diff --git a/webapp/channels/src/components/admin_console/billing/billing_subscriptions/to_yearly_nudge_banner.test.tsx b/webapp/channels/src/components/admin_console/billing/billing_subscriptions/to_yearly_nudge_banner.test.tsx
index af797c5f92..e9061333a5 100644
--- a/webapp/channels/src/components/admin_console/billing/billing_subscriptions/to_yearly_nudge_banner.test.tsx
+++ b/webapp/channels/src/components/admin_console/billing/billing_subscriptions/to_yearly_nudge_banner.test.tsx
@@ -2,11 +2,9 @@
 // See LICENSE.txt for license information.
 
 import React from 'react';
+import {screen} from '@testing-library/react';
 
-import {Provider} from 'react-redux';
-
-import {mountWithIntl} from 'tests/helpers/intl-test-helper';
-import mockStore from 'tests/test_store';
+import {renderWithIntlAndStore} from 'tests/react_testing_utils';
 import {CloudProducts, RecurringIntervals} from 'utils/constants';
 
 import {ToYearlyNudgeBanner, ToYearlyNudgeBannerDismissable} from './to_yearly_nudge_banner';
@@ -42,7 +40,7 @@ const initialState = {
     },
 };
 
-describe('components/admin_console/billing/ToYearlyNudgeBannerDismissable', () => {
+describe('ToYearlyNudgeBannerDismissable', () => {
     test('should show for admins cloud professional monthly', () => {
         const state = JSON.parse(JSON.stringify(initialState));
         state.entities.users.profiles = {
@@ -63,14 +61,9 @@ describe('components/admin_console/billing/ToYearlyNudgeBannerDismissable', () =
             },
         };
 
-        const store = mockStore(state);
-        const wrapper = mountWithIntl(
-            <Provider store={store}>
-                <ToYearlyNudgeBannerDismissable/>
-            </Provider>,
-        );
+        renderWithIntlAndStore(<ToYearlyNudgeBannerDismissable/>, state);
 
-        expect(wrapper.find('AnnouncementBar').exists()).toBe(true);
+        screen.getByTestId('cloud-pro-monthly-deprecation-announcement-bar');
     });
 
     test('should NOT show for NON admins', () => {
@@ -93,14 +86,9 @@ describe('components/admin_console/billing/ToYearlyNudgeBannerDismissable', () =
             },
         };
 
-        const store = mockStore(state);
-        const wrapper = mountWithIntl(
-            <Provider store={store}>
-                <ToYearlyNudgeBannerDismissable/>
-            </Provider>,
-        );
+        renderWithIntlAndStore(<ToYearlyNudgeBannerDismissable/>, state);
 
-        expect(wrapper.find('AnnouncementBar').exists()).toBe(false);
+        expect(() => screen.getByTestId('cloud-pro-monthly-deprecation-announcement-bar')).toThrow();
     });
 
     test('should NOT show for admins on cloud free', () => {
@@ -123,14 +111,9 @@ describe('components/admin_console/billing/ToYearlyNudgeBannerDismissable', () =
             },
         };
 
-        const store = mockStore(state);
-        const wrapper = mountWithIntl(
-            <Provider store={store}>
-                <ToYearlyNudgeBannerDismissable/>
-            </Provider>,
-        );
+        renderWithIntlAndStore(<ToYearlyNudgeBannerDismissable/>, state);
 
-        expect(wrapper.find('AnnouncementBar').exists()).toBe(false);
+        expect(() => screen.getByTestId('cloud-pro-monthly-deprecation-announcement-bar')).toThrow();
     });
 
     test('should NOT show for admins on cloud enterprise', () => {
@@ -153,14 +136,9 @@ describe('components/admin_console/billing/ToYearlyNudgeBannerDismissable', () =
             },
         };
 
-        const store = mockStore(state);
-        const wrapper = mountWithIntl(
-            <Provider store={store}>
-                <ToYearlyNudgeBannerDismissable/>
-            </Provider>,
-        );
+        renderWithIntlAndStore(<ToYearlyNudgeBannerDismissable/>, state);
 
