diff --git a/pylsp/workspace.py b/pylsp/workspace.py
index ea7f55e8..f2e6d43b 100644
--- a/pylsp/workspace.py
+++ b/pylsp/workspace.py
@@ -389,6 +389,11 @@ def jedi_script(self, position=None, use_document_path=False):
             jedi.settings.auto_import_modules = jedi_settings.get('auto_import_modules',
                                                                   DEFAULT_AUTO_IMPORT_MODULES)
             environment_path = jedi_settings.get('environment')
+            # Jedi itself cannot deal with homedir-relative paths.
+            # On systems, where it is expected, expand the home directory.
+            if environment_path and os.name != 'nt':
+                environment_path = os.path.expanduser(environment_path)
+
             extra_paths = jedi_settings.get('extra_paths') or []
             env_vars = jedi_settings.get('env_vars')