diff --git a/resources/js/components/fieldtypes/ButtonGroupFieldtype.vue b/resources/js/components/fieldtypes/ButtonGroupFieldtype.vue
index 36e8988764..f3412db223 100644
--- a/resources/js/components/fieldtypes/ButtonGroupFieldtype.vue
+++ b/resources/js/components/fieldtypes/ButtonGroupFieldtype.vue
@@ -1,5 +1,5 @@
 <template>
-    <ButtonGroup ref="buttonGroup">
+    <ButtonGroup overflow="stack" ref="buttonGroup">
         <Button
             v-for="(option, $index) in options"
             ref="button"
@@ -18,7 +18,6 @@
 <script>
 import Fieldtype from './Fieldtype.vue';
 import HasInputOptions from './HasInputOptions.js';
-import ResizeObserver from 'resize-observer-polyfill';
 import { Button, ButtonGroup } from '@/components/ui';
 
 export default {
@@ -28,20 +27,6 @@ export default {
         ButtonGroup
     },
 
-    data() {
-        return {
-            resizeObserver: null,
-        };
-    },
-
-    mounted() {
-        this.setupResizeObserver();
-    },
-
-    beforeUnmount() {
-        this.resizeObserver.disconnect();
-    },
-
     computed: {
         options() {
             return this.normalizeInputOptions(this.meta.options || this.config.options);
@@ -60,25 +45,6 @@ export default {
             this.update(this.value == newValue && this.config.clearable ? null : newValue);
         },
 
-        setupResizeObserver() {
-            this.resizeObserver = new ResizeObserver(() => {
-                this.handleWrappingOfNode(this.$refs.buttonGroup.$el);
-            });
-            this.resizeObserver.observe(this.$refs.buttonGroup.$el);
-        },
-
-        handleWrappingOfNode(node) {
-            const lastEl = node.lastChild;
-
-            if (!lastEl) return;
-
-            node.classList.remove('btn-vertical');
-
-            if (lastEl.offsetTop > node.clientTop) {
-                node.classList.add('btn-vertical');
-            }
-        },
-
         focus() {
             this.$refs.button[0].focus();
         },
diff --git a/resources/js/components/ui/Button/Group.vue b/resources/js/components/ui/Button/Group.vue
index 45679891c2..e0832d6100 100644
--- a/resources/js/components/ui/Button/Group.vue
+++ b/resources/js/components/ui/Button/Group.vue
@@ -1,40 +1,131 @@
 <template>
-    <div
-        :class="[
-            'group/button inline-flex flex-wrap [[data-floating-toolbar]_&]:justify-center [[data-floating-toolbar]_&]:gap-1 [[data-floating-toolbar]_&]:lg:gap-x-0',
-            '[&>[data-ui-group-target]:not(:first-child):not(:last-child)]:rounded-none',
-            '[&>[data-ui-group-target]:first-child:not(:last-child)]:rounded-e-none',
-            '[&>[data-ui-group-target]:last-child:not(:first-child)]:rounded-s-none',
-            '[&>*:not(:first-child):not(:last-child):not(:only-child)_[data-ui-group-target]]:rounded-none',
-            '[&>*:first-child:not(:last-child)_[data-ui-group-target]]:rounded-e-none',
-            '[&>*:last-child:not(:first-child)_[data-ui-group-target]]:rounded-s-none',
-            'dark:[&_button]:ring-0',
-            'max-lg:[[data-floating-toolbar]_&_button]:rounded-md!',
-            'shadow-ui-sm rounded-lg'
-        ]"
-        data-ui-button-group
-    >
-        <slot />
+    <div ref="wrapper" :class="{ invisible: measuringOverflow }">
+        <div ref="group" :class="groupClasses" :data-measuring="measuringOverflow || undefined" data-ui-button-group>
+            <slot />
+        </div>
     </div>
 </template>
 
