diff --git a/src/test/calendar_test.test.tsx b/src/test/calendar_test.test.tsx
index 81ac627b5d..8d2814668f 100644
--- a/src/test/calendar_test.test.tsx
+++ b/src/test/calendar_test.test.tsx
@@ -45,6 +45,7 @@ import {
   SafeElementWrapper,
   safeQuerySelector,
   safeQuerySelectorAll,
+  setupMockResizeObserver,
 } from "./test_utils";
 
 import type { ReactDatePickerCustomHeaderProps } from "../calendar";
@@ -136,6 +137,10 @@ describe("Calendar", () => {
     };
   }
 
+  beforeAll(() => {
+    setupMockResizeObserver();
+  });
+
   it("should start with the current date in view if no date range", () => {
     const now = newDate();
     const { instance } = getCalendar();
diff --git a/src/test/datepicker_test.test.tsx b/src/test/datepicker_test.test.tsx
index eeb3d83976..21548de05e 100644
--- a/src/test/datepicker_test.test.tsx
+++ b/src/test/datepicker_test.test.tsx
@@ -29,7 +29,11 @@ import DatePicker, { registerLocale } from "../index";
 import CustomInput from "./helper_components/custom_input";
 import ShadowRoot from "./helper_components/shadow_root";
 import TestWrapper from "./helper_components/test_wrapper";
-import { getKey, safeQuerySelector } from "./test_utils";
+import {
+  getKey,
+  safeQuerySelector,
+  setupMockResizeObserver,
+} from "./test_utils";
 
 function getSelectedDayNode(container: HTMLElement) {
   return (
@@ -83,6 +87,10 @@ const showDocument = (calendarInput: HTMLElement) => {
 };
 
 describe("DatePicker", () => {
+  beforeEach(() => {
+    setupMockResizeObserver();
+  });
+
   afterEach(() => {
     jest.resetAllMocks();
   });
diff --git a/src/test/exclude_time_period_test.test.tsx b/src/test/exclude_time_period_test.test.tsx
index 6531bf649f..68bc3acc0f 100644
--- a/src/test/exclude_time_period_test.test.tsx
+++ b/src/test/exclude_time_period_test.test.tsx
@@ -2,9 +2,14 @@ import { render } from "@testing-library/react";
 import React from "react";
 
 import { newDate, setTime } from "../date_utils";
+import { setupMockResizeObserver } from "./test_utils";
 import DatePicker from "../index";
 
 describe("DatePicker", () => {
+  beforeAll(() => {
+    setupMockResizeObserver();
+  });
+
   it("should only display times between minTime and maxTime", () => {
     const now = newDate();
     const { container } = render(
diff --git a/src/test/exclude_times_test.test.tsx b/src/test/exclude_times_test.test.tsx
index 69745a3e3a..d477d80893 100644
--- a/src/test/exclude_times_test.test.tsx
+++ b/src/test/exclude_times_test.test.tsx
@@ -2,11 +2,16 @@ import { render } from "@testing-library/react";
 import React from "react";
 
 import { setTime, newDate } from "../date_utils";
+import { setupMockResizeObserver } from "./test_utils";
 import DatePicker from "../index";
 
 describe("DatePicker", () => {
   let now: Date, excludeTimes: Date[];
 
+  beforeAll(() => {
+    setupMockResizeObserver();
+  });
+
   beforeEach(() => {
     now = newDate();
     excludeTimes = [
diff --git a/src/test/min_time_test.test.tsx b/src/test/min_time_test.test.tsx
index 2eaf280c74..d705695294 100644
--- a/src/test/min_time_test.test.tsx
+++ b/src/test/min_time_test.test.tsx
@@ -3,7 +3,7 @@ import React, { useState } from "react";
 
 import DatePicker from "../index";
 
-import { safeQuerySelector } from "./test_utils";
+import { safeQuerySelector, setupMockResizeObserver } from "./test_utils";
 
 import type { DatePickerProps } from "../index";
 
