diff --git a/interface/src/ui/overlays/ContextOverlayInterface.cpp b/interface/src/ui/overlays/ContextOverlayInterface.cpp
index dd05e5c6a8..aca186a589 100644
--- a/interface/src/ui/overlays/ContextOverlayInterface.cpp
+++ b/interface/src/ui/overlays/ContextOverlayInterface.cpp
@@ -50,7 +50,9 @@ ContextOverlayInterface::ContextOverlayInterface() {
     _entityPropertyFlags += PROP_OWNING_AVATAR_ID;
 
     auto entityScriptingInterface = DependencyManager::get<EntityScriptingInterface>().data();
-    connect(entityScriptingInterface, &EntityScriptingInterface::mousePressOnEntity, this, &ContextOverlayInterface::createOrDestroyContextOverlay);
+    connect(entityScriptingInterface, &EntityScriptingInterface::clickDownOnEntity, this, &ContextOverlayInterface::clickDownOnEntity);
+    connect(entityScriptingInterface, &EntityScriptingInterface::holdingClickOnEntity, this, &ContextOverlayInterface::holdingClickOnEntity);
+    connect(entityScriptingInterface, &EntityScriptingInterface::mouseReleaseOnEntity, this, &ContextOverlayInterface::mouseReleaseOnEntity);
     connect(entityScriptingInterface, &EntityScriptingInterface::hoverEnterEntity, this, &ContextOverlayInterface::contextOverlays_hoverEnterEntity);
     connect(entityScriptingInterface, &EntityScriptingInterface::hoverLeaveEntity, this, &ContextOverlayInterface::contextOverlays_hoverLeaveEntity);
     connect(_tabletScriptingInterface->getTablet("com.highfidelity.interface.tablet.system"), &TabletProxy::tabletShownChanged, this, [&]() {
@@ -97,6 +99,31 @@ void ContextOverlayInterface::setEnabled(bool enabled) {
     _enabled = enabled;
 }
 
+void ContextOverlayInterface::clickDownOnEntity(const EntityItemID& entityItemID, const PointerEvent& event) {
+    if (_enabled && event.getButton() == PointerEvent::SecondaryButton && contextOverlayFilterPassed(entityItemID)) {
+        _mouseDownEntity = entityItemID;
+        _mouseDownEntityTimestamp = usecTimestampNow();
+    } else {
+        if (!_currentEntityWithContextOverlay.isNull()) {
+            disableEntityHighlight(_currentEntityWithContextOverlay);
+            destroyContextOverlay(_currentEntityWithContextOverlay, event);
+        }
+    }
+}
+
+static const float CONTEXT_OVERLAY_CLICK_HOLD_TIME_MSEC = 400.0f;
+void ContextOverlayInterface::holdingClickOnEntity(const EntityItemID& entityItemID, const PointerEvent& event) {
+    if (!_mouseDownEntity.isNull() && ((usecTimestampNow() - _mouseDownEntityTimestamp) > (CONTEXT_OVERLAY_CLICK_HOLD_TIME_MSEC * USECS_PER_MSEC))) {
+        _mouseDownEntity = EntityItemID();
+    }
+}
+
+void ContextOverlayInterface::mouseReleaseOnEntity(const EntityItemID& entityItemID, const PointerEvent& event) {
+    if (_enabled && event.getButton() == PointerEvent::SecondaryButton && contextOverlayFilterPassed(entityItemID) && _mouseDownEntity == entityItemID) {
+        createOrDestroyContextOverlay(entityItemID, event);
+    }
+}
+
 bool ContextOverlayInterface::createOrDestroyContextOverlay(const EntityItemID& entityItemID, const PointerEvent& event) {
     if (_enabled && event.getButton() == PointerEvent::SecondaryButton) {
         if (contextOverlayFilterPassed(entityItemID)) {
diff --git a/interface/src/ui/overlays/ContextOverlayInterface.h b/interface/src/ui/overlays/ContextOverlayInterface.h
index fcdf2d5820..b80a3a70fb 100644
--- a/interface/src/ui/overlays/ContextOverlayInterface.h
+++ b/interface/src/ui/overlays/ContextOverlayInterface.h
@@ -64,6 +64,10 @@ signals:
     void contextOverlayClicked(const QUuid& currentEntityWithContextOverlay);
 
 public slots:
+    void clickDownOnEntity(const EntityItemID& entityItemID, const PointerEvent& event);
+    void holdingClickOnEntity(const EntityItemID& entityItemID, const PointerEvent& event);
+    void mouseReleaseOnEntity(const EntityItemID& entityItemID, const PointerEvent& event);
+
     bool createOrDestroyContextOverlay(const EntityItemID& entityItemID, const PointerEvent& event);
     bool destroyContextOverlay(const EntityItemID& entityItemID, const PointerEvent& event);
     bool destroyContextOverlay(const EntityItemID& entityItemID);
@@ -84,6 +88,8 @@ private:
     };
     bool _verboseLogging{ true };
     bool _enabled { true };
+    EntityItemID _mouseDownEntity{};
+    quint64 _mouseDownEntityTimestamp;
     EntityItemID _currentEntityWithContextOverlay{};
     EntityItemID _lastInspectedEntity{};
     QString _entityMarketplaceID;