diff --git a/test/e2e/README.md b/test/e2e/README.md
index 66c06f4..9541897 100644
--- a/test/e2e/README.md
+++ b/test/e2e/README.md
@@ -27,6 +27,12 @@ End-to-end runs require Cloudinary credentials in `process.env`. The `onPrepare`
 pnpm test:e2e
 ```
 
+To run a specific test file:
+
+```bash
+pnpm test:e2e --spec [FILE_PATH]
+```
+
 This will:
 1. Download a VS Code binary (if not already cached in `.wdio-vscode-service/`)
 2. Launch VS Code with the extension loaded
@@ -56,6 +62,9 @@ test/e2e/
 
 Tests use [Mocha](https://mochajs.org/) as the test framework and the `wdio-vscode-service` page objects to interact with VS Code.
 
+VS Code page object references:
+- [wdio-vscode-service API](https://jubilant-broccoli-www5lem.pages.github.io/vscode-po/index.html) — full API reference for the WebdriverIO VS Code service.
+
 ```ts
 import { activityBarUtils } from '../src/utils/ActivityBarUtils.js'
 import { sideBarViewUtils } from '../src/utils/SideBarViewUtils.js'
diff --git a/test/e2e/package.json b/test/e2e/package.json
index 0242cf8..8a7eded 100644
--- a/test/e2e/package.json
+++ b/test/e2e/package.json
@@ -16,7 +16,7 @@
     "wdio-vscode-service": "^6.1.4"
   },
   "scripts": {
-    "test:e2e": "wdio run ./wdio.conf.ts",
+    "test:e2e": "rm -rf allure-report allure-results && wdio run ./wdio.conf.ts",
     "test:report": "allure generate allure-results -o allure-report --clean && allure open allure-report"
   }
 }
\ No newline at end of file
diff --git a/test/e2e/specs/loadMlAssets.spec.ts b/test/e2e/specs/loadMlAssets.spec.ts
index 69fc2e8..a7cec77 100644
--- a/test/e2e/specs/loadMlAssets.spec.ts
+++ b/test/e2e/specs/loadMlAssets.spec.ts
@@ -1,7 +1,7 @@
 import path from 'node:path';
 import { CloudinarySDK } from '../src/sdks/cloudinarySDK.js';
-import { activityBarUtils } from '../src/utils/ActivityBarUtils.js'
-import { sideBarViewUtils } from '../src/utils/SideBarViewUtils.js'
+import { activityBarUtils } from '../src/vscodeComponentsUtils/ActivityBarUtils.js'
+import { sideBarViewUtils } from '../src/vscodeComponentsUtils/SideBarViewUtils.js'
 import crypto from 'node:crypto';
 import { pathUtils } from '../src/utils/pathUtils.js';
 
@@ -15,12 +15,20 @@ describe('Asset Explorer Tetsts', () => {
     let secondAssetPublicID = `e2e-test-ae-${crypto.randomUUID().substring(0, 8)}`;
 
     beforeEach(async () => {
-        await cloudinarySDK.V2.uploader.upload(path.join(pathUtils.getTestAssetsPath(), 'sample_png.png'), { public_id: firstAssetPublicID });
-        await cloudinarySDK.V2.uploader.upload(path.join(pathUtils.getTestAssetsPath(), 'sample_png.png'), { public_id: secondAssetPublicID });
+        try {
+            await cloudinarySDK.V2.uploader.upload(path.join(pathUtils.getTestAssetsPath(), 'sample_png.png'), { public_id: firstAssetPublicID });
+            await cloudinarySDK.V2.uploader.upload(path.join(pathUtils.getTestAssetsPath(), 'sample_png.png'), { public_id: secondAssetPublicID });
+        } catch (error) {
+            throw new Error('Error uploading assets:', error);
+        }
     });
 
     afterEach(async () => {
-        await cloudinarySDK.V2.api.delete_resources([firstAssetPublicID, secondAssetPublicID]);
+        try {
+            await cloudinarySDK.V2.api.delete_resources([firstAssetPublicID, secondAssetPublicID]);
+        } catch (error) {
+            throw new Error('Error deleting assets:', error);
+        }
     });
 
