diff --git a/src/cdk/drag-drop/directives/drag.spec.ts b/src/cdk/drag-drop/directives/drag.spec.ts
index 5df46aa42222..2ff613f5b6aa 100644
--- a/src/cdk/drag-drop/directives/drag.spec.ts
+++ b/src/cdk/drag-drop/directives/drag.spec.ts
@@ -3299,6 +3299,36 @@ describe('CdkDrag', () => {
         cleanup();
       }));
 
+    it('should be able to re-enable a disabled drop list', fakeAsync(() => {
+      const fixture = createComponent(DraggableInDropZone);
+      fixture.detectChanges();
+      const dragItems = fixture.componentInstance.dragItems;
+      const tryDrag = () => {
+        const firstItem = dragItems.first;
+        const thirdItemRect = dragItems.toArray()[2].element.nativeElement.getBoundingClientRect();
+        dragElementViaMouse(fixture, firstItem.element.nativeElement,
+          thirdItemRect.left + 1, thirdItemRect.top + 1);
+        flush();
+        fixture.detectChanges();
+      };
+
+      expect(dragItems.map(drag => drag.element.nativeElement.textContent!.trim()))
+          .toEqual(['Zero', 'One', 'Two', 'Three']);
+
+      fixture.componentInstance.dropInstance.disabled = true;
+      fixture.detectChanges();
+      tryDrag();
+
+      expect(dragItems.map(drag => drag.element.nativeElement.textContent!.trim()))
+          .toEqual(['Zero', 'One', 'Two', 'Three']);
+
+      fixture.componentInstance.dropInstance.disabled = false;
+      fixture.detectChanges();
+      tryDrag();
+
+      expect(dragItems.map(drag => drag.element.nativeElement.textContent!.trim()))
+          .toEqual(['One', 'Two', 'Zero', 'Three']);
+    }));
   });
 
   describe('in a connected drop container', () => {
diff --git a/src/cdk/drag-drop/directives/drop-list.ts b/src/cdk/drag-drop/directives/drop-list.ts
index ffc629ce19aa..465da130a034 100644
--- a/src/cdk/drag-drop/directives/drop-list.ts
+++ b/src/cdk/drag-drop/directives/drop-list.ts
@@ -104,7 +104,11 @@ export class CdkDropList<T = any> implements AfterContentInit, OnDestroy {
     return this._disabled || (!!this._group && this._group.disabled);
   }
   set disabled(value: boolean) {
-    this._disabled = coerceBooleanProperty(value);
+    // Usually we sync the directive and ref state right before dragging starts, in order to have
+    // a single point of failure and to avoid having to use setters for everything. `disabled` is
+    // a special case, because it can prevent the `beforeStarted` event from firing, which can lock
+    // the user in a disabled state, so we also need to sync it as it's being set.
+    this._dropListRef.disabled = this._disabled = coerceBooleanProperty(value);
   }
   private _disabled = false;
 
@@ -159,7 +163,7 @@ export class CdkDropList<T = any> implements AfterContentInit, OnDestroy {
       return this.enterPredicate(drag.data, drop.data);
     };
 
-    this._syncInputs(this._dropListRef);
+    this._setupInputSyncSubscription(this._dropListRef);
     this._handleEvents(this._dropListRef);
     CdkDropList._dropLists.push(this);
 
@@ -251,7 +255,7 @@ export class CdkDropList<T = any> implements AfterContentInit, OnDestroy {
   }
 
   /** Syncs the inputs of the CdkDropList with the options of the underlying DropListRef. */
-  private _syncInputs(ref: DropListRef<CdkDropList>) {
+  private _setupInputSyncSubscription(ref: DropListRef<CdkDropList>) {
     if (this._dir) {
       this._dir.change
         .pipe(startWith(this._dir.value), takeUntil(this._destroyed))