diff --git a/cypress/e2e/billing.cy.ts b/cypress/e2e/billing.cy.ts
index a21188c0f42d0..a32b416abc39e 100644
--- a/cypress/e2e/billing.cy.ts
+++ b/cypress/e2e/billing.cy.ts
@@ -39,6 +39,7 @@ describe('Billing', () => {
         cy.get('[data-attr=more-button]').first().click()
         cy.contains('.LemonButton', 'Unsubscribe').click()
         cy.get('.LemonModal h3').should('contain', 'Unsubscribe from Product analytics')
+        cy.get('[data-attr=unsubscribe-reason-too-expensive]').click()
 
         cy.get('[data-attr=unsubscribe-reason-survey-textarea]').type('Product analytics')
         cy.contains('.LemonModal .LemonButton', 'Cancel').click()
@@ -46,6 +47,7 @@ describe('Billing', () => {
         cy.get('[data-attr=more-button]').eq(1).click()
         cy.contains('.LemonButton', 'Unsubscribe').click()
         cy.get('.LemonModal h3').should('contain', 'Unsubscribe from Session replay')
+        cy.get('[data-attr=unsubscribe-reason-too-expensive]').click()
         cy.get('[data-attr=unsubscribe-reason-survey-textarea]').type('Session replay')
         cy.contains('.LemonModal .LemonButton', 'Cancel').click()
 
diff --git a/frontend/__snapshots__/scenes-other-billing--billing-unsubscribe-modal--dark.png b/frontend/__snapshots__/scenes-other-billing--billing-unsubscribe-modal--dark.png
index 83009eedca75c..e1b89aae6cea2 100644
Binary files a/frontend/__snapshots__/scenes-other-billing--billing-unsubscribe-modal--dark.png and b/frontend/__snapshots__/scenes-other-billing--billing-unsubscribe-modal--dark.png differ
diff --git a/frontend/__snapshots__/scenes-other-billing--billing-unsubscribe-modal--light.png b/frontend/__snapshots__/scenes-other-billing--billing-unsubscribe-modal--light.png
index 1ef92fbabedfa..37bfc40833416 100644
Binary files a/frontend/__snapshots__/scenes-other-billing--billing-unsubscribe-modal--light.png and b/frontend/__snapshots__/scenes-other-billing--billing-unsubscribe-modal--light.png differ
diff --git a/frontend/__snapshots__/scenes-other-billing--billing-unsubscribe-modal-data-pipelines--dark.png b/frontend/__snapshots__/scenes-other-billing--billing-unsubscribe-modal-data-pipelines--dark.png
index 163316bc42a7e..b725bdd5c50ce 100644
Binary files a/frontend/__snapshots__/scenes-other-billing--billing-unsubscribe-modal-data-pipelines--dark.png and b/frontend/__snapshots__/scenes-other-billing--billing-unsubscribe-modal-data-pipelines--dark.png differ
diff --git a/frontend/__snapshots__/scenes-other-billing--billing-unsubscribe-modal-data-pipelines--light.png b/frontend/__snapshots__/scenes-other-billing--billing-unsubscribe-modal-data-pipelines--light.png
index 2407ed95965c3..c0d570ba527f9 100644
Binary files a/frontend/__snapshots__/scenes-other-billing--billing-unsubscribe-modal-data-pipelines--light.png and b/frontend/__snapshots__/scenes-other-billing--billing-unsubscribe-modal-data-pipelines--light.png differ
diff --git a/frontend/src/scenes/billing/UnsubscribeSurveyModal.tsx b/frontend/src/scenes/billing/UnsubscribeSurveyModal.tsx
index 79d2447260270..18502d80581ec 100644
--- a/frontend/src/scenes/billing/UnsubscribeSurveyModal.tsx
+++ b/frontend/src/scenes/billing/UnsubscribeSurveyModal.tsx
@@ -9,29 +9,20 @@ import {
     LemonModal,
     LemonTextArea,
     Link,
+    Tooltip,
 } from '@posthog/lemon-ui'
 import { useActions, useValues } from 'kea'
 import { HeartHog } from 'lib/components/hedgehogs'
 import { useHogfetti } from 'lib/components/Hogfetti/Hogfetti'
 import { supportLogic } from 'lib/components/Support/supportLogic'
+import { useState } from 'react'
 
