diff --git a/src/db.c b/src/db.c
index 2eacaef3..8e11e9c5 100644
--- a/src/db.c
+++ b/src/db.c
@@ -1524,6 +1524,26 @@ db_files_get_count(void)
   return db_get_count("SELECT COUNT(*) FROM files f WHERE f.disabled = 0;");
 }
 
+int
+db_files_get_count_bypathpattern(char *path)
+{
+  char *query;
+  int count;
+
+  query = sqlite3_mprintf("SELECT COUNT(*) FROM files f WHERE f.path LIKE '%%%q';", path);
+  if (!query)
+    {
+      DPRINTF(E_LOG, L_DB, "Out of memory making count query string.\n");
+
+      return;
+    }
+
+  count = db_get_count(query);
+  sqlite3_free(query);
+
+  return count;
+}
+
 void
 db_files_update_songalbumid(void)
 {
diff --git a/src/db.h b/src/db.h
index 4e96d0e2..99bb9586 100644
--- a/src/db.h
+++ b/src/db.h
@@ -319,6 +319,9 @@ db_query_fetch_string_sort(struct query_params *qp, char **string, char **sortst
 int
 db_files_get_count(void);
 
+int
+db_files_get_count_bypathpattern(char *path);
+
 void
 db_files_update_songalbumid(void);
 
diff --git a/src/filescanner_m3u.c b/src/filescanner_m3u.c
index bd90b297..0031cfb4 100644
--- a/src/filescanner_m3u.c
+++ b/src/filescanner_m3u.c
@@ -171,17 +171,34 @@ scan_m3u_playlist(char *file, time_t mtime)
 	        buf[i] = '/';
 	    }
 
-	  entry = buf;
-	  while (entry && !(mfi_id = db_file_id_bypathpattern(entry)))
+          /* Now search for the library item where the path has closest match to playlist item */
+          /* Succes is when we find an unambiguous match, or when we no longer can expand the  */
+          /* the path to refine our search.                                                    */
+	  entry = NULL;
+	  do
 	    {
-	      DPRINTF(E_DBG, L_SCAN, "Playlist entry is now %s\n", entry);
-	      entry = strchr(entry + 1, '/');
-	    }
+	      ptr = strrchr(buf, '/');
+	      if (entry)
+		*(entry - 1) = '/';
+	      if (ptr)
+		{
+		  *ptr = '\0';
+		  entry = ptr + 1;
+		}
+	      else
+		entry = buf;
 
-	  if (entry && mfi_id > 0)
+	      DPRINTF(E_SPAM, L_SCAN, "Playlist entry is now %s\n", entry);
+	      ret = db_files_get_count_bypathpattern(entry);
+
+	    } while (ptr && (ret > 1));
+
+	  if (ret > 0)
 	    {
+	      mfi_id = db_file_id_bypathpattern(entry);
 	      DPRINTF(E_DBG, L_SCAN, "Found playlist entry match, id is %d, entry is %s\n", mfi_id, entry);
-              filename = db_file_path_byid(mfi_id);
+
+	      filename = db_file_path_byid(mfi_id);
 	      if (!filename)
 		{
 		  DPRINTF(E_LOG, L_SCAN, "Playlist entry %s matches file id %d, but file path is missing.\n", entry, mfi_id);
@@ -190,7 +207,11 @@ scan_m3u_playlist(char *file, time_t mtime)
 		}
 	    }
 	  else
-	    continue;
+	    {
+	      DPRINTF(E_DBG, L_SCAN, "No match for playlist entry %s\n", entry);
+
+	      continue;
+	    }
 	}
 
       ret = db_pl_add_item_bypath(pl_id, filename);