diff --git a/picard/file.py b/picard/file.py
index 410c630d3..53a1e1ec5 100644
--- a/picard/file.py
+++ b/picard/file.py
@@ -369,7 +369,13 @@ class File(QtCore.QObject, Item):
                 if sys.platform == "darwin":
                     new_filename = unicodedata.normalize("NFD", new_filename)
 
-        return os.path.realpath(os.path.join(new_dirname, new_filename))
+        new_path = os.path.join(new_dirname, new_filename)
+        try:
+            return os.path.realpath(new_path)
+        except FileNotFoundError:
+            # os.path.realpath can fail if cwd doesn't exist
+            return new_path
+
 
     def _rename(self, old_filename, metadata):
         new_filename, ext = os.path.splitext(
diff --git a/picard/util/filenaming.py b/picard/util/filenaming.py
index 187bcfac8..6ae23affc 100644
--- a/picard/util/filenaming.py
+++ b/picard/util/filenaming.py
@@ -23,6 +23,7 @@ import struct
 import sys
 import unicodedata
 from picard.util import _io_encoding, decode_filename, encode_filename
+from PyQt5.QtCore import QStandardPaths
 
 
 def _get_utf16_length(text):
@@ -301,7 +302,12 @@ def make_short_filename(basedir, relpath, win_compat=False, relative_to=""):
     """
     # only deal with absolute paths. it saves a lot of grief,
     # and is the right thing to do, even for renames.
-    basedir = os.path.abspath(basedir)
+    try:
+        basedir = os.path.abspath(basedir)
+    except FileNotFoundError:
+        # os.path.abspath raises an exception if basedir is a relative path and
+        # cwd doesn't exist anymore
+        basedir = QStandardPaths.writableLocation(QStandardPaths.MusicLocation)
     # also, make sure the relative path is clean
     relpath = os.path.normpath(relpath)
     if win_compat and relative_to: