diff --git a/frontend/src/component/common/ConstraintsList/ConstraintItemHeader/ConstraintItemHeader.tsx b/frontend/src/component/common/ConstraintsList/ConstraintItemHeader/ConstraintItemHeader.tsx
index 880de40317..4d84dead7f 100644
--- a/frontend/src/component/common/ConstraintsList/ConstraintItemHeader/ConstraintItemHeader.tsx
+++ b/frontend/src/component/common/ConstraintsList/ConstraintItemHeader/ConstraintItemHeader.tsx
@@ -1,12 +1,14 @@
-import type { FC } from 'react';
-import {
-    StrategyEvaluationItem,
-    type StrategyEvaluationItemProps,
-} from '../StrategyEvaluationItem/StrategyEvaluationItem';
+import type { ComponentProps, FC } from 'react';
+import { StrategyEvaluationItem } from '../StrategyEvaluationItem/StrategyEvaluationItem';
 import type { ConstraintSchema } from 'openapi';
 import { formatOperatorDescription } from 'component/common/ConstraintAccordion/ConstraintOperator/formatOperatorDescription';
 import { StrategyEvaluationChip } from '../StrategyEvaluationChip/StrategyEvaluationChip';
 import { styled, Tooltip } from '@mui/material';
+import { Truncator } from 'component/common/Truncator/Truncator';
+import { ValuesList } from '../ValuesList/ValuesList';
+import { useLocationSettings } from 'hooks/useLocationSettings';
+import { formatConstraintValue } from 'utils/formatConstraintValue';
+import { useConstraintTooltips } from './hooks/useConstraintTooltips';
 import { ReactComponent as CaseSensitiveIcon } from 'assets/icons/case-sensitive.svg';
 import { isCaseSensitive } from './isCaseSensitive';
 
@@ -52,32 +54,45 @@ const StyledOperatorGroup = styled('div')(({ theme }) => ({
     gap: theme.spacing(0.5),
 }));
 
+const StyledConstraintName = styled('div')(({ theme }) => ({
+    maxWidth: '150px',
+    paddingRight: theme.spacing(0.5),
+    overflow: 'hidden',
+}));
+
 export const ConstraintItemHeader: FC<
-    ConstraintSchema & Pick<StrategyEvaluationItemProps, 'onSetTruncated'>
-> = ({
-    caseInsensitive,
-    contextName,
-    inverted,
-    operator,
-    value,
-    values,
-    onSetTruncated,
-}) => {
-    const items = value ? [value, ...(values || [])] : values || [];
+    ConstraintSchema & Pick<ComponentProps<typeof ValuesList>, 'onSetTruncated'>
+> = ({ onSetTruncated, ...constraint }) => {
+    const { caseInsensitive, contextName, inverted, operator, value, values } =
+        constraint;
+    const { locationSettings } = useLocationSettings();
+    const items = value
+        ? [
+              formatConstraintValue(constraint, locationSettings) || '',
+              ...(values || []),
+          ]
+        : values || [];
+
+    const tooltips = useConstraintTooltips(contextName, values || []);
 
