apps/client/src/features/editor/extensions/custom-typography.test.ts

@@ -0,0 +1,231 @@
+import { describe, it, expect } from "vitest";
+import { Editor } from "@tiptap/core";
+import { Document } from "@tiptap/extension-document";
+import { Paragraph } from "@tiptap/extension-paragraph";
+import { Text } from "@tiptap/extension-text";
+import { ySyncPluginKey } from "@tiptap/y-tiptap";
+import {
+  CustomTypography,
+  undoGuardKey,
+  findChangedRange,
+  mapRangeThroughChange,
+} from "./custom-typography";
+
+/**
+ * PR #296 — the collab-safe typography undo-guard is exercised through the REAL
+ * editor path: a fresh Editor with the CustomTypography extension, transactions
+ * tagged exactly the way prosemirror-history / y-tiptap tag undo & remote
+ * changes (`setMeta("history$", …)` and `setMeta(ySyncPluginKey, …)`), plus
+ * direct unit tests of the two pure diff helpers. No hand-poke of plugin state.
+ *
+ * ARMING MECHANISM (verified against custom-typography.ts source):
+ *   - A transaction arms the guard only when it is BOTH history/remote
+ *     (`getMeta("history$")` truthy, or `isChangeOrigin` via the ySync meta)
+ *     AND an undo/redo (`getMeta("history$")` truthy, or ySync
+ *     `isUndoRedoOperation`), AND its whole-doc diff is a REPLACE
+ *     (change.oldTo > change.from && change.newTo > change.from).
+ *   - `history$` is the stringified PluginKey of the single prosemirror-history
+ *     plugin; ProseMirror stores meta under `key.key`, so setMeta("history$")
+ *     in a test is read identically by the extension's getMeta("history$").
+ */
+
+const singlePara = (text: string) => ({
+  type: "doc",
+  content: [{ type: "paragraph", content: [{ type: "text", text }] }],
+});
+
+const makeEditor = (text: string) =>
+  new Editor({
+    extensions: [Document, Paragraph, Text, CustomTypography],
+    content: singlePara(text),
+  });
+
+// Build a before/after EditorState pair by applying one plain transaction.
+const mutate = (text: string, apply: (tr: any, schema: any) => void) => {
+  const editor = new Editor({
+    extensions: [Document, Paragraph, Text],
+    content: singlePara(text),
+  });
+  const before = editor.state;
+  const tr = before.tr;
+  apply(tr, before.schema);
+  editor.view.dispatch(tr);
+  const after = editor.state;
+  return { before, after, editor };
+};
+
+describe("findChangedRange", () => {
+  it("returns null for identical docs", () => {
+    const editor = new Editor({
+      extensions: [Document, Paragraph, Text],
+      content: singlePara("hello"),
+    });
+    expect(findChangedRange(editor.state, editor.state)).toBeNull();
+    editor.destroy();
+  });
+
+  it("returns the minimal range for a normal middle insertion", () => {
+    // "hello world" (text at 1..12); insert "there " at pos 6.
+    const { before, after, editor } = mutate("hello world", (tr) =>
+      tr.insertText("there ", 6),
+    );
+    expect(findChangedRange(before, after)).toEqual({
+      from: 6,
+      oldTo: 6,
+      newTo: 12,
+    });
+    editor.destroy();
+  });
+
+  it("normalizes the INSERTION overlapping-bounds branch (repeated content)", () => {
+    // Insert one more 'a' into "aaaaa" at pos 3. findDiffStart lands at the end
+    // (6) while findDiffEnd reports an end BEFORE it ({a:1,b:2}); both ends must
+    // be pushed forward by the same delta -> a non-degenerate range.
+    const { before, after, editor } = mutate("aaaaa", (tr) =>
+      tr.insertText("a", 3),
+    );
+    const change = findChangedRange(before, after)!;
+    expect(change).toEqual({ from: 6, oldTo: 6, newTo: 7 });
+    // Invariant the guard logic relies on: never degenerate.
+    expect(change.from).toBeLessThanOrEqual(change.oldTo);
+    expect(change.from).toBeLessThanOrEqual(change.newTo);
+    editor.destroy();
+  });
+
+  it("normalizes the DELETION overlapping-bounds branch (F2 fix)", () => {
+    // Delete one repeated 'a' from the middle of "aaaaa" ([3,4)). Here
+    // findDiffEnd reports newTo < start, the symmetric case the old one-sided
+    // normalization missed -> it used to yield a degenerate range (newTo < from).
+    const { before, after, editor } = mutate("aaaaa", (tr) => tr.delete(3, 4));
+    const change = findChangedRange(before, after)!;
+    expect(change).toEqual({ from: 5, oldTo: 6, newTo: 5 });
+    // The whole point of F2: from <= newTo (and from <= oldTo) still holds.
