diff --git a/cypress/integration/plugins/dashboards-assistant/chatbot_sidecar_spec.js b/cypress/integration/plugins/dashboards-assistant/chatbot_sidecar_spec.js
new file mode 100644
index 000000000..772685cb4
--- /dev/null
+++ b/cypress/integration/plugins/dashboards-assistant/chatbot_sidecar_spec.js
@@ -0,0 +1,165 @@
+/*
+ * Copyright OpenSearch Contributors
+ * SPDX-License-Identifier: Apache-2.0
+ */
+import { BASE_PATH } from '../../../utils/constants';
+
+if (Cypress.env('DASHBOARDS_ASSISTANT_ENABLED')) {
+  describe('Assistant sidecar spec', () => {
+    beforeEach(() => {
+      // Set welcome screen tracking to false
+      localStorage.setItem('home:welcome:show', 'false');
+      // Set new theme modal to false
+      localStorage.setItem('home:newThemeModal:show', 'false');
+    });
+
+    beforeEach(() => {
+      // Visit ISM OSD
+      cy.visit(`${BASE_PATH}/app/home`);
+
+      // Common text to wait for to confirm page loaded, give up to 60 seconds for initial load
+      cy.get(`input[placeholder="Ask question"]`, { timeout: 120000 }).should(
+        'be.length',
+        1
+      );
+    });
+
+    describe('sidecar spec', () => {
+      it('open sidecar and render normally, support show and hide', () => {
+        // The header may render multiple times, wait for UI to be stable
+        cy.wait(5000);
+
+        // enable to toggle and open sidecar, OSD will be pushed accordingly.
+        cy.get(`img[aria-label="toggle chat flyout icon"]`).click();
+        cy.get('[class~="chatbot-sidecar"]').should('be.visible');
+        cy.get('[class~="chatbot-sidecar"]').should(
+          'have.css',
+          'width',
+          '460px'
+        );
+        //Wrapper and header have related padding style.
+        cy.get('[class~="app-wrapper"]').should(
+          'have.css',
+          'padding-right',
+          '460px'
+        );
+        cy.get('[id="globalHeaderBars"]')
+          .children()
+          .should('have.css', 'padding-right', '460px');
+
+        // click toggle to call sidecar hide, sidecar will be hidden and paddingSize on header and wrapper will be zero.
+        cy.get(`img[aria-label="toggle chat flyout icon"]`).click();
+        cy.get('[class~="chatbot-sidecar"]').should(
+          'have.css',
+          'display',
+          'none'
+        );
+        cy.get('[class~="app-wrapper"]').should(
+          'not.have.attr',
+          'padding-right'
+        );
+        cy.get('[id="globalHeaderBars"]')
+          .children()
+          .should('not.have.attr', 'padding-right');
+
+        // click toggle to call sidecar show
+        cy.get(`img[aria-label="toggle chat flyout icon"]`).click();
+        cy.get('[class~="chatbot-sidecar"]').should('be.visible');
+        cy.get('[class~="app-wrapper"]').should(
+          'have.css',
+          'padding-right',
+          '460px'
+        );
+        cy.get('[id="globalHeaderBars"]')
+          .children()
+          .should('have.css', 'padding-right', '460px');
+      });
+
+      it('open sidecar and support to switch docked mode', () => {
+        // The header may render multiple times, wait for UI to be stable
+        cy.wait(5000);
+
+        // enable to toggle and open sidecar, OSD will be pushed accordingly.
+        cy.get(`img[aria-label="toggle chat flyout icon"]`).click();
+        cy.get('[class~="chatbot-sidecar"]').should('be.visible');
+        cy.get('[class~="app-wrapper"]').should(
+          'have.css',
+          'padding-right',
+          '460px'
+        );
+
+        // switch to docked left
+        cy.get('[id="sidecarModeIcon"]').click();
+        cy.get('[data-test-subj="sidecar-mode-icon-menu-item-left"]').click();
+        cy.get('[class~="app-wrapper"]').should(
+          'have.css',
+          'padding-left',
+          '460px'
+        );
+
+        // switch to docked take over
+        cy.get('[id="sidecarModeIcon"]').click();
+        cy.get(
+          '[data-test-subj="sidecar-mode-icon-menu-item-takeover"]'
+        ).click();
+        cy.get('[class~="app-wrapper"]').should(
+          'not.have.attr',
+          'padding-left'
+        );
+        cy.get('[class~="app-wrapper"]').should(
+          'not.have.attr',
+          'padding-right'
+        );
+      });
+
+      it('open sidecar and support resizable', () => {
+        // The header may render multiple times, wait for UI to be stable
+        cy.wait(5000);
+
+        // enable to toggle and open sidecar, OSD will be pushed accordingly.
+        cy.get(`img[aria-label="toggle chat flyout icon"]`).click();
+        // switch to docked left
+        cy.get('[id="sidecarModeIcon"]').click();
+        cy.get('[data-test-subj="sidecar-mode-icon-menu-item-left"]').click();
+        cy.get('[class~="chatbot-sidecar"]').should('be.visible');
+        cy.get('[class~="chatbot-sidecar"]').should(
+          'have.css',
+          'width',
+          '460px'
+        );
+
+        //drag from left to right
+        cy.get('[data-test-subj="resizableButton"]').trigger('mousedown', {
+          clientX: 0,
+          pageX: 0,
+          pageY: 0,
+        });
+        cy.window().trigger('mousemove', { clientX: 1000, pageX: 0, pageY: 0 });
+        cy.window().trigger('mouseup', { force: true });
+        cy.get('[class~="chatbot-sidecar"]').should(
+          'have.css',
+          'width',
+          `${1000 + 460}px`
+        );
+
+        //drag from right to left
+        cy.get('[data-test-subj="resizableButton"]').trigger('mousedown', {
+          clientX: 0,
+          pageX: 0,
+          pageY: 0,
+        });
+        cy.window().trigger('mousemove', {
+          clientX: -1000,
+          pageX: 0,
+          pageY: 0,
+        });
+        cy.window().trigger('mouseup', { force: true });
+        cy.get('[class~="chatbot-sidecar"]').should(
+          'have.css',
+          'width',
+          `${1460 - 1000}px`
+        );
+      });
+    });
+  });
+}