diff --git a/CHANGELOG.md b/CHANGELOG.md
index 064c6f0eec..40fe9caa9d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,6 +10,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - Replace Twitter logo with X logo within social sharing and social link components [#2387](https://github.com/bigcommerce/cornerstone/pull/2387)
 - Added nvm config [#2389](https://github.com/bigcommerce/cornerstone/pull/2389)
 - Displaying the Hidden cart_order_source Input Field on PDP page [#2392](https://github.com/bigcommerce/cornerstone/pull/2392)
+- 'Please Select a file' popup forces shopper to re-upload file if the option type is 'File Upload' and is set to required [#2409](https://github.com/bigcommerce/cornerstone/pull/2409)
 - Top Global Region Image Widget overlaps the mobile menu [#2402](https://github.com/bigcommerce/cornerstone/pull/2402)
 - Changed default PayPal checkout button color [#2405](https://github.com/bigcommerce/cornerstone/pull/2405)
 - Changed default PayPal checkout button size [#2406](https://github.com/bigcommerce/cornerstone/pull/2406)
diff --git a/templates/components/cart/modals/configure-product.html b/templates/components/cart/modals/configure-product.html
index 6a416a89e4..c829970523 100644
--- a/templates/components/cart/modals/configure-product.html
+++ b/templates/components/cart/modals/configure-product.html
@@ -1,7 +1,7 @@
 <div class="modal-header">
-    <h2 
-        class="modal-header-title" 
-        data-product-variant 
+    <h2
+        class="modal-header-title"
+        data-product-variant
         data-name="{{product_name}}"
         >
         {{lang 'cart.reconfigure_product' name=product_name}}
diff --git a/templates/components/products/options/input-file.html b/templates/components/products/options/input-file.html
index a35a2e81bf..12f9dab4a5 100644
--- a/templates/components/products/options/input-file.html
+++ b/templates/components/products/options/input-file.html
@@ -5,7 +5,13 @@
         {{> components/common/requireness-msg}}
     </label>
 
-    <input class="form-file" type="file" id="attribute_file_{{id}}" name="attribute[{{this.id}}]" {{#if required}}required{{/if}}>
+    <input
+        class="form-file"
+        type="file"
+        id="attribute_file_{{id}}"
+        name="attribute[{{this.id}}]"
+        {{#and required (unless prefill)}}required{{/and}}
+    >
     {{#if original_name}}
         {{{lang 'products.file_option_set' url=file_url name=original_name}}}
         <label>{{lang 'cart.remove_file'}}<input type="checkbox" name="{{file_remove}}"></label>
@@ -19,5 +25,4 @@
             {{lang 'products.filetypes'}} <strong>{{file_types}}</strong>
         {{/if}}
     </p>
-
 </div>