diff --git a/platform/darwin/src/MGLShapeCollection.h b/platform/darwin/src/MGLShapeCollection.h
index 6a21d6fb903..a617223ea75 100644
--- a/platform/darwin/src/MGLShapeCollection.h
+++ b/platform/darwin/src/MGLShapeCollection.h
@@ -19,7 +19,7 @@ NS_ASSUME_NONNULL_BEGIN
 /**
  An array of shapes forming the shape collection.
  */
-@property (nonatomic, copy, readonly) NS_ARRAY_OF(MGLShape <MGLAnnotation> *) *shapes;
+@property (nonatomic, copy, readonly) NS_ARRAY_OF(MGLShape *) *shapes;
 
 /**
  Creates and returns a shape collection consisting of the given shapes.
@@ -28,7 +28,7 @@ NS_ASSUME_NONNULL_BEGIN
     this array is copied to the new object.
  @return A new shape collection object.
  */
-+ (instancetype)shapeCollectionWithShapes:(NS_ARRAY_OF(MGLShape <MGLAnnotation> *) *)shapes;
++ (instancetype)shapeCollectionWithShapes:(NS_ARRAY_OF(MGLShape *) *)shapes;
 
 @end
 
diff --git a/platform/darwin/src/MGLShapeCollection.m b/platform/darwin/src/MGLShapeCollection.m
index 3fc4cdda759..5d42b5a51ca 100644
--- a/platform/darwin/src/MGLShapeCollection.m
+++ b/platform/darwin/src/MGLShapeCollection.m
@@ -2,11 +2,11 @@
 
 @implementation MGLShapeCollection
 
-+ (instancetype)shapeCollectionWithShapes:(NS_ARRAY_OF(MGLShape <MGLAnnotation> *) *)shapes {
++ (instancetype)shapeCollectionWithShapes:(NS_ARRAY_OF(MGLShape *) *)shapes {
     return [[self alloc] initWithShapes:shapes];
 }
 
-- (instancetype)initWithShapes:(NS_ARRAY_OF(MGLShape <MGLAnnotation> *) *)shapes {
+- (instancetype)initWithShapes:(NS_ARRAY_OF(MGLShape *) *)shapes {
     if (self = [super init]) {
         NSAssert(shapes.count, @"Cannot create an empty shape collection");
         _shapes = shapes.copy;
diff --git a/platform/osx/app/Base.lproj/MainMenu.xib b/platform/osx/app/Base.lproj/MainMenu.xib
index 4afb3b244e6..c80428ff00b 100644
--- a/platform/osx/app/Base.lproj/MainMenu.xib
+++ b/platform/osx/app/Base.lproj/MainMenu.xib
@@ -1,5 +1,5 @@
 <?xml version="1.0" encoding="UTF-8" standalone="no"?>
-<document type="com.apple.InterfaceBuilder3.Cocoa.XIB" version="3.0" toolsVersion="10117" systemVersion="15E65" targetRuntime="MacOSX.Cocoa" propertyAccessControl="none" useAutolayout="YES" customObjectInstantitationMethod="direct">
+<document type="com.apple.InterfaceBuilder3.Cocoa.XIB" version="3.0" toolsVersion="10117" systemVersion="15F34" targetRuntime="MacOSX.Cocoa" propertyAccessControl="none" useAutolayout="YES" customObjectInstantitationMethod="direct">
     <dependencies>
         <plugIn identifier="com.apple.InterfaceBuilder.CocoaPlugin" version="10117"/>
     </dependencies>
diff --git a/platform/osx/app/Base.lproj/MapDocument.xib b/platform/osx/app/Base.lproj/MapDocument.xib
index 9a3db47df6a..55d82d21d08 100644
--- a/platform/osx/app/Base.lproj/MapDocument.xib
+++ b/platform/osx/app/Base.lproj/MapDocument.xib
@@ -1,5 +1,5 @@
 <?xml version="1.0" encoding="UTF-8" standalone="no"?>
-<document type="com.apple.InterfaceBuilder3.Cocoa.XIB" version="3.0" toolsVersion="10117" systemVersion="15E65" targetRuntime="MacOSX.Cocoa" propertyAccessControl="none" useAutolayout="YES">
+<document type="com.apple.InterfaceBuilder3.Cocoa.XIB" version="3.0" toolsVersion="10117" systemVersion="15F34" targetRuntime="MacOSX.Cocoa" propertyAccessControl="none" useAutolayout="YES">
     <dependencies>
         <plugIn identifier="com.apple.InterfaceBuilder.CocoaPlugin" version="10117"/>
     </dependencies>
@@ -123,6 +123,12 @@
                         <action selector="removePin:" target="-1" id="w0R-0B-7mG"/>
                     </connections>
                 </menuItem>
+                <menuItem title="Select Features" id="za5-bY-mdf">
+                    <modifierMask key="keyEquivalentModifierMask"/>
+                    <connections>
+                        <action selector="selectFeatures:" target="-1" id="ikt-CZ-yZT"/>
+                    </connections>
+                </menuItem>
             </items>
             <connections>
                 <outlet property="delegate" destination="-2" id="oHe-ZP-lyc"/>
diff --git a/platform/osx/app/MapDocument.m b/platform/osx/app/MapDocument.m
index 6fcfc7ce5d3..4274126747f 100644
--- a/platform/osx/app/MapDocument.m
+++ b/platform/osx/app/MapDocument.m
@@ -14,6 +14,27 @@
     { .latitude = -13.15589555, .longitude = -74.2178961777998 },
 };
 
