diff --git a/packages/app-core/src/lib/cm-format.test.ts b/packages/app-core/src/lib/cm-format.test.ts
index fcc2e447..c50aa600 100644
--- a/packages/app-core/src/lib/cm-format.test.ts
+++ b/packages/app-core/src/lib/cm-format.test.ts
@@ -51,6 +51,29 @@ describe('toggleWrap', () => {
     expect(view.state.selection.main.head).toBe(3) // between == and ==
   })
 
+  it('moves past the closing marker when toggling off an active empty-selection wrap', () => {
+    const view = mount('**bold** text', 6, 6) // cursor before closing **
+    toggleWrap(view, '**')
+    expect(view.state.doc.toString()).toBe('**bold** text')
+    expect(view.state.selection.main.empty).toBe(true)
+    expect(view.state.selection.main.head).toBe(8)
+  })
+
+  it('removes an untouched empty pair when pressing the shortcut again', () => {
+    const view = mount('****', 2, 2) // between the opening and closing **
+    toggleWrap(view, '**')
+    expect(view.state.doc.toString()).toBe('')
+    expect(view.state.selection.main.empty).toBe(true)
+    expect(view.state.selection.main.head).toBe(0)
+  })
+
+  it('does not treat a cursor before a later opening marker as active formatting', () => {
+    const view = mount('**done** **next**', 9, 9) // cursor before the second opening **
+    toggleWrap(view, '**')
+    expect(view.state.doc.toString()).toBe('**done** ******next**')
+    expect(view.state.selection.main.head).toBe(11)
+  })
+
   it('works for the other markers', () => {
     for (const [marker, expected] of [
       ['~~', 'a ~~b~~ c'],
diff --git a/packages/app-core/src/lib/cm-format.ts b/packages/app-core/src/lib/cm-format.ts
index 5b932313..36d347db 100644
--- a/packages/app-core/src/lib/cm-format.ts
+++ b/packages/app-core/src/lib/cm-format.ts
@@ -7,6 +7,23 @@
 import { EditorSelection } from '@codemirror/state'
 import type { EditorView } from '@codemirror/view'
 
+function isInsideUnclosedMarker(text: string, marker: string): boolean {
+  let count = 0
+  let index = 0
+  while (index < text.length) {
+    const found = text.indexOf(marker, index)
+    if (found === -1) break
+    if (
+      marker !== '*' ||
+      (text[found - 1] !== '*' && text[found + marker.length] !== '*')
+    ) {
+      count++
+    }
+    index = found + marker.length
+  }
+  return count % 2 === 1
+}
+
 /**
  * Toggle a symmetric inline marker around each selection range: wrap when it
  * isn't wrapped, unwrap when the markers already sit just outside (or just
@@ -18,6 +35,31 @@ export function toggleWrap(view: EditorView, marker: string): boolean {
     view.state.changeByRange((range) => {
       const { from, to } = range
       if (from === to) {
+        const before = view.state.sliceDoc(Math.max(0, from - m.length), from)
+        const after = view.state.sliceDoc(from, Math.min(view.state.doc.length, from + m.length))
+
+        if (after === m) {
+          if (before === m) {
+            // Empty pair: pressing the shortcut again removes the markers.
+            return {
+              changes: { from: from - m.length, to: from + m.length, insert: '' },
+              range: EditorSelection.cursor(from - m.length)
+            }
+          }
+
+          const line = view.state.doc.lineAt(from)
+          const lineBefore = view.state.sliceDoc(line.from, from)
+          if (isInsideUnclosedMarker(lineBefore, m)) {
+            // Cursor is just before the closing marker from a previously inserted
+            // pair. Treat the shortcut as leaving/toggling off formatting instead
+            // of inserting another marker pair inside it.
+            return {
+              changes: [],
+              range: EditorSelection.cursor(from + m.length)
+            }
+          }
+        }
+
         // No selection: insert the pair and drop the cursor between them.
         return {
           changes: { from, insert: m + m },