diff --git a/frontend/src/components/input/Password.vue b/frontend/src/components/input/Password.vue
index ffd43d788..256083b06 100644
--- a/frontend/src/components/input/Password.vue
+++ b/frontend/src/components/input/Password.vue
@@ -12,8 +12,8 @@
 			:autocomplete="autocomplete"
 			:aria-invalid="isValid !== true ? true : undefined"
 			:aria-describedby="errorId"
-			@keyup.enter="e => $emit('submit', e)"
-			@focusout="() => {validate(); validateAfterFirst = true}"
+			@keyup.enter="handleSubmit"
+			@focusout="e => {handleInput(e); validate(); validateAfterFirst = true}"
 			@keyup="() => {validateAfterFirst ? validate() : null}"
 			@input="handleInput"
 		>
@@ -71,12 +71,19 @@ const isValid = ref<true | string>(true)
 const validateAfterFirst = ref(false)
 const errorId = computed(() => isValid.value !== true ? `${props.id}-error` : undefined)
 
-const validate = useDebounceFn(() => {
-	const valid = validatePassword(props.modelValue, props.validateMinLength)
+function validateValue(value: string) {
+	const valid = validatePassword(value, props.validateMinLength)
 	isValid.value = valid === true ? true : t(valid)
-}, 100)
+}
 
-watchEffect(() => props.validateInitially && validate())
+const validate = useDebounceFn(() => validateValue(props.modelValue), 100)
+
+watchEffect(() => {
+	if (props.validateInitially) {
+		validateAfterFirst.value = true
+		validate()
+	}
+})
 
 function togglePasswordFieldType() {
 	passwordFieldType.value = passwordFieldType.value === 'password'
@@ -87,6 +94,14 @@ function togglePasswordFieldType() {
 function handleInput(e: Event) {
 	emit('update:modelValue', (e.target as HTMLInputElement).value)
 }
+
+function handleSubmit(e: Event) {
+	// Autofill may not fire an input event.
+	handleInput(e)
+	validateValue((e.target as HTMLInputElement).value)
+	validateAfterFirst.value = true
+	emit('submit', e)
+}
 </script>
 
 <style scoped>
diff --git a/frontend/tests/e2e/user/login.spec.ts b/frontend/tests/e2e/user/login.spec.ts
index 6170c3eea..90d25bb8e 100644
--- a/frontend/tests/e2e/user/login.spec.ts
+++ b/frontend/tests/e2e/user/login.spec.ts
@@ -50,6 +50,51 @@ test.describe('Login', () => {
 		await expect(page.locator('main h1')).toContainText(credentials.username)
 	})
 
+	for (const scenario of ['typed', 'blurred', 'retried', 'autofilled'] as const) {
+		test(`Should log in with Enter without flashing a password validation error (${scenario})`, async ({page}) => {
+			await page.goto('/login')
+			await page.locator('#username').fill(credentials.username)
+			if (scenario === 'retried') {
+				await page.getByRole('button', {name: 'Login', exact: true}).click()
+				await expect(page.locator('#password-error')).toBeVisible()
+			}
+			if (scenario === 'autofilled') {
+				await page.locator('#password').evaluate((input: HTMLInputElement, password) => {
+					input.value = password
+				}, credentials.password)
+			} else {
+				await page.locator('#password').pressSequentially(credentials.password)
+			}
+			if (scenario === 'blurred') {
+				await page.locator('#password').press('Tab')
+				await page.locator('#password').focus()
+			}
+			// Keep the form mounted while debounced validation runs.
+			await page.route('**/api/v2/login', async route => {
+				const response = await route.fetch()
+				await new Promise(resolve => setTimeout(resolve, 300))
+				await route.fulfill({response})
+			})
+			const errors = await page.evaluateHandle(() => {
+				const errors: string[] = []
+				const observer = new MutationObserver(() => {
+					const error = document.querySelector('#password-error')
+					if (error) errors.push(error.textContent ?? '')
+				})
+				observer.observe(document.body, {childList: true, subtree: true, characterData: true})
+				return errors
+			})
+
+			await page.locator('#password').press('Enter')
+			await expect(page).toHaveURL('/')
+			await expect(page.locator('main h1')).toContainText(credentials.username)
+			expect(await errors.jsonValue()).toEqual([])
+			await errors.dispose()
+			await page.reload()
+			await expect(page.locator('main h1')).toContainText(credentials.username)
+		})
+	}
+
 	test('Should fail with a bad password', async ({page}) => {
 		const fixture = {
 			username: 'test',