diff --git a/frontend/src/component/common/ConstraintsList/ConstraintItem/ConstraintItem.tsx b/frontend/src/component/common/ConstraintsList/ConstraintItem/ConstraintItem.tsx
index 2a038b3315..222b8f9674 100644
--- a/frontend/src/component/common/ConstraintsList/ConstraintItem/ConstraintItem.tsx
+++ b/frontend/src/component/common/ConstraintsList/ConstraintItem/ConstraintItem.tsx
@@ -1,5 +1,8 @@
 import type { FC } from 'react';
-import { StrategyEvaluationItem } from '../StrategyEvaluationItem/StrategyEvaluationItem';
+import {
+    StrategyEvaluationItem,
+    type StrategyEvaluationItemProps,
+} from '../StrategyEvaluationItem/StrategyEvaluationItem';
 import type { ConstraintSchema } from 'openapi';
 import { formatOperatorDescription } from 'component/common/ConstraintAccordion/ConstraintOperator/formatOperatorDescription';
 import { StrategyEvaluationChip } from '../StrategyEvaluationChip/StrategyEvaluationChip';
@@ -29,18 +32,25 @@ const StyledOperatorGroup = styled('div')(({ theme }) => ({
     gap: theme.spacing(0.5),
 }));
 
-export const ConstraintItem: FC<ConstraintSchema> = ({
+export const ConstraintItem: FC<
+    ConstraintSchema & Pick<StrategyEvaluationItemProps, 'onSetTruncated'>
+> = ({
     caseInsensitive,
     contextName,
     inverted,
     operator,
     value,
     values,
+    onSetTruncated,
 }) => {
     const items = value ? [value, ...(values || [])] : values || [];
 
     return (
-        <StrategyEvaluationItem type='Constraint' values={items}>
+        <StrategyEvaluationItem
+            type='Constraint'
+            values={items}
+            onSetTruncated={onSetTruncated}
+        >
             {contextName}
             <StyledOperatorGroup>
                 {inverted ? <Inverted /> : null}
diff --git a/frontend/src/component/common/ConstraintsList/StrategyEvaluationItem/StrategyEvaluationItem.tsx b/frontend/src/component/common/ConstraintsList/StrategyEvaluationItem/StrategyEvaluationItem.tsx
index 5f26e7e4a6..9bf97c46ab 100644
--- a/frontend/src/component/common/ConstraintsList/StrategyEvaluationItem/StrategyEvaluationItem.tsx
+++ b/frontend/src/component/common/ConstraintsList/StrategyEvaluationItem/StrategyEvaluationItem.tsx
@@ -1,11 +1,15 @@
-import { Chip, type ChipProps, styled } from '@mui/material';
+import { styled } from '@mui/material';
+import {
+    Truncator,
+    type TruncatorProps,
+} from 'component/common/Truncator/Truncator';
 import type { FC, ReactNode } from 'react';
 
-type StrategyItemProps = {
+export type StrategyEvaluationItemProps = {
     type?: ReactNode;
     children?: ReactNode;
     values?: string[];
-};
+} & Pick<TruncatorProps, 'onSetTruncated'>;
 
 const StyledContainer = styled('div')(({ theme }) => ({
     display: 'flex',
@@ -17,7 +21,6 @@ const StyledContainer = styled('div')(({ theme }) => ({
 const StyledContent = styled('div')(({ theme }) => ({
     display: 'flex',
     gap: theme.spacing(1),
-    flexWrap: 'wrap',
     alignItems: 'center',
 }));
 
@@ -30,37 +33,33 @@ const StyledType = styled('span')(({ theme }) => ({
     width: theme.spacing(10),
 }));
 