     return (
-        <StrategyEvaluationItem
-            type='Constraint'
-            values={items}
-            onSetTruncated={onSetTruncated}
-        >
-            {contextName}
+        <StrategyEvaluationItem type='Constraint'>
+            <StyledConstraintName>
+                <Truncator lines={2} title={contextName} arrow>
+                    {contextName}
+                </Truncator>
+            </StyledConstraintName>
             <StyledOperatorGroup>
                 <Operator label={operator} inverted={inverted} />
                 {isCaseSensitive(operator, caseInsensitive) ? (
                     <CaseSensitive />
                 ) : null}
             </StyledOperatorGroup>
+            <ValuesList
+                values={items}
+                onSetTruncated={onSetTruncated}
+                tooltips={tooltips}
+            />
         </StrategyEvaluationItem>
     );
 };
diff --git a/frontend/src/component/common/ConstraintsList/ConstraintItemHeader/hooks/useConstraintTooltips.test.ts b/frontend/src/component/common/ConstraintsList/ConstraintItemHeader/hooks/useConstraintTooltips.test.ts
new file mode 100644
index 0000000000..76fb8a6c69
--- /dev/null
+++ b/frontend/src/component/common/ConstraintsList/ConstraintItemHeader/hooks/useConstraintTooltips.test.ts
@@ -0,0 +1,99 @@
+import { vi } from 'vitest';
+import { renderHook } from '@testing-library/react';
+import { useConstraintTooltips } from './useConstraintTooltips';
+import useUnleashContext from 'hooks/api/getters/useUnleashContext/useUnleashContext';
+
+vi.mock('hooks/api/getters/useUnleashContext/useUnleashContext', () => ({
+    default: vi.fn(),
+}));
+
+describe('useConstraintTooltips', () => {
+    beforeEach(() => {
+        vi.resetAllMocks();
+    });
+
+    it('returns tooltip mapping for legal values with descriptions', () => {
+        (
+            useUnleashContext as unknown as ReturnType<typeof vi.fn>
+        ).mockReturnValue({
+            context: [
+                {
+                    name: 'contextA',
+                    description: 'Test context A',
+                    createdAt: '2021-01-01',
+                    sortOrder: 1,
+                    stickiness: false,
+                    legalValues: [
+                        { value: 'value1', description: 'Tooltip 1' },
+                        { value: 'value2', description: 'Tooltip 2' },
+                        { value: 'value3' }, // No description provided
+                    ],
+                },
+            ],
+        });
+
+        const { result } = renderHook(() =>
+            useConstraintTooltips('contextA', [
+                'value1',
+                'value2',
+                'value3',
+                'nonExisting',
+            ]),
+        );
+
+        expect(result.current).toEqual({
+            value1: 'Tooltip 1',
+            value2: 'Tooltip 2',
+        });
+    });
+
+    it('returns an empty object when the context is not found', () => {
+        (
+            useUnleashContext as unknown as ReturnType<typeof vi.fn>
+        ).mockReturnValue({
+            context: [
+                {
+                    name: 'otherContext',
+                    description: 'Other context',
+                    createdAt: '2021-01-01',
+                    sortOrder: 1,
+                    stickiness: false,
+                    legalValues: [
+                        { value: 'value1', description: 'Tooltip 1' },
+                    ],
+                },
+            ],
+        });
+
+        const { result } = renderHook(() =>
+            useConstraintTooltips('contextA', ['value1']),
+        );
+
+        expect(result.current).toEqual({});
+    });
+
+    it('returns an empty object when no values are provided', () => {
+        (
+            useUnleashContext as unknown as ReturnType<typeof vi.fn>
+        ).mockReturnValue({
+            context: [
+                {
+                    name: 'contextA',
+                    description: 'Test context A',
+                    createdAt: '2021-01-01',
+                    sortOrder: 1,
+                    stickiness: false,
+                    legalValues: [
+                        { value: 'value1', description: 'Tooltip 1' },
+                    ],
+                },
+            ],
+        });
+
+        const { result } = renderHook(() =>
+            useConstraintTooltips('contextA', []),
+        );
+
+        expect(result.current).toEqual({});
+    });
+});
diff --git a/frontend/src/component/common/ConstraintsList/ConstraintItemHeader/hooks/useConstraintTooltips.ts b/frontend/src/component/common/ConstraintsList/ConstraintItemHeader/hooks/useConstraintTooltips.ts
new file mode 100644
index 0000000000..1e0b7ca774
--- /dev/null
+++ b/frontend/src/component/common/ConstraintsList/ConstraintItemHeader/hooks/useConstraintTooltips.ts
@@ -0,0 +1,27 @@
+import useUnleashContext from 'hooks/api/getters/useUnleashContext/useUnleashContext';
+import { useMemo } from 'react';
+
+export const useConstraintTooltips = (
+    contextName: string,
+    values: string[],
+) => {
+    const { context } = useUnleashContext();
+    const contextDefinition = useMemo(
+        () => context.find(({ name }) => name === contextName),
+        [contextName, context],
+    );
+    return useMemo<Record<string, string>>(
+        () =>
+            Object.fromEntries(
+                values
+                    ?.map((item) => [
+                        item,
+                        contextDefinition?.legalValues?.find(
+                            ({ value }) => value === item,
+                        )?.description,
+                    ])
+                    .filter(([_, tooltip]) => !!tooltip) || [],
+            ),
+        [context, values],
+    );
+};
diff --git a/frontend/src/component/common/ConstraintsList/StrategyEvaluationItem/StrategyEvaluationItem.tsx b/frontend/src/component/common/ConstraintsList/StrategyEvaluationItem/StrategyEvaluationItem.tsx
index 239fe69968..2fc8948c9a 100644
--- a/frontend/src/component/common/ConstraintsList/StrategyEvaluationItem/StrategyEvaluationItem.tsx
+++ b/frontend/src/component/common/ConstraintsList/StrategyEvaluationItem/StrategyEvaluationItem.tsx
@@ -1,16 +1,11 @@
-import { styled } from '@mui/material';
-import {
-    Truncator,
-    type TruncatorProps,
-} from 'component/common/Truncator/Truncator';
-import { disabledStrategyClassName } from 'component/common/StrategyItemContainer/disabled-strategy-utils';
 import type { FC, ReactNode } from 'react';
+import { styled } from '@mui/material';
+import { disabledStrategyClassName } from 'component/common/StrategyItemContainer/disabled-strategy-utils';
 
