diff --git a/src/js/_enqueues/admin/postbox.js b/src/js/_enqueues/admin/postbox.js
index b6d1b6569dc84..fc339afd14d2b 100644
--- a/src/js/_enqueues/admin/postbox.js
+++ b/src/js/_enqueues/admin/postbox.js
@@ -394,6 +394,24 @@
 				opacity: 0.65,
 				start: function() {
 					$( 'body' ).addClass( 'is-dragging-metaboxes' );
+
+					/*
+					 * Equalize the height of the dashboard sortable drop areas to the
+					 * tallest column. The drop placeholder only appears where the dragged
+					 * item overlaps a `.meta-box-sortables` area, so without this a widget
+					 * dragged past the end of a shorter column gets no drop indicator.
+					 */
+					var $dashboardSortables = $( '#dashboard-widgets .meta-box-sortables' ),
+						maxSortableHeight = 0;
+
+					$dashboardSortables.each( function() {
+						maxSortableHeight = Math.max( maxSortableHeight, $( this ).height() );
+					});
+
+					if ( maxSortableHeight ) {
+						$dashboardSortables.css( 'min-height', maxSortableHeight + 'px' );
+					}
+
 					// Refresh the cached positions of all the sortable items so that the min-height set while dragging works.
 					$( '.meta-box-sortables' ).sortable( 'refreshPositions' );
 				},
@@ -402,6 +420,9 @@
 
 					$( 'body' ).removeClass( 'is-dragging-metaboxes' );
 
+					// Remove the temporary equal-height drop areas set in `start`.
+					$( '#dashboard-widgets .meta-box-sortables' ).css( 'min-height', '' );
+
 					if ( $el.find( '#dashboard_browser_nag' ).is( ':visible' ) && 'dashboard_browser_nag' != this.firstChild.id ) {
 						$el.sortable('cancel');
 						return;
diff --git a/src/wp-admin/css/common.css b/src/wp-admin/css/common.css
index 63e960b482c00..bc264e14f7936 100644
--- a/src/wp-admin/css/common.css
+++ b/src/wp-admin/css/common.css
@@ -2258,12 +2258,25 @@ html.wp-toolbar {
 	color: #a7aaad;
 }
 
-.sortable-placeholder:not(.empty-container .sortable-placeholder) {
-	border: 1px dashed #c3c4c7;
+.sortable-placeholder {
+	box-sizing: border-box;
+	border: 2px dashed var(--wp-admin-theme-color, #c3c4c7);
+	background: rgba(var(--wp-admin-theme-color--rgb, 56, 88, 233), 0.08);
 	border-radius: 8px;
 	margin-bottom: 20px;
 }
 
+/*
+ * Empty containers render their own drop outline, so the placeholder inside
+ * them is redundant. Kept as a separate rule (instead of a `:not()` with a
+ * descendant combinator) so unsupported-selector engines can't drop the main
+ * placeholder styles and leave the drop indicator invisible.
+ */
+.empty-container .sortable-placeholder {
+	border: none;
+	background: none;
+}
+
 .postbox,
 .stuffbox {
 	margin-bottom: 20px;
diff --git a/src/wp-admin/css/dashboard.css b/src/wp-admin/css/dashboard.css
index ab73f828f7067..4018ff7262df3 100644
--- a/src/wp-admin/css/dashboard.css
+++ b/src/wp-admin/css/dashboard.css
@@ -39,7 +39,13 @@
 }
 
 #dashboard-widgets-wrap {
-	overflow: hidden;
+	/*
+	 * Use flow-root to contain the floated postbox columns without clipping.
+	 * `overflow: hidden` would clip the jQuery UI Sortable drag helper when it
+	 * leaves the wrap bounds (e.g. while scroll-dragging near the edges),
+	 * making the drop zone glitch or disappear.
+	 */
+	display: flow-root;
 	margin: 0 -8px;
 }
 
@@ -87,13 +93,13 @@
 
 #dashboard-widgets .postbox-container .empty-container:after {
 	content: attr(data-emptystring);
-	margin: auto;
 	position: absolute;
-	top: 50%;
+	top: 0;
 	left: 0;
 	right: 0;
-	transform: translateY( -50% );
-	padding: 0 2em;
+	/* Keep the hint near the top of the drop zone instead of floating it to the
+	   vertical center of a tall empty column. */
+	padding: 32px 2em;
 	text-align: center;
 	color: #646970;
 	font-size: 16px;