Undo a Slash pick with one Mod-z, and hide rows that lift their own block #332

Parent

#328. Related: #251

What to build

After /h2 and Enter, one Mod-z gives different results by typing speed, because a Slash pick has no undo boundary of its own. It can also remove the typing before the /, and in a shared pad that lands on shared text. Two rows also undo their own block: "Bullet List" in an empty bullet item, and "Blockquote" inside a blockquote, each lift the line out.

After the fix, a pick is exactly one undo step, and each row does what its label says.

Acceptance criteria

• Type /h2 and press Enter. The pick adds exactly one step to the undo stack, at any typing speed.
• Text typed right after a pick is its own undo step. It does not merge into the pick.
• On desktop, one Mod-z after the pick gives back the /h2 paragraph, and the Slash menu opens on it again.
• In an empty item, the row whose type equals the nearest list is absent. Example: /bul in a bullet item shows no "Bullet List" row.
• The other list rows stay. "Ordered List" inside a bullet list still shows, as the toolbar button does.
• Inside any blockquote, including a list item inside a quote, the "Blockquote" row is absent.
• Two new Cypress cases pass. Each case fails when its fix is removed (prove it by sabotage).

Blocked by

None — can start now.

Agent brief

Type: AFK — an agent can finish this alone.

Category: bug

Current behavior:

• The pick runs deleteRange(range), then item.run(editor), and sets no undo boundary (apps/webapp/src/components/TipTap/extensions/slash-menu/slash-menu.ts:63-70).
• The Yjs UndoManager merges changes less than 500 ms apart (captureTimeout = 500, yjs 13.6.32 dist/yjs.mjs:3580). The pad's yUndoPlugin sets no other value (@tiptap/y-tiptap dist/y-tiptap.js:2866-2869).
• So a fast /h2 Enter merges the pick into the typing. A slow one does not. This is code-traced. No browser run has shown it yet; the new test does that first.
• The Bullet List, Ordered List, Task List and Blockquote rows use can: always (apps/webapp/src/components/TipTap/slash/slashItems.ts:55-86).
• toggleList with the same list type calls liftListItem (@tiptap/core src/commands/toggleList.ts). toggleWrap calls lift when a blockquote is already active (@tiptap/core src/commands/toggleWrap.ts:25-28).

Desired behavior:

• Stop Yjs capture before deleteRange and again after item.run. The first call keeps the pick apart from the typing. The second keeps the next keys apart from the pick.
• The heading toc-id stamp runs in appendTransaction (@tiptap/extension-unique-id 3.31.3 dist/index.js:118). That lands in the same dispatch, so the second call does not split it from the heading.
• After a pick, @tiptap/suggestion 3.31.3 sets no dismissed range. It sets one only on exit. So the restored /h2 opens the list again. The test pins that.
• Hide a list row when the nearest list ancestor has the same type. Hide Blockquote when editor.isActive('blockquote').

Where to start: Line numbers are hints as of 2026-09-28; the agent searches by symbol.

• Add apps/webapp/src/components/TipTap/slash/pickUndoBoundary.ts. It exports one function that calls yUndoPluginKey.getState(editor.state)?.undoManager.stopCapturing(). The same handle is used at toolbar/desktop/applyImportedContent.ts:20. The webapp and @tiptap/extension-collaboration resolve the same @tiptap/y-tiptap copy (3.0.9), so this key finds the pad's undo plugin. Optional chaining covers the UndoRedo path, where there is no Yjs undo.
• Keep the helper in its own file. The pad @ list (Add a pad @ list where Members open a Comment and Headings insert a link #349) will use the same undo boundary.
• In slash-menu.ts command, call the helper before deleteRange and after item.run.
• Add apps/webapp/src/components/TipTap/slash/slashContext.ts. It is the one home for caret checks that row can functions use. Put nearestListType(editor) there. Build it with findParentNode from @tiptap/core over bulletList, orderedList and taskList.
• Do not use isActive for lists. Lists nest, and isActive is true for any list ancestor.
• In slashItems.ts, replace can: always on the three list rows and on Blockquote.

