diff --git a/.changeset/listbox-checkbox-primary-line.md b/.changeset/listbox-checkbox-primary-line.md
new file mode 100644
index 000000000..79fe0d826
--- /dev/null
+++ b/.changeset/listbox-checkbox-primary-line.md
@@ -0,0 +1,5 @@
+---
+'@launchpad-ui/components': patch
+---
+
+Align the multi-select `ListBoxItem` checkbox to the item's primary line instead of vertically centering it against the whole item, so items with a stacked label and description keep the checkbox next to the label.
diff --git a/packages/components/src/ListBox.tsx b/packages/components/src/ListBox.tsx
index 5d0e13f9d..64391d11c 100644
--- a/packages/components/src/ListBox.tsx
+++ b/packages/components/src/ListBox.tsx
@@ -70,7 +70,7 @@ const ListBoxItem = <T extends object>({ ref, ...props }: ListBoxItemProps<T>) =
 				<>
 					{selectionMode === 'multiple' && (
 						<div
-							className={checkboxStyles()}
+							className={checkboxStyles({ className: styles.checkbox })}
 							data-selected={isSelected || undefined}
 							data-disabled={isDisabled || undefined}
 						>
diff --git a/packages/components/src/styles/ListBox.module.css b/packages/components/src/styles/ListBox.module.css
index 75525ec05..aacad0233 100644
--- a/packages/components/src/styles/ListBox.module.css
+++ b/packages/components/src/styles/ListBox.module.css
@@ -4,6 +4,15 @@
 
 .item {
 	composes: item from './Menu.module.css';
+
+	&:has(.checkbox) {
+		align-items: start;
+	}
+
+	& .checkbox {
+		height: 1lh;
+		align-items: center;
+	}
 }
 
 .content {