diff --git a/apps/web/src/components/ChatMarkdown.test.tsx b/apps/web/src/components/ChatMarkdown.test.tsx
index 9499ee5a6915..a8c82552f9bb 100644
--- a/apps/web/src/components/ChatMarkdown.test.tsx
+++ b/apps/web/src/components/ChatMarkdown.test.tsx
@@ -24,13 +24,21 @@ describe("orderedListGutterStyle", () => {
   it("accounts for a non-default start attribute", () => {
     // start=95 + 9 items => last marker is "103", three digits.
     expect(orderedListGutterStyle(9, 95)).toEqual({ "--list-gutter": "4ch" });
+    expect(orderedListGutterStyle(5, "999995")).toEqual({ "--list-gutter": "7ch" });
   });
 
   it("scales further for four-digit markers", () => {
     expect(orderedListGutterStyle(1000, undefined)).toEqual({ "--list-gutter": "5ch" });
   });
 
+  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();
+  });
+
   it("treats a missing/zero item count as a single item", () => {
     expect(orderedListGutterStyle(0, undefined)).toBeUndefined();
+    expect(orderedListGutterStyle(0, 100)).toEqual({ "--list-gutter": "4ch" });
   });
 });
diff --git a/apps/web/src/components/ChatMarkdown.tsx b/apps/web/src/components/ChatMarkdown.tsx
index c3e1c5288da7..74cc76afd498 100644
--- a/apps/web/src/components/ChatMarkdown.tsx
+++ b/apps/web/src/components/ChatMarkdown.tsx
@@ -157,22 +157,24 @@ function findTaskListMarkerOffset(markdown: string, listItemStart: number): numb
 }
 
 /**
- * The default `1.25rem` marker gutter (`.chat-markdown ol`) fits two-digit
- * decimal markers. Once a list's last item reaches three digits (item 100+),
- * `list-style-position: outside` paints the marker wider than that gutter and
- * the leading digit gets clipped by the item's own overflow. Rather than
- * widening the gutter for every list, only lists whose last marker is 3+
- * digits get a wider `--list-gutter`, sized to that marker's digit count.
+ * 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.
  */
 export function orderedListGutterStyle(
   itemCount: number,
-  start: number | undefined,
+  start: unknown,
 ): { "--list-gutter": string } | undefined {
-  const firstNumber = typeof start === "number" && Number.isFinite(start) ? start : 1;
+  const parsedStart = Number.parseInt(String(start ?? 1), 10);
+  const firstNumber = Number.isNaN(parsedStart) ? 1 : parsedStart;
   const lastNumber = firstNumber + Math.max(itemCount - 1, 0);
-  const digits = String(Math.abs(lastNumber)).length;
-  if (digits <= 2) return undefined;
-  return { "--list-gutter": `${digits + 1}ch` };
+  const markerWidth = Math.max(String(firstNumber).length, String(lastNumber).length);
+  if (markerWidth <= 2) return undefined;
+  return { "--list-gutter": `${markerWidth + 1}ch` };
 }
 
 const CHAT_MARKDOWN_SANITIZE_SCHEMA = {
diff --git a/apps/web/src/index.css b/apps/web/src/index.css
index b602758d09ca..63751f589019 100644
--- a/apps/web/src/index.css
+++ b/apps/web/src/index.css
@@ -2040,7 +2040,7 @@ 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
-   last marker is 3+ digits, so item 100+ isn't clipped by list-style-position:
+   widest marker is 3+ characters, so item 100+ 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 {
@@ -2049,6 +2049,10 @@ code {
   list-style-type: decimal;
 }
 
+.chat-markdown ol > li::marker {
+  font-variant-numeric: tabular-nums;
+}
+
 .chat-markdown ul ul {
   list-style-type: circle;
 }
@@ -2114,7 +2118,6 @@ code {
 
 .chat-markdown section[data-footnotes] ol {
   margin: 0;
-  padding-left: 1.25rem;
 }
 
 .chat-markdown section[data-footnotes] li + li {