diff --git a/x-pack/plugins/alerting/public/pages/maintenance_windows/components/maintenance_windows_list.tsx b/x-pack/plugins/alerting/public/pages/maintenance_windows/components/maintenance_windows_list.tsx
index 33a36a2bc0dea..9d4fc521c3f66 100644
--- a/x-pack/plugins/alerting/public/pages/maintenance_windows/components/maintenance_windows_list.tsx
+++ b/x-pack/plugins/alerting/public/pages/maintenance_windows/components/maintenance_windows_list.tsx
@@ -12,12 +12,15 @@ import {
   EuiBasicTableColumn,
   EuiButton,
   useEuiBackgroundColor,
+  EuiFlexGroup,
+  EuiFlexItem,
   SearchFilterConfig,
 } from '@elastic/eui';
 import { css } from '@emotion/react';
 import { MaintenanceWindowFindResponse, SortDirection } from '../types';
 import * as i18n from '../translations';
 import { useEditMaintenanceWindowsNavigation } from '../../../hooks/use_navigation';
+import { UpcomingEventsPopover } from './upcoming_events_popover';
 import { StatusColor, STATUS_DISPLAY, STATUS_SORT } from '../constants';
 import { MaintenanceWindowStatus } from '../../../../common';
 import { StatusFilter } from './status_filter';
@@ -61,7 +64,18 @@ const columns: Array<EuiBasicTableColumn<MaintenanceWindowFindResponse>> = [
     field: 'eventStartTime',
     name: i18n.TABLE_START_TIME,
     dataType: 'date',
-    render: (startDate: string) => formatDate(startDate, 'MM/DD/YY HH:mm A'),
+    render: (startDate: string, item: MaintenanceWindowFindResponse) => {
+      return (
+        <EuiFlexGroup responsive={false} alignItems="center">
+          <EuiFlexItem grow={false}>{formatDate(startDate, 'MM/DD/YY HH:mm A')}</EuiFlexItem>
+          {item.events.length > 1 ? (
+            <EuiFlexItem grow={false}>
+              <UpcomingEventsPopover maintenanceWindowFindResponse={item} />
+            </EuiFlexItem>
+          ) : null}
+        </EuiFlexGroup>
+      );
+    },
     sortable: true,
   },
   {
diff --git a/x-pack/plugins/alerting/public/pages/maintenance_windows/components/upcoming_events_popover.test.tsx b/x-pack/plugins/alerting/public/pages/maintenance_windows/components/upcoming_events_popover.test.tsx
new file mode 100644
index 0000000000000..574bb7d1f7549
--- /dev/null
+++ b/x-pack/plugins/alerting/public/pages/maintenance_windows/components/upcoming_events_popover.test.tsx
@@ -0,0 +1,67 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+import { fireEvent } from '@testing-library/react';
+import * as React from 'react';
+import { AppMockRenderer, createAppMockRenderer } from '../../../lib/test_utils';
+import { UpcomingEventsPopover } from './upcoming_events_popover';
+import { MaintenanceWindowStatus } from '../../../../common';
+
+describe('rule_actions_popover', () => {
+  let appMockRenderer: AppMockRenderer;
+
+  beforeEach(() => {
+    jest.clearAllMocks();
+    appMockRenderer = createAppMockRenderer();
+  });
+
+  it('renders the top 3 events', () => {
+    const result = appMockRenderer.render(
+      <UpcomingEventsPopover
+        maintenanceWindowFindResponse={{
+          title: 'test MW',
+          enabled: true,
+          duration: 0,
+          events: [
+            { gte: '2023-04-14T14:58:40.243Z', lte: '2023-04-14T14:58:40.243Z' },
+            { gte: '2023-04-21T14:58:40.243Z', lte: '2023-04-21T14:58:40.243Z' },
+            { gte: '2023-04-28T14:58:40.243Z', lte: '2023-04-28T14:58:40.243Z' },
+            { gte: '2023-05-05T14:58:40.243Z', lte: '2023-05-05T14:58:40.243Z' },
+            { gte: '2023-05-12T14:58:40.243Z', lte: '2023-05-12T14:58:40.243Z' },
+            { gte: '2023-05-19T14:58:40.243Z', lte: '2023-05-19T14:58:40.243Z' },
+          ],
+          id: 'dccedda0-dad4-11ed-9f8d-2b13e6c2138e',
+          status: MaintenanceWindowStatus.Upcoming,
+          expirationDate: '2024-04-14T14:58:58.997Z',
+          rRule: {
+            dtstart: '2023-04-14T14:58:40.243Z',
+            tzid: 'America/New_York',
+            freq: 3,
+            interval: 1,
+            byweekday: ['FR'],
+          },
+          createdBy: 'elastic',
+          updatedBy: 'elastic',
+          createdAt: '2023-04-14T14:58:58.997Z',
+          updatedAt: '2023-04-14T14:58:58.997Z',
+          eventStartTime: '2023-04-21T14:58:40.243Z',
+          eventEndTime: '2023-04-21T14:58:40.243Z',
+          total: 1000,
