Installation macOS (Terminal) - trakt/Plex-Trakt-Scrobbler GitHub Wiki
Table of Contents:
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Download the latest release of the WebTools plugin from here 
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Extract the downloaded ZIP archive unzip WebTools.bundle.zip 
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Copy the WebTools.bundlefolder to thePlug-insfolder on your system:cp -r WebTools.bundle ~/Library/Application\ Support/Plex\ Media\ Server/Plug-ins/ 
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Restart Plex Media Server   
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Open the WebTools interface at http://<System IP>:33400orhttp://<System IP>:33443and login with your Plex.tv account 
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Open the "Unsupported AppStore" module:  
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Find the "Trakt.tv" plugin listed under "Application", and click "Install":  
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The "Trakt.tv" plugin should appear at Settings > Manage > Pluginsin about one minute. (but can vary depending on the speed of your system)If the plugin doesn't appear after waiting a few minutes: the plugin may not be installed correctly, or has crashed on startup. Please post an issue here with the latest plugin log file for support. 
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Configure the plugin by clicking on the plugin settings button at Settings > Manage > Plugins: 
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Download the latest release of the Trakt.tv plugin - 
Stable (recommended) curl "https://github.com/trakt/Plex-Trakt-Scrobbler/archive/master.zip" -Lo Plex-Trakt-Scrobbler.zip
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Beta curl "https://github.com/trakt/Plex-Trakt-Scrobbler/archive/beta.zip" -Lo Plex-Trakt-Scrobbler.zip
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Development curl "https://github.com/trakt/Plex-Trakt-Scrobbler/archive/develop.zip" -Lo Plex-Trakt-Scrobbler.zip
 
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Extract the downloaded ZIP archive unzip Plex-Trakt-Scrobbler.zip 
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Copy the Trakttv.bundlefolder to thePlug-insfolder on your system:sudo cp -r Plex-Trakt-Scrobbler-*/Trakttv.bundle ~/Library/Application\ Support/Plex\ Media\ Server/Plug-ins/ 
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Restart Plex Media Server   
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The "Trakt.tv" plugin should appear at Settings > Manage > Pluginsin about one minute. (but can vary depending on the speed of your system)If the plugin doesn't appear after waiting a few minutes: the plugin may not be installed correctly, or has crashed on startup. Please post an issue here with the latest plugin log file for support. 
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Configure the plugin by clicking on the plugin settings button at Settings > Manage > Plugins: 
Copying the plugin into the Plug-ins folder may result in incorrect permissions on the Trakttv.bundle folder, permissions can be fixed with the following steps:
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Determine the user + group which has ownership of Plex Media Server: stat -f '%u:%g' ~/Library/Application\ Support/Plex\ Media\ Server 
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Update ownership of the Trakttv.bundlefoldersudo chown -R <uid>:<gid> ~/Library/Application\ Support/Plex\ Media\ Server/Plug-ins/Trakttv.bundle (Replace <uid>:<gid>with the output from step 1)
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Update permissions on the Trakttv.bundlefoldersudo chmod -R 770 ~/Library/Application\ Support/Plex\ Media\ Server/Plug-ins/Trakttv.bundle