 export type StrategyEvaluationItemProps = {
     type?: ReactNode;
     children?: ReactNode;
-    values?: string[];
-} & Pick<TruncatorProps, 'onSetTruncated'>;
+};
 
 const StyledContainer = styled('div')(({ theme }) => ({
     display: 'flex',
@@ -38,35 +33,17 @@ const StyledType = styled('span')(({ theme }) => ({
     color: theme.palette.text.secondary,
     width: theme.spacing(10),
 }));
-
 /**
  * Abstract building block for a list of constraints, segments and other items inside a strategy
  */
 export const StrategyEvaluationItem: FC<StrategyEvaluationItemProps> = ({
     type,
     children,
-    values,
-    onSetTruncated,
-}) => (
-    <StyledContainer>
-        <StyledType>{type}</StyledType>
-        <StyledContent>
-            {children}
-            {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>
-);
+}) => {
+    return (
+        <StyledContainer>
+            <StyledType>{type}</StyledType>
+            <StyledContent>{children}</StyledContent>
+        </StyledContainer>
+    );
+};
diff --git a/frontend/src/component/common/ConstraintsList/ValuesList/ValuesList.tsx b/frontend/src/component/common/ConstraintsList/ValuesList/ValuesList.tsx
new file mode 100644
index 0000000000..394cd1302d
--- /dev/null
+++ b/frontend/src/component/common/ConstraintsList/ValuesList/ValuesList.tsx
@@ -0,0 +1,66 @@
+import type { FC } from 'react';
+import { styled, Tooltip } from '@mui/material';
+import {
+    Truncator,
+    type TruncatorProps,
+} from 'component/common/Truncator/Truncator';
+
+export type ValuesListProps = {
+    values?: string[];
+    tooltips?: Record<string, string | undefined>;
+} & Pick<TruncatorProps, 'onSetTruncated'>;
+
+const StyledValuesContainer = styled('div')({
+    flex: '1 1 0',
+});
+
+const StyledValueItem = styled('span')(({ theme }) => ({
+    padding: theme.spacing(0.25),
+    display: 'inline-block',
+    span: {
+        background: theme.palette.background.elevation2,
+        borderRadius: theme.shape.borderRadiusLarge,
+        display: 'inline-block',
+        padding: theme.spacing(0.25, 1),
+    },
+}));
+
+const StyledSingleValue = styled('div')(({ theme }) => ({
+    padding: theme.spacing(0.25, 1),
+    background: theme.palette.background.elevation2,
+    borderRadius: theme.shape.borderRadiusLarge,
+}));
+
+export const ValuesList: FC<ValuesListProps> = ({
+    values,
+    tooltips,
+    onSetTruncated,
+}) => (
+    <StyledValuesContainer>
+        {values && values?.length === 1 ? (
+            <StyledSingleValue>
+                <Truncator
+                    title={values[0]}
+                    arrow
+                    lines={2}
+                    onSetTruncated={() => onSetTruncated?.(false)}
+                >
+                    <Tooltip title={tooltips?.[values[0]] || ''}>
+                        <span>{values[0]}</span>
+                    </Tooltip>
+                </Truncator>
+            </StyledSingleValue>
+        ) : null}
+        {values && values?.length > 1 ? (
+            <Truncator title='' lines={2} onSetTruncated={onSetTruncated}>
+                {values.map((value) => (
+                    <Tooltip title={tooltips?.[value] || ''} key={value}>
+                        <StyledValueItem>
+                            <span>{value}</span>
+                        </StyledValueItem>
+                    </Tooltip>
+                ))}
+            </Truncator>
+        ) : null}
+    </StyledValuesContainer>
+);
diff --git a/frontend/src/component/common/SegmentItem/SegmentItem.tsx b/frontend/src/component/common/SegmentItem/SegmentItem.tsx
index 610b422fb7..33f2c2666b 100644
--- a/frontend/src/component/common/SegmentItem/SegmentItem.tsx
+++ b/frontend/src/component/common/SegmentItem/SegmentItem.tsx
@@ -45,8 +45,7 @@ const StyledAccordionSummary = styled(AccordionSummary)(({ theme }) => ({
 }));
 