-const StyledValuesGroup = styled('div')(({ theme }) => ({
-    display: 'flex',
-    alignItems: 'center',
-    gap: theme.spacing(0.5),
-}));
-
-const StyledValue = styled(({ ...props }: ChipProps) => (
-    <Chip size='small' {...props} />
-))(({ theme }) => ({
-    padding: theme.spacing(0.5),
-    background: theme.palette.background.elevation1,
-}));
-
 /**
  * Abstract building block for a list of constraints, segments and other items inside a strategy
  */
-export const StrategyEvaluationItem: FC<StrategyItemProps> = ({
+export const StrategyEvaluationItem: FC<StrategyEvaluationItemProps> = ({
     type,
     children,
     values,
+    onSetTruncated,
 }) => (
     <StyledContainer>
         <StyledType>{type}</StyledType>
         <StyledContent>
             {children}
-            {values && values?.length > 0 ? (
-                <StyledValuesGroup>
-                    {values?.map((value, index) => (
-                        <StyledValue key={`${value}#${index}`} label={value} />
-                    ))}
-                </StyledValuesGroup>
+            {values && values?.length === 1 ? (
+                <Truncator
+                    title={values[0]}
+                    arrow
+                    lines={2}
+                    onSetTruncated={() => onSetTruncated?.(false)}
+                >
+                    {values[0]}
+                </Truncator>
+            ) : null}
+            {values && values?.length > 1 ? (
+                <Truncator title='' lines={2} onSetTruncated={onSetTruncated}>
+                    {values.join(', ')}
+                </Truncator>
             ) : null}
         </StyledContent>
     </StyledContainer>
diff --git a/frontend/src/component/common/NewConstraintAccordion/ConstraintAccordionView/ConstraintAccordionViewHeader/ConstraintAccordionViewHeader.tsx b/frontend/src/component/common/NewConstraintAccordion/ConstraintAccordionView/ConstraintAccordionViewHeader/ConstraintAccordionViewHeader.tsx
index 633aa3dd19..e7a80d8e87 100644
--- a/frontend/src/component/common/NewConstraintAccordion/ConstraintAccordionView/ConstraintAccordionViewHeader/ConstraintAccordionViewHeader.tsx
+++ b/frontend/src/component/common/NewConstraintAccordion/ConstraintAccordionView/ConstraintAccordionViewHeader/ConstraintAccordionViewHeader.tsx
@@ -4,6 +4,7 @@ import { ConstraintAccordionViewHeaderInfo } from './ConstraintAccordionViewHead
 import { ConstraintAccordionHeaderActions } from '../../ConstraintAccordionHeaderActions/ConstraintAccordionHeaderActions';
 import { styled } from '@mui/system';
 import useUnleashContext from 'hooks/api/getters/useUnleashContext/useUnleashContext';
+import { useUiFlag } from 'hooks/useUiFlag';
 
 interface IConstraintAccordionViewHeaderProps {
     constraint: IConstraint;
@@ -38,6 +39,7 @@ export const ConstraintAccordionViewHeader = ({
     disabled,
 }: IConstraintAccordionViewHeaderProps) => {
     const { context } = useUnleashContext();
+    const flagOverviewRedesign = useUiFlag('flagOverviewRedesign');
     const { contextName } = constraint;
 
     const disableEdit = !context
@@ -46,7 +48,9 @@ export const ConstraintAccordionViewHeader = ({
 
     return (
         <StyledContainer>
-            <ConstraintIcon compact={compact} disabled={disabled} />
+            {!flagOverviewRedesign ? (
+                <ConstraintIcon compact={compact} disabled={disabled} />
+            ) : null}
             <ConstraintAccordionViewHeaderInfo
                 constraint={constraint}
                 singleValue={singleValue}
diff --git a/frontend/src/component/common/NewConstraintAccordion/ConstraintAccordionView/ConstraintAccordionViewHeader/ConstraintAccordionViewHeaderInfo.tsx b/frontend/src/component/common/NewConstraintAccordion/ConstraintAccordionView/ConstraintAccordionViewHeader/ConstraintAccordionViewHeaderInfo.tsx
index f7a4f09912..569678dce9 100644
--- a/frontend/src/component/common/NewConstraintAccordion/ConstraintAccordionView/ConstraintAccordionViewHeader/ConstraintAccordionViewHeaderInfo.tsx
+++ b/frontend/src/component/common/NewConstraintAccordion/ConstraintAccordionView/ConstraintAccordionViewHeader/ConstraintAccordionViewHeaderInfo.tsx
@@ -1,29 +1,9 @@
-import { styled, Tooltip } from '@mui/material';
-import { ConstraintViewHeaderOperator } from './ConstraintViewHeaderOperator';
-import { ConditionallyRender } from 'component/common/ConditionallyRender/ConditionallyRender';
-import { ConstraintAccordionViewHeaderSingleValue } from './ConstraintAccordionViewHeaderSingleValue';
-import { ConstraintAccordionViewHeaderMultipleValues } from './ConstraintAccordionViewHeaderMultipleValues';
+import { IconButton, styled } from '@mui/material';
 import type { IConstraint } from 'interfaces/strategy';
-
-const StyledHeaderText = styled('span')(({ theme }) => ({
-    display: '-webkit-box',
-    WebkitLineClamp: 3,
-    WebkitBoxOrient: 'vertical',
-    overflow: 'hidden',
-    maxWidth: '100px',
-    minWidth: '100px',
-    marginRight: '10px',
-    marginTop: 'auto',
-    marginBottom: 'auto',
-    wordBreak: 'break-word',
-    fontSize: theme.fontSizes.smallBody,
-    [theme.breakpoints.down(710)]: {
-        textAlign: 'center',
-        padding: theme.spacing(1, 0),
-        marginRight: 'inherit',
-        maxWidth: 'inherit',
-    },
-}));
+import { ConstraintItem } from 'component/common/ConstraintsList/ConstraintItem/ConstraintItem';
+import { useState } from 'react';
+import VisibilityIcon from '@mui/icons-material/Visibility';
+import VisibilityOffIcon from '@mui/icons-material/VisibilityOff';
 
