diff --git a/CHANGES.rst b/CHANGES.rst
index 44512451..dc3f5cbf 100644
--- a/CHANGES.rst
+++ b/CHANGES.rst
@@ -17,6 +17,8 @@ Unreleased
     :issue:`4150`
 -   ``jsonify`` handles ``decimal.Decimal`` by encoding to ``str``.
     :issue:`4157`
+-   Correctly handle raising deferred errors in CLI lazy loading.
+    :issue:`4096`
 
 
 Version 2.0.1
diff --git a/src/flask/cli.py b/src/flask/cli.py
index d9e810da..81191a1a 100644
--- a/src/flask/cli.py
+++ b/src/flask/cli.py
@@ -312,7 +312,7 @@ class DispatchingApp:
         self.loader = loader
         self._app = None
         self._lock = Lock()
-        self._bg_loading_exc_info = None
+        self._bg_loading_exc = None
 
         if use_eager_loading is None:
             use_eager_loading = os.environ.get("WERKZEUG_RUN_MAIN") != "true"
@@ -328,23 +328,24 @@ class DispatchingApp:
             with self._lock:
                 try:
                     self._load_unlocked()
-                except Exception:
-                    self._bg_loading_exc_info = sys.exc_info()
+                except Exception as e:
+                    self._bg_loading_exc = e
 
         t = Thread(target=_load_app, args=())
         t.start()
 
     def _flush_bg_loading_exception(self):
         __traceback_hide__ = True  # noqa: F841
-        exc_info = self._bg_loading_exc_info
-        if exc_info is not None:
-            self._bg_loading_exc_info = None
-            raise exc_info
+        exc = self._bg_loading_exc
+
+        if exc is not None:
+            self._bg_loading_exc = None
+            raise exc
 
     def _load_unlocked(self):
         __traceback_hide__ = True  # noqa: F841
         self._app = rv = self.loader()
-        self._bg_loading_exc_info = None
+        self._bg_loading_exc = None
         return rv
 
     def __call__(self, environ, start_response):
diff --git a/tests/test_cli.py b/tests/test_cli.py
index ebf8d1f5..5a666d8a 100644
--- a/tests/test_cli.py
+++ b/tests/test_cli.py
@@ -17,6 +17,7 @@ from flask import Blueprint
 from flask import current_app
 from flask import Flask
 from flask.cli import AppGroup
+from flask.cli import DispatchingApp
 from flask.cli import dotenv
 from flask.cli import find_best_app
 from flask.cli import FlaskGroup
@@ -310,6 +311,23 @@ def test_scriptinfo(test_apps, monkeypatch):
     assert app.name == "testapp"
 
 
+def test_lazy_load_error(monkeypatch):
+    """When using lazy loading, the correct exception should be
+    re-raised.
+    """
+
+    class BadExc(Exception):
+        pass
+
+    def bad_load():
+        raise BadExc
+
+    lazy = DispatchingApp(bad_load, use_eager_loading=False)
+
+    with pytest.raises(BadExc):
+        lazy._flush_bg_loading_exception()
+
+
 def test_with_appcontext(runner):
     @click.command()
     @with_appcontext