-        expect(wrapper.find('AnnouncementBar').exists()).toBe(false);
+        expect(() => screen.getByTestId('cloud-pro-monthly-deprecation-announcement-bar')).toThrow();
     });
 
     test('should NOT show for admins on cloud pro annual', () => {
@@ -182,15 +160,9 @@ describe('components/admin_console/billing/ToYearlyNudgeBannerDismissable', () =
                 },
             },
         };
+        renderWithIntlAndStore(<ToYearlyNudgeBannerDismissable/>, state);
 
-        const store = mockStore(state);
-        const wrapper = mountWithIntl(
-            <Provider store={store}>
-                <ToYearlyNudgeBannerDismissable/>
-            </Provider>,
-        );
-
-        expect(wrapper.find('AnnouncementBar').exists()).toBe(false);
+        expect(() => screen.getByTestId('cloud-pro-monthly-deprecation-announcement-bar')).toThrow();
     });
 
     test('should NOT show for admins when banner was dismissed in preferences', () => {
@@ -200,10 +172,10 @@ describe('components/admin_console/billing/ToYearlyNudgeBannerDismissable', () =
         };
         state.entities.preferences = {
             myPreferences: {
-                'cloud_yearly_nudge_banner--nudge_to_yearly_banner_dismissed': {
-                    category: 'cloud_yearly_nudge_banner',
-                    name: 'nudge_to_yearly_banner_dismissed',
-                    value: 'true',
+                'to_cloud_yearly_plan_nudge--nudge_to_cloud_yearly_plan_snoozed': {
+                    category: 'to_cloud_yearly_plan_nudge',
+                    name: 'nudge_to_cloud_yearly_plan_snoozed',
+                    value: '{"range": 0, "show": false}',
                 },
             },
         };
@@ -221,19 +193,13 @@ describe('components/admin_console/billing/ToYearlyNudgeBannerDismissable', () =
                 },
             },
         };
+        renderWithIntlAndStore(<ToYearlyNudgeBannerDismissable/>, state);
 
-        const store = mockStore(state);
-        const wrapper = mountWithIntl(
-            <Provider store={store}>
-                <ToYearlyNudgeBannerDismissable/>
-            </Provider>,
-        );
-
-        expect(wrapper.find('AnnouncementBar').exists()).toBe(false);
+        expect(() => screen.getByTestId('cloud-pro-monthly-deprecation-announcement-bar')).toThrow();
     });
 });
 
-describe('components/admin_console/billing/ToYearlyNudgeBanner', () => {
+describe('ToYearlyNudgeBanner', () => {
     test('should show for cloud professional monthly', () => {
         const state = JSON.parse(JSON.stringify(initialState));
         state.entities.cloud = {
@@ -251,14 +217,9 @@ describe('components/admin_console/billing/ToYearlyNudgeBanner', () => {
             },
         };
 
-        const store = mockStore(state);
-        const wrapper = mountWithIntl(
-            <Provider store={store}>
-                <ToYearlyNudgeBanner/>
-            </Provider>,
-        );
+        renderWithIntlAndStore(<ToYearlyNudgeBanner/>, state);
 
-        expect(wrapper.find('AlertBanner').exists()).toBe(true);
+        screen.getByTestId('cloud-pro-monthly-deprecation-alert-banner');
     });
 
     test('should NOT show for non cloud professional monthly', () => {
@@ -278,13 +239,9 @@ describe('components/admin_console/billing/ToYearlyNudgeBanner', () => {
             },
         };
 
-        const store = mockStore(state);
-        const wrapper = mountWithIntl(
-            <Provider store={store}>
-                <ToYearlyNudgeBanner/>
-            </Provider>,
-        );
+        renderWithIntlAndStore(<ToYearlyNudgeBanner/>, state);
 
-        expect(wrapper.find('AlertBanner').exists()).toBe(false);
+        expect(() => screen.getByTestId('cloud-pro-monthly-deprecation-alert-banner')).toThrow();
     });
 });
+
diff --git a/webapp/channels/src/components/admin_console/billing/billing_subscriptions/to_yearly_nudge_banner.tsx b/webapp/channels/src/components/admin_console/billing/billing_subscriptions/to_yearly_nudge_banner.tsx
index 3cc1e8aa75..f2eac86e69 100644
--- a/webapp/channels/src/components/admin_console/billing/billing_subscriptions/to_yearly_nudge_banner.tsx
+++ b/webapp/channels/src/components/admin_console/billing/billing_subscriptions/to_yearly_nudge_banner.tsx
@@ -1,9 +1,10 @@
 // Copyright (c) 2015-present Mattermost, Inc. All Rights Reserved.
 // See LICENSE.txt for license information.
 
