diff --git a/web/src/hotkey.js b/web/src/hotkey.js
index 4b42051e8d..cec1778497 100644
--- a/web/src/hotkey.js
+++ b/web/src/hotkey.js
@@ -45,6 +45,7 @@ import * as reactions from "./reactions";
 import * as recent_view_ui from "./recent_view_ui";
 import * as recent_view_util from "./recent_view_util";
 import * as scheduled_messages_overlay_ui from "./scheduled_messages_overlay_ui";
+import * as scheduled_messages_popover from "./scheduled_messages_popover";
 import * as search from "./search";
 import * as settings_data from "./settings_data";
 import * as sidebar_ui from "./sidebar_ui";
@@ -486,7 +487,7 @@ export function process_enter_key(e) {
     // it since it is the trigger for the popover. <button> is already used
     // to trigger the tooltip so it cannot be used to trigger the popover.
     if (e.target.id === "send_later") {
-        $("#send_later i").trigger("click");
+        scheduled_messages_popover.toggle();
         return true;
     }
 
diff --git a/web/src/scheduled_messages_popover.js b/web/src/scheduled_messages_popover.js
index 1193cd419d..2b4f532494 100644
--- a/web/src/scheduled_messages_popover.js
+++ b/web/src/scheduled_messages_popover.js
@@ -5,6 +5,7 @@ import render_send_later_popover from "../templates/popovers/send_later_popover.
 import render_send_later_modal from "../templates/send_later_modal.hbs";
 import render_send_later_modal_options from "../templates/send_later_modal_options.hbs";
 
+import * as blueslip from "./blueslip";
 import * as channel from "./channel";
 import * as common from "./common";
 import * as compose from "./compose";
@@ -19,6 +20,8 @@ import {user_settings} from "./user_settings";
 export const SCHEDULING_MODAL_UPDATE_INTERVAL_IN_MILLISECONDS = 60 * 1000;
 const ENTER_SENDS_SELECTION_DELAY = 600;
 
+let send_later_popover_keyboard_toggle = false;
+
 function set_compose_box_schedule(element) {
     const selected_send_at_time = element.dataset.sendStamp / 1000;
     return selected_send_at_time;
@@ -114,6 +117,28 @@ export function do_schedule_message(send_at_time) {
     compose.finish(true);
 }
 
+function get_send_later_menu_items() {
+    const $current_schedule_popover_elem = $("[data-tippy-root] #send_later_popover");
+    if (!$current_schedule_popover_elem) {
+        blueslip.error("Trying to get menu items when schedule popover is closed.");
+        return undefined;
+    }
+
+    return $current_schedule_popover_elem.find("li:not(.divider):visible a");
+}
+
+function focus_first_send_later_popover_item() {
+    // It is recommended to only call this when the user opens the menu with a hotkey.
+    // Our popup menus act kind of funny when you mix keyboard and mouse.
+    const $items = get_send_later_menu_items();
+    popover_menus.focus_first_popover_item($items);
+}
+
+export function toggle() {
+    send_later_popover_keyboard_toggle = true;
+    $("#send_later i").trigger("click");
+}
+
 export function initialize() {
     delegate("body", {
         ...popover_menus.default_popover_props,
@@ -136,6 +161,10 @@ export function initialize() {
             popover_menus.popover_instances.send_later = instance;
         },
         onMount(instance) {
+            if (send_later_popover_keyboard_toggle) {
+                focus_first_send_later_popover_item();
+                send_later_popover_keyboard_toggle = false;
+            }
             const $popper = $(instance.popper);
             common.adjust_mac_kbd_tags(".enter_sends_choices kbd");
             $popper.one("click", ".send_later_selected_send_later_time", () => {
@@ -175,6 +204,7 @@ export function initialize() {
         onHidden(instance) {
             instance.destroy();
             popover_menus.popover_instances.send_later = undefined;
+            send_later_popover_keyboard_toggle = false;
         },
     });
 }