diff --git a/cypress/integration/plugins/dashboards-assistant/conversation_history_spec.js b/cypress/integration/plugins/dashboards-assistant/conversation_history_spec.js
new file mode 100644
index 000000000..0349481b9
--- /dev/null
+++ b/cypress/integration/plugins/dashboards-assistant/conversation_history_spec.js
@@ -0,0 +1,212 @@
+/*
+ * Copyright OpenSearch Contributors
+ * SPDX-License-Identifier: Apache-2.0
+ */
+import { BASE_PATH } from '../../../utils/constants';
+import { setStorageItem } from '../../../utils/plugins/dashboards-assistant/helpers';
+
+if (Cypress.env('DASHBOARDS_ASSISTANT_ENABLED')) {
+  describe('Assistant conversation history spec', () => {
+    let restoreShowHome;
+    let restoreNewThemeModal;
+
+    before(() => {
+      // Set welcome screen tracking to false
+      restoreShowHome = setStorageItem(
+        localStorage,
+        'home:welcome:show',
+        'false'
+      );
+      // Hide new theme modal
+      restoreNewThemeModal = setStorageItem(
+        localStorage,
+        'home:newThemeModal:show',
+        'false'
+      );
+      // Visit 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: 60000 }).should(
+        'be.length',
+        1
+      );
+
+      // Open assistant flyout
+      // The flyout button will be detached and can't be clicked, add 10s delayed fix it.
+      cy.wait(10000);
+      cy.get('img[aria-label="toggle chat flyout icon"]').click();
+    });
+    after(() => {
+      if (restoreShowHome) {
+        restoreShowHome();
+      }
+      if (restoreNewThemeModal) {
+        restoreNewThemeModal();
+      }
+      // Close assistant flyout
+      cy.get('img[aria-label="toggle chat flyout icon"]').click();
+    });
+
+    beforeEach(() => {
+      cy.get('.llm-chat-flyout', { timeout: 60000 }).should('be.visible');
+    });
+
+    describe('panel operations', () => {
+      it('should toggle history list', () => {
+        cy.get('.llm-chat-flyout button[aria-label="history"]')
+          .should('be.visible')
+          .click();
+        cy.get('.llm-chat-flyout-body')
+          .contains('Conversations')
+          .should('be.visible');
+
+        cy.get('.llm-chat-flyout button[aria-label="history"]')
+          .should('be.visible')
+          .click();
+        cy.get('textarea[placeholder="Ask me anything..."]').should('exist');
+        cy.get('.llm-chat-flyout-body')
+          .contains('Conversations')
+          .should('not.be.visible');
+      });
+
+      it('should back to chat panel', () => {
+        cy.get('.llm-chat-flyout button[aria-label="history"]').click();
+        cy.get('.llm-chat-flyout')
+          .contains('Conversations')
+          .should('be.visible');
+
+        cy.get('.llm-chat-flyout-body').contains('Back').click();
+        cy.get('textarea[placeholder="Ask me anything..."]').should('exist');
+      });
+
+      it('should hide back button in fullscreen mode', () => {
+        cy.get('.llm-chat-flyout button[aria-label="fullScreen"]').click();
+        cy.get('.llm-chat-flyout button[aria-label="history"]').click();
+
+        cy.get('.llm-chat-flyout')
+          .contains('Conversations')
+          .should('be.visible');
+        cy.get('textarea[placeholder="Ask me anything..."]').should('exist');
+        cy.get('.llm-chat-flyout-body')
+          .contains('Back', { timeout: 3000 })
+          .should('not.exist');
+
+        // Back to default mode
+        cy.get('.llm-chat-flyout button[aria-label="fullScreen"]').click();
+        cy.get('.llm-chat-flyout button[aria-label="history"]').click();
+      });
+    });
+    describe('history item operations', () => {
+      const conversations = [];
+
+      before(() => {
+        // Create conversations data
+        cy.sendAssistantMessage({
+          input: {
+            type: 'input',
+            content: 'What are the indices in my cluster?',
+            contentType: 'text',
+          },
+        }).then((result) => {
+          if (result.status !== 200) {
+            throw result.body;
+          }
+          conversations.push(result.body);
+        });
+      });
+
+      after(() => {
+        // Clear created conversations in tests
+        conversations.map(({ conversationId }) =>
+          cy.deleteConversation(conversationId)
+        );
+      });
+
+      it('should show created conversation in the history list', () => {
+        cy.get('.llm-chat-flyout button[aria-label="history"]').click();
+
+        cy.get('.llm-chat-flyout').contains('Conversations');
+        conversations.forEach(({ conversationId }) => {
+          cy.getElementByTestId(`chatHistoryItem-${conversationId}`).should(
+            'exist'
+          );
+        });
+        cy.contains('What are the indices in my cluster?');
+        cy.get('.llm-chat-flyout button[aria-label="history"]').click();
+      });
+
+      it('should load conversation in chat panel', () => {
+        cy.get('.llm-chat-flyout button[aria-label="history"]').click();
+
+        const conversationToLoad = conversations[0];