-import React from 'react';
+import React, {useEffect} from 'react';
 import {useDispatch, useSelector} from 'react-redux';
 import {useIntl, FormattedMessage} from 'react-intl';
+import moment from 'moment';
 
 import AlertBanner from 'components/alert_banner';
 import useOpenCloudPurchaseModal from 'components/common/hooks/useOpenCloudPurchaseModal';
@@ -22,12 +23,35 @@ import {GlobalState} from '@mattermost/types/store';
 
 import './to_yearly_nudge_banner.scss';
 
+enum DismissShowRange {
+    GreaterThanEqual90 = '>=90',
+    BetweenNinetyAnd60 = '89-61',
+    SixtyTo31 = '60-31',
+    ThirtyTo11 = '30-11',
+    TenTo1 = '10-1',
+    Zero = '0'
+}
+
+const cloudProMonthlyCloseMoment = '20230727';
+
+interface ToYearlyPlanDismissPreference {
+
+    // range represents the range for the days to the deprecation of cloud free e.g. in 30 to 10 days to deprecate cloud free
+    // Incase of dismissing the banner, range represents the time (days) period when this banner was dismissed.
+    // This is important because in case the banner was dismissed for a certain period, it helps us know that we should not show it again for that period.
+    range: DismissShowRange;
+    show: boolean;
+}
+
 const ToYearlyNudgeBannerDismissable = () => {
     const dispatch = useDispatch();
 
     const openPurchaseModal = useOpenCloudPurchaseModal({});
 
-    const nudgeDismissed = useSelector((state: GlobalState) => getPreference(state, Preferences.CLOUD_YEARLY_NUDGE_BANNER, CloudBanners.NUDGE_TO_YEARLY_BANNER_DISMISSED)) === 'true';
+    const snoozePreferenceVal = useSelector((state: GlobalState) => getPreference(state, Preferences.TO_CLOUD_YEARLY_PLAN_NUDGE, CloudBanners.NUDGE_TO_CLOUD_YEARLY_PLAN_SNOOZED, '{"range": 0, "show": true}'));
+    const snoozeInfo = JSON.parse(snoozePreferenceVal) as ToYearlyPlanDismissPreference;
+    const show = snoozeInfo.show;
+
     const currentUser = useSelector(getCurrentUser);
     const isAdmin = useSelector(isCurrentUserSystemAdmin);
     const product = useSelector(selectSubscriptionProduct);
@@ -35,16 +59,75 @@ const ToYearlyNudgeBannerDismissable = () => {
     const currentProductIsMonthly = product?.recurring_interval === RecurringIntervals.MONTH;
     const currentProductProMonthly = currentProductProfessional && currentProductIsMonthly;
 