+    expect(change.from).toBeLessThanOrEqual(change.newTo);
+    expect(change.from).toBeLessThanOrEqual(change.oldTo);
+    editor.destroy();
+  });
+
+  it("normalizes a multi-char repeated deletion (F2 fix)", () => {
+    const { before, after, editor } = mutate("aaaaa", (tr) => tr.delete(2, 4));
+    const change = findChangedRange(before, after)!;
+    expect(change).toEqual({ from: 4, oldTo: 6, newTo: 4 });
+    expect(change.from).toBeLessThanOrEqual(change.newTo);
+    editor.destroy();
+  });
+});
+
+describe("mapRangeThroughChange", () => {
+  const range = { from: 5, to: 10 };
+
+  it("RELEASES on a strict intersection (edit inside the guarded range)", () => {
+    // change straddles the interior of the guard.
+    expect(
+      mapRangeThroughChange(range, { from: 6, oldTo: 8, newTo: 7 }),
+    ).toBeNull();
+  });
+
+  it("does NOT release on a boundary touch at the guard END", () => {
+    // Edit begins exactly at range.to (10): from < to is false -> no intersect.
+    expect(
+      mapRangeThroughChange(range, { from: 10, oldTo: 10, newTo: 12 }),
+    ).toEqual(range);
+  });
+
+  it("does NOT release on a boundary touch at the guard START", () => {
+    // Edit ends exactly at range.from (5): oldTo > from is false -> no intersect;
+    // it is treated as a change fully before, shifting the guard.
+    expect(
+      mapRangeThroughChange(range, { from: 3, oldTo: 5, newTo: 8 }),
+    ).toEqual({ from: 8, to: 13 });
+  });
+
+  it("SHIFTS the guard for a change fully before it", () => {
+    // Insert 2 chars entirely before the range (oldTo 3 <= from 5): +2 delta.
+    expect(
+      mapRangeThroughChange(range, { from: 2, oldTo: 3, newTo: 5 }),
+    ).toEqual({ from: 7, to: 12 });
+  });
+
+  it("leaves the guard untouched for a change fully after it", () => {
+    expect(
+      mapRangeThroughChange(range, { from: 12, oldTo: 14, newTo: 16 }),
+    ).toBe(range);
+  });
+});
+
+describe("undo-guard arming (integration)", () => {
+  it("arms {from, to:newTo} on a LOCAL undo-replace (history meta)", () => {
+    // Undo of an em-dash substitution: "a—b" restored to "a--b" — the em-dash
+    // (pos 2..3) is REPLACED by "--", tagged with the history plugin's meta.
+    const editor = makeEditor("a—b");
+    const { state } = editor;
+    const tr = state.tr
+      .replaceWith(2, 3, state.schema.text("--"))
+      .setMeta("history$", { redo: false });
+    editor.view.dispatch(tr);
+
+    expect(editor.state.doc.textContent).toBe("a--b");
+    // from = diff start (2), to = newTo = end of the inserted "--" (4).
+    expect(undoGuardKey.getState(editor.state)).toEqual({ from: 2, to: 4 });
+    editor.destroy();
+  });
+
+  it("does NOT arm on a REMOTE change-origin replace (no undo meta)", () => {
+    // Same replace, but tagged only as a y-sync remote change: history/remote
+    // yes, undo/redo NO -> must not arm.
+    const editor = makeEditor("a—b");
+    const { state } = editor;
+    const tr = state.tr
+      .replaceWith(2, 3, state.schema.text("--"))
+      .setMeta(ySyncPluginKey, { isChangeOrigin: true });
+    editor.view.dispatch(tr);
+
+    expect(editor.state.doc.textContent).toBe("a--b");
+    expect(undoGuardKey.getState(editor.state)).toBeNull();
+    editor.destroy();
+  });
+
+  it("does NOT arm on an ordinary local edit", () => {
+    const editor = makeEditor("a—b");
+    editor.view.dispatch(
+      editor.state.tr.replaceWith(2, 3, editor.state.schema.text("--")),
+    );
+    expect(undoGuardKey.getState(editor.state)).toBeNull();
+    editor.destroy();
+  });
+});
+
+describe("undo-guard release / shift (integration)", () => {
+  it("RELEASES when a later edit lands inside the guarded region", () => {
+    const editor = makeEditor("a—b");
+    editor.view.dispatch(
+      editor.state.tr
+        .replaceWith(2, 3, editor.state.schema.text("--"))
+        .setMeta("history$", { redo: false }),
+    );
+    const guard = undoGuardKey.getState(editor.state)!;
+    expect(guard).toEqual({ from: 2, to: 4 });
+
+    // Type a character inside the restored region -> guard is dropped.
