diff --git a/frontend/src/component/feature/FeatureView/FeatureOverview/ReleasePlan/MilestoneProgressionForm/MilestoneProgressionForm.tsx b/frontend/src/component/feature/FeatureView/FeatureOverview/ReleasePlan/MilestoneProgressionForm/MilestoneProgressionForm.tsx
index b862900db9..4b19be755a 100644
--- a/frontend/src/component/feature/FeatureView/FeatureOverview/ReleasePlan/MilestoneProgressionForm/MilestoneProgressionForm.tsx
+++ b/frontend/src/component/feature/FeatureView/FeatureOverview/ReleasePlan/MilestoneProgressionForm/MilestoneProgressionForm.tsx
@@ -4,6 +4,7 @@ import { useMilestoneProgressionForm } from '../hooks/useMilestoneProgressionFor
 import { MilestoneProgressionTimeInput } from './MilestoneProgressionTimeInput.tsx';
 import type { ChangeMilestoneProgressionSchema } from 'openapi';
 import type { MilestoneStatus } from '../ReleasePlanMilestone/ReleasePlanMilestoneStatus.tsx';
+import { useMilestoneProgressionInfo } from '../hooks/useMilestoneProgressionInfo.ts';
 
 const StyledFormContainer = styled('div')(({ theme }) => ({
     display: 'flex',
@@ -54,6 +55,13 @@ const StyledErrorMessage = styled('span')(({ theme }) => ({
     paddingLeft: theme.spacing(3.25),
 }));
 
+const StyledInfoLine = styled('span')(({ theme }) => ({
+    color: theme.palette.text.secondary,
+    fontSize: theme.typography.caption.fontSize,
+    paddingLeft: theme.spacing(3.25),
+    fontStyle: 'italic',
+}));
+
 interface IMilestoneProgressionFormProps {
     sourceMilestoneId: string;
     targetMilestoneId: string;
@@ -81,6 +89,12 @@ export const MilestoneProgressionForm = ({
         status,
     );
 
+    const progressionInfo = useMilestoneProgressionInfo(
+        form.getIntervalMinutes(),
+        sourceMilestoneStartedAt,
+        status,
+    );
+
     const handleSubmit = async () => {
         if (!form.validate()) {
             return;
@@ -103,14 +117,18 @@ export const MilestoneProgressionForm = ({
         <StyledFormContainer onKeyDown={handleKeyDown}>
             <StyledTopRow>
                 <StyledIcon />
-                <StyledLabel>Proceed to the next milestone after</StyledLabel>
+                <StyledLabel>Proceed after</StyledLabel>
                 <MilestoneProgressionTimeInput
                     timeValue={form.timeValue}
                     timeUnit={form.timeUnit}
                     onTimeValueChange={form.handleTimeValueChange}
                     onTimeUnitChange={form.handleTimeUnitChange}
                 />
+                <StyledLabel>from milestone start</StyledLabel>
             </StyledTopRow>
+            {progressionInfo && (
+                <StyledInfoLine>{progressionInfo}</StyledInfoLine>
+            )}
             {form.errors.time && (
                 <StyledErrorMessage>{form.errors.time}</StyledErrorMessage>
             )}
diff --git a/frontend/src/component/feature/FeatureView/FeatureOverview/ReleasePlan/ReleasePlanMilestone/MilestoneTransitionDisplay.tsx b/frontend/src/component/feature/FeatureView/FeatureOverview/ReleasePlan/ReleasePlanMilestone/MilestoneTransitionDisplay.tsx
index 3b8dedbb67..780c7013cd 100644
--- a/frontend/src/component/feature/FeatureView/FeatureOverview/ReleasePlan/ReleasePlanMilestone/MilestoneTransitionDisplay.tsx
+++ b/frontend/src/component/feature/FeatureView/FeatureOverview/ReleasePlan/ReleasePlanMilestone/MilestoneTransitionDisplay.tsx
@@ -10,6 +10,7 @@ import {
 import type { ChangeMilestoneProgressionSchema } from 'openapi';
 import type { ReactNode } from 'react';
 import { useEffect } from 'react';
+import { useMilestoneProgressionInfo } from '../hooks/useMilestoneProgressionInfo.ts';
 
 const StyledFormWrapper = styled('div', {
     shouldForwardProp: (prop) => prop !== 'hasChanged',
@@ -97,6 +98,13 @@ const StyledErrorMessage = styled('span')(({ theme }) => ({
     paddingLeft: theme.spacing(3.25),
 }));
 