@@ -44,6 +44,10 @@ const DatePickerWithState = (
 };
 
 describe("Datepicker minTime", () => {
+  beforeAll(() => {
+    setupMockResizeObserver();
+  });
+
   it("should select time 12:00 AM when no minTime constraint is set.", () => {
     const { getByText, container } = render(<DatePickerWithState />);
 
diff --git a/src/test/show_time_test.test.tsx b/src/test/show_time_test.test.tsx
index 0fdfbf442d..a64a4785e6 100644
--- a/src/test/show_time_test.test.tsx
+++ b/src/test/show_time_test.test.tsx
@@ -4,9 +4,13 @@ import React from "react";
 import DatePicker from "../index";
 import TimeComponent from "../time";
 
-import { safeQuerySelector } from "./test_utils";
+import { safeQuerySelector, setupMockResizeObserver } from "./test_utils";
 
 describe("DatePicker", () => {
+  beforeAll(() => {
+    setupMockResizeObserver();
+  });
+
   it("should show time component when showTimeSelect prop is present", () => {
     const { container } = render(<DatePicker showTimeSelect open />);
     const timeComponent = container.querySelector(
diff --git a/src/test/test_utils.ts b/src/test/test_utils.ts
index 54f8073c57..83e075a00d 100644
--- a/src/test/test_utils.ts
+++ b/src/test/test_utils.ts
@@ -123,6 +123,37 @@ export const safeQuerySelectorAll = <T extends HTMLElement = HTMLElement>(
   return elements;
 };
 
+let _resizeObserverCallbackFn: ResizeObserverCallback | null;
+
+export const getResizeObserverCallback = () => _resizeObserverCallbackFn;
+
+export const setupMockResizeObserver = () => {
+  const mockObserve = jest.fn();
+  const mockDisconnect = jest.fn();
+  const mockUnobserve = jest.fn();
+
+  const ResizeObserverMock = jest.fn((fn) => {
+    _resizeObserverCallbackFn = fn;
+
+    return {
+      observe: mockObserve,
+      disconnect: () => {
+        _resizeObserverCallbackFn = null;
+        mockDisconnect();
+      },
+      unobserve: jest.fn(),
+    };
+  });
+
+  global.ResizeObserver = ResizeObserverMock;
+
+  return {
+    observe: mockObserve,
+    disconnect: mockDisconnect,
+    unobserve: mockUnobserve,
+  };
+};
+
 export class SafeElementWrapper<T extends HTMLElement> {
   constructor(private element: T) {}
 
diff --git a/src/test/time_input_test.test.tsx b/src/test/time_input_test.test.tsx
index bc332753ec..ef4bf1d7bc 100644
--- a/src/test/time_input_test.test.tsx
+++ b/src/test/time_input_test.test.tsx
@@ -5,9 +5,13 @@ import DatePicker from "../index";
 import InputTimeComponent from "../input_time";
 
 import CustomTimeInput from "./helper_components/custom_time_input";
-import { safeQuerySelector } from "./test_utils";
+import { safeQuerySelector, setupMockResizeObserver } from "./test_utils";
 
 describe("timeInput", () => {
+  beforeEach(() => {
+    setupMockResizeObserver();
+  });
+
   afterEach(() => {
     jest.resetAllMocks();
   });
diff --git a/src/test/timepicker_test.test.tsx b/src/test/timepicker_test.test.tsx
index 3ed6d043e5..b4c8010f44 100644
--- a/src/test/timepicker_test.test.tsx
+++ b/src/test/timepicker_test.test.tsx
@@ -6,9 +6,11 @@ import DatePicker from "../index";
 
 import {
   getKey,
+  getResizeObserverCallback,
   SafeElementWrapper,
   safeQuerySelector,
   safeQuerySelectorAll,
+  setupMockResizeObserver,
 } from "./test_utils";
 
 const MIN_TIME_LI_LEN = 2;
@@ -19,10 +21,65 @@ describe("TimePicker", () => {
   let onChangeMoment: Date | undefined;
   let instance: DatePicker | null = null;
 
