diff --git a/server/objects/LibraryItem.js b/server/objects/LibraryItem.js
index 95674288..a6d620f8 100644
--- a/server/objects/LibraryItem.js
+++ b/server/objects/LibraryItem.js
@@ -197,9 +197,15 @@ class LibraryItem {
       if (key === 'libraryFiles') {
         this.libraryFiles = payload.libraryFiles.map(lf => lf.clone())
 
-        // Use first image library file as cover
-        const firstImageFile = this.libraryFiles.find(lf => lf.fileType === 'image')
-        if (firstImageFile) this.media.coverPath = firstImageFile.metadata.path
+        // Set cover image
+        const imageFiles = this.libraryFiles.filter(lf => lf.fileType === 'image')
+        const coverMatch = imageFiles.find(iFile => /\/cover\.[^.\/]*$/.test(iFile.metadata.path))
+        if (coverMatch) {
+          this.media.coverPath = coverMatch.metadata.path
+        } else if (imageFiles.length) {
+          this.media.coverPath = imageFiles[0].metadata.path
+        }
+
       } else if (this[key] !== undefined && key !== 'media') {
         this[key] = payload[key]
       }
@@ -444,8 +450,14 @@ class LibraryItem {
     // Set cover image if not set
     const imageFiles = this.libraryFiles.filter(lf => lf.fileType === 'image')
     if (imageFiles.length && !this.media.coverPath) {
-      this.media.coverPath = imageFiles[0].metadata.path
-      Logger.debug('[LibraryItem] Set media cover path', this.media.coverPath)
+      // attempt to find a file called cover.<ext> otherwise just fall back to the first image found
+      const coverMatch = imageFiles.find(iFile => /\/cover\.[^.\/]*$/.test(iFile.metadata.path))
+      if (coverMatch) {
+        this.media.coverPath = coverMatch.metadata.path
+      } else {
+        this.media.coverPath = imageFiles[0].metadata.path
+      }
+      Logger.info('[LibraryItem] Set media cover path', this.media.coverPath)
       hasUpdated = true
     }