diff --git a/web/src/settings_components.ts b/web/src/settings_components.ts
index 130a949c51..66992e0746 100644
--- a/web/src/settings_components.ts
+++ b/web/src/settings_components.ts
@@ -1417,6 +1417,21 @@ export function initialize_disable_btn_hint_popover(
     tippy.default(util.the($btn_wrapper), tippy_opts);
 }
 
+export function enable_opening_typeahead_on_clicking_label($container: JQuery): void {
+    const $group_setting_labels = $container.find(".group-setting-label");
+    $group_setting_labels.on("click", (e) => {
+        // Click opens the typeahead.
+        $(e.target).siblings(".pill-container").find(".input").expectOne().trigger("click");
+        // Focus puts the cursor into the input.
+        $(e.target).siblings(".pill-container").find(".input").expectOne().trigger("focus");
+    });
+}
+
+export function disable_opening_typeahead_on_clicking_label($container: JQuery): void {
+    const $group_setting_labels = $container.find(".group-setting-label");
+    $group_setting_labels.off("click");
+}
+
 export const group_setting_widget_map = new Map<string, GroupSettingPillContainer | null>([
     ["can_add_members_group", null],
     ["can_join_group", null],
diff --git a/web/src/user_group_create.ts b/web/src/user_group_create.ts
index 1790d6f79a..51b9c2e7e9 100644
--- a/web/src/user_group_create.ts
+++ b/web/src/user_group_create.ts
@@ -253,6 +253,9 @@ export function set_up_handlers(): void {
         }
     });
 
+    // This will always be enabled when creating a user group.
+    settings_components.enable_opening_typeahead_on_clicking_label($container);
+
     can_add_members_group_widget = settings_components.create_group_setting_widget({
         $pill_container: $container.find(".can-add-members-group-container .pill-container"),
         setting_name: "can_add_members_group",
diff --git a/web/src/user_group_edit.js b/web/src/user_group_edit.js
index e300184873..3e79358969 100644
--- a/web/src/user_group_edit.js
+++ b/web/src/user_group_edit.js
@@ -121,6 +121,7 @@ function update_group_permission_settings_elements(group) {
         $permission_pill_container_elements.each(function () {
             $(this)[0]._tippy?.destroy();
         });
+        settings_components.enable_opening_typeahead_on_clicking_label($group_permission_settings);
     } else {
         $permission_pill_container_elements.find(".input").prop("contenteditable", false);
 
@@ -132,6 +133,7 @@ function update_group_permission_settings_elements(group) {
                 $t({defaultMessage: "You do not have permission to edit this setting."}),
             );
         });
+        settings_components.disable_opening_typeahead_on_clicking_label($group_permission_settings);
     }
 }