+  let mockObserve: jest.Mock, mockDisconnect: jest.Mock;
+
+  beforeAll(() => {
+    const { observe, disconnect } = setupMockResizeObserver();
+    mockObserve = observe;
+    mockDisconnect = disconnect;
+  });
+
   beforeEach(() => {
     div = document.createElement("div");
   });
 
+  describe("Re-adjust height on Calendar Height Change", () => {
+    beforeEach(() => {
+      mockObserve.mockReset();
+      mockDisconnect.mockReset();
+    });
+
+    it("calls observe on mount", async () => {
+      render(
+        <DatePicker
+          inline
+          selected={new Date()}
+          showTimeSelect
+          timeIntervals={15}
+        />,
+      );
+      await waitFor(() => {
+        expect(mockObserve).toHaveBeenCalledTimes(1);
+
+        const resizeObserverCallback = getResizeObserverCallback();
+        const mockObserveElement = mockObserve.mock.calls[0][0];
+        expect(typeof resizeObserverCallback).toBe("function");
+
+        if (resizeObserverCallback) {
+          resizeObserverCallback([], mockObserveElement);
+        }
+      });
+    });
+
+    it("calls disconnect on unmount", async () => {
+      const component = render(
+        <DatePicker
+          inline
+          selected={new Date()}
+          showTimeSelect
+          timeIntervals={15}
+        />,
+      );
+
+      component.unmount();
+      await waitFor(() => {
+        expect(mockDisconnect).toHaveBeenCalledTimes(1);
+        const resizeObserverCallback = getResizeObserverCallback();
+        expect(resizeObserverCallback).toBe(null);
+      });
+    });
+  });
+
   it("should update on input time change", () => {
     renderDatePicker("February 28, 2018 4:43 PM");
     expect(getInputString()).toBe("February 28, 2018 4:43 PM");
diff --git a/src/time.tsx b/src/time.tsx
index 4e1bb3d513..c6ed61e4b1 100644
--- a/src/time.tsx
+++ b/src/time.tsx
@@ -62,6 +62,7 @@ export default class Time extends Component<TimeProps, TimeState> {
     );
   };
 
+  private resizeObserver?: ResizeObserver;
   state: TimeState = {
     height: null,
   };
@@ -69,11 +70,11 @@ export default class Time extends Component<TimeProps, TimeState> {
   componentDidMount(): void {
     // code to ensure selected time will always be in focus within time window when it first appears
     this.scrollToTheSelectedTime();
-    if (this.props.monthRef && this.header) {
-      this.setState({
-        height: this.props.monthRef.clientHeight - this.header.clientHeight,
-      });
-    }
+    this.observeDatePickerHeightChanges();
+  }
+
+  componentWillUnmount(): void {
+    this.resizeObserver?.disconnect();
   }
 
   private header?: HTMLDivElement;
@@ -82,6 +83,27 @@ export default class Time extends Component<TimeProps, TimeState> {
 
   private centerLi?: HTMLLIElement;
 
+  private observeDatePickerHeightChanges(): void {
+    const { monthRef } = this.props;
+    this.updateContainerHeight();
+
+    if (monthRef) {
+      this.resizeObserver = new ResizeObserver(() => {
+        this.updateContainerHeight();
+      });
+
+      this.resizeObserver.observe(monthRef);
+    }
+  }
+
+  private updateContainerHeight(): void {
+    if (this.props.monthRef && this.header) {
+      this.setState({
+        height: this.props.monthRef.clientHeight - this.header.clientHeight,
+      });
+    }
+  }
+
   scrollToTheSelectedTime = (): void => {
     requestAnimationFrame((): void => {
       if (!this.list) return;