diff --git a/apps/playlist.c b/apps/playlist.c
index c64fc229b5..3eb0949cc2 100644
--- a/apps/playlist.c
+++ b/apps/playlist.c
@@ -855,14 +855,14 @@ static int directory_search_callback(char* filename, void* context)
 
     if (insert_pos < 0)
         return -1;
-    
+
     (c->count)++;
-    
-    /* Make sure tracks are inserted in correct order if user requests
-       INSERT_FIRST */
-    if (c->position == PLAYLIST_INSERT_FIRST || c->position >= 0)
-        c->position = insert_pos + 1;
-    
+
+    /* After first INSERT_FIRST switch to INSERT so that all the
+    rest of the tracks get inserted one after the other */
+    if (c->position == PLAYLIST_INSERT_FIRST)
+        c->position = PLAYLIST_INSERT;
+
     if (((c->count)%PLAYLIST_DISPLAY_COUNT) == 0)
     {
         unsigned char* count_str;
@@ -3179,7 +3179,7 @@ int playlist_insert_playlist(struct playlist_info* playlist, const char *filenam
                 result = -1;
                 break;
             }
-            
+
             insert_pos = add_track_to_playlist(playlist, trackname, position,
                 queue, -1);
 
@@ -3189,13 +3189,13 @@ int playlist_insert_playlist(struct playlist_info* playlist, const char *filenam
                 break;
             }
 
-            /* Make sure tracks are inserted in correct order if user
-               requests INSERT_FIRST */
-            if (position == PLAYLIST_INSERT_FIRST || position >= 0)
-                position = insert_pos + 1;
+            /* After first INSERT_FIRST switch to INSERT so that all the
+            rest of the tracks get inserted one after the other */
+            if (position == PLAYLIST_INSERT_FIRST)
+                position = PLAYLIST_INSERT;
 
             count++;
-            
+
             if ((count%PLAYLIST_DISPLAY_COUNT) == 0)
             {
                 display_playlist_count(count, count_str, false);
diff --git a/apps/tagtree.c b/apps/tagtree.c
index f006baa581..97e0c67b62 100644
--- a/apps/tagtree.c
+++ b/apps/tagtree.c
@@ -2018,18 +2018,9 @@ static bool insert_all_playlist(struct tree_context *c, int position, bool queue
         }
     }
 
-    if (position == PLAYLIST_INSERT_FIRST)
-    {
-        from = c->filesindir - 1;
-        to = -1;
-        direction = -1;
-    }
-    else
-    {
-        from = 0;
-        to = c->filesindir;
-        direction = 1;
-    }
+    from = 0;
+    to = c->filesindir;
+    direction = 1;
 
     for (i = from; i != to; i += direction)
     {
@@ -2049,6 +2040,11 @@ static bool insert_all_playlist(struct tree_context *c, int position, bool queue
             break;
         }
         yield();
+
+        if (position == PLAYLIST_INSERT_FIRST)
+        {
+            position = PLAYLIST_INSERT;
+        }
     }
     playlist_sync(NULL);
     tagcache_search_finish(&tcs);