diff --git a/cli/src/main/groovy/com/jdbernard/wdiwtlt/cli/CommandLineInterface.groovy b/cli/src/main/groovy/com/jdbernard/wdiwtlt/cli/CommandLineInterface.groovy
index 78392c5..8efcc85 100644
--- a/cli/src/main/groovy/com/jdbernard/wdiwtlt/cli/CommandLineInterface.groovy
+++ b/cli/src/main/groovy/com/jdbernard/wdiwtlt/cli/CommandLineInterface.groovy
@@ -327,6 +327,7 @@ Configuration:
             case 'remove':      return processRemove(rest, currentSelection)
             case 'tag':         return processTag(rest, currentSelection)
             case 'untag':       return processTag(rest, currentSelection, false)
+            case 'randomize':   return processRandomize(rest)
             case 'clear':       return processClear(rest)
             case 'pause':       return processPause()
             case 'stop':        return processStop()
@@ -566,6 +567,44 @@ Configuration:
         msg "Removed ${toRemove.size()} files."
         return toRemove }
 
+    private def processRandomize(String options) {
+        Playlist p
+        switch (options) {
+            case 'queue': p = playQueue; break
+            case ~/playlist (.+)/:
+                String idOrName = Matcher.lastMatcher[0][1]
+                p = getExactlyOne(Playlist, idOrName)
+                break
+            default: invalidOptionsErr('randomize') }
+
+        library.randomizePlaylist(p) }
+
+    private def processReorder(String options) {
+        Playlist p
+        int startingIdx = -1
+
+        String[] parts = options.split(/ as | starting at /)
+
+        if (parts.size() < 2) invalidOptionsErr('reorder');
+
+        // Playlist or queue?
+        switch (parts[0].trim()) {
+            case 'queue': p = playQueue; break
+            case ~/playlist (.+)/:
+                String idOrName = Matcher.lastMatcher[0][1]
+                p = getExactlyOne(Playlist, idOrName)
+                break
+            default: invalidOptionsErr('reorder') }
+
+        // What files in order?
+        List<MediaFile> playlistFiles = library.getMediaFilesWhere(playlistId: p.id)
+        String[] fileIds = parts[1].split(/[,;\s]/)
+        List<MediaFile> files = fileIds.collect { library.getMediaFileById(it) }
+                                  .findAll()
+
+        if (parts.size() == 3) startingIdx = safeToInteger(parts[2])
+    }
+
     private def processTag(String options, List<Model> selection,
     boolean addTags = true) {
 
@@ -722,6 +761,8 @@ Available commands:
     enqueue     Enqueue requested media to the end of the play queue.
     add         Append requested media to the end of a playlist.
     remove      Remove requested from the play queue or playlist.
+    randomize   Re-order the files in a play queue or a playlist randomly.
+    reorder     Re-order the files in a play queue or a playlist.
     tag         Associate tags with requested media.
     untag       Remove the association between the given tags and media.
     clear       Clear the selection, play queue, playlist, or screen.
@@ -900,7 +941,36 @@ remove <select-criteria> from playlist <id | name>
 
 """
 
-            // tag
+            // RANDOMIZE
+            // --------------
+            case 'randomize': return """\
+randomize queue
+randomize playlist <id | name>
+
+    Randomize the order of all elements in either the current play queue or the
+    named playlist.
+
+"""
+
+            // REORDER
+            // --------------
+            case 'reorder': return """\
+reorder queue move <file id | name> to <position>
+reorder playlist <id | name> move <file id | name> to <position>
+
+    Move a single file from  its current position to the named position in the
+    play queue/playlist.
+
+reorder queue as <file id>... starting at <position>
+reorder playlist <id | name> as <file id>... starting at <position>
+
+    Take a set of files in the playlist, reorder them into given order, and
+    move them to the given starting position (defaults to the end of the
+    playlist)
+
+"""
+
+            // TAG
             // --------------
             case 'tag': return """\
 tag <tag>...
@@ -1053,6 +1123,14 @@ Playlist and Queue Management:
     create bookmark <id | name>
     update bookmark <id | name>
 
+    randomize queue
+    randomize playlist
+
+    reorder queue move <file id | name> to <position>
+    reorder playlist <id | name> move <file id | name> to <position>
+    reorder queue as <file id>...
+    reorder playlist <id | name> as <file id>...
+
     clear
     clear queue
     clear selection