+
+        cy.getElementByTestId(
+          `chatHistoryItem-${conversationToLoad.conversationId}`
+        )
+          .contains(conversationToLoad.title)
+          .click();
+        cy.get('textarea[placeholder="Ask me anything..."]').should('exist');
+        cy.get('div.llm-chat-bubble-panel-input').contains(
+          conversationToLoad.title
+        );
+      });
+
+      it('should able to update conversation title', () => {
+        cy.get('.llm-chat-flyout button[aria-label="history"]').click();
+
+        const conversationToUpdate = conversations[0];
+        const newTitle = 'New title';
+
+        cy.getElementByTestId(
+          `chatHistoryItem-${conversationToUpdate.conversationId}`
+        )
+          .find('button[aria-label="Edit conversation name"]')
+          .click();
+        cy.contains('Edit conversation name');
+
+        cy.get('input[aria-label="Conversation name input"').type(newTitle);
+        cy.getElementByTestId('confirmModalConfirmButton')
+          .contains('Confirm name')
+          .click();
+
+        conversationToUpdate.title = newTitle;
+        cy.getElementByTestId(
+          `chatHistoryItem-${conversationToUpdate.conversationId}`
+        ).contains(conversationToUpdate.title);
+        cy.contains('Edit conversation name', { timeout: 3000 }).should(
+          'not.exist'
+        );
+
+        // Reset to chat panel
+        cy.get('.llm-chat-flyout button[aria-label="history"]').click();
+      });
+
+      it('should able to delete conversation', () => {
+        cy.get('.llm-chat-flyout button[aria-label="history"]').click();
+
+        const conversationToDelete = conversations[0];
+
+        cy.getElementByTestId(
+          `chatHistoryItem-${conversationToDelete.conversationId}`
+        )
+          .find('button[aria-label="Delete conversation"]')
+          .click();
+        cy.getElementByTestId('confirmModalTitleText').contains(
+          'Delete conversation'
+        );
+
+        cy.getElementByTestId('confirmModalConfirmButton')
+          .contains('Delete conversation')
+          .click();
+
+        cy.getElementByTestId(
+          `chatHistoryItem-${conversationToDelete.conversationId}`
+        ).should('not.exist');
+        conversations.shift();
+
+        // Reset to chat panel
+        cy.get('.llm-chat-flyout button[aria-label="history"]').click();
+      });
+    });
+  });
+}
diff --git a/cypress/utils/plugins/dashboards-assistant/commands.js b/cypress/utils/plugins/dashboards-assistant/commands.js
index 51df1be8a..8197c9d80 100644
--- a/cypress/utils/plugins/dashboards-assistant/commands.js
+++ b/cypress/utils/plugins/dashboards-assistant/commands.js
@@ -4,9 +4,10 @@
  */
 
 import FlowTemplateJSON from '../../../fixtures/plugins/dashboards-assistant/flow-template.json';
-import { BACKEND_BASE_PATH } from '../../constants';
-import { ML_COMMONS_API } from './constants';
+import { BACKEND_BASE_PATH, BASE_PATH } from '../../constants';
+import { ML_COMMONS_API, ASSISTANT_API } from './constants';
 import clusterSettings from '../../../fixtures/plugins/dashboards-assistant/cluster_settings.json';
+import { apiRequest } from '../../helpers';
 
 Cypress.Commands.add('addAssistantRequiredSettings', () => {
   cy.request('PUT', `${BACKEND_BASE_PATH}/_cluster/settings`, clusterSettings);
@@ -152,3 +153,14 @@ Cypress.Commands.add('stopDummyServer', () => {
     }
   });
 });
+
+Cypress.Commands.add('sendAssistantMessage', (body) =>
+  apiRequest(`${BASE_PATH}${ASSISTANT_API.SEND_MESSAGE}`, 'POST', body)
+);
+
+Cypress.Commands.add('deleteConversation', (conversationId) =>
+  apiRequest(
+    `${BASE_PATH}${ASSISTANT_API.CONVERSATION}/${conversationId}`,
+    'DELETE'
+  )
+);
diff --git a/cypress/utils/plugins/dashboards-assistant/constants.js b/cypress/utils/plugins/dashboards-assistant/constants.js
index 16592accb..c8340b5ed 100644
--- a/cypress/utils/plugins/dashboards-assistant/constants.js
+++ b/cypress/utils/plugins/dashboards-assistant/constants.js
@@ -15,3 +15,10 @@ export const ML_COMMONS_API = {
   CREATE_MODEL: `${ML_COMMONS_API_PREFIX}/models/_register`,
   CREATE_AGENT: `${ML_COMMONS_API_PREFIX}/agents/_register`,
 };
+
+export const ASSISTANT_API_BASE = '/api/assistant';
+
+export const ASSISTANT_API = {
+  SEND_MESSAGE: `${ASSISTANT_API_BASE}/send_message`,
+  CONVERSATION: `${ASSISTANT_API_BASE}/conversation`,
+};
diff --git a/cypress/utils/plugins/dashboards-assistant/helpers.js b/cypress/utils/plugins/dashboards-assistant/helpers.js
new file mode 100644
index 000000000..53093a530
--- /dev/null
+++ b/cypress/utils/plugins/dashboards-assistant/helpers.js
@@ -0,0 +1,16 @@
+/*
+ * Copyright OpenSearch Contributors
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+export const setStorageItem = (storage, key, value) => {
+  const oldValue = storage.getItem(key);
+  storage.setItem(key, value);
+  return () => {
+    if (oldValue === null) {
+      storage.removeItem(key);
+    } else {
+      storage.setItem(key, oldValue);
+    }
+  };
+};