diff --git a/CHANGELOG.md b/CHANGELOG.md
index 26962b4eee..8efbf4a53a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -69,6 +69,8 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
   ([#3517](https://github.com/open-telemetry/opentelemetry-python-contrib/pull/3517))
 - `opentelemetry-instrumentation-httpx` Add support for HTTP metrics
   ([#3513](https://github.com/open-telemetry/opentelemetry-python-contrib/pull/3513))
+- `opentelemetry-instrumentation` Allow re-raising exception when instrumentation fails
+  ([#3545](https://github.com/open-telemetry/opentelemetry-python-contrib/pull/3545))
 
 ### Deprecated
 
diff --git a/opentelemetry-instrumentation/src/opentelemetry/instrumentation/auto_instrumentation/__init__.py b/opentelemetry-instrumentation/src/opentelemetry/instrumentation/auto_instrumentation/__init__.py
index 69af0b4cea..8571d0e5a2 100644
--- a/opentelemetry-instrumentation/src/opentelemetry/instrumentation/auto_instrumentation/__init__.py
+++ b/opentelemetry-instrumentation/src/opentelemetry/instrumentation/auto_instrumentation/__init__.py
@@ -118,8 +118,12 @@ def run() -> None:
     execl(executable, executable, *args.command_args)
 
 
-def initialize():
-    """Setup auto-instrumentation, called by the sitecustomize module"""
+def initialize(*, swallow_exceptions: bool = True) -> None:
+    """
+    Setup auto-instrumentation, called by the sitecustomize module
+
+    :param swallow_exceptions: Whether or not to propagate instrumentation exceptions to the caller. Exceptions are logged and swallowed by default.
+    """
     # prevents auto-instrumentation of subprocesses if code execs another python process
     if "PYTHONPATH" in environ:
         environ["PYTHONPATH"] = _python_path_without_directory(
@@ -131,5 +135,7 @@ def initialize():
         distro.configure()
         _load_configurators()
         _load_instrumentors(distro)
-    except Exception:  # pylint: disable=broad-except
+    except Exception as exc:  # pylint: disable=broad-except
         _logger.exception("Failed to auto initialize OpenTelemetry")
+        if not swallow_exceptions:
+            raise exc
diff --git a/opentelemetry-instrumentation/tests/auto_instrumentation/test_initialize.py b/opentelemetry-instrumentation/tests/auto_instrumentation/test_initialize.py
index 6d05a69c8e..715da0d2f6 100644
--- a/opentelemetry-instrumentation/tests/auto_instrumentation/test_initialize.py
+++ b/opentelemetry-instrumentation/tests/auto_instrumentation/test_initialize.py
@@ -59,3 +59,16 @@ def test_handles_exceptions(self, load_distro_mock, logger_mock):
         logger_mock.exception.assert_called_once_with(
             "Failed to auto initialize OpenTelemetry"
         )
+
+    @patch("opentelemetry.instrumentation.auto_instrumentation._logger")
+    @patch("opentelemetry.instrumentation.auto_instrumentation._load_distro")
+    def test_reraises_exceptions(self, load_distro_mock, logger_mock):
+        # pylint:disable=no-self-use
+        load_distro_mock.side_effect = ValueError("inner exception")
+        with self.assertRaises(ValueError) as em:
+            auto_instrumentation.initialize(swallow_exceptions=False)
+            logger_mock.exception.assert_called_once_with(
+                "Failed to auto initialize OpenTelemetry"
+            )
+
+        self.assertEqual("inner exception", str(em.exception))