diff --git a/web/src/group_setting_pill.ts b/web/src/group_setting_pill.ts
index 771b1ef60e..7cfe003d47 100644
--- a/web/src/group_setting_pill.ts
+++ b/web/src/group_setting_pill.ts
@@ -139,6 +139,7 @@ export function create_pills(
             setting_name,
             setting_type,
         },
+        show_outline_on_invalid_input: true,
     });
     return pill_widget;
 }
diff --git a/web/src/input_pill.ts b/web/src/input_pill.ts
index 96ae1c4032..0db01c28df 100644
--- a/web/src/input_pill.ts
+++ b/web/src/input_pill.ts
@@ -35,6 +35,7 @@ type InputPillCreateOptions<ItemType> = {
         all_pills: InputPill<ItemType>[],
         remove_pill: (pill: HTMLElement) => void,
     ) => void;
+    show_outline_on_invalid_input?: boolean;
 };
 
 export type InputPill<ItemType> = {
@@ -58,6 +59,7 @@ type InputPillStore<ItemType> = {
     createPillonPaste?: () => void;
     split_text_on_comma: boolean;
     convert_to_pill_on_enter: boolean;
+    show_outline_on_invalid_input: boolean;
 };
 
 // These are the functions that are exposed to other modules.
@@ -98,6 +100,7 @@ export function create<ItemType extends {type: string}>(
         convert_to_pill_on_enter: opts.convert_to_pill_on_enter ?? true,
         generate_pill_html: opts.generate_pill_html,
         on_pill_exit: opts.on_pill_exit,
+        show_outline_on_invalid_input: opts.show_outline_on_invalid_input ?? false,
     };
 
     // a dictionary of internal functions. Some of these are exposed as well,
@@ -133,12 +136,14 @@ export function create<ItemType extends {type: string}>(
         create_item(text: string) {
             const existing_items = funcs.items();
             const item = store.create_item_from_text(text, existing_items, store.pill_config);
-
             if (!item) {
                 store.$input.addClass("shake");
+
+                if (store.show_outline_on_invalid_input) {
+                    store.$parent.addClass("invalid");
+                }
                 return undefined;
             }
-
             return item;
         },
 
@@ -161,6 +166,15 @@ export function create<ItemType extends {type: string}>(
             store.pills.push(payload);
             store.$input.before(payload.$element);
 
+            if (store.show_outline_on_invalid_input && store.$parent.hasClass("invalid")) {
+                store.$parent.removeClass("invalid");
+            }
+
+            // If we check is_pending just after adding a pill, the
+            // text is still present until further input, so we
+            // manually clear it here.
+            this.clear_text();
+
             if (store.onPillCreate !== undefined) {
                 store.onPillCreate();
             }
@@ -359,6 +373,13 @@ export function create<ItemType extends {type: string}>(
         // the hook receives the updated text content of the input unlike the "keydown"
         // event which does not have the updated text content.
         store.$parent.on("input", ".input", () => {
+            if (
+                store.show_outline_on_invalid_input &&
+                funcs.value(store.$input[0]!).length === 0 &&
+                store.$parent.hasClass("invalid")
+            ) {
+                store.$parent.removeClass("invalid");
+            }
             store.onTextInputHook?.();
         });
 
diff --git a/web/src/settings_components.ts b/web/src/settings_components.ts
index 35c7babe89..8cda156136 100644
--- a/web/src/settings_components.ts
+++ b/web/src/settings_components.ts
@@ -1395,13 +1395,16 @@ function should_disable_save_button_for_group_settings(settings: string[]): bool
             );
         }
         assert(group_setting_config !== undefined);
-        if (group_setting_config.allow_nobody_group) {
-            continue;
-        }
 
         const pill_widget = get_group_setting_widget(setting_name);
         assert(pill_widget !== null);
+        if (pill_widget.is_pending()) {
+            return true;
+        }
 
+        if (group_setting_config.allow_nobody_group) {
+            continue;
+        }
         const setting_value = get_group_setting_widget_value(pill_widget);
         const nobody_group = user_groups.get_user_group_from_name("role:nobody")!;
         if (setting_value === nobody_group.id) {
@@ -1595,6 +1598,9 @@ export function create_group_setting_widget({
     if (group !== undefined) {
         set_group_setting_widget_value(pill_widget, group[setting_name]);
 
