diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml
index 3c3ddd20c4..f580432f8b 100644
--- a/.pre-commit-config.yaml
+++ b/.pre-commit-config.yaml
@@ -11,6 +11,7 @@ repos:
         exclude: ^projects/control-service/projects/helm_charts
       - id: check-json
       - id: check-ast
+        exclude: ^projects/vdk-core/tests/functional/run/jobs/syntax-error-job/1_step.py
       - id: check-added-large-files
       - id: end-of-file-fixer
       - id: trailing-whitespace
@@ -27,6 +28,7 @@ repos:
     hooks:
       - id: black
         language_version: python3
+        exclude: ^projects/vdk-core/tests/functional/run/jobs/syntax-error-job/1_step.py
   # ensure pydoc is up-to standard
   - repo: https://github.com/pycqa/pydocstyle
     rev: 6.1.1
diff --git a/projects/vdk-core/src/vdk/internal/builtin_plugins/run/file_based_step.py b/projects/vdk-core/src/vdk/internal/builtin_plugins/run/file_based_step.py
index 511cae2b6c..6bff73cc07 100644
--- a/projects/vdk-core/src/vdk/internal/builtin_plugins/run/file_based_step.py
+++ b/projects/vdk-core/src/vdk/internal/builtin_plugins/run/file_based_step.py
@@ -74,8 +74,27 @@ def run(job_input)
             sys.path.insert(0, str(step.job_dir))
             filename = step.file_path.name
             namespace = "step_" + str(filename).lower().strip(".py")
-            python_module = imp.load_source(namespace, str(step.file_path))
             success = False
+
+            try:
+                log.debug("Loading %s ..." % filename)
+                python_module = imp.load_source(namespace, str(step.file_path))
+                log.debug("Loading %s SUCCESS" % filename)
+            except BaseException as e:
+                log.info("Loading %s FAILURE" % filename)
+                errors.log_and_rethrow(
+                    to_be_fixed_by=errors.ResolvableBy.USER_ERROR,
+                    log=log,
+                    what_happened="Failed loading job sources of %s" % filename,
+                    why_it_happened=errors.MSG_WHY_FROM_EXCEPTION(e),
+                    consequences=errors.MSG_CONSEQUENCE_TERMINATING_APP,
+                    countermeasures=errors.MSG_COUNTERMEASURE_FIX_PARENT_EXCEPTION
+                    + " Most likely importing a dependency or data job step failed, see"
+                    + " logs for details and fix the failed step (details in stacktrace).",
+                    exception=e,
+                    wrap_in_vdk_error=True,
+                )
+
             for _, func in inspect.getmembers(python_module, inspect.isfunction):
                 if func.__name__ == "run":
                     try:
diff --git a/projects/vdk-core/tests/functional/run/jobs/syntax-error-job/1_step.py b/projects/vdk-core/tests/functional/run/jobs/syntax-error-job/1_step.py
new file mode 100644
index 0000000000..e059a2491b
--- /dev/null
+++ b/projects/vdk-core/tests/functional/run/jobs/syntax-error-job/1_step.py
@@ -0,0 +1,7 @@
+# Copyright 2021 VMware, Inc.
+# SPDX-License-Identifier: Apache-2.0
+from vdk.api.job_input import IJobInput
+
+
+def run(job_input: IJobInput):
+    syntax error # type: ignore
diff --git a/projects/vdk-core/tests/functional/run/test_run_errors.py b/projects/vdk-core/tests/functional/run/test_run_errors.py
index 748ae2cf4b..4bd5aba26a 100644
--- a/projects/vdk-core/tests/functional/run/test_run_errors.py
+++ b/projects/vdk-core/tests/functional/run/test_run_errors.py
@@ -28,6 +28,15 @@ def tmp_termination_msg_file(tmpdir) -> pathlib.Path:
         yield pathlib.Path(out_file)
 
 
+def test_initialize_step_user_error(tmp_termination_msg_file):
+    errors.clear_intermediate_errors()
+    runner = CliEntryBasedTestRunner()
+
+    result: Result = runner.invoke(["run", util.job_path("syntax-error-job")])
+    cli_assert_equal(1, result)
+    assert (json.loads(tmp_termination_msg_file.read_text())["status"]) == "User error"
+
+
 def test_run_user_error(tmp_termination_msg_file):
     errors.clear_intermediate_errors()
     runner = CliEntryBasedTestRunner()