diff --git a/apps/desktop/src/app/chat/composer/empty-composer.test.ts b/apps/desktop/src/app/chat/composer/empty-composer.test.ts
index 4e5146c174d..fe8305d2c45 100644
--- a/apps/desktop/src/app/chat/composer/empty-composer.test.ts
+++ b/apps/desktop/src/app/chat/composer/empty-composer.test.ts
@@ -1,6 +1,11 @@
 import { describe, expect, it } from 'vitest'
 
-import { composerPlainText, normalizeComposerEditorDom, RICH_INPUT_SLOT } from './rich-editor'
+import {
+  composerPlainText,
+  normalizeComposerEditorDom,
+  renderComposerContents,
+  RICH_INPUT_SLOT
+} from './rich-editor'
 
 function editor(): HTMLDivElement {
   const el = document.createElement('div')
@@ -69,3 +74,66 @@ describe('an emptied composer reads as empty', () => {
     expect(composerPlainText(el)).toBe('one\n\n')
   })
 })
+
+/** The rule the stylesheet paints the placeholder with. `:empty` alone goes
+ *  false the instant the scaffolding <br> lands. */
+const PLACEHOLDER_SHOWS = ':is(:empty, [data-empty])'
+
+describe('an emptied composer shows its placeholder again', () => {
+  it('advertises emptiness once the scaffolding break is in place', () => {
+    expect(emptied().matches(PLACEHOLDER_SHOWS)).toBe(true)
+  })
+
+  it('advertises emptiness for a truly childless editor', () => {
+    expect(editor().matches(PLACEHOLDER_SHOWS)).toBe(true)
+  })
+
+  it('stops advertising it once something is typed', () => {
+    const el = emptied()
+
+    el.replaceChildren(document.createTextNode('hi'))
+    normalizeComposerEditorDom(el)
+
+    expect(el.matches(PLACEHOLDER_SHOWS)).toBe(false)
+  })
+
+  // A text node is invisible to selectors, so `one<br>` and `<br>` are the same
+  // shape to any pure-CSS rule (`:has(> br:only-child)` matches both and paints
+  // the placeholder straight over the user's text). The DOM writer has to say.
+  it('does not advertise emptiness for a trailing break after text', () => {
+    const el = editor()
+
+    el.append(document.createTextNode('one'), document.createElement('br'))
+    normalizeComposerEditorDom(el)
+
+    expect(el.matches(PLACEHOLDER_SHOWS)).toBe(false)
+  })
+
+  it('does not advertise emptiness for a Shift+Enter break between text', () => {
+    const el = editor()
+
+    el.append(document.createTextNode('one'), document.createElement('br'), document.createTextNode('two'))
+    normalizeComposerEditorDom(el)
+
+    expect(el.matches(PLACEHOLDER_SHOWS)).toBe(false)
+  })
+
+  // Repainting from text (restored draft, undo, completion rebuild) is the
+  // other writer that reshapes the editor root — it must not strand the marker.
+  it('drops the marker when a draft is painted back in', () => {
+    const el = emptied()
+
+    renderComposerContents(el, 'restored draft')
+
+    expect(el.matches(PLACEHOLDER_SHOWS)).toBe(false)
+  })
+
+  it('re-advertises emptiness when a draft is painted back out', () => {
+    const el = editor()
+
+    renderComposerContents(el, 'temporary')
+    renderComposerContents(el, '')
+
+    expect(el.matches(PLACEHOLDER_SHOWS)).toBe(true)
+  })
+})
diff --git a/apps/desktop/src/app/chat/composer/index.tsx b/apps/desktop/src/app/chat/composer/index.tsx
index b05b563c528..74717759228 100644
--- a/apps/desktop/src/app/chat/composer/index.tsx
+++ b/apps/desktop/src/app/chat/composer/index.tsx
@@ -57,6 +57,7 @@ import { ActionBadges } from './micro-actions'
 import { chipTypedPathOnSpace, pathifyRefs } from './path-refs'
 import { QueuePanel } from './queue-panel'
 import {
+  COMPOSER_PLACEHOLDER_CLASS,
   composerPlainText,
   deleteChipBeforeCaret,
   deleteSelectionInEditor,
@@ -946,7 +947,7 @@ export function ChatBar({
         autoCorrect="off"
         className={cn(
           'min-h-[1.625rem] min-h-(--composer-input-min-height) max-h-(--composer-input-max-height) cursor-text overflow-y-auto whitespace-pre-wrap break-words [overflow-wrap:anywhere] bg-transparent pb-1 pr-1 pt-1 leading-normal text-foreground outline-none disabled:cursor-not-allowed',
-          'empty:before:content-[attr(data-placeholder)] empty:before:text-muted-foreground/60',
+          COMPOSER_PLACEHOLDER_CLASS,
           '**:data-ref-text:cursor-default',
           stacked && 'pl-3',
           stacked ? 'w-full' : 'min-w-(--composer-input-inline-min-width) flex-1'
diff --git a/apps/desktop/src/app/chat/composer/rich-editor.ts b/apps/desktop/src/app/chat/composer/rich-editor.ts
index d7ef6c30820..0c9c7098870 100644
--- a/apps/desktop/src/app/chat/composer/rich-editor.ts
+++ b/apps/desktop/src/app/chat/composer/rich-editor.ts
@@ -21,6 +21,28 @@ import { slashCommandMatches, type SlashCommandScanOptions } from './slash-refs'
 
 export const RICH_INPUT_SLOT = 'composer-rich-input'
 
