diff --git a/frontend/editor/src/core/tools/formFill/FieldInput.tsx b/frontend/editor/src/core/tools/formFill/FieldInput.tsx
index 9662298dc4..9a8943ea47 100644
--- a/frontend/editor/src/core/tools/formFill/FieldInput.tsx
+++ b/frontend/editor/src/core/tools/formFill/FieldInput.tsx
@@ -68,8 +68,11 @@ function FieldInputInner({
       );
 
     case "checkbox": {
-      const isChecked = !!value && value !== "Off";
-      const onValue = (field.widgets && field.widgets[0]?.exportValue) || "Yes";
+      const exportVal = field.widgets && field.widgets[0]?.exportValue;
+      const isChecked = exportVal
+        ? value === exportVal || value === "Yes"
+        : !!value && value !== "Off";
+      const onValue = exportVal || "Yes";
       return (
         <Checkbox
           size="xs"
diff --git a/frontend/editor/src/core/tools/formFill/FormFieldOverlay.tsx b/frontend/editor/src/core/tools/formFill/FormFieldOverlay.tsx
index 40f9cdf603..45b658d69d 100644
--- a/frontend/editor/src/core/tools/formFill/FormFieldOverlay.tsx
+++ b/frontend/editor/src/core/tools/formFill/FormFieldOverlay.tsx
@@ -338,9 +338,11 @@ function WidgetInputInner({
       );
 
     case "checkbox": {
-      // Checkbox is checked when value is anything other than 'Off' or empty
-      const isChecked = !!value && value !== "Off";
-      // When toggling on, use the widget's exportValue (e.g. 'Red', 'Blue') or fall back to 'Yes'
+      // Checkbox is checked when value matches exportValue if present, or is non-empty and not 'Off'
+      const isChecked = widget.exportValue
+        ? value === widget.exportValue || value === "Yes"
+        : !!value && value !== "Off";
+      // When toggling on, use the widget's exportValue (e.g. 'Red', 'Blue', 'Pass') or fall back to 'Yes'
       const onValue = widget.exportValue || "Yes";
       return (
         <div
@@ -433,6 +435,7 @@ function WidgetInputInner({
             multiple={field.multiSelect}
             style={{
               ...inputBaseStyle,
+              minWidth: "100%",
               padding: 0,
               paddingLeft: 2,
               appearance: "auto",
diff --git a/frontend/editor/src/core/tools/formFill/providers/PdfiumFormProvider.ts b/frontend/editor/src/core/tools/formFill/providers/PdfiumFormProvider.ts
index 87d18c3f2f..471bba5e43 100644
--- a/frontend/editor/src/core/tools/formFill/providers/PdfiumFormProvider.ts
+++ b/frontend/editor/src/core/tools/formFill/providers/PdfiumFormProvider.ts
@@ -92,7 +92,7 @@ function toFormField(
   // Derive value string
   let value = f.value;
   if (type === "checkbox") {
-    value = f.isChecked ? "Yes" : "Off";
+    value = f.isChecked ? f.widgets[0]?.exportValue || "Yes" : "Off";
   } else if (type === "radio") {
     // Use widget index as the canonical radio value.
     // This avoids issues with duplicate exportValues across widgets