+        }}
+      />
+    );
+
+    const popoverButton = result.getByTestId('upcoming-events-icon-button');
+    expect(popoverButton).toBeInTheDocument();
+    fireEvent.click(popoverButton);
+
+    expect(result.getByTestId('upcoming-events-popover-title')).toBeInTheDocument();
+    expect(result.getByTestId('upcoming-events-popover-title')).toHaveTextContent(
+      'Repeats every Friday'
+    );
+    expect(result.getAllByTestId('upcoming-events-popover-item').length).toBe(3);
+  });
+});
diff --git a/x-pack/plugins/alerting/public/pages/maintenance_windows/components/upcoming_events_popover.tsx b/x-pack/plugins/alerting/public/pages/maintenance_windows/components/upcoming_events_popover.tsx
new file mode 100644
index 0000000000000..a20907a2e1236
--- /dev/null
+++ b/x-pack/plugins/alerting/public/pages/maintenance_windows/components/upcoming_events_popover.tsx
@@ -0,0 +1,127 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import React, { useCallback, useMemo, useState } from 'react';
+import moment from 'moment';
+import { findIndex } from 'lodash';
+import {
+  EuiButtonIcon,
+  EuiFlexGroup,
+  EuiFlexItem,
+  EuiHorizontalRule,
+  EuiIcon,
+  EuiPopover,
+  EuiPopoverTitle,
+  EuiSpacer,
+  EuiText,
+  formatDate,
+} from '@elastic/eui';
+import * as i18n from '../translations';
+import { recurringSummary } from '../helpers/recurring_summary';
+import { getPresets } from '../helpers/get_presets';
+import { MaintenanceWindowFindResponse } from '../types';
+import { convertFromMaintenanceWindowToForm } from '../helpers/convert_from_maintenance_window_to_form';
+
+interface UpcomingEventsPopoverProps {
+  maintenanceWindowFindResponse: MaintenanceWindowFindResponse;
+}
+
+export const UpcomingEventsPopover: React.FC<UpcomingEventsPopoverProps> = React.memo(
+  ({ maintenanceWindowFindResponse }) => {
+    const [isPopoverOpen, setIsPopoverOpen] = useState(false);
+
+    const onButtonClick = useCallback(() => {
+      setIsPopoverOpen((open) => !open);
+    }, []);
+    const closePopover = useCallback(() => {
+      setIsPopoverOpen(false);
+    }, []);
+
+    const { startDate, recurringSchedule, topEvents, presets } = useMemo(() => {
+      const maintenanceWindow = convertFromMaintenanceWindowToForm(maintenanceWindowFindResponse);
+      const date = moment(maintenanceWindow.startDate);
+      const currentEventIndex = findIndex(
+        maintenanceWindowFindResponse.events,
+        (event) =>
+          event.gte === maintenanceWindowFindResponse.eventStartTime &&
+          event.lte === maintenanceWindowFindResponse.eventEndTime
+      );
+      return {
+        startDate: date,
+        recurringSchedule: maintenanceWindow.recurringSchedule,
+        topEvents: maintenanceWindowFindResponse.events.slice(
+          currentEventIndex + 1,
+          currentEventIndex + 4
+        ),
+        presets: getPresets(date),
+      };
+    }, [maintenanceWindowFindResponse]);
+
+    return (
+      <EuiPopover
+        button={
+          <EuiButtonIcon
+            data-test-subj="upcoming-events-icon-button"
+            color="text"
+            display="base"
+            iconType="calendar"
+            size="s"
+            aria-label="Upcoming events"
+            onClick={onButtonClick}
+          />
+        }
+        isOpen={isPopoverOpen}
+        closePopover={closePopover}
+        anchorPosition="downCenter"
+      >
+        <EuiPopoverTitle data-test-subj="upcoming-events-popover-title">
+          {i18n.CREATE_FORM_RECURRING_SUMMARY_PREFIX(
+            recurringSummary(startDate, recurringSchedule, presets)
+          )}
+        </EuiPopoverTitle>
+        <EuiFlexGroup direction="column" responsive={false} gutterSize="none">
+          <EuiFlexItem grow={false}>
+            <EuiText style={{ fontWeight: 700 }} color="subdued" size="s">
+              {i18n.UPCOMING}
+            </EuiText>
+            <EuiSpacer size="m" />
+          </EuiFlexItem>
+          {topEvents.map((event, index) => (
+            <EuiFlexItem
+              data-test-subj="upcoming-events-popover-item"
+              key={`startDate.${index}`}
+              grow={false}
+            >
+              <EuiFlexGroup
+                responsive={false}
+                alignItems="center"