Rules that apply:

• CONTEXT.md §Pad tools: each Slash row runs an existing editor command.
• apps/webapp/src/components/TipTap/CLAUDE.md §Editor Performance: items() runs on every keystroke, so keep the new checks cheap. Walk only the caret depth.
• AGENTS.md §Test Policy: the undo case is allowed under (c), an ordering bug that hand checks cannot pin. The rows case is allowed under (b): the defect is on main since commit e7271cc54. Prove each by sabotage.
• AGENTS.md §Test Orchestration And Authoring: use realType. cy.realPress is a parent command, so gate on editor focus first.

Verify:

• Add the undo case to apps/webapp/cypress/e2e/editor/slash/slash-menu.cy.ts:
  • The spec's beforeEach visits /editor with persist: true. That loads Collaboration on a local Y.Doc, so the pad has a Yjs undo manager. Without it the playground uses plain UndoRedo (apps/webapp/src/components/TipTap/TipTap.tsx:249). Keep persist: true.
  • After startIn, stop capture once, because its setContent would merge with fast typing.
  • Reach the undo manager through window._editor.state.plugins. Find the plugin whose key starts with y-undo$, then call getState(state).undoManager. new PluginKey('y-undo') (@tiptap/y-tiptap dist/y-tiptap.js:35) gives the key y-undo$, or y-undo$1 if a second copy loads. Fail the test when the lookup finds nothing. Add no window globals.
  • realType('/h2'). Read undoStack.length as L. Press Enter, then realType('x') at once. Assert the length is L + 2.
  • Pick the modifier like cypress/e2e/editor/find/caret-find.cy.ts:18: Meta on darwin, Control elsewhere. keyboard-shortcuts.cy.js presses Mod-z but asserts nothing, so do not copy it.
  • Mod-z once: the block is Heading 2 with empty text. Mod-z again: the block is a paragraph /h2, and [data-testid="slash-menu"] exists.
  • Do not add a timed wait.
• Add the rows case to the same spec:
  • Start in <h1>Doc</h1><ul><li><p></p></li></ul> and type /. Assert no [data-slash-item="bulletList"], and assert orderedList and taskList are present.
  • Start in <h1>Doc</h1><blockquote><p></p></blockquote> and type /. Assert no [data-slash-item="blockquote"].
• From the repo root, run bun run check.
• Start the local stack with make dev-local from the repo root. On first run it writes .env.local, which bun run dev in apps/webapp needs. Note the webapp port; it is not always 3000 (AGENTS.md §Test Policy; README.md local development).
• From apps/webapp, run bunx cypress run --spec cypress/e2e/editor/slash/slash-menu.cy.ts --env EDITOR_BASE_URL=http://localhost:<port>. All cases pass.
• Sabotage, one at a time, and watch a case fail each time:
  • Remove the helper call before deleteRange.
  • Remove the helper call after item.run.
  • Restore can: always on Bullet List.
  • Restore can: always on Blockquote.
    Put each fix back after it fails. Run the sabotage locally: a slow runner can stretch the gap before Enter past 500 ms and hide the merge.
• No look changes, so no light and dark check is needed. The phone sheet uses the same filterSlashItems, so it gets the same rows.

Out of scope

• Code Block in a list item lifts the item before it converts (@tiptap/core src/commands/setNode.ts falls back to clearNodes). The toolbar does the same. Accept it.
• "Ordered List" in a bullet list changes the whole list. That matches the toolbar.
• A second can check at pick time. On failure it would close the list and leave a dead /query.
• The empty-result status and option ids — Announce an empty Slash menu result, and give each option a stable id #333.
• Markdown hints on rows — Show the Markdown shortcut on each Slash menu row that has one #346.