     /**
@@ -35,6 +43,6 @@ describe('Asset Explorer Tetsts', () => {
         await sideBarViewUtils.validateSideBarViewTitle(expectedTitle);
 
         await sideBarViewUtils.validateContentItemsExist(expectedItems);
-        });
+    });
 });
 
diff --git a/test/e2e/specs/searchAssetFromSideBar.spec.ts b/test/e2e/specs/searchAssetFromSideBar.spec.ts
new file mode 100644
index 0000000..1c14386
--- /dev/null
+++ b/test/e2e/specs/searchAssetFromSideBar.spec.ts
@@ -0,0 +1,44 @@
+import path from 'node:path';
+import crypto from 'node:crypto';
+import { CloudinarySDK } from '../src/sdks/cloudinarySDK.js';
+import { activityBarUtils } from '../src/vscodeComponentsUtils/ActivityBarUtils.js';
+import { SideBarViewActions, sideBarViewUtils } from '../src/vscodeComponentsUtils/SideBarViewUtils.js';
+import { pathUtils } from '../src/utils/pathUtils.js';
+import { inputBoxUtils } from '../src/vscodeComponentsUtils/InputBoxUtils.js';
+import { browser } from '@wdio/globals';
+
+describe('Search asset from side bar', () => {
+
+    const cloudinarySDK = new CloudinarySDK();
+    const assetPublicID = `${crypto.randomUUID().substring(0, 8)}`;
+
+    beforeEach(async () => {
+        try {
+            await cloudinarySDK.V2.uploader.upload(
+                path.join(pathUtils.getTestAssetsPath(), 'sample_png.png'),
+                { public_id: assetPublicID }
+            );
+        } catch (error) {
+            throw new Error('Error uploading asset:', error);
+        }
+    });
+
+    afterEach(async () => {
+        try {
+            await cloudinarySDK.V2.api.delete_resources([assetPublicID]);
+        } catch (error) {
+            throw new Error('Error deleting asset:', error);
+        }
+    });
+
+    it('should find the uploaded asset via sidebar search', async () => {
+        await activityBarUtils.openView('Cloudinary');
+
+        await sideBarViewUtils.clickAction(SideBarViewActions.SEARCH);
+
+        await inputBoxUtils.fillAndConfirm(assetPublicID);
+
+        await sideBarViewUtils.validateContentItemsExist(['Clear Search', assetPublicID]);
+        await sideBarViewUtils.validateContentItemsNumber(2);
+    });
+});
diff --git a/test/e2e/specs/uploadFromSideBarView.spec.ts b/test/e2e/specs/uploadFromSideBarView.spec.ts
new file mode 100644
index 0000000..2ee7aa6
--- /dev/null
+++ b/test/e2e/specs/uploadFromSideBarView.spec.ts
@@ -0,0 +1,61 @@
+import path from "path";
+import { CloudinarySDK } from "../src/sdks/cloudinarySDK.js";
+import { pathUtils } from "../src/utils/pathUtils.js";
+import { SideBarViewActions, sideBarViewUtils } from "../src/vscodeComponentsUtils/SideBarViewUtils.js";
+import { activityBarUtils } from "../src/vscodeComponentsUtils/ActivityBarUtils.js";
+import { uploadToCloudinaryTab } from "../src/webViewTabs/UploadToCloudinaryTab.js";
+import * as fs from 'node:fs';
+import { expect } from "@wdio/globals";
+import allureReporter from '@wdio/allure-reporter'
+
+describe('Upload asset from side bar Upload button', () => {
+
+    const cloudinarySDK = new CloudinarySDK();
+    const assetPath = path.join(pathUtils.getTestAssetsPath(), 'sample_png.png');
+
+    const newFileName = `${crypto.randomUUID().substring(0, 8)}.png`;    
+    const newFilePath = path.join(pathUtils.getTempFolderPath(), newFileName);
+
+    const firstAssetPublicID = `e2e-test-ae-${crypto.randomUUID().substring(0, 8)}`;
+
+    beforeEach(async () => {
+        try {
+            // Copy with a unique name so the sidebar shows the display name (not the public ID) in dynamic folder environments
+            fs.copyFileSync(assetPath, newFilePath);
+        } catch (error) {
+            throw new Error('Error copying asset:', error);
+        }
+    });
+
+    afterEach(async () => {
+        try {
+            await cloudinarySDK.V2.api.delete_resources([firstAssetPublicID]);
+        } catch (error) {
+            throw new Error('Error deleting assets:', error);
+        }
+    });
+
+    it('should upload an asset using the side bar Upload button with custom public ID', async () => {
+        await activityBarUtils.openView('Cloudinary');
+        await sideBarViewUtils.clickAction(SideBarViewActions.UPLOAD);
+
+        await uploadToCloudinaryTab.switchTo();
+        await uploadToCloudinaryTab.openAdvancedOptions();
+        await uploadToCloudinaryTab.fillCustomPublicId(firstAssetPublicID);
+        
+        await uploadToCloudinaryTab.uploadLocalFile(newFilePath);
+
+        await uploadToCloudinaryTab.switchBack();
+
+        await activityBarUtils.openView('Cloudinary');
+        
+        await sideBarViewUtils.clickAction(SideBarViewActions.REFRESH);
+
+        await sideBarViewUtils.validateContentItemsExist([newFileName.replace('.png', '')]);
+
+        await allureReporter.addStep('Validate that the asset was uploaded with the correct display name');
+        const byPublicId = await cloudinarySDK.V2.api.resource(firstAssetPublicID);
+        expect(byPublicId.display_name).toBe(newFileName.replace('.png', ''));
+    });
+});
+
diff --git a/test/e2e/src/utils/pathUtils.ts b/test/e2e/src/utils/pathUtils.ts
index b9d5bc7..f25d8a1 100644
--- a/test/e2e/src/utils/pathUtils.ts
+++ b/test/e2e/src/utils/pathUtils.ts
@@ -1,5 +1,6 @@
 import path from 'node:path';
 import { fileURLToPath } from 'node:url';
+import * as fs from 'node:fs';
 
