diff --git a/packages/lwc-engine/src/faux-shadow/events.ts b/packages/lwc-engine/src/faux-shadow/events.ts
index ae5b8e181a..c2623f1c68 100644
--- a/packages/lwc-engine/src/faux-shadow/events.ts
+++ b/packages/lwc-engine/src/faux-shadow/events.ts
@@ -69,15 +69,17 @@ const EventPatchDescriptors: PropertyDescriptorMap = {
                 return outerMostElement;
             }
             const eventContext = eventToContextMap.get(this);
-            // Executing event listener on component, target is always currentTarget
+
+            // Retarget to currentTarget if the listener was added to a custom element.
             if (eventContext === EventListenerContext.CUSTOM_ELEMENT_LISTENER) {
                 return patchShadowDomTraversalMethods(currentTarget as Element);
             }
-            const currentTargetRootNode = getRootNode.call(currentTarget, GET_ROOT_NODE_CONFIG_FALSE); // x-child
 
-            // Before we can process any events, we need to first determine three things:
-            // 1) What VM context was the event attached to? (e.g. in what VM context was addEventListener called in).
-            // 2) What VM owns the context where the event was attached? (e.g. who rendered the VM context from step 1).
+            const currentTargetRootNode = getRootNode.call(currentTarget, GET_ROOT_NODE_CONFIG_FALSE);
+
+            // We need to determine three things in order to retarget correctly:
+            // 1) What VM context was the listener added? (e.g. in what VM context was addEventListener called in).
+            // 2) What VM owns the context where the listener was added? (e.g. who rendered the VM context from step 1).
             // 3) What is the event's original target's relationship to 1 and 2?
 
             // Determining Number 1:
@@ -86,8 +88,8 @@ const EventPatchDescriptors: PropertyDescriptorMap = {
             // // x-parent.html
             // <template>
             //  <!--
-            //    The event below is attached inside of x-parent's template
-            //    so vm context will be <x-parent>'s owner VM
+            //    This listener is added inside of <x-parent>'s template
+            //    so its VM context will be <x-parent>'s VM
             //  -->
             //  <div onclick={handleClick}</div>
             // </template>
@@ -145,8 +147,15 @@ const EventPatchDescriptors: PropertyDescriptorMap = {
             // </template>
             //
             let closestTarget = originalTarget;
-            while (getNodeOwnerKey(closestTarget as Node) !== myCurrentShadowKey && getNodeOwnerKey(closestTarget as Node) !== myOwnerKey) {
+            let nodeOwnerKey = getNodeOwnerKey(closestTarget as Node);
+            while (nodeOwnerKey !== myCurrentShadowKey && nodeOwnerKey !== myOwnerKey) {
                 closestTarget = parentNodeGetter.call(closestTarget);
+                // In this case, the original target is in a detached root, making it
+                // impossible to retarget (unless we figure out something clever).
+                if (closestTarget === null) {
+                    return originalTarget;
+                }
+                nodeOwnerKey = getNodeOwnerKey(closestTarget as Node);
             }
 
             /**