@@ -360,13 +360,13 @@ describe("orderedListGutterStyle", () => {
     expect(orderedListGutterStyle(9, undefined)).toBeUndefined();
   });
 
-  it("leaves the default gutter alone for two-digit lists", () => {
-    expect(orderedListGutterStyle(99, undefined)).toBeUndefined();
+  it("widens the gutter for two-digit lists", () => {
+    expect(orderedListGutterStyle(99, undefined)).toEqual({ "--list-gutter": "3ch" });
   });
 
-  it("leaves the default gutter alone for a two-digit list that starts above 1", () => {
+  it("widens the gutter for a two-digit list that starts above 1", () => {
     // start=50 + 49 items => last marker is "98", still two digits.
-    expect(orderedListGutterStyle(49, 50)).toBeUndefined();
+    expect(orderedListGutterStyle(49, 50)).toEqual({ "--list-gutter": "3ch" });
   });
 
   it("widens the gutter once the last marker reaches three digits", () => {
@@ -387,7 +387,7 @@ describe("orderedListGutterStyle", () => {
   it("uses the widest marker and includes a negative start's minus sign", () => {
     expect(orderedListGutterStyle(1001, -1000)).toEqual({ "--list-gutter": "6ch" });
     expect(orderedListGutterStyle(3, -15)).toEqual({ "--list-gutter": "4ch" });
-    expect(orderedListGutterStyle(3, -5)).toBeUndefined();
+    expect(orderedListGutterStyle(3, -5)).toEqual({ "--list-gutter": "3ch" });
   });
 
   it("treats a missing/zero item count as a single item", () => {
 
@@ -328,13 +328,10 @@ function findTaskListMarkerOffset(markdown: string, listItemStart: number): numb
 }
 
 /**
- * The default `1.25rem` marker gutter (`.chat-markdown ol`) fits markers up to
- * two characters wide. Once a marker reaches three characters (item 100+),
- * `list-style-position: outside` paints it wider than that gutter and clips
- * the leading character against the item's own overflow. Rather than widening
- * the gutter for every list, only lists whose widest marker is 3+ characters
- * get a wider `--list-gutter`. The width includes a negative marker's minus
- * sign.
+ * The default `1.25rem` marker gutter (`.chat-markdown ol`) fits one-character
+ * markers. Wider markers can extend past it and get clipped by a collapsed
+ * message's overflow. Widen the gutter to fit the widest marker, including a
+ * negative marker's minus sign.
  */
 export function orderedListGutterStyle(
   itemCount: number,
@@ -344,7 +341,7 @@ export function orderedListGutterStyle(
   const firstNumber = Number.isNaN(parsedStart) ? 1 : parsedStart;
   const lastNumber = firstNumber + Math.max(itemCount - 1, 0);
   const markerWidth = Math.max(String(firstNumber).length, String(lastNumber).length);
-  if (markerWidth <= 2) return undefined;
+  if (markerWidth <= 1) return undefined;
   return { "--list-gutter": `${markerWidth + 1}ch` };
 }
 
 
@@ -1643,8 +1643,8 @@ code {
 }
 
 .chat-markdown ul {
-  /* Reset for nested uls under a widened ol — --list-gutter is an inherited
-     custom property, so without this a task-list under a 3+ digit ordered
+  /* Reset for nested uls under a widened ol. --list-gutter is an inherited
+     custom property, so without this a task-list under a multi-digit ordered
      list would inherit the outer gutter instead of its own default. */
   --list-gutter: 1.25rem;
   padding-left: 1.25rem;
@@ -1653,7 +1653,7 @@ code {
 
 /* --list-gutter defaults to the same 1.25rem as .chat-markdown ul, but
    ChatMarkdown's `ol` renderer widens it (via inline style) for lists whose
-   widest marker is 3+ characters, so item 100+ isn't clipped by list-style-position:
+   widest marker has multiple characters so it isn't clipped by list-style-position:
    outside painting the marker past the padding box. Reset it here too so a
    nested ol without its own widened marker doesn't inherit the outer one. */
 .chat-markdown ol {