 const __filename = fileURLToPath(import.meta.url);
 const __dirname = path.dirname(__filename);
@@ -22,6 +23,17 @@ class PathUtils {
   public getTestAssetsPath() {
     return path.join(__dirname, '..', '..', 'assets');
   }
+
+  /**
+   * Gets the path to the temp folder.
+   */
+  public getTempFolderPath() {
+    const tempFolderPath = path.join(__dirname, '..', '..', 'temp');
+    if (!fs.existsSync(tempFolderPath)) {
+      fs.mkdirSync(tempFolderPath, { recursive: true });
+    }
+    return tempFolderPath;
+  }
 }
 
 export const pathUtils = new PathUtils();
diff --git a/test/e2e/src/utils/ActivityBarUtils.ts b/test/e2e/src/vscodeComponentsUtils/ActivityBarUtils.ts
similarity index 100%
rename from test/e2e/src/utils/ActivityBarUtils.ts
rename to test/e2e/src/vscodeComponentsUtils/ActivityBarUtils.ts
diff --git a/test/e2e/src/vscodeComponentsUtils/InputBoxUtils.ts b/test/e2e/src/vscodeComponentsUtils/InputBoxUtils.ts
new file mode 100644
index 0000000..e84f9bf
--- /dev/null
+++ b/test/e2e/src/vscodeComponentsUtils/InputBoxUtils.ts
@@ -0,0 +1,32 @@
+import { browser } from "@wdio/globals"
+import { InputBox } from "wdio-vscode-service"
+import allureReporter from '@wdio/allure-reporter'
+
+/**
+ * Utility class for interacting with the VS Code InputBox / Command Palette.
+ */
+class InputBoxUtils {
+
+    /**
+     * Opens the VS Code command palette.
+     */
+    public async getInputBox() {
+        await allureReporter.addStep('Get Input Box instance');
+        const inputBox = await browser.$('.quick-input-widget input');
+        await inputBox.waitForDisplayed();
+        return inputBox;
+    }
+
+    /**
+     * Fills an already-visible InputBox with text and confirms.
+     * Use when an action (e.g. Search) has already opened an InputBox.
+     */
+    public async fillAndConfirm(text: string) {
+        await allureReporter.addStep(`Fill input box "${text}"`);
+        const inputBox = await this.getInputBox();
+        await inputBox.setValue(text);
+        await browser.keys('Enter');
+    }
+}
+
+export const inputBoxUtils = new InputBoxUtils()
diff --git a/test/e2e/src/utils/SideBarViewUtils.ts b/test/e2e/src/vscodeComponentsUtils/SideBarViewUtils.ts
similarity index 65%
rename from test/e2e/src/utils/SideBarViewUtils.ts
rename to test/e2e/src/vscodeComponentsUtils/SideBarViewUtils.ts
index 2e571d3..34dbaab 100644
--- a/test/e2e/src/utils/SideBarViewUtils.ts
+++ b/test/e2e/src/vscodeComponentsUtils/SideBarViewUtils.ts
@@ -2,6 +2,15 @@ import { browser, expect } from "@wdio/globals"
 import { TreeItem } from "wdio-vscode-service"
 import allureReporter from '@wdio/allure-reporter'
 
+/**
+ * Actions available in the Side Bar View.
+ */
+export enum SideBarViewActions {
+    UPLOAD = ' Upload',
+    SEARCH = ' Search',
+    REFRESH = '  Refresh',
+}
+
 /**
  * Utility class for interacting with the Side Bar View in VS Code.
  */
@@ -53,11 +62,42 @@ class SideBarViewUtils {
         const itemLabels = await Promise.all(
             visibleItems.map(item => item.getLabel())
         );
+
         for (const expected of expectedItems) {
             expect(itemLabels).toContain(expected);
         }
     }
 
