diff --git a/gateway/field_presence.go b/gateway/field_presence.go
index 8992fb89..e531cd98 100644
--- a/gateway/field_presence.go
+++ b/gateway/field_presence.go
@@ -15,23 +15,21 @@ import (
 	"google.golang.org/grpc/metadata"
 )
 
-const fieldPresenceMetaKey = "field-paths"
+const (
+	fieldPresenceMetaKey = "field-paths"
+	pathsSeparator       = "$"
+	bulkField            = "objects"
+)
 
-// PresenceAnnotator will parse the JSON input and then add the paths to the
+// NewPresenceAnnotator will parse the JSON input and then add the paths to the
 // metadata to be pulled from context later
 func NewPresenceAnnotator(methods ...string) func(context.Context, *http.Request) metadata.MD {
 	return func(ctx context.Context, req *http.Request) metadata.MD {
 		if req == nil {
 			return nil
 		}
-		validMethod := false
-		for _, m := range methods {
-			if req.Method == m {
-				validMethod = true
-				break
-			}
-		}
-		if !validMethod {
+
+		if !isValidMethod(req, methods...) {
 			return nil
 		}
 
@@ -49,43 +47,95 @@ func NewPresenceAnnotator(methods ...string) func(context.Context, *http.Request
 			return md
 		}
 
-		var paths []string
 		var root interface{}
-
 		if err := json.Unmarshal(body, &root); err != nil {
 			return nil
 		}
 
-		queue := []pathItem{{node: root}}
-		for len(queue) > 0 {
-			// dequeue an item
-			item := queue[0]
-			queue = queue[1:]
-			if m, ok := item.node.(map[string]interface{}); ok {
-				l := len(item.path)
-				// if the item is an object, then enqueue all of its children
-				for k, v := range m {
-					newPath := make([]string, l+1)
-					copy(newPath, item.path)
-					newPath[l] = generator.CamelCase(k)
-					queue = append(queue, pathItem{path: newPath, node: v})
-				}
+		roots := getRoots(root)
+		for _, r := range roots {
+			queue := []pathItem{{node: r}}
+
+			paths := []string{}
+			for len(queue) > 0 {
+				// dequeue an item
+				item := queue[0]
+				queue = queue[1:]
 
-				if len(m) == 0 && l > 0 {
-					// otherwise, it's a leaf node so print its path
+				if isLeaf(item) {
 					paths = append(paths, strings.Join(item.path, "."))
+				} else {
+					if m, ok := item.node.(map[string]interface{}); ok {
+						// if the item is an object, then enqueue all of its children
+						for k, v := range m {
+							newPath := extendPath(item.path, k, v)
+							queue = append(queue, pathItem{path: newPath, node: v})
+						}
+					}
 				}
-			} else if len(item.path) > 0 {
-				// otherwise, it's a leaf node so print its path
-				paths = append(paths, strings.Join(item.path, "."))
 			}
+
+			entry := strings.Join(paths, pathsSeparator)
+			if len(entry) == 0 {
+				continue
+			}
+
+			md[fieldPresenceMetaKey] = append(md[fieldPresenceMetaKey], strings.Join(paths, pathsSeparator))
 		}
 
-		md[fieldPresenceMetaKey] = paths
 		return md
 	}
 }
 
+func extendPath(parrent []string, key string, value interface{}) []string {
+	newPath := make([]string, len(parrent)+1)
+	copy(newPath, parrent)
+	newPath[len(newPath)-1] = generator.CamelCase(key)
+	return newPath
+}
+
+func isLeaf(item pathItem) bool {
+	if m, ok := item.node.(map[string]interface{}); ok {
+		if len(m) == 0 && len(item.path) > 0 {
+			return true
+		}
+	} else if len(item.path) > 0 {
+		return true
+	}
+
+	return false
+}
+
+func getRoots(root interface{}) []interface{} {
+	defaultRoot := []interface{}{root}
+	m, ok := root.(map[string]interface{})
+	if !ok {
+		return defaultRoot
+	}
+
+	bulk, ok := m[bulkField]
+	if !ok {
+		return defaultRoot
+	}
+
+	slice, ok := bulk.([]interface{})
+	if !ok {
+		return defaultRoot
+	}
+
+	return slice
+}
+
+func isValidMethod(req *http.Request, methods ...string) bool {
+	for _, m := range methods {
+		if req.Method == m {
+			return true
+		}
+	}
+
+	return false
+}
+
 // pathItem stores a in-progress deconstruction of a path for a fieldmask
 type pathItem struct {
 	// the list of prior fields leading up to node
@@ -110,17 +160,19 @@ func PresenceClientInterceptor() grpc.UnaryClientInterceptor {
 		if !found {
 			return
 		}
-		fieldMask := &field_mask.FieldMask{Paths: paths}
 
