diff --git a/app/assets/javascripts/polaris_view_components.js b/app/assets/javascripts/polaris_view_components.js
index e1475bd8..531637d1 100644
--- a/app/assets/javascripts/polaris_view_components.js
+++ b/app/assets/javascripts/polaris_view_components.js
@@ -451,8 +451,8 @@ class Dropzone extends Controller {
   onChange(e) {
     this.stopEvent(e);
     if (this.disabled) return;
-    this.clearFiles();
     const fileList = getDataTransferFiles(e);
+    this.clearFiles();
     const {files: files, acceptedFiles: acceptedFiles, rejectedFiles: rejectedFiles} = this.getValidatedFiles(fileList);
     this.dragTargets = [];
     this.files = files;
diff --git a/app/assets/javascripts/polaris_view_components/dropzone_controller.js b/app/assets/javascripts/polaris_view_components/dropzone_controller.js
index c9f66e95..c784a2ab 100644
--- a/app/assets/javascripts/polaris_view_components/dropzone_controller.js
+++ b/app/assets/javascripts/polaris_view_components/dropzone_controller.js
@@ -94,9 +94,9 @@ export default class extends Controller {
     this.stopEvent(e)
     if (this.disabled) return
 
+    const fileList = getDataTransferFiles(e)
     this.clearFiles()
 
-    const fileList = getDataTransferFiles(e)
     const { files, acceptedFiles, rejectedFiles } = this.getValidatedFiles(fileList)
     this.dragTargets = []
 
diff --git a/test/system/dropzone_component_test.rb b/test/system/dropzone_component_test.rb
index d4cbd25b..f4d238c4 100644
--- a/test/system/dropzone_component_test.rb
+++ b/test/system/dropzone_component_test.rb
@@ -115,6 +115,35 @@ def test_multiple_direct_uploads
     assert_text "Attachments (2)"
   end
 
+  def test_reselect_file
+    with_preview("dropzone_component/with_file_upload")
+
+    find(".Polaris-DropZone").drop(fixture_file("file.txt"), fixture_file("image.png"))
+    assert_selector ".Polaris-DropZone__Preview > .Polaris-LegacyStack > .Polaris-LegacyStack__Item", count: 2
+    within ".Polaris-DropZone__Preview > .Polaris-LegacyStack" do
+      assert_selector ".Polaris-LegacyStack__Item:nth-child(1)" do
+        assert_text "file.txt"
+        assert_text "10 Bytes"
+      end
+      assert_selector ".Polaris-LegacyStack__Item:nth-child(2)" do
+        assert_text "image.png"
+        assert_text "11.37 KB"
+      end
+    end
+
+    page.attach_file(fixture_file("image.png")) do
+      page.find(".Polaris-DropZone").click
+    end
+
+    assert_selector ".Polaris-DropZone__Preview > .Polaris-LegacyStack > .Polaris-LegacyStack__Item", count: 1
+    within ".Polaris-DropZone__Preview > .Polaris-LegacyStack" do
+      assert_selector ".Polaris-LegacyStack__Item:nth-child(1)" do
+        assert_text "image.png"
+        assert_text "11.37 KB"
+      end
+    end
+  end
+
   def fixture_file(name)
     Rails.root.join("../test/fixtures/#{name}")
   end