diff --git a/django/forms/jinja2/django/forms/widgets/clearable_file_input.html b/django/forms/jinja2/django/forms/widgets/clearable_file_input.html
index 93812837f010..4f3a93627f50 100644
--- a/django/forms/jinja2/django/forms/widgets/clearable_file_input.html
+++ b/django/forms/jinja2/django/forms/widgets/clearable_file_input.html
@@ -1,5 +1,5 @@
 {% if widget.is_initial %}{{ widget.initial_text }}: <a href="{{ widget.value.url }}">{{ widget.value }}</a>{% if not widget.required %}
-<input type="checkbox" name="{{ widget.checkbox_name }}" id="{{ widget.checkbox_id }}"{% if widget.attrs.disabled %} disabled{% endif %}>
+<input type="checkbox" name="{{ widget.checkbox_name }}" id="{{ widget.checkbox_id }}"{% if widget.attrs.disabled %} disabled{% endif %}{% if widget.attrs.checked %} checked{% endif %}>
 <label for="{{ widget.checkbox_id }}">{{ widget.clear_checkbox_label }}</label>{% endif %}<br>
 {{ widget.input_text }}:{% endif %}
 <input type="{{ widget.type }}" name="{{ widget.name }}"{% include "django/forms/widgets/attrs.html" %}>
diff --git a/django/forms/templates/django/forms/widgets/clearable_file_input.html b/django/forms/templates/django/forms/widgets/clearable_file_input.html
index 93812837f010..4f3a93627f50 100644
--- a/django/forms/templates/django/forms/widgets/clearable_file_input.html
+++ b/django/forms/templates/django/forms/widgets/clearable_file_input.html
@@ -1,5 +1,5 @@
 {% if widget.is_initial %}{{ widget.initial_text }}: <a href="{{ widget.value.url }}">{{ widget.value }}</a>{% if not widget.required %}
-<input type="checkbox" name="{{ widget.checkbox_name }}" id="{{ widget.checkbox_id }}"{% if widget.attrs.disabled %} disabled{% endif %}>
+<input type="checkbox" name="{{ widget.checkbox_name }}" id="{{ widget.checkbox_id }}"{% if widget.attrs.disabled %} disabled{% endif %}{% if widget.attrs.checked %} checked{% endif %}>
 <label for="{{ widget.checkbox_id }}">{{ widget.clear_checkbox_label }}</label>{% endif %}<br>
 {{ widget.input_text }}:{% endif %}
 <input type="{{ widget.type }}" name="{{ widget.name }}"{% include "django/forms/widgets/attrs.html" %}>
diff --git a/tests/forms_tests/widget_tests/test_clearablefileinput.py b/tests/forms_tests/widget_tests/test_clearablefileinput.py
index 53b84cc0ecfd..ae54cc4b5da9 100644
--- a/tests/forms_tests/widget_tests/test_clearablefileinput.py
+++ b/tests/forms_tests/widget_tests/test_clearablefileinput.py
@@ -111,6 +111,21 @@ def test_render_disabled(self):
             ),
         )
 
+    def test_render_checked(self):
+        self.widget.checked = True
+        self.check_html(
+            self.widget,
+            "myfile",
+            FakeFieldFile(),
+            html=(
+                'Currently: <a href="something">something</a>'
+                '<input type="checkbox" name="myfile-clear" id="myfile-clear_id" '
+                "checked>"
+                '<label for="myfile-clear_id">Clear</label><br>Change: '
+                '<input type="file" name="myfile" checked>'
+            ),
+        )
+
     def test_render_no_disabled(self):
         class TestForm(Form):
             clearable_file = FileField(