+        pill_widget.onTextInputHook(() => {
+            save_discard_group_widget_status_handler($("#group_permission_settings"), group);
+        });
         pill_widget.onPillCreate(() => {
             save_discard_group_widget_status_handler($("#group_permission_settings"), group);
         });
@@ -1668,6 +1674,12 @@ export function create_realm_group_setting_widget({
     const $save_discard_widget_container = $(`#id_realm_${CSS.escape(setting_name)}`).closest(
         ".settings-subsection-parent",
     );
+    pill_widget.onTextInputHook(() => {
+        if (pill_update_callback !== undefined) {
+            pill_update_callback();
+        }
+        save_discard_realm_settings_widget_status_handler($save_discard_widget_container);
+    });
     pill_widget.onPillCreate(() => {
         if (pill_update_callback !== undefined) {
             pill_update_callback();
@@ -1712,6 +1724,9 @@ export function create_stream_group_setting_widget({
         const $edit_container = stream_settings_containers.get_edit_container(sub);
         const $subsection = $edit_container.find(".advanced-configurations-container");
 
+        pill_widget.onTextInputHook(() => {
+            save_discard_stream_settings_widget_status_handler($subsection, sub);
+        });
         pill_widget.onPillCreate(() => {
             save_discard_stream_settings_widget_status_handler($subsection, sub);
         });
diff --git a/web/src/stream_create.ts b/web/src/stream_create.ts
index 5049036e01..53a5fa0fae 100644
--- a/web/src/stream_create.ts
+++ b/web/src/stream_create.ts
@@ -70,6 +70,11 @@ export function maybe_update_error_message(): void {
     }
 }
 
+const group_setting_widget_map = new Map<string, GroupSettingPillContainer | null>([
+    ["can_administer_channel_group", null],
+    ["can_remove_subscribers_group", null],
+]);
+
 class StreamSubscriptionError {
     report_no_subs_to_stream(): void {
         $("#stream_subscription_error").text(
@@ -200,7 +205,23 @@ $("body").on("click", ".settings-sticky-footer #stream_creation_go_to_subscriber
     let invite_only = false;
     let is_web_public = false;
 
-    if (is_stream_name_valid) {
+    let is_any_stream_group_widget_pending = false;
+    const permission_settings = Object.keys(realm.server_supported_permission_settings.stream);
+    for (const setting_name of permission_settings) {
+        const widget = group_setting_widget_map.get(setting_name);
+        assert(widget !== undefined);
+        assert(widget !== null);
+        if (widget.is_pending()) {
+            is_any_stream_group_widget_pending = true;
+            // We are not appending any value here, but instead this is
+            // a proxy to invoke the error state for a group widget
+            // that would usually get triggered on clicking enter.
+            widget.appendValue(widget.getCurrentText()!);
+            break;
+        }
+    }
+
+    if (is_stream_name_valid && !is_any_stream_group_widget_pending) {
         if (privacy_type === "invite-only" || privacy_type === "invite-only-public-history") {
             invite_only = true;
         } else if (privacy_type === "web-public") {
@@ -520,6 +541,7 @@ function set_up_group_setting_widgets(): void {
                 $pill_container: $("#id_new_" + setting_name),
                 setting_name: stream_permission_group_settings_schema.parse(setting_name),
             });
+        group_setting_widget_map.set(setting_name, group_setting_widgets[setting_name]);
     }
 }
 
diff --git a/web/src/user_group_create.ts b/web/src/user_group_create.ts
index fb2ef008da..68aadfe45a 100644
--- a/web/src/user_group_create.ts
+++ b/web/src/user_group_create.ts
@@ -108,7 +108,23 @@ $("body").on("click", ".settings-sticky-footer #user_group_go_to_members", (e) =
     const group_name = $<HTMLInputElement>("input#create_user_group_name").val()!.trim();
     const is_user_group_name_valid = user_group_name_error.validate_for_submit(group_name);
 