-    const savedDismissedPref = () => {
+    const now = moment(Date.now());
+    const proMonthlyEndDate = moment(cloudProMonthlyCloseMoment, 'YYYYMMDD');
+    const daysToProMonthlyEnd = proMonthlyEndDate.diff(now, 'days');
+
+    const snoozedForRange = (range: DismissShowRange) => {
+        return snoozeInfo.range === range;
+    };
+
+    useEffect(() => {
+        if (!snoozeInfo.show) {
+            if (daysToProMonthlyEnd >= 90 && !snoozedForRange(DismissShowRange.GreaterThanEqual90)) {
+                showBanner(true);
+            }
+
+            if (daysToProMonthlyEnd < 90 && daysToProMonthlyEnd > 60 && !snoozedForRange(DismissShowRange.BetweenNinetyAnd60)) {
+                showBanner(true);
+            }
+
+            if (daysToProMonthlyEnd <= 60 && daysToProMonthlyEnd > 30 && !snoozedForRange(DismissShowRange.SixtyTo31)) {
+                showBanner(true);
+            }
+
+            if (daysToProMonthlyEnd <= 30 && daysToProMonthlyEnd > 10 && !snoozedForRange(DismissShowRange.ThirtyTo11)) {
+                showBanner(true);
+            }
+
+            if (daysToProMonthlyEnd <= 10) {
+                showBanner(true);
+            }
+        }
+    }, []);
+
+    const showBanner = (show = false) => {
+        let dRange = DismissShowRange.Zero;
+        if (daysToProMonthlyEnd >= 90) {
+            dRange = DismissShowRange.GreaterThanEqual90;
+        }
+
+        if (daysToProMonthlyEnd < 90 && daysToProMonthlyEnd > 60) {
+            dRange = DismissShowRange.BetweenNinetyAnd60;
+        }
+
+        if (daysToProMonthlyEnd <= 60 && daysToProMonthlyEnd > 30) {
+            dRange = DismissShowRange.SixtyTo31;
+        }
+
+        if (daysToProMonthlyEnd <= 30 && daysToProMonthlyEnd > 10) {
+            dRange = DismissShowRange.ThirtyTo11;
+        }
+
+        // ideally this case should not happen because snooze button is not shown when TenTo1 days are remaining
+        if (daysToProMonthlyEnd <= 10 && daysToProMonthlyEnd > 0) {
+            dRange = DismissShowRange.TenTo1;
+        }
+
+        const snoozeInfo: ToYearlyPlanDismissPreference = {
+            range: dRange,
+            show,
+        };
+
         dispatch(savePreferences(currentUser.id, [{
-            category: Preferences.CLOUD_YEARLY_NUDGE_BANNER,
-            name: CloudBanners.NUDGE_TO_YEARLY_BANNER_DISMISSED,
+            category: Preferences.TO_CLOUD_YEARLY_PLAN_NUDGE,
+            name: CloudBanners.NUDGE_TO_CLOUD_YEARLY_PLAN_SNOOZED,
             user_id: currentUser.id,
-            value: 'true',
+            value: JSON.stringify(snoozeInfo),
         }]));
     };
 
-    if (nudgeDismissed) {
+    if (!show) {
         return null;
     }
 
@@ -56,21 +139,30 @@ const ToYearlyNudgeBannerDismissable = () => {
         return null;
     }
 
-    const message = {
-        id: 'cloud_billing.nudge_to_yearly.announcement_bar',
-        defaultMessage: 'Simplify your billing and switch to an annual plan today',
-    };
+    const message = (
+        <FormattedMessage
+            id='cloud_billing.nudge_to_yearly.announcement_bar'
+            defaultMessage='Monthly billing will be discontinued in {days} days . Switch to annual billing'
+            values={{
+                days: daysToProMonthlyEnd,
+
+            }}
+        />
+    );
+
+    const announcementType = (daysToProMonthlyEnd <= 10) ? AnnouncementBarTypes.CRITICAL : AnnouncementBarTypes.ANNOUNCEMENT;
 
     return (
         <AnnouncementBar
-            type={AnnouncementBarTypes.ANNOUNCEMENT}
-            showCloseButton={true}
+            id='cloud-pro-monthly-deprecation-announcement-bar'
+            type={announcementType}
+            showCloseButton={daysToProMonthlyEnd > 10}
             onButtonClick={() => openPurchaseModal({trackingLocation: 'to_yearly_nudge_annoucement_bar'})}
             modalButtonText={t('cloud_billing.nudge_to_yearly.learn_more')}
             modalButtonDefaultText='Learn more'
-            message={<FormattedMessage {...message}/>}
+            message={message}
             showLinkAsButton={true}
-            handleClose={savedDismissedPref}
+            handleClose={showBanner}
         />
     );
 };
@@ -90,17 +182,22 @@ const ToYearlyNudgeBanner = () => {
         return null;
     }
 
