diff --git a/beets/importer.py b/beets/importer.py
index 4b5284fec8..18e4bf0f12 100644
--- a/beets/importer.py
+++ b/beets/importer.py
@@ -392,7 +392,8 @@ def mark_merged(self, paths):
         """Mark paths and directories as merged for future reimport tasks.
         """
         self._merged_items.update(paths)
-        dirs = {os.path.dirname(path) if os.path.isfile(path) else path
+        dirs = {os.path.dirname(path)
+                if os.path.isfile(syspath(path)) else path
                 for path in paths}
         self._merged_dirs.update(dirs)
 
@@ -921,7 +922,7 @@ def prune(self, filename):
         the file still exists, no pruning is performed, so it's safe to
         call when the file in question may not have been removed.
         """
-        if self.toppath and not os.path.exists(filename):
+        if self.toppath and not os.path.exists(syspath(filename)):
             util.prune_dirs(os.path.dirname(filename),
                             self.toppath,
                             clutter=config['clutter'].as_str_seq())
@@ -1131,7 +1132,7 @@ def cleanup(self, **kwargs):
         if self.extracted:
             log.debug('Removing extracted directory: {0}',
                       displayable_path(self.toppath))
-            shutil.rmtree(self.toppath)
+            shutil.rmtree(syspath(self.toppath))
 
     def extract(self):
         """Extracts the archive to a temporary directory and sets
diff --git a/beets/library.py b/beets/library.py
index 7600c25044..bdd747b000 100644
--- a/beets/library.py
+++ b/beets/library.py
@@ -1215,7 +1215,7 @@ def move_art(self, operation=MoveOperation.MOVE):
         if not old_art:
             return
 
-        if not os.path.exists(old_art):
+        if not os.path.exists(syspath(old_art)):
             log.error('removing reference to missing album art file {}',
                       util.displayable_path(old_art))
             self.artpath = None
diff --git a/beets/ui/commands.py b/beets/ui/commands.py
index 1377ad0c5a..c921ecffa6 100755
--- a/beets/ui/commands.py
+++ b/beets/ui/commands.py
@@ -1272,7 +1272,7 @@ def update_items(lib, query, album, move, pretend, fields):
 
 def update_func(lib, opts, args):
     # Verify that the library folder exists to prevent accidental wipes.
-    if not os.path.isdir(lib.directory):
+    if not os.path.isdir(syspath(lib.directory)):
         ui.print_("Library path is unavailable or does not exist.")
         ui.print_(lib.directory)
         if not ui.input_yn("Are you sure you want to continue (y/n)?", True):
@@ -1666,8 +1666,10 @@ def move_func(lib, opts, args):
     dest = opts.dest
     if dest is not None:
         dest = normpath(dest)
-        if not os.path.isdir(dest):
-            raise ui.UserError('no such directory: %s' % dest)
+        if not os.path.isdir(syspath(dest)):
+            raise ui.UserError('no such directory: {}'.format(
+                displayable_path(dest)
+            ))
 
     move_items(lib, dest, decargs(args), opts.copy, opts.album, opts.pretend,
                opts.timid, opts.export)