+    /**
+     * Waits for the content of the Side Bar View to load.
+     */
+    public async clickAction(action: SideBarViewActions) {
+        await allureReporter.addStep(`Click the "${action.trim()}" action button`);
+        const sideBarView = await this.getSideBarView();
+        const titlePart = sideBarView.getTitlePart();
+        const actionButton = await titlePart.elem.$(`.//*[@title='${action}' or @aria-label='${action}']`);
+        await actionButton.waitForClickable();
+        await actionButton.click();
+    }
+
+    /**
+     * Validates that the Side Bar View contains exactly the expected items and no others.
+     */
+    public async validateContentItemsNumber(expectedItemsNumber: number) {
+        await allureReporter.addStep(`Validate only ${expectedItemsNumber} items are visible`);
+        await this.waitContentToLoad();
+        const content = await this.getSideBarViewContent();
+        const sections = await content.getSections();
+        const visibleItems = await sections[0].getVisibleItems() as TreeItem[];
+        const itemLabels = await Promise.all(
+            visibleItems.map(item => item.getLabel())
+        );
+
+        await browser.waitUntil(async () => {
+            return itemLabels.length === expectedItemsNumber;
+        }, { timeout: 15000, timeoutMsg: `Expected ${itemLabels.length} items, but got ${expectedItemsNumber} items` })
+    }
+
     /**
      * Waits for the content of the Side Bar View to load.
      */
diff --git a/test/e2e/src/vscodeComponentsUtils/WebViewUtils.ts b/test/e2e/src/vscodeComponentsUtils/WebViewUtils.ts
new file mode 100644
index 0000000..b1ea8a4
--- /dev/null
+++ b/test/e2e/src/vscodeComponentsUtils/WebViewUtils.ts
@@ -0,0 +1,16 @@
+import { browser } from "@wdio/globals"
+
+
+class WebViewUtils {
+    /**
+     * Gets the WebView instance.
+     */
+    public async getWebView(title: string) {
+        const workbench = await browser.getWorkbench()
+        return browser.waitUntil(() => workbench.getWebviewByTitle(title), {
+            timeoutMsg: `WebView with title "${title}" not found`,
+        })
+    }
+}
+
+export const webViewUtils = new WebViewUtils()
\ No newline at end of file
diff --git a/test/e2e/src/webViewTabs/UploadToCloudinaryTab.ts b/test/e2e/src/webViewTabs/UploadToCloudinaryTab.ts
new file mode 100644
index 0000000..5acd973
--- /dev/null
+++ b/test/e2e/src/webViewTabs/UploadToCloudinaryTab.ts
@@ -0,0 +1,72 @@
+import { browser } from "@wdio/globals"
+import allureReporter from '@wdio/allure-reporter'
+import { WebViewTabBase } from "./WebViewTabBase.js";
+
+/**
+ * Utility class for interacting with the Upload to Cloudinary webview.
+ */
+class UploadToCloudinaryTab extends WebViewTabBase {
+
+    constructor() {
+        super('Upload to Cloudinary');
+    }
+
+    /**
+     * Uploads a local file via the upload widget's file input.
+     * Uses the wdio-vscode-service WebView page object for iframe switching.
+     */
+    public async uploadLocalFile(absoluteFilePath: string) {
