlytemp/PlexConnect/.git/info/",
"/Applications/onlytemp/PlexConnect/.git/objects/",
"/Applications/onlytemp/PlexConnect/.git/"
))- delaying uninstall detection.
23/06/14 08:43:12,988 Intego Uninstaller[7809]: Error loading /Library/ScriptingAdditions/Adobe Unit Types.osax/Contents/MacOS/Adobe Unit Types: dlopen(/Library/ScriptingAdditions/Adobe Unit Types.osax/Contents/MacOS/Adobe Unit Types, 262): no suitable image found. Did find:
/Library/ScriptingAdditions/Adobe Unit Types.osax/Contents/MacOS/Adobe Unit Types: no matching architecture in universal wrapper
23/06/14 08:43:12,990 Intego Uninstaller[7809]: Performance: Please update this scripting addition to supply a value for ThreadSafe for each event handler: "/Library/ScriptingAdditions/SIMBL.osax"
23/06/14 08:43:13,000 kernel[0]: Intego Uninstall (map: 0xffffff803623a2d0) triggered DYLD shared region unnest for map: 0xffffff803623a2d0, region 0x7fff92000000->0x7fff92200000. While not abnormal for debuggers, this increases system memory footprint until the target exits.
23/06/14 08:43:13,589 Intego Uninstaller[7809]: Activity on Intego folders ((
"/Applications/onlytemp/PlexConnect/.git/"
))- delaying uninstall detection.
23/06/14 08:43:14,471 Intego Uninstaller[7809]: Activity on Intego folders ((
"/Applications/onlytemp/PlexConnect/.git/objects/pack/"
))- delaying uninstall detection.
23/06/14 08:43:16,544 Intego Uninstaller[7809]: No applications seem to have been manually uninstalled.
23/06/14 08:43:28,292 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/onlytemp/PlexConnect/assets/templates/"
))- delaying uninstall detection.
23/06/14 08:43:28,403 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/onlytemp/PlexConnect/assets/templates/"
))- delaying uninstall detection.
23/06/14 08:43:28,502 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/onlytemp/PlexConnect/assets/templates/"
))- delaying uninstall detection.
23/06/14 08:43:28,604 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/onlytemp/PlexConnect/assets/templates/"
))- delaying uninstall detection.
23/06/14 08:43:28,708 Intego Uninstaller[7822]: Error loading /Library/ScriptingAdditions/Adobe Unit Types.osax/Contents/MacOS/Adobe Unit Types: dlopen(/Library/ScriptingAdditions/Adobe Unit Types.osax/Contents/MacOS/Adobe Unit Types, 262): no suitable image found. Did find:
/Library/ScriptingAdditions/Adobe Unit Types.osax/Contents/MacOS/Adobe Unit Types: no matching architecture in universal wrapper
23/06/14 08:43:28,710 Intego Uninstaller[7822]: Performance: Please update this scripting addition to supply a value for ThreadSafe for each event handler: "/Library/ScriptingAdditions/SIMBL.osax"
23/06/14 08:43:28,000 kernel[0]: Intego Uninstall (map: 0xffffff80386291e0) triggered DYLD shared region unnest for map: 0xffffff80386291e0, region 0x7fff92000000->0x7fff92200000. While not abnormal for debuggers, this increases system memory footprint until the target exits.
23/06/14 08:43:28,968 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/onlytemp/PlexConnect/assets/templates/"
))- delaying uninstall detection.
23/06/14 08:43:28,976 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/onlytemp/PlexConnect/assets/templates/",
"/Applications/onlytemp/PlexConnect/assets/",
"/Applications/onlytemp/PlexConnect/assets/thumbnails/"
))- delaying uninstall detection.
23/06/14 08:43:28,976 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/onlytemp/PlexConnect/assets/thumbnails/"
))- delaying uninstall detection.
23/06/14 08:43:29,021 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/onlytemp/PlexConnect/assets/thumbnails/"
))- delaying uninstall detection.
23/06/14 08:43:29,125 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/onlytemp/PlexConnect/assets/thumbnails/"
))- delaying uninstall detection.
23/06/14 08:43:29,232 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/onlytemp/PlexConnect/assets/thumbnails/"
))- delaying uninstall detection.
23/06/14 08:43:29,332 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/onlytemp/PlexConnect/assets/thumbnails/",
"/Applications/onlytemp/PlexConnect/support/IOS_jailbreak/",
"/Applications/onlytemp/PlexConnect/support/OSX/",
"/Applications/onlytemp/PlexConnect/support/",
"/Applications/onlytemp/PlexConnect/support/aTV_jailbreak/",
"/Applications/onlytemp/PlexConnect/",
"/Applications/onlytemp/PlexConnect/update/",
"/Applications/onlytemp/PlexConnect/update/OSX/",
"/Applications/onlytemp/PlexConnect/update/OSX/Gradient/"
))- delaying uninstall detection.