-    if (is_user_group_name_valid) {
+    let is_any_group_widget_pending = false;
+    const permission_settings = Object.keys(realm.server_supported_permission_settings.group);
+    for (const setting_name of permission_settings) {
+        const widget = group_setting_widget_map.get(setting_name);
+        assert(widget !== undefined);
+        assert(widget !== null);
+        if (widget.is_pending()) {
+            is_any_group_widget_pending = true;
+            // We are not appending any value here, but instead this is
+            // a proxy to invoke the error state for a group widget
+            // that would usually get triggered on clicking enter.
+            widget.appendValue(widget.getCurrentText()!);
+            break;
+        }
+    }
+
+    if (is_user_group_name_valid && !is_any_group_widget_pending) {
         user_group_components.show_user_group_settings_pane.create_user_group(
             "user_group_members_container",
             group_name,
diff --git a/web/styles/app_variables.css b/web/styles/app_variables.css
index 8174132613..54de42baa3 100644
--- a/web/styles/app_variables.css
+++ b/web/styles/app_variables.css
@@ -686,6 +686,8 @@
     --color-background-animated-button: hsl(0deg 0% 90%);
     --color-animated-button-text: hsl(0deg 0% 0%);
     --color-background-animated-button-hover: hsl(240deg 96% 68%);
+    --color-invalid-input-border: hsl(3deg 57% 33%);
+    --color-invalid-input-box-shadow: 0 0 2px hsl(3deg 57% 33%);
 
     /* Recent view */
     --color-border-recent-view-row: hsl(0deg 0% 87%);
@@ -1443,6 +1445,8 @@
     --color-background-animated-button: hsl(211deg 29% 14%);
     --color-animated-button-text: hsl(0deg 0% 100%);
     --color-background-animated-button-hover: hsl(240deg 96% 68%);
+    --color-invalid-input-border: hsl(3deg 73% 74%);
+    --color-invalid-input-box-shadow: 0 0 2px hsl(3deg 73% 74%);
 
     /* Recent view */
     --color-border-recent-view-row: hsl(0deg 0% 0% / 20%);
diff --git a/web/styles/compose.css b/web/styles/compose.css
index d8e5ab2222..d636b89d95 100644
--- a/web/styles/compose.css
+++ b/web/styles/compose.css
@@ -329,8 +329,8 @@
 
     &:has(.new_message_textarea.invalid),
     &:has(.new_message_textarea.invalid:focus) {
-        border-color: hsl(3deg 57% 33%);
-        box-shadow: 0 0 2px hsl(3deg 57% 33%);
+        border-color: var(--color-invalid-input-border);
+        box-shadow: var(--color-invalid-input-box-shadow);
     }
 }
 
diff --git a/web/styles/dark_theme.css b/web/styles/dark_theme.css
index 285f8e8eff..6bfa24b9e3 100644
--- a/web/styles/dark_theme.css
+++ b/web/styles/dark_theme.css
@@ -273,14 +273,6 @@
         }
     }
 
-    #message-content-container {
-        &:has(textarea.new_message_textarea.invalid),
-        &:has(textarea.new_message_textarea.invalid:focus) {
-            border-color: hsl(3deg 73% 74%);
-            box-shadow: 0 0 2px hsl(3deg 73% 74%);
-        }
-    }
-
     #stream-actions-menu-popover .sp-container {
         background-color: transparent;
 
diff --git a/web/styles/input_pill.css b/web/styles/input_pill.css
index c8a98efcef..34010568e5 100644
--- a/web/styles/input_pill.css
+++ b/web/styles/input_pill.css
@@ -177,6 +177,11 @@
             display: none;
         }
     }
+
+    &.invalid {
+        border-color: var(--color-invalid-input-border);
+        box-shadow: var(--color-invalid-input-box-shadow);
+    }
 }
 
 #compose-direct-recipient .pill-container {
diff --git a/web/tests/input_pill.test.cjs b/web/tests/input_pill.test.cjs
index 6cd2cf2f64..9eb57de9ec 100644
--- a/web/tests/input_pill.test.cjs
+++ b/web/tests/input_pill.test.cjs
@@ -60,6 +60,7 @@ run_test("basics", ({mock_template}) => {
     };
 
     widget.appendValidatedData(item);
+    assert.ok(!widget.is_pending());
     assert.ok(inserted_before);
 
     assert.deepEqual(widget.items(), [item]);