+    editor.view.dispatch(editor.state.tr.insertText("x", guard.from + 1));
+    expect(undoGuardKey.getState(editor.state)).toBeNull();
+    editor.destroy();
+  });
+
+  it("keeps and SHIFTS the guard when a later edit lands before it", () => {
+    const editor = makeEditor("zz a—b");
+    // "zz a—b": em-dash at pos 5; replace the 'a' at 4..5 with "--" to arm.
+    editor.view.dispatch(
+      editor.state.tr
+        .replaceWith(4, 5, editor.state.schema.text("--"))
+        .setMeta("history$", { redo: false }),
+    );
+    const guard = undoGuardKey.getState(editor.state)!;
+    expect(guard).toEqual({ from: 4, to: 6 });
+
+    // Insert one char at the very start (before the guard) -> guard shifts +1.
+    editor.view.dispatch(editor.state.tr.insertText("Q", 1));
+    expect(undoGuardKey.getState(editor.state)).toEqual({ from: 5, to: 7 });
+    editor.destroy();
+  });
+});

apps/client/src/features/editor/extensions/custom-typography.ts

@@ -0,0 +1,193 @@
+import { InputRule } from "@tiptap/core";
+import {
+  Plugin,
+  PluginKey,
+  type EditorState,
+  type Transaction,
+} from "@tiptap/pm/state";
+import { Typography } from "@tiptap/extension-typography";
+import { isChangeOrigin } from "@tiptap/extension-collaboration";
+import { ySyncPluginKey } from "@tiptap/y-tiptap";
+
+// Region restored by the latest undo — while it is intact, typography
+// input rules overlapping it must not fire again.
+interface UndoGuardRange {
+  from: number;
+  to: number;
+}
+
+// Exported for tests: the plugin key lets a test read the armed guard state,
+// and the two pure helpers below are unit-tested directly.
+export const undoGuardKey = new PluginKey<UndoGuardRange | null>(
+  "typographyUndoGuard",
+);
+
+// prosemirror-history does not export its plugin key, so template-editor
+// undo/redo is detected via the stable stringified key. Only one
+// PluginKey("history") exists in the dependency tree, so "history$" is stable.
+const HISTORY_META = "history$";
+
+const isUndoRedoTransaction = (tr: Transaction): boolean => {
+  if (tr.getMeta(HISTORY_META)) {
+    return true;
+  }
+  // Read yjs undo/redo meta via the real ySyncPluginKey object (imported, not
+  // a fragile stringified key), which y-tiptap sets on Y.UndoManager changes.
+  const ySyncMeta = tr.getMeta(ySyncPluginKey) as
+    | { isUndoRedoOperation?: boolean }
+    | undefined;
+  return !!ySyncMeta?.isUndoRedoOperation;
+};
+
+interface DocChange {
+  from: number;
+  oldTo: number;
+  newTo: number;
+}
+
+// Compute the minimal changed region between two docs. yjs undo/redo (and any
+// remote change) arrives as a whole-document replace step, so the transaction
+// step maps are useless — diff the docs to recover the real minimal change.
+// Returns null when the docs are identical.
+export const findChangedRange = (
+  oldState: EditorState,
+  newState: EditorState,
+): DocChange | null => {
+  const start = oldState.doc.content.findDiffStart(newState.doc.content);
+  const end = oldState.doc.content.findDiffEnd(newState.doc.content);
+  if (start == null || end == null) {
+    return null;
+  }
+  let { a: oldTo, b: newTo } = end;
+  // findDiffEnd can report an end BEFORE the diff start when the changed text
+  // abuts repeated content (insertion -> oldTo<start, deletion -> newTo<start).
+  // Push both ends forward by the same delta so the range stays non-degenerate
+  // (from <= oldTo and from <= newTo), matching ProseMirror's own diff bounds.
+  const minTo = Math.min(oldTo, newTo);
+  if (minTo < start) {
+    const delta = start - minTo;
+    oldTo += delta;
+    newTo += delta;
+  }
+  return { from: start, oldTo, newTo };
+};
+
+// Map an armed guard range across a single document change described by a diff.
+// Returns null when the change touches the guarded text itself (the restored
+// substitution was edited, so the guard must be released).
+export const mapRangeThroughChange = (
+  range: UndoGuardRange,
+  change: DocChange,
+): UndoGuardRange | null => {
+  // Strict intersection: an edit exactly at a guard boundary (e.g. the user
+  // typing the suppressed space right after the restored text, or deleting it)
+  // must NOT drop the guard.
