diff --git a/frontend/src/component/common/ConstraintAccordion/ConstraintAccordionEdit/ConstraintAccordionEditHeader/ConstraintAccordionEditHeader.tsx b/frontend/src/component/common/ConstraintAccordion/ConstraintAccordionEdit/ConstraintAccordionEditHeader/ConstraintAccordionEditHeader.tsx
index 76d6b37519..b4688363ef 100644
--- a/frontend/src/component/common/ConstraintAccordion/ConstraintAccordionEdit/ConstraintAccordionEditHeader/ConstraintAccordionEditHeader.tsx
+++ b/frontend/src/component/common/ConstraintAccordion/ConstraintAccordionEdit/ConstraintAccordionEditHeader/ConstraintAccordionEditHeader.tsx
@@ -9,6 +9,7 @@ import {
     DATE_AFTER,
     IN,
     stringOperators,
+    inOperators,
 } from 'constants/operators';
 import { resolveText } from './helpers';
 import { oneOf } from 'utils/oneOf';
@@ -123,7 +124,7 @@ export const ConstraintAccordionEditHeader = ({
             setOperator(IN);
         }
 
-        if (oneOf(stringOperators, operator)) {
+        if (oneOf([...stringOperators, ...inOperators], operator)) {
             setShowCaseSensitiveButton(true);
         } else {
             setShowCaseSensitiveButton(false);
diff --git a/src/lib/util/feature-evaluator/constraint.ts b/src/lib/util/feature-evaluator/constraint.ts
index 72c7c3976b..c39cf17fe5 100644
--- a/src/lib/util/feature-evaluator/constraint.ts
+++ b/src/lib/util/feature-evaluator/constraint.ts
@@ -39,10 +39,15 @@ const cleanValues = (values: string[]) =>
 
 const InOperator = (constraint: Constraint, context: Context) => {
     const field = constraint.contextName;
+    const caseInsensitive = Boolean(constraint.caseInsensitive);
     const values = cleanValues(constraint.values);
     const contextValue = resolveContextValue(context, field);
 
-    const isIn = values.some((val) => val === contextValue);
+    const isIn = values.some((val) =>
+        caseInsensitive
+            ? val.toLowerCase() === contextValue?.toLowerCase()
+            : val === contextValue,
+    );
     return constraint.operator === Operator.IN ? isIn : !isIn;
 };