diff --git a/frontend/src/component/common/ConstraintAccordion/ConstraintAccordionEdit/ConstraintAccordionEditHeader/ConstraintAccordionEditHeader.tsx b/frontend/src/component/common/ConstraintAccordion/ConstraintAccordionEdit/ConstraintAccordionEditHeader/ConstraintAccordionEditHeader.tsx
index b4688363ef..cde0213c7a 100644
--- a/frontend/src/component/common/ConstraintAccordion/ConstraintAccordionEdit/ConstraintAccordionEditHeader/ConstraintAccordionEditHeader.tsx
+++ b/frontend/src/component/common/ConstraintAccordion/ConstraintAccordionEdit/ConstraintAccordionEditHeader/ConstraintAccordionEditHeader.tsx
@@ -24,6 +24,7 @@ import { InvertedOperatorButton } from '../StyledToggleButton/InvertedOperatorBu
 import { CaseSensitiveButton } from '../StyledToggleButton/CaseSensitiveButton/CaseSensitiveButton';
 import { ConstraintAccordionHeaderActions } from '../../ConstraintAccordionHeaderActions/ConstraintAccordionHeaderActions';
 import { styled } from '@mui/material';
+import useUiConfig from 'hooks/api/getters/useUiConfig/useUiConfig';
 
 interface IConstraintAccordionViewHeader {
     localConstraint: IConstraint;
@@ -101,6 +102,11 @@ export const ConstraintAccordionEditHeader = ({
     const { contextName, operator } = localConstraint;
     const [showCaseSensitiveButton, setShowCaseSensitiveButton] =
         useState(false);
+    const { uiConfig } = useUiConfig();
+
+    const caseInsensitiveInOperators = Boolean(
+        uiConfig.flags.caseInsensitiveInOperators
+    );
 
     /* We need a special case to handle the currenTime context field. Since
     this field will be the only one to allow DATE_BEFORE and DATE_AFTER operators
@@ -124,12 +130,21 @@ export const ConstraintAccordionEditHeader = ({
             setOperator(IN);
         }
 
-        if (oneOf([...stringOperators, ...inOperators], operator)) {
+        if (
+            oneOf(stringOperators, operator) ||
+            (oneOf(inOperators, operator) && caseInsensitiveInOperators)
+        ) {
             setShowCaseSensitiveButton(true);
         } else {
             setShowCaseSensitiveButton(false);
         }
-    }, [contextName, setOperator, operator, setLocalConstraint]);
+    }, [
+        contextName,
+        setOperator,
+        operator,
+        setLocalConstraint,
+        caseInsensitiveInOperators,
+    ]);
 
     if (!context) {
         return null;
@@ -140,7 +155,10 @@ export const ConstraintAccordionEditHeader = ({
     });
 
     const onOperatorChange = (operator: Operator) => {
-        if (oneOf(stringOperators, operator)) {
+        if (
+            oneOf(stringOperators, operator) ||
+            (oneOf(inOperators, operator) && caseInsensitiveInOperators)
+        ) {
             setShowCaseSensitiveButton(true);
         } else {
             setShowCaseSensitiveButton(false);
diff --git a/frontend/src/interfaces/uiConfig.ts b/frontend/src/interfaces/uiConfig.ts
index 0f7c06185a..7a0f96bcde 100644
--- a/frontend/src/interfaces/uiConfig.ts
+++ b/frontend/src/interfaces/uiConfig.ts
@@ -46,6 +46,7 @@ export interface IFlags {
     serviceAccounts?: boolean;
     featuresExportImport?: boolean;
     newProjectOverview?: boolean;
+    caseInsensitiveInOperators?: boolean;
 }
 
 export interface IVersionInfo {
diff --git a/src/lib/__snapshots__/create-config.test.ts.snap b/src/lib/__snapshots__/create-config.test.ts.snap
index 358d94852c..82783012cb 100644
--- a/src/lib/__snapshots__/create-config.test.ts.snap
+++ b/src/lib/__snapshots__/create-config.test.ts.snap
@@ -70,6 +70,7 @@ exports[`should create default config 1`] = `
       "ENABLE_DARK_MODE_SUPPORT": false,
       "anonymiseEventLog": false,
       "batchMetrics": false,
+      "caseInsensitiveInOperators": false,
       "embedProxy": true,
       "embedProxyFrontend": true,
       "featuresExportImport": false,
@@ -89,6 +90,7 @@ exports[`should create default config 1`] = `
       "ENABLE_DARK_MODE_SUPPORT": false,
       "anonymiseEventLog": false,
       "batchMetrics": false,
+      "caseInsensitiveInOperators": false,
       "embedProxy": true,
       "embedProxyFrontend": true,
       "featuresExportImport": false,
diff --git a/src/lib/types/experimental.ts b/src/lib/types/experimental.ts
index c35f25180b..b058d79e8b 100644
--- a/src/lib/types/experimental.ts
+++ b/src/lib/types/experimental.ts
@@ -58,6 +58,10 @@ const flags = {
         process.env.UNLEASH_EXPERIMENTAL_FEATURES_EXPORT_IMPORT,
         false,
     ),
+    caseInsensitiveInOperators: parseEnvVarBoolean(
+        process.env.UNLEASH_EXPERIMENTAL_CASE_INSENSITIVE_IN_OPERATORS,
+        false,
+    ),
 };
 
 export const defaultExperimentalOptions: IExperimentalOptions = {