 const StyledAccordionDetails = styled(AccordionDetails)(({ theme }) => ({
-    borderTop: `1px dashed ${theme.palette.divider}`,
-    padding: theme.spacing(1.5, 3, 2.5),
+    padding: theme.spacing(0.5, 3, 2.5),
 }));
 
 const StyledLink = styled(Link)({
diff --git a/frontend/src/component/feature/FeatureView/FeatureOverview/FeatureOverviewEnvironments/FeatureOverviewEnvironment/EnvironmentAccordionBody/StrategyDraggableItem/StrategyItem/StrategyExecution/hooks/useCustomStrategyParameters.tsx b/frontend/src/component/feature/FeatureView/FeatureOverview/FeatureOverviewEnvironments/FeatureOverviewEnvironment/EnvironmentAccordionBody/StrategyDraggableItem/StrategyItem/StrategyExecution/hooks/useCustomStrategyParameters.tsx
index 2d7fd503a2..ba5bd6de5c 100644
--- a/frontend/src/component/feature/FeatureView/FeatureOverview/FeatureOverviewEnvironments/FeatureOverviewEnvironment/EnvironmentAccordionBody/StrategyDraggableItem/StrategyItem/StrategyExecution/hooks/useCustomStrategyParameters.tsx
+++ b/frontend/src/component/feature/FeatureView/FeatureOverview/FeatureOverviewEnvironments/FeatureOverviewEnvironment/EnvironmentAccordionBody/StrategyDraggableItem/StrategyItem/StrategyExecution/hooks/useCustomStrategyParameters.tsx
@@ -13,6 +13,7 @@ import type {
     StrategySchemaParametersItem,
 } from 'openapi';
 import type { IFeatureStrategyPayload } from 'interfaces/strategy';
+import { ValuesList } from 'component/common/ConstraintsList/ValuesList/ValuesList';
 
 export const useCustomStrategyParameters = (
     strategy: Pick<
@@ -48,14 +49,11 @@ export const useCustomStrategyParameters = (
                 }
 
                 return (
-                    <StrategyEvaluationItem
-                        key={key}
-                        type={typeItem}
-                        values={values}
-                    >
+                    <StrategyEvaluationItem key={key} type={typeItem}>
                         {values.length === 1
                             ? 'has 1 item:'
                             : `has ${values.length} items:`}
+                        <ValuesList values={values} />
                     </StrategyEvaluationItem>
                 );
             }
@@ -82,12 +80,11 @@ export const useCustomStrategyParameters = (
                 const value = parseParameterString(parameters[name]);
 