+    const now = moment(Date.now());
+    const proMonthlyEndDate = moment(cloudProMonthlyCloseMoment, 'YYYYMMDD');
+    const daysToProMonthlyEnd = proMonthlyEndDate.diff(now, 'days');
+
     const title = (
         <FormattedMessage
             id='cloud_billing.nudge_to_yearly.title'
-            defaultMessage='Switch to an annual plan today'
+            defaultMessage='Action required: Switch to annual billing to keep your workspace.'
         />
     );
 
     const description = (
         <FormattedMessage
             id='cloud_billing.nudge_to_yearly.description'
-            defaultMessage='Simplify your billing by switching to an annual subscription.'
+            defaultMessage='Monthly billing will be discontinued on {date}. To keep your workspace, switch to annual billing.'
+            values={{date: moment(cloudProMonthlyCloseMoment, 'YYYYMMDD').format('MMMM DD, YYYY')}}
         />
     );
 
@@ -122,9 +219,12 @@ const ToYearlyNudgeBanner = () => {
         </button>
     );
 
+    const bannerMode = (daysToProMonthlyEnd <= 10) ? 'danger' : 'info';
+
     return (
         <AlertBanner
-            mode='info'
+            id='cloud-pro-monthly-deprecation-alert-banner'
+            mode={bannerMode}
             title={title}
             message={description}
             className='ToYearlyNudgeBanner'
diff --git a/webapp/channels/src/i18n/en.json b/webapp/channels/src/i18n/en.json
index a22b676e6e..249111c8b5 100644
--- a/webapp/channels/src/i18n/en.json
+++ b/webapp/channels/src/i18n/en.json
@@ -3039,10 +3039,11 @@
   "cloud_billing.nudge_to_paid.learn_more": "Upgrade",
   "cloud_billing.nudge_to_paid.title": "Upgrade to paid plan to keep your workspace",
   "cloud_billing.nudge_to_paid.view_plans": "View plans",
+  "cloud_billing.nudge_to_yearly.announcement_bar": "Monthly billing will be discontinued in {days} days . Switch to annual billing",
   "cloud_billing.nudge_to_yearly.contact_sales": "Contact sales",
-  "cloud_billing.nudge_to_yearly.description": "Simplify your billing by switching to an annual subscription.",
+  "cloud_billing.nudge_to_yearly.description": "Monthly billing will be discontinued on {date}. To keep your workspace, switch to annual billing.",
   "cloud_billing.nudge_to_yearly.learn_more": "Learn more",
-  "cloud_billing.nudge_to_yearly.title": "Switch to an annual plan today",
+  "cloud_billing.nudge_to_yearly.title": "Action required: Switch to annual billing to keep your workspace.",
   "cloud_delinquency.banner.buttonText": "Update billing now",
   "cloud_delinquency.banner.end_user_notify_admin_button": "Notify admin",
   "cloud_delinquency.banner.end_user_notify_admin_title": "Your workspace has been downgraded. Notify your admin to fix billing issues",
diff --git a/webapp/channels/src/utils/constants.tsx b/webapp/channels/src/utils/constants.tsx
index 4bb243003c..cffc537c84 100644
--- a/webapp/channels/src/utils/constants.tsx
+++ b/webapp/channels/src/utils/constants.tsx
@@ -157,7 +157,7 @@ export const Preferences = {
     CONFIGURATION_BANNERS: 'configuration_banners',
     NOTIFY_ADMIN_REVOKE_DOWNGRADED_WORKSPACE: 'admin_revoke_downgraded_instance',
     OVERAGE_USERS_BANNER: 'overage_users_banner',
-    CLOUD_YEARLY_NUDGE_BANNER: 'cloud_yearly_nudge_banner',
+    TO_CLOUD_YEARLY_PLAN_NUDGE: 'to_cloud_yearly_plan_nudge',
     TO_PAID_PLAN_NUDGE: 'to_paid_plan_nudge',
 };
 
@@ -726,7 +726,7 @@ export const CloudBanners = {
     TRIAL: 'trial',
     UPGRADE_FROM_TRIAL: 'upgrade_from_trial',
     THREE_DAYS_LEFT_TRIAL_MODAL_DISMISSED: 'dismiss_3_days_left_trial_modal',
-    NUDGE_TO_YEARLY_BANNER_DISMISSED: 'nudge_to_yearly_banner_dismissed',
+    NUDGE_TO_CLOUD_YEARLY_PLAN_SNOOZED: 'nudge_to_cloud_yearly_plan_snoozed',
     NUDGE_TO_PAID_PLAN_SNOOZED: 'nudge_to_paid_plan_snoozed',
 };