23/06/14 08:43:29,435 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/onlytemp/PlexConnect/update/OSX/Gradient/",
"/Applications/onlytemp/PlexConnect/update/OSX/GradientMovies/",
"/Applications/onlytemp/PlexConnect/update/OSX/GradientTV/",
"/Applications/onlytemp/PlexConnect/update/OSX/Web Sharing.prefPane/",
"/Applications/onlytemp/PlexConnect/update/OSX/Web Sharing.prefPane/Contents/MacOS/",
"/Applications/onlytemp/PlexConnect/update/OSX/Web Sharing.prefPane/Contents/Resources/",
"/Applications/onlytemp/PlexConnect/update/OSX/Web Sharing.prefPane/Contents/Resources/en.lproj/",
"/Applications/onlytemp/PlexConnect/update/OSX/Web Sharing.prefPane/Contents/",
"/Applications/onlytemp/PlexConnect/update/OSX/Web Sharing.prefPane/Contents/_CodeSignature/",
"/Applications/onlytemp/PlexConnect/update/OSX/",
"/Applications/onlytemp/PlexConnect/update/OSX/thumbnails/"
))- delaying uninstall detection.
23/06/14 08:43:29,540 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/onlytemp/PlexConnect/update/OSX/thumbnails/",
"/Applications/onlytemp/PlexConnect/update/OSX/",
"/Applications/onlytemp/PlexConnect/.git/",
"/Applications/PlexConnect/update/OSX/Gradient/",
"/Applications/PlexConnect/update/OSX/GradientMovies/",
"/Applications/PlexConnect/update/OSX/GradientTV/",
"/Applications/PlexConnect/update/OSX/Web Sharing.prefPane/",
"/Applications/PlexConnect/update/OSX/Web Sharing.prefPane/Contents/_CodeSignature/",
"/Applications/PlexConnect/update/OSX/Web Sharing.prefPane/Contents/MacOS/",
"/Applications/PlexConnect/update/OSX/Web Sharing.prefPane/Contents/",
"/Applications/PlexConnect/update/OSX/Web Sharing.prefPane/Contents/Resources/en.lproj/",
"/Applications/PlexConnect/update/OSX/Web Sharing.prefPane/Contents/Resources/",
"/Applications/PlexConnect/update/OSX/"
))- delaying uninstall detection.
23/06/14 08:43:29,712 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/PlexConnect/update/OSX/",
"/Applications/PlexConnect/update/OSX/thumbnails/"
))- delaying uninstall detection.
23/06/14 08:43:29,930 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/PlexConnect/update/OSX/thumbnails/"
))- delaying uninstall detection.
23/06/14 08:43:30,030 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/PlexConnect/update/OSX/thumbnails/",
"/Applications/PlexConnect/update/OSX/",
"/Applications/onlytemp/PlexConnect/.git/",
"/Applications/onlytemp/PlexConnect/",
"/Applications/onlytemp/PlexConnect/assets/certificates/",
"/Applications/onlytemp/PlexConnect/assets/js/"
))- delaying uninstall detection.
23/06/14 08:43:30,030 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/onlytemp/PlexConnect/assets/locales/",
"/Applications/onlytemp/PlexConnect/assets/templates/",
"/Applications/onlytemp/PlexConnect/assets/",
"/Applications/onlytemp/PlexConnect/assets/thumbnails/"
))- delaying uninstall detection.
23/06/14 08:43:30,084 sudo[7826]: tommasoavati : TTY=unknown ; PWD=/ ; USER=root ; COMMAND=/usr/bin/install.bash
23/06/14 08:43:30,204 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/onlytemp/",
"/Applications/",
"/Applications/PlexConnect/update/OSX/"
))- delaying uninstall detection.
23/06/14 08:43:30,345 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/PlexConnect/update/OSX/"
))- delaying uninstall detection.
23/06/14 08:43:30,517 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/PlexConnect/update/OSX/"
))- delaying uninstall detection.
23/06/14 08:43:30,622 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/PlexConnect/update/OSX/"
))- delaying uninstall detection.
23/06/14 08:43:30,794 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/PlexConnect/update/OSX/"
))- delaying uninstall detection.
23/06/14 08:43:32,736 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/PlexConnect/update/OSX/"
))- delaying uninstall detection.
23/06/14 08:43:32,911 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/PlexConnect/update/OSX/"
))- delaying uninstall detection.
23/06/14 08:43:34,579 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/PlexConnect/update/OSX/"
))- delaying uninstall detection.
23/06/14 08:43:34,751 Intego Uninstaller[7822]: Activity on Intego folders ((
"/Applications/PlexConnect/update/OSX/"
))- delaying uninstall detection.
