diff --git a/changelog/5444.bugfix.rst b/changelog/5444.bugfix.rst
new file mode 100644
index 00000000000..230d4b49eb6
--- /dev/null
+++ b/changelog/5444.bugfix.rst
@@ -0,0 +1 @@
+Fix ``--stepwise`` mode when the first file passed on the command-line fails to collect.
diff --git a/src/_pytest/stepwise.py b/src/_pytest/stepwise.py
index 0427cd0ea45..81b9fa0f433 100644
--- a/src/_pytest/stepwise.py
+++ b/src/_pytest/stepwise.py
@@ -29,6 +29,7 @@ def __init__(self, config):
         self.config = config
         self.active = config.getvalue("stepwise")
         self.session = None
+        self.report_status = ""
 
         if self.active:
             self.lastfailed = config.cache.get("cache/stepwise", None)
@@ -70,12 +71,6 @@ def pytest_collection_modifyitems(self, session, config, items):
 
         config.hook.pytest_deselected(items=already_passed)
 
-    def pytest_collectreport(self, report):
-        if self.active and report.failed:
-            self.session.shouldstop = (
-                "Error when collecting test, stopping test execution."
-            )
-
     def pytest_runtest_logreport(self, report):
         # Skip this hook if plugin is not active or the test is xfailed.
         if not self.active or "xfail" in report.keywords:
@@ -104,7 +99,7 @@ def pytest_runtest_logreport(self, report):
                     self.lastfailed = None
 
     def pytest_report_collectionfinish(self):
-        if self.active and self.config.getoption("verbose") >= 0:
+        if self.active and self.config.getoption("verbose") >= 0 and self.report_status:
             return "stepwise: %s" % self.report_status
 
     def pytest_sessionfinish(self, session):
diff --git a/testing/test_stepwise.py b/testing/test_stepwise.py
index 68e5989ecdb..b27dd02993e 100644
--- a/testing/test_stepwise.py
+++ b/testing/test_stepwise.py
@@ -157,14 +157,12 @@ def test_change_testfile(stepwise_testdir):
     assert "test_success PASSED" in stdout
 
 
-def test_stop_on_collection_errors(broken_testdir):
-    result = broken_testdir.runpytest(
-        "-v",
-        "--strict-markers",
-        "--stepwise",
-        "working_testfile.py",
-        "broken_testfile.py",
-    )
-
-    stdout = result.stdout.str()
-    assert "errors during collection" in stdout
+@pytest.mark.parametrize("broken_first", [True, False])
+def test_stop_on_collection_errors(broken_testdir, broken_first):
+    """Stop during collection errors. Broken test first or broken test last
+    actually surfaced a bug (#5444), so we test both situations."""
+    files = ["working_testfile.py", "broken_testfile.py"]
+    if broken_first:
+        files.reverse()
+    result = broken_testdir.runpytest("-v", "--strict-markers", "--stepwise", *files)
+    result.stdout.fnmatch_lines("*errors during collection*")