+  if (change.from < range.to && change.oldTo > range.from) {
+    return null;
+  }
+  // Change fully before the guard: shift the guard by the length delta.
+  if (change.oldTo <= range.from) {
+    const delta = change.newTo - change.oldTo;
+    return { from: range.from + delta, to: range.to + delta };
+  }
+  // Change fully after the guard: positions are unaffected.
+  return range;
+};
+
+// Detect history/remote transactions that may arrive as a whole-document
+// replace step: prosemirror-history undo/redo, or any yjs remote-origin change
+// (isChangeOrigin is the canonical predicate already used across the app).
+const isHistoryOrRemoteTransaction = (tr: Transaction): boolean =>
+  !!tr.getMeta(HISTORY_META) || isChangeOrigin(tr);
+
+export const CustomTypography = Typography.extend({
+  addProseMirrorPlugins() {
+    return [
+      ...(this.parent?.() ?? []),
+      new Plugin({
+        key: undoGuardKey,
+        state: {
+          init: () => null,
+          apply(tr, prev, oldState, newState): UndoGuardRange | null {
+            if (tr.docChanged && isHistoryOrRemoteTransaction(tr)) {
+              const change = findChangedRange(oldState, newState);
+              if (change == null) {
+                // Attribute-only or otherwise content-neutral change: keep the
+                // guard.
+                return prev;
+              }
+              // Arm the guard only when the LOCAL user's undo/redo REPLACED text
+              // (deleted + inserted) — the signature of reverting an input-rule
+              // substitution. Pure insertions/deletions and remote peer edits
+              // must not arm it.
+              if (
+                isUndoRedoTransaction(tr) &&
+                change.oldTo > change.from &&
+                change.newTo > change.from
+              ) {
+                return { from: change.from, to: change.newTo };
+              }
+              // Non-arming history/remote change: map the existing guard through
+              // the real diff instead of the (whole-document) step map.
+              if (!prev) {
+                return null;
+              }
+              return mapRangeThroughChange(prev, change);
+            }
+            if (!prev) {
+              return null;
+            }
+            if (!tr.docChanged) {
+              return prev;
+            }
+            // Ordinary local edit: minimal step maps are accurate and cheap.
+            let range: UndoGuardRange | null = prev;
+            for (const stepMap of tr.mapping.maps) {
+              const { from: rangeFrom, to: rangeTo } = range;
+              let touched = false;
+              stepMap.forEach((fromA, toA) => {
+                if (fromA < rangeTo && toA > rangeFrom) {
+                  touched = true;
+                }
+              });
+              if (touched) {
+                range = null;
+                break;
+              }
+              range = {
+                from: stepMap.map(rangeFrom, 1),
+                to: stepMap.map(rangeTo, -1),
+              };
+            }
+            return range && range.to > range.from ? range : null;
+          },
+        },
+      }),
+    ];
+  },
+
+  addInputRules() {
+    // Wrap every typography rule: skip it when its match overlaps the text
+    // just restored by undo, so an undone substitution is not re-applied.
+    return (this.parent?.() ?? []).map(
+      (rule) =>
+        new InputRule({
+          find: rule.find,
+          undoable: rule.undoable,
+          handler: (props) => {
+            const guard = undoGuardKey.getState(props.state);
+            if (
+              guard &&
+              props.range.from < guard.to &&
+              props.range.to > guard.from
+            ) {
+              // Returning null skips this rule and lets the typed character
+              // be inserted as plain text.
+              return null;
+            }
+            return rule.handler(props);
+          },
+        }),
+    );
+  },
+});

apps/client/src/features/editor/extensions/extensions.ts

@@ -6,7 +6,7 @@ import { TaskList, TaskItem } from "@tiptap/extension-list";
 import { Placeholder, CharacterCount, UndoRedo } from "@tiptap/extensions";
 import { Superscript } from "@tiptap/extension-superscript";
 import SubScript from "@tiptap/extension-subscript";
-import { Typography } from "@tiptap/extension-typography";
+import { CustomTypography } from "./custom-typography";
 import { TextStyle } from "@tiptap/extension-text-style";
 import { Color } from "@tiptap/extension-color";
 import { Youtube } from "@tiptap/extension-youtube";
@@ -245,7 +245,9 @@ export const mainExtensions = [
       return ReactMarkViewRenderer(SpoilerView);
     },
   }),
-  Typography,
+  // Typography with an undo guard: does not re-apply a substitution the user
+  // just undid (e.g. Ctrl+Z on "1/2" -> "½" followed by another space).
+  CustomTypography,
   TrailingNode,
   GlobalDragHandle.configure({
     customNodes: ["transclusionSource", "transclusionReference", "pageEmbed"],