23/06/14 08:43:36,817 Intego Uninstaller[7822]: No applications seem to have been manually uninstalled.
23/06/14 08:43:42,213 Intego Uninstaller[7863]: Activity on Intego folders ((
"/Applications/PlexConnect/update/OSX/Web Sharing.prefPane/",
"/Applications/PlexConnect/update/OSX/Web Sharing.prefPane/Contents/_CodeSignature/",
"/Applications/PlexConnect/update/OSX/Web Sharing.prefPane/Contents/MacOS/",
"/Applications/PlexConnect/update/OSX/Web Sharing.prefPane/Contents/",
"/Applications/PlexConnect/update/OSX/Web Sharing.prefPane/Contents/Resources/en.lproj/",
"/Applications/PlexConnect/update/OSX/Web Sharing.prefPane/Contents/Resources/",
"/Applications/PlexConnect/update/OSX/"
))- delaying uninstall detection.
23/06/14 08:43:42,315 Intego Uninstaller[7863]: Activity on Intego folders ((
"/Applications/PlexConnect/update/OSX/"
))- delaying uninstall detection.
23/06/14 08:43:42,589 Intego Uninstaller[7863]: Error loading /Library/ScriptingAdditions/Adobe Unit Types.osax/Contents/MacOS/Adobe Unit Types: dlopen(/Library/ScriptingAdditions/Adobe Unit Types.osax/Contents/MacOS/Adobe Unit Types, 262): no suitable image found. Did find:
/Library/ScriptingAdditions/Adobe Unit Types.osax/Contents/MacOS/Adobe Unit Types: no matching architecture in universal wrapper
23/06/14 08:43:42,590 Intego Uninstaller[7863]: Performance: Please update this scripting addition to supply a value for ThreadSafe for each event handler: "/Library/ScriptingAdditions/SIMBL.osax"
23/06/14 08:43:42,000 kernel[0]: Intego Uninstall (map: 0xffffff8036bb5a50) triggered DYLD shared region unnest for map: 0xffffff8036bb5a50, region 0x7fff92000000->0x7fff92200000. While not abnormal for debuggers, this increases system memory footprint until the target exits.
23/06/14 08:43:43,687 Intego Uninstaller[7863]: Activity on Intego folders ((
"/Applications/PlexConnect/update/OSX/"
))- delaying uninstall detection.
23/06/14 08:43:45,738 sudo[8073]: tommasoavati : TTY=unknown ; PWD=/ ; USER=root ; COMMAND=/usr/bin/sudoersfix.bash
23/06/14 08:43:45,756 Intego Uninstaller[7863]: No applications seem to have been manually uninstalled.
23/06/14 08:43:59,959 osascript[8079]: Error loading /Library/ScriptingAdditions/Adobe Unit Types.osax/Contents/MacOS/Adobe Unit Types: dlopen(/Library/ScriptingAdditions/Adobe Unit Types.osax/Contents/MacOS/Adobe Unit Types, 262): no suitable image found. Did find:
/Library/ScriptingAdditions/Adobe Unit Types.osax/Contents/MacOS/Adobe Unit Types: no matching architecture in universal wrapper
23/06/14 08:43:59,961 osascript[8079]: Performance: Please update this scripting addition to supply a value for ThreadSafe for each event handler: "/Library/ScriptingAdditions/SIMBL.osax"
23/06/14 08:44:02,229 Terminal[8080]: Error loading /Library/ScriptingAdditions/Adobe Unit Types.osax/Contents/MacOS/Adobe Unit Types: dlopen(/Library/ScriptingAdditions/Adobe Unit Types.osax/Contents/MacOS/Adobe Unit Types, 262): no suitable image found. Did find:
/Library/ScriptingAdditions/Adobe Unit Types.osax/Contents/MacOS/Adobe Unit Types: no matching architecture in universal wrapper
23/06/14 08:44:02,233 Terminal[8080]: Performance: Please update this scripting addition to supply a value for ThreadSafe for each event handler: "/Library/ScriptingAdditions/SIMBL.osax"
23/06/14 08:44:02,000 kernel[0]: Terminal (map: 0xffffff80498d3960) triggered DYLD shared region unnest for map: 0xffffff80498d3960, region 0x7fff92000000->0x7fff92200000. While not abnormal for debuggers, this increases system memory footprint until the target exits.
23/06/14 08:44:02,606 System Events[8081]: .sdef warning for part of complex type 'any | number | boolean | date | list | record | text | data' used in suite 'Property List Suite': 'data' is not a valid type name.
23/06/14 08:44:02,607 System Events[8081]: .sdef warning for type 'text | missing value | any' attribute 'uniqueID' of class 'XML element' in suite 'XML Suite': AppleScript ID references may not work for this property because its type is not NSNumber- or NSString-derived.