 import { BillingProductV2AddonType, BillingProductV2Type } from '~/types'
 
 import { billingLogic } from './billingLogic'
-import { billingProductLogic } from './billingProductLogic'
+import { billingProductLogic, randomizeReasons, UNSUBSCRIBE_REASONS } from './billingProductLogic'
 import { ExportsUnsubscribeTable, exportsUnsubscribeTableLogic } from './ExportsUnsubscribeTable'
 
-const UNSUBSCRIBE_REASONS = [
-    'Too expensive',
-    'Not getting enough value',
-    'Not using the product',
-    'Found a better alternative',
-    'Poor customer support',
-    'Too difficult to use',
-    'Not enough hedgehogs',
-    'Other (let us know below!)',
-]
-
 export const UnsubscribeSurveyModal = ({
     product,
 }: {
@@ -39,7 +30,7 @@ export const UnsubscribeSurveyModal = ({
 }): JSX.Element | null => {
     const { trigger, HogfettiComponent } = useHogfetti()
 
-    const { surveyID, surveyResponse, isAddonProduct, unsubscribeModalStep } = useValues(
+    const { surveyID, surveyResponse, isAddonProduct, unsubscribeModalStep, unsubscribeReasonQuestions } = useValues(
         billingProductLogic({ product, hogfettiTrigger: trigger })
     )
     const {
@@ -55,6 +46,7 @@ export const UnsubscribeSurveyModal = ({
     const { unsubscribeError, billingLoading, billing } = useValues(billingLogic)
     const { unsubscribeDisabledReason, itemsToDisable } = useValues(exportsUnsubscribeTableLogic)
     const { openSupportForm } = useActions(supportLogic)
+    const [randomizedReasons] = useState(randomizeReasons(UNSUBSCRIBE_REASONS))
 
     const textAreaNotEmpty = surveyResponse['$survey_response']?.length > 0
     const includesPipelinesAddon =
@@ -152,7 +144,15 @@ export const UnsubscribeSurveyModal = ({
                             </LemonButton>
                             <LemonButton
                                 type={textAreaNotEmpty ? 'primary' : 'secondary'}
-                                disabledReason={includesPipelinesAddon && unsubscribeDisabledReason}
+                                disabledReason={
+                                    surveyResponse['$survey_response_2'].length === 0
+                                        ? 'Please select a reason'
+                                        : !textAreaNotEmpty
+                                        ? 'Please share your feedback'
+                                        : includesPipelinesAddon
+                                        ? unsubscribeDisabledReason
+                                        : undefined
+                                }
                                 onClick={handleUnsubscribe}
                                 loading={billingLoading}
                             >
@@ -192,30 +192,35 @@ export const UnsubscribeSurveyModal = ({
                                 ? `Why are you ${actionVerb}?`
                                 : `Why are you ${actionVerb} from ${product.name}?`}{' '}
                             <i className="text-muted">(you can select multiple)</i>
+                            <Tooltip title="Required">
+                                <span className="text-danger">*</span>
+                            </Tooltip>
                         </LemonLabel>
                         <div className="grid grid-cols-2 gap-2">
-                            {UNSUBSCRIBE_REASONS.map((reason) => (
+                            {randomizedReasons.map((reason) => (
                                 <LemonCheckbox
                                     bordered
-                                    key={reason}
-                                    label={reason}
-                                    dataAttr={`unsubscribe-reason-${reason.toLowerCase().replace(' ', '-')}`}
-                                    checked={surveyResponse['$survey_response_2'].includes(reason)}
-                                    onChange={() => toggleSurveyReason(reason)}
+                                    key={reason.reason}
+                                    label={reason.reason}
+                                    dataAttr={`unsubscribe-reason-${reason.reason.toLowerCase().replace(' ', '-')}`}
+                                    checked={surveyResponse['$survey_response_2'].includes(reason.reason)}
+                                    onChange={() => toggleSurveyReason(reason.reason)}
                                     className="w-full"
                                     labelClassName="w-full"
                                 />
                             ))}
                         </div>
 
