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diff --git a/spec/frontend/content_editor/components/toolbar_image_button_spec.js b/spec/frontend/content_editor/components/toolbar_image_button_spec.js
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+++ b/spec/frontend/content_editor/components/toolbar_image_button_spec.js
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+import { GlButton, GlFormInputGroup } from '@gitlab/ui';
+import { mountExtended } from 'helpers/vue_test_utils_helper';
+import ToolbarImageButton from '~/content_editor/components/toolbar_image_button.vue';
+import { configure as configureImageExtension } from '~/content_editor/extensions/image';
+import { createTestEditor, mockChainedCommands } from '../test_utils';
+
+describe('content_editor/components/toolbar_image_button', () => {
+  let wrapper;
+  let editor;
+
+  const buildWrapper = () => {
+    wrapper = mountExtended(ToolbarImageButton, {
+      propsData: {
+        tiptapEditor: editor,
+      },
+    });
+  };
+
+  const findImageURLInput = () =>
+    wrapper.findComponent(GlFormInputGroup).find('input[type="text"]');
+  const findApplyImageButton = () => wrapper.findComponent(GlButton);
+
+  const selectFile = async (file) => {
+    const input = wrapper.find({ ref: 'fileSelector' });
+
+    // override the property definition because `input.files` isn't directly modifyable
+    Object.defineProperty(input.element, 'files', { value: [file], writable: true });
+    await input.trigger('change');
+  };
+
+  beforeEach(() => {
+    const { tiptapExtension: Image } = configureImageExtension({
+      renderMarkdown: jest.fn(),
+      uploadsPath: '/uploads/',
+    });
+
+    editor = createTestEditor({
+      extensions: [Image],
+    });
+
+    buildWrapper();
+  });
+
+  afterEach(() => {
+    editor.destroy();
+    wrapper.destroy();
+  });
+
+  it('sets the image to the value in the URL input when "Insert" button is clicked', async () => {
+    const commands = mockChainedCommands(editor, ['focus', 'setImage', 'run']);
+
+    await findImageURLInput().setValue('https://example.com/img.jpg');
+    await findApplyImageButton().trigger('click');
+
+    expect(commands.focus).toHaveBeenCalled();
+    expect(commands.setImage).toHaveBeenCalledWith({
+      alt: 'img',
+      src: 'https://example.com/img.jpg',
+      canonicalSrc: 'https://example.com/img.jpg',
+    });
+    expect(commands.run).toHaveBeenCalled();
+
+    expect(wrapper.emitted().execute[0]).toEqual([{ contentType: 'image', value: 'url' }]);
+  });
+
+  it('uploads the selected image when file input changes', async () => {
+    const commands = mockChainedCommands(editor, ['focus', 'uploadImage', 'run']);
+    const file = new File(['foo'], 'foo.png', { type: 'image/png' });
+
+    await selectFile(file);
+
+    expect(commands.focus).toHaveBeenCalled();
+    expect(commands.uploadImage).toHaveBeenCalledWith({ file });
+    expect(commands.run).toHaveBeenCalled();
+
+    expect(wrapper.emitted().execute[0]).toEqual([{ contentType: 'image', value: 'upload' }]);
+  });
+});