 const StyledHeaderWrapper = styled('div')(({ theme }) => ({
     display: 'flex',
@@ -55,49 +35,26 @@ interface ConstraintAccordionViewHeaderMetaInfoProps {
 
 export const ConstraintAccordionViewHeaderInfo = ({
     constraint,
-    singleValue,
     allowExpand,
     expanded,
-    disabled = false,
-    maxLength = 112, //The max number of characters in the values text for NOT allowing expansion
 }: ConstraintAccordionViewHeaderMetaInfoProps) => {
+    const [expandable, setExpandable] = useState(false);
+
     return (
         <StyledHeaderWrapper>
             <StyledHeaderMetaInfo>
-                <Tooltip title={constraint.contextName} arrow>
-                    <StyledHeaderText
-                        sx={(theme) => ({
-                            color: disabled
-                                ? theme.palette.text.secondary
-                                : 'inherit',
-                        })}
-                    >
-                        {constraint.contextName}
-                    </StyledHeaderText>
-                </Tooltip>
-                <ConstraintViewHeaderOperator
-                    constraint={constraint}
-                    disabled={disabled}
-                />
-                <ConditionallyRender
-                    condition={singleValue}
-                    show={
-                        <ConstraintAccordionViewHeaderSingleValue
-                            constraint={constraint}
-                            allowExpand={allowExpand}
-                            disabled={disabled}
-                        />
-                    }
-                    elseShow={
-                        <ConstraintAccordionViewHeaderMultipleValues
-                            constraint={constraint}
-                            expanded={expanded}
-                            allowExpand={allowExpand}
-                            maxLength={maxLength}
-                            disabled={disabled}
-                        />
-                    }
+                <ConstraintItem
+                    {...constraint}
+                    onSetTruncated={(state: boolean) => {
+                        setExpandable(state);
+                        allowExpand(state);
+                    }}
                 />
+                {expandable ? (
+                    <IconButton type='button'>
+                        {expanded ? <VisibilityOffIcon /> : <VisibilityIcon />}
+                    </IconButton>
+                ) : null}
             </StyledHeaderMetaInfo>
         </StyledHeaderWrapper>
     );
diff --git a/frontend/src/component/common/Truncator/Truncator.tsx b/frontend/src/component/common/Truncator/Truncator.tsx
index 8302845f12..77d69b76f7 100644
--- a/frontend/src/component/common/Truncator/Truncator.tsx
+++ b/frontend/src/component/common/Truncator/Truncator.tsx
@@ -25,13 +25,14 @@ const StyledTruncatorContainer = styled(Box, {
 
 type OverridableTooltipProps = Omit<TooltipProps, 'children'>;
 
-interface ITruncatorProps extends BoxProps {
+export type TruncatorProps = {
     lines?: number;
     title?: string;
     arrow?: boolean;
     tooltipProps?: OverridableTooltipProps;
     children: React.ReactNode;
-}
+    onSetTruncated?: (isTruncated: boolean) => void;
+} & BoxProps;
 
 export const Truncator = ({
     lines = 1,
@@ -40,8 +41,9 @@ export const Truncator = ({
     tooltipProps,
     children,
     component = 'span',
+    onSetTruncated,
     ...props
-}: ITruncatorProps) => {
+}: TruncatorProps) => {
     const [isTruncated, setIsTruncated] = useState(false);
     const ref = useRef<HTMLDivElement>(null);
 
