diff --git a/frontend/tests/e2e/editor/emoji-autocomplete.spec.ts b/frontend/tests/e2e/editor/emoji-autocomplete.spec.ts
new file mode 100644
index 000000000..1476ce7bb
--- /dev/null
+++ b/frontend/tests/e2e/editor/emoji-autocomplete.spec.ts
@@ -0,0 +1,85 @@
+import {test, expect} from '../../support/fixtures'
+import {ProjectFactory} from '../../factories/project'
+import {TaskFactory} from '../../factories/task'
+import {BucketFactory} from '../../factories/bucket'
+import {createDefaultViews} from '../project/prepareProjects'
+
+test.describe('Emoji Autocomplete', () => {
+	let projectId: number
+	test.beforeEach(async () => {
+		const projects = await ProjectFactory.create(1) as Array<{id: number}>
+		projectId = projects[0].id
+		const views = await createDefaultViews(projectId)
+		await BucketFactory.create(1, {
+			project_view_id: views[3].id,
+		})
+	})
+
+	test('Inserts the unicode glyph when selecting from the popup', async ({authenticatedPage: page}) => {
+		const tasks = await TaskFactory.create(1, {
+			id: 1,
+			project_id: projectId,
+			description: 'x',
+			index: 1,
+		})
+
+		await page.goto(`/tasks/${tasks[0].id}`)
+		await page.waitForLoadState('networkidle')
+
+		const editButton = page.locator('.task-view .details.content.description .tiptap button.done-edit').filter({hasText: 'Edit'})
+		await expect(editButton).toBeVisible({timeout: 10000})
+		await editButton.click()
+
+		const editor = page.locator('.task-view .details.content.description [contenteditable="true"]').first()
+		await expect(editor).toBeVisible({timeout: 10000})
+		await editor.click()
+		await page.keyboard.press('ControlOrMeta+a')
+		await page.keyboard.press('Delete')
+
+		await editor.pressSequentially(':smi', {delay: 50})
+
+		const popup = page.locator('.emoji-items')
+		await expect(popup).toBeVisible()
+
+		await page.keyboard.press('Enter')
+
+		await expect(popup).toBeHidden()
+		await expect(editor).not.toContainText(':smi')
+		const text = await editor.innerText()
+		let hasNonAscii = false
+		for (let i = 0; i < text.length; i++) {
+			if (text.charCodeAt(i) > 127) {
+				hasNonAscii = true
+				break
+			}
+		}
+		expect(hasNonAscii).toBe(true)
+	})
+
+	test('Does not open the popup when ":" follows a non-whitespace char', async ({authenticatedPage: page}) => {
+		const tasks = await TaskFactory.create(1, {
+			id: 2,
+			project_id: projectId,
+			description: 'x',
+			index: 1,
+		})
+
+		await page.goto(`/tasks/${tasks[0].id}`)
+		await page.waitForLoadState('networkidle')
+
+		const editButton = page.locator('.task-view .details.content.description .tiptap button.done-edit').filter({hasText: 'Edit'})
+		await expect(editButton).toBeVisible({timeout: 10000})
+		await editButton.click()
+
+		const editor = page.locator('.task-view .details.content.description [contenteditable="true"]').first()
+		await expect(editor).toBeVisible({timeout: 10000})
+		await editor.click()
+		await page.keyboard.press('ControlOrMeta+a')
+		await page.keyboard.press('Delete')
+
+		await editor.pressSequentially('word:foo', {delay: 50})
+
+		const popup = page.locator('.emoji-items')
+		await expect(popup).toBeHidden()
+	})
+})