+NS_ARRAY_OF(id <MGLAnnotation>) *MBXFlattenedShapes(NS_ARRAY_OF(id <MGLAnnotation>) *shapes) {
+    NSMutableArray *flattenedShapes = [NSMutableArray arrayWithCapacity:shapes.count];
+    for (id <MGLAnnotation> shape in shapes) {
+        NSArray *subshapes;
+        if ([shape isKindOfClass:[MGLMultiPolyline class]]) {
+            subshapes = [(MGLMultiPolyline *)shape polylines];
+        } else if ([shape isKindOfClass:[MGLMultiPolygon class]]) {
+            subshapes = [(MGLMultiPolygon *)shape polygons];
+        } else if ([shape isKindOfClass:[MGLShapeCollection class]]) {
+            subshapes = MBXFlattenedShapes([(MGLShapeCollection *)shape shapes]);
+        }
+        
+        if (subshapes) {
+            [flattenedShapes addObjectsFromArray:subshapes];
+        } else {
+            [flattenedShapes addObject:shape];
+        }
+    }
+    return flattenedShapes;
+}
+
 @interface MapDocument () <NSWindowDelegate, NSSharingServicePickerDelegate, NSMenuDelegate, MGLMapViewDelegate>
 
 @property (weak) IBOutlet NSMenu *mapViewContextMenu;
@@ -420,8 +441,7 @@ - (void)handlePressGesture:(NSPressGestureRecognizer *)gestureRecognizer {
         if (!NSPointInRect([gestureRecognizer locationInView:self.mapView.compass], self.mapView.compass.bounds)
             && !NSPointInRect([gestureRecognizer locationInView:self.mapView.zoomControls], self.mapView.zoomControls.bounds)
             && !NSPointInRect([gestureRecognizer locationInView:self.mapView.attributionView], self.mapView.attributionView.bounds)) {
-            NSArray *features = [self.mapView visibleFeaturesAtPoint:location];
-            [self.mapView addAnnotations:features];
+            [self dropPinAtPoint:location];
         }
     }
 }
@@ -464,6 +484,16 @@ - (void)removePinAtPoint:(NSPoint)point {
     [self.mapView removeAnnotation:[self.mapView annotationAtPoint:point]];
 }
 
+- (IBAction)selectFeatures:(id)sender {
+    [self selectFeaturesAtPoint:_mouseLocationForMapViewContextMenu];
+}
+
+- (void)selectFeaturesAtPoint:(NSPoint)point {
+    NSArray *features = [self.mapView visibleFeaturesAtPoint:point];
+    NSArray *flattenedFeatures = MBXFlattenedShapes(features);
+    [self.mapView addAnnotations:flattenedFeatures];
+}
+
 #pragma mark User interface validation
 
 - (BOOL)validateMenuItem:(NSMenuItem *)menuItem {
@@ -521,6 +551,9 @@ - (BOOL)validateMenuItem:(NSMenuItem *)menuItem {
         menuItem.hidden = annotationUnderCursor == nil;
         return YES;
     }
+    if (menuItem.action == @selector(selectFeatures:)) {
+        return YES;
+    }
     if (menuItem.action == @selector(toggleTileBoundaries:)) {
         BOOL isShown = self.mapView.debugMask & MGLMapDebugTileBoundariesMask;
         menuItem.title = isShown ? @"Hide Tile Boundaries" : @"Show Tile Boundaries";