+/** Paints `data-placeholder` while the editor is empty.
+ *
+ *  `:empty` can't be the whole test: a cleared editor keeps a scaffolding <br>
+ *  so the contenteditable doesn't collapse, and that break makes `:empty`
+ *  false. Nor can CSS infer it on its own — a text node is invisible to
+ *  selectors, so `one<br>` and a lone `<br>` are the same shape, and
+ *  `:has(> br:only-child)` would paint the placeholder straight over the
+ *  user's text. The code that empties the editor is what knows, so it marks it.
+ *
+ *  @see markEditorEmptiness */
+export const COMPOSER_PLACEHOLDER_CLASS =
+  '[&:is(:empty,[data-empty])]:before:content-[attr(data-placeholder)] [&:is(:empty,[data-empty])]:before:text-muted-foreground/60'
+
+/** Keep that marker in step with the editor root's contents. */
+export function markEditorEmptiness(editor: HTMLElement) {
+  if (editor.childNodes.length === 0) {
+    editor.dataset.empty = ''
+  } else {
+    delete editor.dataset.empty
+  }
+}
+
 /** @see referenceRe — the shared pattern every surface recognises a reference
  *  with. Module-level `/g` regexes carry `lastIndex`, so call sites reset it. */
 export const REF_RE = referenceRe()
@@ -165,6 +187,10 @@ export function renderComposerContents(target: HTMLElement, text: string, option
   // typed (`/wor`) and must stay editable. Callers repainting inert text (a
   // restored draft, a sent message opened for edit) pass `trailingCommitted`.
   appendComposerContents(target, text, options)
+
+  // The other writer that reshapes the editor root: painting a restored draft
+  // in clears the marker, clearing back to '' sets it.
+  markEditorEmptiness(target)
 }
 
 /** Caret range when the selection lives inside `editor`; else null. */
@@ -681,6 +707,9 @@ export function normalizeComposerEditorDom(editor: HTMLElement) {
   // composer to appear as a tiny dot/pixel. Ensure there's always at least
   // one <br> so the element maintains intrinsic height. The CSS min-height
   // is a belt; the <br> is suspenders — together they prevent the shrink.
+  // That break is also why emptiness has to be marked, not inferred.
+  markEditorEmptiness(editor)
+
   if (editor.childNodes.length === 0) {
     editor.appendChild(document.createElement('br'))
   }
diff --git a/apps/desktop/src/components/assistant-ui/thread/user-edit-composer.tsx b/apps/desktop/src/components/assistant-ui/thread/user-edit-composer.tsx
index 16ec52cf0d2..1e6ec792d01 100644
--- a/apps/desktop/src/components/assistant-ui/thread/user-edit-composer.tsx
+++ b/apps/desktop/src/components/assistant-ui/thread/user-edit-composer.tsx
@@ -35,6 +35,7 @@ import {
 } from '@/app/chat/composer/inline-refs'
 import { chipTypedPathOnSpace, pathifyRefs } from '@/app/chat/composer/path-refs'
 import {
+  COMPOSER_PLACEHOLDER_CLASS,
   composerPlainText,
   insertComposerContentsAtCaret,
   placeCaretEnd,
@@ -772,7 +773,7 @@ export const UserEditComposer: FC<UserEditComposerProps> = ({ cwd, gateway, sess
               autoCorrect="off"
               className={cn(
                 'ui-prompt-input-editor__input max-h-48 w-full resize-none bg-transparent p-0 pr-7 text-[length:var(--conversation-text-font-size)] text-foreground/95 outline-none',
-                'empty:before:content-[attr(data-placeholder)] empty:before:text-muted-foreground/60',
+                COMPOSER_PLACEHOLDER_CLASS,
                 '**:data-ref-text:cursor-default',
                 expanded ? 'min-h-16' : 'min-h-[1.25rem]'
               )}
diff --git a/apps/desktop/src/styles.css b/apps/desktop/src/styles.css
index 95eeebe29ac..4017644307b 100644
--- a/apps/desktop/src/styles.css
+++ b/apps/desktop/src/styles.css
@@ -1436,7 +1436,7 @@ text-* variant utilities. */ .btn-arc {
   font-size: 0.8125rem;
 }
 
-[data-slot='composer-rich-input']:empty::before {
+[data-slot='composer-rich-input']:is(:empty, [data-empty])::before {
   color: var(--ui-text-tertiary) !important;
 }