diff --git a/app/components/InputSelect.tsx b/app/components/InputSelect.tsx
index ae27a55431..7111993fcb 100644
--- a/app/components/InputSelect.tsx
+++ b/app/components/InputSelect.tsx
@@ -21,6 +21,7 @@ import {
   InputSelectContent,
   InputSelectItem,
   InputSelectSeparator,
+  InputSelectHeading,
   InputSelectTrigger,
   type TriggerButtonProps,
 } from "./primitives/InputSelect";
@@ -35,6 +36,13 @@ type Separator = {
   type: "separator";
 };
 
+type Heading = {
+  /* Denotes a non-selectable heading rendered above a group of options. */
+  type: "heading";
+  /* Text shown as the heading label. */
+  label: string;
+};
+
 export type Item = {
   /* Denotes a selectable option in the menu. */
   type: "item";
@@ -48,7 +56,7 @@ export type Item = {
   icon?: React.ReactElement;
 };
 
-export type Option = Item | Separator;
+export type Option = Item | Separator | Heading;
 
 type Props = Omit<React.HTMLAttributes<HTMLButtonElement>, "onChange"> & {
   /* Options to display in the select menu. */
@@ -118,6 +126,14 @@ export const InputSelect = React.forwardRef<HTMLButtonElement, Props>(
           return <InputSelectSeparator key={`separator-${idx}`} />;
         }
 
+        if (option.type === "heading") {
+          return (
+            <InputSelectHeading key={`heading-${option.label}`}>
+              {option.label}
+            </InputSelectHeading>
+          );
+        }
+
         return (
           <InputSelectItem key={option.value} value={option.value}>
             <Option option={option} optionsHaveIcon={optionsHaveIcon} />
@@ -244,6 +260,14 @@ const MobileSelect = React.forwardRef<HTMLButtonElement, MobileSelectProps>(
           return <InputSelectSeparator key={`separator-${idx}`} />;
         }
 
+        if (option.type === "heading") {
+          return (
+            <InputSelectHeading key={`heading-${option.label}`}>
+              {option.label}
+            </InputSelectHeading>
+          );
+        }
+
         const isSelected = option === selectedOption;
 
         return (
diff --git a/app/components/primitives/InputSelect.tsx b/app/components/primitives/InputSelect.tsx
index 14d1c1ebb2..dbafe63786 100644
--- a/app/components/primitives/InputSelect.tsx
+++ b/app/components/primitives/InputSelect.tsx
@@ -1,6 +1,7 @@
 import * as InputSelectPrimitive from "@radix-ui/react-select";
 import * as React from "react";
 import styled from "styled-components";
+import Text from "@shared/components/Text";
 import { depths, s } from "@shared/styles";
 import type { Props as ButtonProps } from "~/components/Button";
 import { fadeAndSlideDown, fadeAndSlideUp } from "~/styles/animations";
@@ -110,6 +111,31 @@ const Separator = styled.hr`
   margin: 6px 0;
 `;
 
+/** Non-selectable heading rendered to group options in the menu. */
+const InputSelectHeading = React.forwardRef<
+  HTMLSpanElement,
+  { children?: React.ReactNode }
+>(({ children }, ref) => (
+  <InputSelectPrimitive.Group>
+    <InputSelectPrimitive.Label asChild>
+      <Heading ref={ref}>{children}</Heading>
+    </InputSelectPrimitive.Label>
+  </InputSelectPrimitive.Group>
+));
+InputSelectHeading.displayName = "InputSelectHeading";
+
+const Heading = styled(Text).attrs({
+  type: "tertiary",
+  size: "xsmall",
+  weight: "bold",
+})`
+  display: block;
+  padding-block: 8px 4px;
+  padding-inline: 8px;
+  text-transform: uppercase;
+  letter-spacing: 0.04em;
+`;
+
 /** Styled components. */
 const StyledContent = styled(InputSelectPrimitive.Content)`
   z-index: ${depths.menu};
@@ -143,4 +169,5 @@ export {
   InputSelectContent,
   InputSelectItem,
   InputSelectSeparator,
+  InputSelectHeading,
 };
diff --git a/app/scenes/Document/components/History/HighlightChangesControl.tsx b/app/scenes/Document/components/History/HighlightChangesControl.tsx
index 517a2adac1..c6df7bde9e 100644
--- a/app/scenes/Document/components/History/HighlightChangesControl.tsx
+++ b/app/scenes/Document/components/History/HighlightChangesControl.tsx
@@ -63,12 +63,26 @@ export function HighlightChangesControl({
       ? RevisionHelper.latestId(document.id)
       : undefined;
 
+    const currentYear = new Date().getFullYear();
+    let lastHeadingYear: number | undefined;
+
     for (const rev of revisionItems) {
       if (rev.id === resolvedSelectedId) {
         continue;
       }
 
-      const dateLabel = formatDate(new Date(rev.createdAt), "MMM do, h:mm a", {
+      const revDate = new Date(rev.createdAt);
+      const revYear = revDate.getFullYear();
+
+      if (revYear !== currentYear && revYear !== lastHeadingYear) {
+        options.push({
+          type: "heading",
+          label: String(revYear),
+        });
+        lastHeadingYear = revYear;
+      }
+
+      const dateLabel = formatDate(revDate, "MMM do, h:mm a", {
         locale,
       });
       const collaboratorText = revisionCollaboratorText(rev, t);