diff --git a/e2e/cypress/integration/files_and_attachments/image_link_preview_new_window_spec.js b/e2e/cypress/integration/files_and_attachments/image_link_preview_new_window_spec.js
new file mode 100644
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+++ b/e2e/cypress/integration/files_and_attachments/image_link_preview_new_window_spec.js
@@ -0,0 +1,70 @@
+// Copyright (c) 2015-present Mattermost, Inc. All Rights Reserved.
+// See LICENSE.txt for license information.
+
+// ***************************************************************
+// - [#] indicates a test step (e.g. # Go to a page)
+// - [*] indicates an assertion (e.g. * Check the title)
+// - Use element ID when selecting an element. Create one if none.
+// ***************************************************************
+
+// Group: @file_and_attachments
+
+describe('Image Link Preview', () => {
+    let testTeam;
+
+    before(() => {
+        // # Enable Link Previews
+        cy.apiUpdateConfig({
+            ServiceSettings: {
+                EnableLinkPreviews: true,
+            },
+        });
+
+        // # Create new team and new user and visit Town Square channel
+        cy.apiInitSetup({loginAfter: true}).then(({team}) => {
+            testTeam = team;
+
+            // # For test user, enable link previews and expand image previews
+            cy.apiSaveLinkPreviewsPreference('true');
+            cy.apiSaveCollapsePreviewsPreference('false');
+
+            cy.visit(`/${testTeam.name}/channels/town-square`);
+        });
+    });
+
+    it('MM-T329 Image link preview', () => {
+        const link = 'http://www.traveller.com.au/content/dam/images/g/u/n/q/h/0/image.related.articleLeadwide.620x349.gunpvd.png/1488330286332.png';
+        const baseUrl = Cypress.config('baseUrl');
+        const encodedIconUrl = encodeURIComponent(link);
+
+        // # Post a link to an externally hosted image
+        cy.postMessage(link);
+
+        cy.findByLabelText('file thumbnail').click().then(() => {
+            // * Assert that the image has the correct url
+            cy.findByTestId('imagePreview').should('have.attr', 'src', `${baseUrl}/api/v4/image?url=${encodedIconUrl}`);
+
+            // * Assert container elements
+            cy.findByTestId('fileCountFooter').should('be.visible');
+            cy.findByText('File 1 of 1').should('be.visible');
+            cy.findByText('Open').should('be.visible');
+
+            // * Assert that clicking the image will open in a new tab
+            cy.get('a[href*="image"]').should('have.attr', 'target', '_blank');
+
+            // * Assert image is available to be clicked (cypress limitation for opening new child window)
+            cy.findByTestId('imagePreview').then((el) => {
+                const imageUrl = el.prop('src');
+                cy.request(imageUrl).then((res) => {
+                    expect(res.status).equal(200);
+                });
+            });
+
+            // * Close the image then assert that it is closed
+            cy.findByTestId('imagePreview').trigger('mouseover').then(() => {
+                cy.get('div.modal-close').click();
+                cy.findByTestId('imagePreview').should('not.exist');
+            });
+        });
+    });
+});