-                        <LemonTextArea
-                            data-attr="unsubscribe-reason-survey-textarea"
-                            placeholder="Share your feedback here so we can improve PostHog!"
-                            value={surveyResponse['$survey_response']}
-                            onChange={(value) => {
-                                setSurveyResponse('$survey_response', value)
-                            }}
-                        />
+                        {surveyResponse['$survey_response_2'].length > 0 && (
+                            <LemonTextArea
+                                data-attr="unsubscribe-reason-survey-textarea"
+                                placeholder={unsubscribeReasonQuestions}
+                                value={surveyResponse['$survey_response']}
+                                onChange={(value) => {
+                                    setSurveyResponse('$survey_response', value)
+                                }}
+                            />
+                        )}
 
                         <LemonBanner type="info">
                             <p>
diff --git a/frontend/src/scenes/billing/billingProductLogic.ts b/frontend/src/scenes/billing/billingProductLogic.ts
index 3d6a3bed351fa..a36bde1a388ec 100644
--- a/frontend/src/scenes/billing/billingProductLogic.ts
+++ b/frontend/src/scenes/billing/billingProductLogic.ts
@@ -15,6 +15,28 @@ import { BillingGaugeItemKind, BillingGaugeItemType } from './types'
 
 const DEFAULT_BILLING_LIMIT: number = 500
 
+type UnsubscribeReason = {
+    reason: string
+    question: string
+}
+
+export const UNSUBSCRIBE_REASONS: UnsubscribeReason[] = [
+    { reason: 'Too expensive', question: 'What will you be using instead?' },
+    { reason: 'Not getting enough value', question: 'What prevented you from getting more value out of PostHog?' },
+    { reason: 'Not using the product', question: 'Why are you not using the product?' },
+    { reason: 'Found a better alternative', question: 'What service will you be moving to?' },
+    { reason: 'Poor customer support', question: 'Please provide details on your support experience.' },
+    { reason: 'Too difficult to use', question: 'What was difficult to use?' },
+    { reason: 'Not enough hedgehogs', question: 'How many hedgehogs do you need? (but really why are you leaving)' },
+    { reason: 'Other (let us know below!)', question: 'Why are you leaving?' },
+]
+
+export const randomizeReasons = (reasons: UnsubscribeReason[]): UnsubscribeReason[] => {
+    const shuffledReasons = reasons.slice(0, -1).sort(() => Math.random() - 0.5)
+    shuffledReasons.push(reasons[reasons.length - 1])
+    return shuffledReasons
+}
+
 export interface BillingProductLogicProps {
     product: BillingProductV2Type | BillingProductV2AddonType
     productRef?: React.MutableRefObject<HTMLDivElement | null>
@@ -298,6 +320,18 @@ export const billingProductLogic = kea<billingProductLogicType>([
             (billing, product): boolean =>
                 !!billing?.products?.some((p) => p.addons?.some((addon) => addon.type === product?.type)),
         ],
+        unsubscribeReasonQuestions: [
+            (s) => [s.surveyResponse],
+            (surveyResponse): string => {
+                return surveyResponse['$survey_response_2']
+                    .map((reason) => {
+                        const reasonObject = UNSUBSCRIBE_REASONS.find((r) => r.reason === reason)
+                        return reasonObject?.question
+                    })
+                    .join(' ')
+                    .concat(' (required)')
+            },
+        ],
     })),
     listeners(({ actions, values, props }) => ({
         updateBillingLimitsSuccess: () => {