+        await allureReporter.addStep(`Upload file: ${absoluteFilePath}`);
+
+        const fileInput = await browser.$('#fileInput');
+        await fileInput.waitForExist();
+        await browser.execute((el: any) => {
+            el.style.display = 'block';
+            el.style.opacity = '1';
+        }, fileInput as any);
+        await fileInput.setValue(absoluteFilePath);
+
+        await this.waitForAllUploadsToComplete();
+    }
+
+    /**
+     * Waits for all uploads to complete.
+     */
+    public async waitForAllUploadsToComplete() {
+        await browser.waitUntil(async () => {
+            const statuses = await browser.$$('.queue-item__status');
+            const count = await statuses.length;
+            if (count === 0) {
+                return false
+            };
+
+            const textPromises = await statuses.map(el => el.getText());
+            const texts = await Promise.all(textPromises);
+            return texts.every(text => text === 'Complete');
+        }, { timeoutMsg: 'Not all uploads completed in time' });
+    }
+
+    /**
+     * Opens the Advanced Options section.
+     */
+    public async openAdvancedOptions() {
+        await allureReporter.addStep('Open Advanced Options');
+
+        const header = await browser.$('#advancedHeader');
+        await header.waitForClickable();
+        await header.click();
+    }
+
+    /**
+     * Fills the Custom Public ID input.
+     */
+    public async fillCustomPublicId(publicId: string) {
+        await allureReporter.addStep(`Fill Custom Public ID: ${publicId}`);
+
+        const input = await browser.$('#publicIdInput');
+        await input.waitForExist();
+        await input.setValue(publicId);
+    }
+}
+
+export const uploadToCloudinaryTab = new UploadToCloudinaryTab()
diff --git a/test/e2e/src/webViewTabs/WebViewTabBase.ts b/test/e2e/src/webViewTabs/WebViewTabBase.ts
new file mode 100644
index 0000000..62712d8
--- /dev/null
+++ b/test/e2e/src/webViewTabs/WebViewTabBase.ts
@@ -0,0 +1,38 @@
+import { WebView } from "wdio-vscode-service";
+import { webViewUtils } from "../vscodeComponentsUtils/WebViewUtils.js";
+
+
+/**
+ * Base class for all webview tabs.
+ */
+export abstract class WebViewTabBase {
+    protected title: string;
+    protected webview: WebView | null = null;
+
+    /**
+     * Constructor.
+     * @param title - The title of the webview tab.
+     */
+    constructor(title: string) {
+        this.title = title;
+    }
+
+    /**
+     * Switches to the webview tab.
+     */
+    public async switchTo() {
+        this.webview = await webViewUtils.getWebView(this.title);
+        await this.webview.open();
+    }
+
+    /**
+     * Switches back to the main view.
+     */
+    public async switchBack() {
+        if (!this.webview) {
+            throw new Error('WebView not opened. Call switchTo() first.');
+        }
+        await this.webview.close();
+        this.webview = null;
+    }
+}
\ No newline at end of file