diff --git a/client/plugins/init.client.js b/client/plugins/init.client.js
index bf3a6734..bdc1b2f5 100644
--- a/client/plugins/init.client.js
+++ b/client/plugins/init.client.js
@@ -1,4 +1,5 @@
 import Vue from 'vue'
+import Path from 'path'
 import vClickOutside from 'v-click-outside'
 import { formatDistance, format, addDays, isDate } from 'date-fns'
 
@@ -119,20 +120,36 @@ Vue.prototype.$sanitizeFilename = (input, colonReplacement = ' - ') => {
   if (typeof input !== 'string') {
     return false
   }
+
+  // Max is actually 255-260 for windows but this leaves padding incase ext wasnt put on yet
+  const MAX_FILENAME_LEN = 240
+
   var replacement = ''
-  var illegalRe = /[\/\?<>\\:\*\|"]/g;
-  var controlRe = /[\x00-\x1f\x80-\x9f]/g;
-  var reservedRe = /^\.+$/;
-  var windowsReservedRe = /^(con|prn|aux|nul|com[0-9]|lpt[0-9])(\..*)?$/i;
-  var windowsTrailingRe = /[\. ]+$/;
+  var illegalRe = /[\/\?<>\\:\*\|"]/g
+  var controlRe = /[\x00-\x1f\x80-\x9f]/g
+  var reservedRe = /^\.+$/
+  var windowsReservedRe = /^(con|prn|aux|nul|com[0-9]|lpt[0-9])(\..*)?$/i
+  var windowsTrailingRe = /[\. ]+$/
+  var lineBreaks = /[\n\r]/g
 
   var sanitized = input
     .replace(':', colonReplacement) // Replace first occurrence of a colon
     .replace(illegalRe, replacement)
     .replace(controlRe, replacement)
     .replace(reservedRe, replacement)
+    .replace(lineBreaks, replacement)
     .replace(windowsReservedRe, replacement)
-    .replace(windowsTrailingRe, replacement);
+    .replace(windowsTrailingRe, replacement)
+
+
+  if (sanitized.length > MAX_FILENAME_LEN) {
+    var lenToRemove = sanitized.length - MAX_FILENAME_LEN
+    var ext = Path.extname(sanitized)
+    var basename = Path.basename(sanitized, ext)
+    basename = basename.slice(0, basename.length - lenToRemove)
+    sanitized = basename + ext
+  }
+
   return sanitized
 }
 
diff --git a/server/objects/PodcastEpisodeDownload.js b/server/objects/PodcastEpisodeDownload.js
index fd083abf..09b9d71d 100644
--- a/server/objects/PodcastEpisodeDownload.js
+++ b/server/objects/PodcastEpisodeDownload.js
@@ -21,7 +21,6 @@ class PodcastEpisodeDownload {
   toJSONForClient() {
     return {
       id: this.id,
-      // podcastEpisode: this.podcastEpisode ? this.podcastEpisode.toJSON() : null,
       episodeDisplayTitle: this.podcastEpisode ? this.podcastEpisode.bestFilename : null,
       url: this.url,
       libraryItemId: this.libraryItem ? this.libraryItem.id : null,
diff --git a/server/utils/fileUtils.js b/server/utils/fileUtils.js
index a0db36ee..b2b0a85b 100644
--- a/server/utils/fileUtils.js
+++ b/server/utils/fileUtils.js
@@ -181,19 +181,33 @@ module.exports.sanitizeFilename = (filename, colonReplacement = ' - ') => {
     return false
   }
 
+  // Max is actually 255-260 for windows but this leaves padding incase ext wasnt put on yet
+  const MAX_FILENAME_LEN = 240
+
   var replacement = ''
-  var illegalRe = /[\/\?<>\\:\*\|"]/g;
-  var controlRe = /[\x00-\x1f\x80-\x9f]/g;
-  var reservedRe = /^\.+$/;
-  var windowsReservedRe = /^(con|prn|aux|nul|com[0-9]|lpt[0-9])(\..*)?$/i;
-  var windowsTrailingRe = /[\. ]+$/;
+  var illegalRe = /[\/\?<>\\:\*\|"]/g
+  var controlRe = /[\x00-\x1f\x80-\x9f]/g
+  var reservedRe = /^\.+$/
+  var windowsReservedRe = /^(con|prn|aux|nul|com[0-9]|lpt[0-9])(\..*)?$/i
+  var windowsTrailingRe = /[\. ]+$/
+  var lineBreaks = /[\n\r]/g
 
   sanitized = filename
     .replace(':', colonReplacement) // Replace first occurrence of a colon
     .replace(illegalRe, replacement)
     .replace(controlRe, replacement)
     .replace(reservedRe, replacement)
+    .replace(lineBreaks, replacement)
     .replace(windowsReservedRe, replacement)
-    .replace(windowsTrailingRe, replacement);
+    .replace(windowsTrailingRe, replacement)
+
+  if (sanitized.length > MAX_FILENAME_LEN) {
+    var lenToRemove = sanitized.length - MAX_FILENAME_LEN
+    var ext = Path.extname(sanitized)
+    var basename = Path.basename(sanitized, ext)
+    basename = basename.slice(0, basename.length - lenToRemove)
+    sanitized = basename + ext
+  }
+
   return sanitized
 }
\ No newline at end of file