-		// If a field with type *FieldMask exists, set the paths in it
+		fieldMask := fieldMaskFromPaths(paths)
+		// If a field with type *FieldMask or []*FieldMask exists, set the paths in it
 		t := reflect.ValueOf(req)
 		if t.Kind() != reflect.Interface && t.Kind() != reflect.Ptr {
 			return
 		}
+
 		t = t.Elem()
 		if t.Kind() != reflect.Struct { // only Structs can have their fields enumerated
 			return
 		}
+
 		for i := 0; i < t.NumField(); i++ {
 			f := t.Field(i)
 			if f.Type() == reflect.TypeOf(fieldMask) && f.IsNil() {
@@ -130,3 +182,19 @@ func PresenceClientInterceptor() grpc.UnaryClientInterceptor {
 		return
 	}
 }
+
+func fieldMaskFromPaths(paths []string) interface{} {
+	if len(paths) == 0 {
+		return &field_mask.FieldMask{}
+	}
+
+	if len(paths) > 1 {
+		bulkFieldMasks := make([]*field_mask.FieldMask, len(paths))
+		for i, p := range paths {
+			bulkFieldMasks[i] = &field_mask.FieldMask{Paths: strings.Split(p, pathsSeparator)}
+		}
+		return bulkFieldMasks
+	}
+
+	return &field_mask.FieldMask{Paths: strings.Split(paths[0], pathsSeparator)}
+}
diff --git a/gateway/field_presence_test.go b/gateway/field_presence_test.go
index 3de86951..96de41dd 100644
--- a/gateway/field_presence_test.go
+++ b/gateway/field_presence_test.go
@@ -2,6 +2,7 @@ package gateway
 
 import (
 	"context"
+	"fmt"
 	"io/ioutil"
 	"net/http"
 	"reflect"
@@ -20,8 +21,9 @@ func TestAnnotator(t *testing.T) {
 		``:   metadata.MD{fieldPresenceMetaKey: nil},
 		`{}`: metadata.MD{fieldPresenceMetaKey: nil},
 		`{`:  nil,
-		`{"one":{"two":"a", "three":[]}, "four": 5}`: {fieldPresenceMetaKey: []string{"Four", "One.Two", "One.Three"}},
-		`{"one": {}}`:                                {fieldPresenceMetaKey: []string{"One"}},
+		`{"objects":[{"one": {"two":"a", "three":[]}, "four": 5}, {"one":{"two":"a", "three":[]}, "four": 5}]}`: {fieldPresenceMetaKey: []string{"Four$One.Two$One.Three", "Four$One.Two$One.Three"}},
+		`{"one":{"two":"a", "three":[]}, "four": 5}`:                                                            {fieldPresenceMetaKey: []string{"Four$One.Two$One.Three"}},
+		`{"one": {}}`:                                                                                           {fieldPresenceMetaKey: []string{"One"}},
 		`{
   "name": "atlas",
   "burden": {
@@ -40,9 +42,7 @@ func TestAnnotator(t *testing.T) {
 			"mortals": []
 		}
   }
-}`: {fieldPresenceMetaKey: []string{"Name", "Burden.Duration", "Burden.Weight",
-			"Burden.Breaks", "Burden.Replacements.Hero.Name", "Burden.Replacements.Hero.Duration",
-			"Burden.Replacements.Hero.Lineage.Mother", "Burden.Replacements.Hero.Lineage.Father", "Burden.Replacements.Mortals"}},
+}`: {fieldPresenceMetaKey: []string{"Name$Burden.Duration$Burden.Weight$Burden.Breaks$Burden.Replacements.Hero.Name$Burden.Replacements.Hero.Duration$Burden.Replacements.Hero.Lineage.Mother$Burden.Replacements.Hero.Lineage.Father$Burden.Replacements.Mortals"}},
 	} {
 		postReq := &http.Request{
 			Method: "POST",
@@ -54,15 +54,33 @@ func TestAnnotator(t *testing.T) {
 			continue
 		}
 		// Because the order of objects at the same depth is not guaranteed
-		sort.Strings(md[fieldPresenceMetaKey])
-		sort.Strings(expect[fieldPresenceMetaKey])
-		if !reflect.DeepEqual(md, expect) {
+		if !isEqualFieldMasks(md[fieldPresenceMetaKey], expect[fieldPresenceMetaKey]) {
 			t.Errorf("Did not produce expected metadata %+v, got %+v", expect, md)
 		}
 
 	}
 }
 
+func isEqualFieldMasks(s1 []string, s2 []string) bool {
+	if len(s1) != len(s2) {
+		fmt.Println("len(s1) != len(s2)", len(s1), len(s2))
+		return false
+	}
+
+	for i := 0; i < len(s1); i++ {
+		mask1, mask2 := strings.Split(s1[i], "$"), strings.Split(s2[i], "$")
+		sort.Strings(mask1)
+		sort.Strings(mask2)
+
+		if !reflect.DeepEqual(mask1, mask2) {
+			fmt.Println("!reflect.DeepEqual(mask1, mask2)")
+			return false
+		}
+	}
+
+	return true
+}
+
 type dummyReq struct {
 	SomeFieldMaskField *field_mask.FieldMask
 }
@@ -80,7 +98,7 @@ func TestUnaryServerInterceptor(t *testing.T) {
 	interceptor := PresenceClientInterceptor()
 	md := runtime.ServerMetadata{
 		HeaderMD: metadata.MD{
-			fieldPresenceMetaKey: []string{"one.two.three", "one.four"},
+			fieldPresenceMetaKey: []string{"one.two.three$one.four"},
 		},
 	}
 	ctx := runtime.NewServerMetadataContext(context.Background(), md)
@@ -112,7 +130,7 @@ func TestUnaryServerInterceptor(t *testing.T) {
 		if req == nil {
 			t.Fatal("For some reason it deleted the request object")
 		}
-		got, want := req.SomeFieldMaskField, &field_mask.FieldMask{Paths: nil}
+		got, want := req.SomeFieldMaskField, &field_mask.FieldMask{}
 		if !reflect.DeepEqual(got, want) {
 			t.Errorf("Didn't properly set the fieldmask in the request.\ngot :%v\nwant:%v", got, want)
 		}