                 return (
-                    <StrategyEvaluationItem
-                        key={key}
-                        type={typeItem}
-                        values={value === '' ? undefined : [value]}
-                    >
+                    <StrategyEvaluationItem key={key} type={typeItem}>
                         {value === '' ? 'is an empty string' : 'is set to'}
+                        <ValuesList
+                            values={value === '' ? undefined : [value]}
+                        />
                     </StrategyEvaluationItem>
                 );
             }
@@ -95,12 +92,9 @@ export const useCustomStrategyParameters = (
             case 'number': {
                 const value = parseParameterNumber(parameters[name]);
                 return (
-                    <StrategyEvaluationItem
-                        key={key}
-                        type={typeItem}
-                        values={[`${value}`]}
-                    >
+                    <StrategyEvaluationItem key={key} type={typeItem}>
                         is a number set to
+                        <ValuesList values={[`${value}`]} />
                     </StrategyEvaluationItem>
                 );
             }
diff --git a/frontend/src/component/feature/FeatureView/FeatureOverview/FeatureOverviewEnvironments/FeatureOverviewEnvironment/EnvironmentAccordionBody/StrategyDraggableItem/StrategyItem/StrategyExecution/hooks/useStrategyParameters.tsx b/frontend/src/component/feature/FeatureView/FeatureOverview/FeatureOverviewEnvironments/FeatureOverviewEnvironment/EnvironmentAccordionBody/StrategyDraggableItem/StrategyItem/StrategyExecution/hooks/useStrategyParameters.tsx
index f867c04a4f..ba081d8cd8 100644
--- a/frontend/src/component/feature/FeatureView/FeatureOverview/FeatureOverviewEnvironments/FeatureOverviewEnvironment/EnvironmentAccordionBody/StrategyDraggableItem/StrategyItem/StrategyExecution/hooks/useStrategyParameters.tsx
+++ b/frontend/src/component/feature/FeatureView/FeatureOverview/FeatureOverviewEnvironments/FeatureOverviewEnvironment/EnvironmentAccordionBody/StrategyDraggableItem/StrategyItem/StrategyExecution/hooks/useStrategyParameters.tsx
@@ -1,8 +1,9 @@
 import { useMemo } from 'react';
-import { parseParameterStrings } from 'utils/parseParameter';
 import { StrategyEvaluationItem } from 'component/common/ConstraintsList/StrategyEvaluationItem/StrategyEvaluationItem';
 import type { FeatureStrategySchema } from 'openapi';
 import { RolloutParameter } from '../RolloutParameter/RolloutParameter';
+import { ValuesList } from 'component/common/ConstraintsList/ValuesList/ValuesList';
+import { parseParameterStrings } from 'utils/parseParameter';
 
 export const useStrategyParameters = (
     strategy: Partial<
@@ -36,11 +37,9 @@ export const useStrategyParameters = (
 
         if (['userids', 'hostnames', 'ips'].includes(type)) {
             return (
-                <StrategyEvaluationItem
-                    key={key}
-                    type={key}
-                    values={parseParameterStrings(value)}
-                />
+                <StrategyEvaluationItem key={key} type={key}>
+                    <ValuesList values={parseParameterStrings(value)} />
+                </StrategyEvaluationItem>
             );
         }
 
diff --git a/frontend/src/utils/formatConstraintValue.ts b/frontend/src/utils/formatConstraintValue.ts
index b7a73748a7..c4a098716b 100644
--- a/frontend/src/utils/formatConstraintValue.ts
+++ b/frontend/src/utils/formatConstraintValue.ts
@@ -1,10 +1,10 @@
-import type { IConstraint } from 'interfaces/strategy';
 import { formatDateYMDHMS } from 'utils/formatDate';
 import type { ILocationSettings } from 'hooks/useLocationSettings';
 import { CURRENT_TIME_CONTEXT_FIELD } from 'utils/operatorsForContext';
+import type { ConstraintSchema } from 'openapi';
 
 export const formatConstraintValue = (
-    constraint: IConstraint,
+    constraint: Pick<ConstraintSchema, 'value' | 'contextName'>,
     locationSettings: ILocationSettings,
 ): string | undefined => {
     if (