+const StyledInfoLine = styled('span')(({ theme }) => ({
+    color: theme.palette.text.secondary,
+    fontSize: theme.typography.caption.fontSize,
+    paddingLeft: theme.spacing(3.25),
+    fontStyle: 'italic',
+}));
+
 interface IMilestoneTransitionDisplayProps {
     intervalMinutes: number;
     targetMilestoneId: string;
@@ -129,6 +137,7 @@ export const ReadonlyMilestoneTransitionDisplay = ({
                 <span style={{ fontSize: 'inherit' }}>
                     {initial.value} {initial.unit}
                 </span>
+                <StyledLabel status={status}>from milestone start</StyledLabel>
             </StyledContentGroup>
         </StyledDisplayContainer>
     );
@@ -159,6 +168,12 @@ export const MilestoneTransitionDisplay = ({
     const currentIntervalMinutes = form.getIntervalMinutes();
     const hasChanged = currentIntervalMinutes !== intervalMinutes;
 
+    const progressionInfo = useMilestoneProgressionInfo(
+        currentIntervalMinutes,
+        sourceMilestoneStartedAt ?? null,
+        status,
+    );
+
     useEffect(() => {
         const newInitial = getTimeValueAndUnitFromMinutes(intervalMinutes);
         form.setTimeValue(newInitial.value);
@@ -214,15 +229,16 @@ export const MilestoneTransitionDisplay = ({
             <StyledDisplayContainer>
                 <StyledContentGroup>
                     <StyledIcon status={status} />
-                    <StyledLabel status={status}>
-                        Proceed to the next milestone after
-                    </StyledLabel>
+                    <StyledLabel status={status}>Proceed after</StyledLabel>
                     <MilestoneProgressionTimeInput
                         timeValue={form.timeValue}
                         timeUnit={form.timeUnit}
                         onTimeValueChange={form.handleTimeValueChange}
                         onTimeUnitChange={form.handleTimeUnitChange}
                     />
+                    <StyledLabel status={status}>
+                        from milestone start
+                    </StyledLabel>
                 </StyledContentGroup>
                 {!hasChanged && (
                     <StyledButtonGroup hasChanged={false}>
@@ -238,6 +254,9 @@ export const MilestoneTransitionDisplay = ({
                     </StyledButtonGroup>
                 )}
             </StyledDisplayContainer>
+            {progressionInfo && (
+                <StyledInfoLine>{progressionInfo}</StyledInfoLine>
+            )}
             {form.errors.time && (
                 <StyledErrorMessage>{form.errors.time}</StyledErrorMessage>
             )}
diff --git a/frontend/src/component/feature/FeatureView/FeatureOverview/ReleasePlan/hooks/getMilestoneProgressionInfo.test.ts b/frontend/src/component/feature/FeatureView/FeatureOverview/ReleasePlan/hooks/getMilestoneProgressionInfo.test.ts
new file mode 100644
index 0000000000..a1c4f7f4e3
--- /dev/null
+++ b/frontend/src/component/feature/FeatureView/FeatureOverview/ReleasePlan/hooks/getMilestoneProgressionInfo.test.ts
@@ -0,0 +1,30 @@
+import { describe, it, expect } from 'vitest';
+import { getMilestoneProgressionInfo } from './getMilestoneProgressionInfo.js';
+
+describe('getMilestoneProgressionInfo', () => {
+    const currentTime = new Date('2025-10-31T15:00:00.000Z');
+
+    it('returns immediate proceed message when elapsed >= interval', () => {