+<script setup>
+import { ref, computed, nextTick, onMounted, onBeforeUnmount } from 'vue';
+import { cva } from 'cva';
+
+import debounce from '@/util/debounce';
+
+const props = defineProps({
+    /* When 'stack', switch to vertical layout when overflowing. When 'gap', switch to normal buttons with gaps when overflowing. */
+    overflow: {
+        type: String,
+        default: null,
+        validator: (v) => [null, 'stack', 'gap'].includes(v),
+    },
+    orientation: {
+        type: String,
+        default: 'horizontal',
+    },
+    gap: {
+        type: [String, Boolean],
+        default: false,
+    },
+    justify: {
+        type: String,
+        default: 'start',
+    },
+});
+
+const hasOverflow = ref(false);
+const needsOverflowObserver = computed(() => props.overflow === 'stack' || props.overflow === 'gap');
+const measuringOverflow = ref(false);
+
+const groupClasses = computed(() => {
+    const collapseHorizontally = [
+        '[&>[data-ui-group-target]:first-child:not(:last-child)]:rounded-e-none',
+        '[&>:first-child:not(:last-child)_[data-ui-group-target]]:rounded-e-none',
+        '[&>[data-ui-group-target]:last-child:not(:first-child)]:rounded-s-none',
+        '[&>:last-child:not(:first-child)_[data-ui-group-target]]:rounded-s-none',
+        '[&>[data-ui-group-target]:not(:first-child)]:border-s-0',
+        '[&>:not(:first-child)_[data-ui-group-target]]:border-s-0',
+    ];
+
+    const collapseVertically = [
+        'flex-col',
+        '[&>[data-ui-group-target]:first-child:not(:last-child)]:rounded-b-none',
+        '[&>:first-child:not(:last-child)_[data-ui-group-target]]:rounded-b-none',
+        '[&>[data-ui-group-target]:last-child:not(:first-child)]:rounded-t-none',
+        '[&>:last-child:not(:first-child)_[data-ui-group-target]]:rounded-t-none',
+        '[&>[data-ui-group-target]:not(:last-child)]:border-b-0',
+        '[&>:not(:last-child)_[data-ui-group-target]]:border-b-0',
+    ];
+
+    return cva({
+        base: [
+            'group/button inline-flex flex-wrap relative',
+            'dark:[&_button]:ring-0',
+            'rounded-lg shadow-ui-sm [&_[data-ui-group-target]]:shadow-none',
+            '[&>[data-ui-group-target]:not(:first-child):not(:last-child)]:rounded-none',
+            '[&>:not(:first-child):not(:last-child)_[data-ui-group-target]]:rounded-none',
+        ],
+        variants: {
+            orientation: {
+                vertical: collapseVertically,
+            },
+            justify: {
+                center: 'justify-center',
+            },
+        },
+        compoundVariants: [
+            { overflow: 'stack', hasOverflow: false, class: collapseHorizontally },
+            { overflow: 'stack', hasOverflow: true, class: collapseVertically },
+            { overflow: 'gap', hasOverflow: true, class: 'gap-1' },
+            { overflow: 'gap', hasOverflow: false, class: collapseHorizontally },
+            { overflow: null, orientation: 'horizontal', gap: false, class: collapseHorizontally },
+        ],
+    })({
+        gap: props.gap,
+        justify: props.justify,
+        orientation: props.orientation,
+        overflow: props.overflow,
+        hasOverflow: hasOverflow.value,
+    });
+});
+
+const wrapper = ref(null);
+const group = ref(null);
+let resizeObserver = null;
+
+async function checkOverflow() {
+    if (!group.value?.children.length) return;
+
+    // Enter measuring mode: force horizontal wrap
+    measuringOverflow.value = true;
+    await nextTick();
+
+    // Check if any child has wrapped to a new line
+    const children = Array.from(group.value.children);
+    const firstTop = children[0].offsetTop;
+    const lastTop = children[children.length - 1].offsetTop;
+    hasOverflow.value = lastTop > firstTop;
+
+    // Exit measuring mode
+    measuringOverflow.value = false;
+}
+
+onMounted(() => {
+    if (needsOverflowObserver.value) {
+        checkOverflow();
+        resizeObserver = new ResizeObserver(debounce(checkOverflow, 50));
+        resizeObserver.observe(wrapper.value);
+    }
+});
+
+onBeforeUnmount(() => {
+    resizeObserver?.disconnect();
+});
+</script>
+
 <style>
-    /* GROUP FLOATING TOOLBAR / BUTTON GROUP BORDERS
-    =================================================== */
-    [data-ui-button-group] [data-ui-group-target] {
-        @apply shadow-none;
-
-        &:not(:first-child):not([data-floating-toolbar] &) {
-            border-inline-start: 0;
-        }
-
-        /* Account for button groups being split apart on small screens */
-        [data-floating-toolbar] & {
-            @media (width >= 1024px) {
-                &:not(:first-child) {
-                    border-inline-start: 0;
-                }
-            }
-        }
+    /* Force horizontal wrap layout during measurement to detect overflow */
+    [data-ui-button-group][data-measuring] {
+        @apply flex! flex-row!;
     }
 </style>
diff --git a/resources/js/components/ui/Listing/BulkActionsFloatingToolbar.vue b/resources/js/components/ui/Listing/BulkActionsFloatingToolbar.vue
index 4bee4b1195..17e3d8f2f0 100644
--- a/resources/js/components/ui/Listing/BulkActionsFloatingToolbar.vue
+++ b/resources/js/components/ui/Listing/BulkActionsFloatingToolbar.vue
@@ -118,7 +118,7 @@ onUnmounted(() => document.removeEventListener('keydown', onKeydown, true));
         :transition="{ duration: 0.2, ease: 'easeInOut' }"
     >
         <div class="pointer-events-auto space-y-3 rounded-xl border border-gray-300/60 dark:border-gray-700 p-1 bg-gray-200/55 shadow-[0_1px_16px_-2px_rgba(63,63,71,0.2)] dark:bg-gray-800 dark:shadow-[0_10px_15px_rgba(0,0,0,.5)] dark:inset-shadow-2xs dark:inset-shadow-white/10">
-            <ButtonGroup>
+            <ButtonGroup overflow="gap" justify="center">
                 <Button
                     class="text-blue-500!"
                     @click="clearSelections?.()"