diff --git a/Casks/plex-media-server.rb b/Casks/plex-media-server.rb
index 94d526950a6..d2bc58236de 100644
--- a/Casks/plex-media-server.rb
+++ b/Casks/plex-media-server.rb
@@ -1,10 +1,10 @@
 cask 'plex-media-server' do
-  version '1.4.3.3433-03e4cfa35'
-  sha256 '0b543f12a8a0aeecc89fe39b9cf300bd2acf3bd00ef46c3e02ccb6e2fb91a06f'
+  version '1.4.4.3495-edef59192'
+  sha256 '7a7a0b90e4245e05a012a1c10f55b7de7b6d146a7004d60f7b7c2692d34057f7'
 
   url "https://downloads.plex.tv/plex-media-server/#{version}/PlexMediaServer-#{version}-OSX.zip"
   appcast 'https://plex.tv/api/downloads/1.json',
-          checkpoint: '4f407637442bd7e311732eca7ebf8fca7f9e7b05edba7721a09edc353ef852ec'
+          checkpoint: 'c3c840fec0acc30d142b2c846c1b2771b111372f67d7476f53e68337b860ba0d'
   name 'Plex Media Server'
   homepage 'https://www.plex.tv/'