+                justifyContent="flexStart"
+                style={{ width: '300px' }}
+              >
+                <EuiFlexItem grow={false}>
+                  <EuiIcon color="subdued" type="calendar" />
+                </EuiFlexItem>
+                <EuiFlexItem grow={false}>
+                  <EuiText color="subdued" size="s">
+                    {formatDate(event.gte, 'MM/DD/YY HH:mm A')}
+                  </EuiText>
+                </EuiFlexItem>
+              </EuiFlexGroup>
+              {index < topEvents.length - 1 ? (
+                <EuiHorizontalRule
+                  style={{ inlineSize: 'unset', marginInline: '-16px' }}
+                  margin="s"
+                />
+              ) : null}
+            </EuiFlexItem>
+          ))}
+        </EuiFlexGroup>
+      </EuiPopover>
+    );
+  }
+);
+UpcomingEventsPopover.displayName = 'UpcomingEventsPopover';
diff --git a/x-pack/plugins/alerting/public/pages/maintenance_windows/helpers/convert_from_maintenance_window_to_form.test.ts b/x-pack/plugins/alerting/public/pages/maintenance_windows/helpers/convert_from_maintenance_window_to_form.test.ts
index fd2627d2478f1..c892f7db66729 100644
--- a/x-pack/plugins/alerting/public/pages/maintenance_windows/helpers/convert_from_maintenance_window_to_form.test.ts
+++ b/x-pack/plugins/alerting/public/pages/maintenance_windows/helpers/convert_from_maintenance_window_to_form.test.ts
@@ -194,7 +194,7 @@ describe('convertFromMaintenanceWindowToForm', () => {
         tzid: 'UTC',
         freq: RRuleFrequency.YEARLY,
         interval: 1,
-        bymonth: [2],
+        bymonth: [3],
         bymonthday: [22],
       },
     });
@@ -307,7 +307,7 @@ describe('convertFromMaintenanceWindowToForm', () => {
         tzid: 'UTC',
         freq: RRuleFrequency.YEARLY,
         interval: 3,
-        bymonth: [2],
+        bymonth: [3],
         bymonthday: [22],
       },
     });
diff --git a/x-pack/plugins/alerting/public/pages/maintenance_windows/helpers/convert_to_rrule.test.ts b/x-pack/plugins/alerting/public/pages/maintenance_windows/helpers/convert_to_rrule.test.ts
index 737bb47f4aa33..7eaecba5169b8 100644
--- a/x-pack/plugins/alerting/public/pages/maintenance_windows/helpers/convert_to_rrule.test.ts
+++ b/x-pack/plugins/alerting/public/pages/maintenance_windows/helpers/convert_to_rrule.test.ts
@@ -121,7 +121,7 @@ describe('convertToRRule', () => {
       tzid: 'UTC',
       freq: RRuleFrequency.YEARLY,
       interval: 1,
-      bymonth: [2],
+      bymonth: [3],
       bymonthday: [22],
     });
   });
@@ -209,7 +209,7 @@ describe('convertToRRule', () => {
       tzid: 'UTC',
       freq: RRuleFrequency.YEARLY,
       interval: 3,
-      bymonth: [2],
+      bymonth: [3],
       bymonthday: [22],
     });
   });
diff --git a/x-pack/plugins/alerting/public/pages/maintenance_windows/helpers/convert_to_rrule.ts b/x-pack/plugins/alerting/public/pages/maintenance_windows/helpers/convert_to_rrule.ts
index b284e50579deb..90706165c717b 100644
--- a/x-pack/plugins/alerting/public/pages/maintenance_windows/helpers/convert_to_rrule.ts
+++ b/x-pack/plugins/alerting/public/pages/maintenance_windows/helpers/convert_to_rrule.ts
@@ -68,7 +68,8 @@ export const convertToRRule = (
   }
 
   if (frequency === Frequency.YEARLY) {
-    rRule.bymonth = [startDate.month()];
+    // rRule expects 1 based indexing for months
+    rRule.bymonth = [startDate.month() + 1];
     rRule.bymonthday = [startDate.date()];
   }
 
diff --git a/x-pack/plugins/alerting/public/pages/maintenance_windows/translations.ts b/x-pack/plugins/alerting/public/pages/maintenance_windows/translations.ts
index 1b3317d9182b2..30b83963cc5b7 100644
--- a/x-pack/plugins/alerting/public/pages/maintenance_windows/translations.ts
+++ b/x-pack/plugins/alerting/public/pages/maintenance_windows/translations.ts
@@ -468,3 +468,7 @@ export const EXPERIMENTAL_DESCRIPTION = i18n.translate(
       'This functionality is in technical preview and may be changed or removed completely in a future release. Elastic will take a best effort approach to fix any issues, but features in technical preview are not subject to the support SLA of official GA features.',
   }
 );
+
+export const UPCOMING = i18n.translate('xpack.alerting.maintenanceWindows.upcoming', {
+  defaultMessage: 'Upcoming',
+});