diff --git a/pkg/parser/fsreader.go b/pkg/parser/fsreader.go
index ff0927a45..a9c7cd40d 100644
--- a/pkg/parser/fsreader.go
+++ b/pkg/parser/fsreader.go
@@ -24,6 +24,14 @@ import (
 	"github.com/spf13/afero"
 )
 
+var _ AnnotatedReadCloser = &FsReadCloser{}
+
+// FsReadCloserAnnotation annotates data for an FsReadCloser.
+type FsReadCloserAnnotation struct {
+	path     string
+	position int
+}
+
 // FsReadCloser implements io.ReadCloser for an Afero filesystem.
 type FsReadCloser struct {
 	fs         afero.Fs
@@ -32,6 +40,7 @@ type FsReadCloser struct {
 	index      int
 	position   int
 	writeBreak bool
+	wroteBreak bool
 }
 
 // A FilterFn filters files when the FsReadCloser walks the filesystem.
@@ -56,6 +65,13 @@ func SkipDirs() FilterFn {
 	}
 }
 
+// SkipEmpty skips empty files.
+func SkipEmpty() FilterFn {
+	return func(path string, info os.FileInfo) (bool, error) {
+		return info.Size() == 0, nil
+	}
+}
+
 // SkipNotYAML skips files that do not have YAML extension.
 func SkipNotYAML() FilterFn {
 	return func(path string, info os.FileInfo) (bool, error) {
@@ -94,24 +110,29 @@ func NewFsReadCloser(fs afero.Fs, dir string, fns ...FilterFn) (*FsReadCloser, e
 		index:      0,
 		position:   0,
 		writeBreak: false,
+		wroteBreak: false,
 	}, err
 }
 
 func (r *FsReadCloser) Read(p []byte) (n int, err error) {
+	if r.wroteBreak {
+		r.index++
+		r.position = 0
+		r.wroteBreak = false
+	}
 	if r.index == len(r.paths) {
 		return 0, io.EOF
 	}
 	if r.writeBreak {
 		n = copy(p, "\n---\n")
 		r.writeBreak = false
+		r.wroteBreak = true
 		return n, nil
 	}
 	b, err := afero.ReadFile(r.fs, r.paths[r.index])
 	n = copy(p, b[r.position:])
 	r.position += n
 	if err == io.EOF || n == 0 {
-		r.position = 0
-		r.index++
 		r.writeBreak = true
 		err = nil
 	}
@@ -122,3 +143,17 @@ func (r *FsReadCloser) Read(p []byte) (n int, err error) {
 func (r *FsReadCloser) Close() error {
 	return nil
 }
+
+// Annotate returns additional about the data currently being read.
+func (r *FsReadCloser) Annotate() interface{} {
+	// Index will be out of bounds if we error after the final file has been
+	// read.
+	index := r.index
+	if index == len(r.paths) {
+		index--
+	}
+	return FsReadCloserAnnotation{
+		path:     r.paths[index],
+		position: r.position,
+	}
+}
diff --git a/pkg/parser/parser.go b/pkg/parser/parser.go
index ea9b36097..13a3ea2ec 100644
--- a/pkg/parser/parser.go
+++ b/pkg/parser/parser.go
@@ -19,10 +19,12 @@ package parser
 import (
 	"bufio"
 	"context"
+	"fmt"
 	"io"
 	"io/ioutil"
 	"strings"
 
+	"github.com/pkg/errors"
 	"github.com/spf13/afero"
 	corev1 "k8s.io/api/core/v1"
 	"k8s.io/apimachinery/pkg/runtime"
@@ -31,6 +33,13 @@ import (
 	"k8s.io/client-go/kubernetes"
 )
 
+// AnnotatedReadCloser is a wrapper around io.ReadCloser that allows
+// implementations to supply additional information about data that is read.
+type AnnotatedReadCloser interface {
+	io.ReadCloser
+	Annotate() interface{}
+}
+
 // ObjectCreaterTyper know how to create and determine the type of objects.
 type ObjectCreaterTyper interface {
 	runtime.ObjectCreater
@@ -105,6 +114,9 @@ func (p *PackageParser) Parse(ctx context.Context, reader io.ReadCloser) (*Packa
 		if err != nil {
 			o, _, err := do.Decode(bytes, nil, nil)
 			if err != nil {
+				if anno, ok := reader.(AnnotatedReadCloser); ok {
+					return pkg, errors.Wrap(err, fmt.Sprintf("%+v", anno.Annotate()))
+				}
 				return pkg, err
 			}
 			pkg.objects = append(pkg.objects, o)
diff --git a/pkg/parser/parser_test.go b/pkg/parser/parser_test.go
index 50bc363b2..dc97c0cbf 100644
--- a/pkg/parser/parser_test.go
+++ b/pkg/parser/parser_test.go
@@ -131,7 +131,7 @@ func TestParser(t *testing.T) {
 		"FsBackendSkip": {
 			reason:  "should skip empty files and files without yaml extension",
 			parser:  New(metaScheme, objScheme),
-			backend: NewFsBackend(emptyFs, FsDir("."), FsFilters(SkipDirs(), SkipNotYAML())),
+			backend: NewFsBackend(emptyFs, FsDir("."), FsFilters(SkipDirs(), SkipEmpty(), SkipNotYAML())),
 			pkg:     NewPackage(),
 		},
 	}