diff --git a/Makefile b/Makefile
index dc40d45f2..9767d86d1 100644
--- a/Makefile
+++ b/Makefile
@@ -6,7 +6,7 @@ test-all: lint test
 
 .PHONY: test
 test:
-	go test -race ./...
+	go test -race -count=1 ./...
 
 .PHONY: lint
 lint:
diff --git a/file/readfile.go b/file/readfile.go
index 93054c8e3..d72b0742e 100644
--- a/file/readfile.go
+++ b/file/readfile.go
@@ -20,44 +20,48 @@ import (
 // file, depending on the type of each item in filenames, merges the content of
 // these files and renders a Content.
 func getContent(filenames []string) (*Content, error) {
-	var allReaders []io.Reader
 	var workspaces []string
+	var res Content
+	var errs []error
 	for _, fileOrDir := range filenames {
 		readers, err := getReaders(fileOrDir)
 		if err != nil {
 			return nil, err
 		}
-		allReaders = append(allReaders, readers...)
-	}
-	var res Content
-	for _, r := range allReaders {
-		content, err := readContent(r)
-		if err != nil {
-			return nil, fmt.Errorf("reading file: %w", err)
-		}
-		if content.Workspace != "" {
-			workspaces = append(workspaces, content.Workspace)
-		}
-		err = mergo.Merge(&res, content, mergo.WithAppendSlice)
-		if err != nil {
-			return nil, fmt.Errorf("merging file contents: %w", err)
+
+		for filename, r := range readers {
+			content, err := readContent(r)
+			if err != nil {
+				errs = append(errs, fmt.Errorf("reading file %s: %w", filename, err))
+				continue
+			}
+			if content.Workspace != "" {
+				workspaces = append(workspaces, content.Workspace)
+			}
+			err = mergo.Merge(&res, content, mergo.WithAppendSlice)
+			if err != nil {
+				return nil, fmt.Errorf("merging file contents: %w", err)
+			}
 		}
 	}
+	if len(errs) > 0 {
+		return nil, utils.ErrArray{Errors: errs}
+	}
 	if err := validateWorkspaces(workspaces); err != nil {
 		return nil, err
 	}
 	return &res, nil
 }
 
-// getReaders returns back io.Readers representing all the YAML and JSON
-// files in a directory. If fileOrDir is a single file, then it
+// getReaders returns back a map of filename:io.Reader representing all the
+// YAML and JSON files in a directory. If fileOrDir is a single file, then it
 // returns back the reader for the file.
 // If fileOrDir is equal to "-" string, then it returns back a io.Reader
 // for the os.Stdin file descriptor.
-func getReaders(fileOrDir string) ([]io.Reader, error) {
+func getReaders(fileOrDir string) (map[string]io.Reader, error) {
 	// special case where `-` means stdin
 	if fileOrDir == "-" {
-		return []io.Reader{os.Stdin}, nil
+		return map[string]io.Reader{"STDIN": os.Stdin}, nil
 	}
 
 	finfo, err := os.Stat(fileOrDir)
@@ -75,13 +79,13 @@ func getReaders(fileOrDir string) ([]io.Reader, error) {
 		files = append(files, fileOrDir)
 	}
 
-	var res []io.Reader
+	res := make(map[string]io.Reader, len(files))
 	for _, file := range files {
 		f, err := os.Open(file)
 		if err != nil {
 			return nil, fmt.Errorf("opening file: %w", err)
 		}
-		res = append(res, bufio.NewReader(f))
+		res[file] = bufio.NewReader(f)
 	}
 	return res, nil
 }
diff --git a/file/readfile_test.go b/file/readfile_test.go
index df2a49285..eb5e65e10 100644
--- a/file/readfile_test.go
+++ b/file/readfile_test.go
@@ -6,9 +6,10 @@ import (
 	"reflect"
 	"testing"
 
+	"github.com/google/go-cmp/cmp"
+	"github.com/google/go-cmp/cmp/cmpopts"
 	"github.com/kong/deck/utils"
 	"github.com/kong/go-kong/kong"
-	"github.com/stretchr/testify/require"
 )
 
 func Test_configFilesInDir(t *testing.T) {
@@ -66,15 +67,17 @@ func Test_getReaders(t *testing.T) {
 	tests := []struct {
 		name string
 		args args
-		want []io.Reader
+		want map[string]io.Reader
 		// length of returned array
 		wantLen int
 		wantErr bool
 	}{
 		{
-			name:    "read from standard input",
-			args:    args{"-"},
-			want:    []io.Reader{os.Stdin},
+			name: "read from standard input",
+			args: args{"-"},
+			want: map[string]io.Reader{
+				"STDIN": os.Stdin,
+			},
 			wantLen: 1,
 			wantErr: false,
 		},
@@ -126,6 +129,29 @@ func Test_getReaders(t *testing.T) {
 	}
 }
 
+func sortSlices(x, y interface{}) bool {
+	var xName, yName string
+	switch xEntity := x.(type) {
+	case FService:
+		yEntity := y.(FService)
+		xName = *xEntity.Name
+		yName = *yEntity.Name
+	case FRoute:
+		yEntity := y.(FRoute)
+		xName = *xEntity.Name
+		yName = *yEntity.Name
+	case FConsumer:
+		yEntity := y.(FConsumer)
+		xName = *xEntity.Username
+		yName = *yEntity.Username
+	case FPlugin:
+		yEntity := y.(FPlugin)
+		xName = *xEntity.Name
+		yName = *yEntity.Name
+	}
+	return xName < yName
+}
+
 func Test_getContent(t *testing.T) {
 	type args struct {
 		filenames []string
@@ -556,7 +582,15 @@ kong.log.set_serialize_value("span_id", parse_traceid(ngx.ctx.KONG_SPANS[1].span
 				t.Errorf("getContent() error = %v, wantErr %v", err, tt.wantErr)
 				return
 			}
-			require.Equal(t, tt.want, got)
+
+			opt := []cmp.Option{
+				cmpopts.SortSlices(sortSlices),
+				cmpopts.SortSlices(func(a, b *string) bool { return *a < *b }),
+				cmpopts.EquateEmpty(),
+			}
+			if diff := cmp.Diff(got, tt.want, opt...); diff != "" {
+				t.Errorf(diff)
+			}
 		})
 	}
 }
diff --git a/file/validate.go b/file/validate.go
index 14076950c..1f3eb977a 100644
--- a/file/validate.go
+++ b/file/validate.go
@@ -1,6 +1,8 @@
 package file
 
 import (
+	"encoding/json"
+	"errors"
 	"fmt"
 
 	"github.com/kong/deck/utils"
@@ -8,6 +10,15 @@ import (
 	"sigs.k8s.io/yaml"
 )
 
+type ValidationError struct {
+	Object string `json:"object"`
+	Err    error  `json:"error"`
+}
+
+func (e *ValidationError) Error() string {
+	return fmt.Sprintf("validation error: object=%s, err=%v", e.Object, e.Err)
+}
+
 func validate(content []byte) error {
 	var c map[string]interface{}
 	err := yaml.Unmarshal(content, &c)
@@ -24,10 +35,14 @@ func validate(content []byte) error {
 	if result.Valid() {
 		return nil
 	}
+
 	var errs utils.ErrArray
 	for _, desc := range result.Errors() {
-		err := fmt.Errorf(desc.String())
-		errs.Errors = append(errs.Errors, err)
+		jsonString, err := json.Marshal(desc.Value())
+		if err != nil {
+			return err
+		}
+		errs.Errors = append(errs.Errors, &ValidationError{Object: string(jsonString), Err: errors.New(desc.String())})
 	}
 	return errs
 }