@@ -50,7 +52,6 @@ export const Truncator = ({
             setIsTruncated(ref.current.scrollHeight > ref.current.offsetHeight);
         }
     };
-
     useEffect(() => {
         const resizeObserver = new ResizeObserver(checkTruncation);
         if (ref.current) {
@@ -59,6 +60,10 @@ export const Truncator = ({
         return () => resizeObserver.disconnect();
     }, [title, children]);
 
+    useEffect(() => {
+        onSetTruncated?.(isTruncated);
+    }, [isTruncated]);
+
     const overridableTooltipProps: OverridableTooltipProps = {
         title,
         arrow,
diff --git a/frontend/src/component/feature/FeatureView/FeatureOverview/FeatureOverviewEnvironments/FeatureOverviewEnvironment/EnvironmentAccordionBody/StrategyDraggableItem/StrategyItem/StrategyExecution/RolloutParameter/RolloutVariants/RolloutVariants.tsx b/frontend/src/component/feature/FeatureView/FeatureOverview/FeatureOverviewEnvironments/FeatureOverviewEnvironment/EnvironmentAccordionBody/StrategyDraggableItem/StrategyItem/StrategyExecution/RolloutParameter/RolloutVariants/RolloutVariants.tsx
index d8b560b251..2f57913745 100644
--- a/frontend/src/component/feature/FeatureView/FeatureOverview/FeatureOverviewEnvironments/FeatureOverviewEnvironment/EnvironmentAccordionBody/StrategyDraggableItem/StrategyItem/StrategyExecution/RolloutParameter/RolloutVariants/RolloutVariants.tsx
+++ b/frontend/src/component/feature/FeatureView/FeatureOverview/FeatureOverviewEnvironments/FeatureOverviewEnvironment/EnvironmentAccordionBody/StrategyDraggableItem/StrategyItem/StrategyExecution/RolloutParameter/RolloutVariants/RolloutVariants.tsx
@@ -29,6 +29,12 @@ const StyledPayloadHeader = styled('div')(({ theme }) => ({
     marginBottom: theme.spacing(1),
 }));
 
+const StyledValuesContainer = styled('div')(({ theme }) => ({
+    display: 'flex',
+    gap: theme.spacing(0.75, 0.5),
+    flexWrap: 'wrap',
+}));
+
 export const RolloutVariants: FC<{
     variants?: StrategyVariantSchema[];
 }> = ({ variants }) => {
@@ -38,34 +44,36 @@ export const RolloutVariants: FC<{
 
     return (
         <StrategyEvaluationItem type={`Variants (${variants.length})`}>
-            {variants.map((variant, i) => (
-                <HtmlTooltip
-                    arrow
-                    title={
-                        variant.payload?.value ? (
-                            <div>
-                                <StyledPayloadHeader>
-                                    Payload:
-                                </StyledPayloadHeader>
-                                <code>{variant.payload?.value}</code>
-                            </div>
-                        ) : null
-                    }
-                    key={variant.name}
-                >
-                    <StyledVariantChip
-                        key={variant.name}
-                        order={i}
-                        label={
-                            <>
-                                <span>
-                                    {variant.weight / 10}% – {variant.name}
-                                </span>
-                            </>
+            <StyledValuesContainer>
+                {variants.map((variant, i) => (
+                    <HtmlTooltip
+                        arrow
+                        title={
+                            variant.payload?.value ? (
+                                <div>
+                                    <StyledPayloadHeader>
+                                        Payload:
+                                    </StyledPayloadHeader>
+                                    <code>{variant.payload?.value}</code>
+                                </div>
+                            ) : null
                         }
-                    />
-                </HtmlTooltip>
-            ))}
+                        key={variant.name}
+                    >
+                        <StyledVariantChip
+                            key={variant.name}
+                            order={i}
+                            label={
+                                <>
+                                    <span>
+                                        {variant.weight / 10}% – {variant.name}
+                                    </span>
+                                </>
+                            }
+                        />
+                    </HtmlTooltip>
+                ))}
+            </StyledValuesContainer>
         </StrategyEvaluationItem>
     );
 };