+        const startedAt = '2025-10-31T14:00:00.000Z';
+        const res = getMilestoneProgressionInfo(
+            30,
+            startedAt,
+            'en-US',
+            currentTime,
+        );
+        expect(res).toBeTruthy();
+        expect(res as string).toMatch(/^Already .* in this milestone\.$/);
+    });
+
+    it('returns proceed time and remaining message when elapsed < interval', () => {
+        const startedAt = '2025-10-31T14:00:00.000Z';
+        const res = getMilestoneProgressionInfo(
+            120,
+            startedAt,
+            'en-US',
+            currentTime,
+        );
+        expect(res).toBeTruthy();
+        expect(res as string).toMatch(/^Will proceed at .* \(in .*\)\.$/);
+    });
+});
diff --git a/frontend/src/component/feature/FeatureView/FeatureOverview/ReleasePlan/hooks/getMilestoneProgressionInfo.ts b/frontend/src/component/feature/FeatureView/FeatureOverview/ReleasePlan/hooks/getMilestoneProgressionInfo.ts
new file mode 100644
index 0000000000..54cbcb21b8
--- /dev/null
+++ b/frontend/src/component/feature/FeatureView/FeatureOverview/ReleasePlan/hooks/getMilestoneProgressionInfo.ts
@@ -0,0 +1,32 @@
+import { addMinutes, differenceInMinutes, formatDistance } from 'date-fns';
+import { formatDateYMDHM } from 'utils/formatDate.ts';
+
+export const getMilestoneProgressionInfo = (
+    intervalMinutes: number,
+    sourceMilestoneStartedAt: string | null | undefined,
+    locale: string,
+    currentTime: Date = new Date(),
+): string | null => {
+    if (!sourceMilestoneStartedAt) {
+        return null;
+    }
+
+    const startDate = new Date(sourceMilestoneStartedAt);
+    const elapsedMinutes = differenceInMinutes(currentTime, startDate);
+    const proceedDate = addMinutes(startDate, intervalMinutes);
+
+    if (elapsedMinutes >= intervalMinutes) {
+        const elapsedTime = formatDistance(startDate, currentTime, {
+            addSuffix: false,
+        });
+        return `Already ${elapsedTime} in this milestone.`;
+    }
+
+    const proceedTime = formatDateYMDHM(proceedDate, locale);
+    const remainingTime = formatDistance(proceedDate, currentTime, {
+        addSuffix: false,
+    });
+    return `Will proceed at ${proceedTime} (in ${remainingTime}).`;
+};
+
+export default getMilestoneProgressionInfo;
diff --git a/frontend/src/component/feature/FeatureView/FeatureOverview/ReleasePlan/hooks/useMilestoneProgressionInfo.ts b/frontend/src/component/feature/FeatureView/FeatureOverview/ReleasePlan/hooks/useMilestoneProgressionInfo.ts
new file mode 100644
index 0000000000..2f986f3769
--- /dev/null
+++ b/frontend/src/component/feature/FeatureView/FeatureOverview/ReleasePlan/hooks/useMilestoneProgressionInfo.ts
@@ -0,0 +1,20 @@
+import { useLocationSettings } from 'hooks/useLocationSettings';
+import { getMilestoneProgressionInfo } from './getMilestoneProgressionInfo.ts';
+import type { MilestoneStatus } from '../ReleasePlanMilestone/ReleasePlanMilestoneStatus.tsx';
+
+export const useMilestoneProgressionInfo = (
+    intervalMinutes: number,
+    sourceMilestoneStartedAt?: string | null,
+    status?: MilestoneStatus,
+) => {
+    const { locationSettings } = useLocationSettings();
+    if (!status || status.type !== 'active') {
+        return null;
+    }
+
+    return getMilestoneProgressionInfo(
+        intervalMinutes,
+        sourceMilestoneStartedAt,
+        locationSettings.locale,
+    );
+};