diff --git a/pkg/loader/fileloader.go b/pkg/loader/fileloader.go
index 9ed39af49..038d8599b 100644
--- a/pkg/loader/fileloader.go
+++ b/pkg/loader/fileloader.go
@@ -190,8 +190,9 @@ func newGitLoader(
 // seenBefore tests whether the current or any previously
 // visited root begins with the given path.
 func (l *fileLoader) seenBefore(path string) error {
+	terminated := path + string(filepath.Separator)
 	for _, r := range l.roots {
-		if strings.HasPrefix(r, path) {
+		if r == path || strings.HasPrefix(r, terminated) {
 			return fmt.Errorf(
 				"cycle detected: new root '%s' contains previous root '%s'",
 				path, r)
diff --git a/pkg/target/kusttarget.go b/pkg/target/kusttarget.go
index 6c2caf552..75066d974 100644
--- a/pkg/target/kusttarget.go
+++ b/pkg/target/kusttarget.go
@@ -243,7 +243,7 @@ func (kt *KustTarget) loadCustomizedBases() (resmap.ResMap, *interror.Kustomizat
 	for _, path := range kt.kustomization.Bases {
 		ldr, err := kt.ldr.New(path)
 		if err != nil {
-			errs.Append(errors.Wrap(err, "couldn't make ldr for "+path))
+			errs.Append(errors.Wrap(err, "couldn't make loader for "+path))
 			continue
 		}
 		target, err := NewKustTarget(
diff --git a/pkg/target/kusttarget_test.go b/pkg/target/kusttarget_test.go
index 8a916a1fe..9db44abc4 100644
--- a/pkg/target/kusttarget_test.go
+++ b/pkg/target/kusttarget_test.go
@@ -18,6 +18,7 @@ package target
 
 import (
 	"encoding/base64"
+	"path/filepath"
 	"reflect"
 	"strings"
 	"testing"
@@ -298,3 +299,40 @@ func TestDisableNameSuffixHash(t *testing.T) {
 		t.Errorf("unexpected secret resource name: %s", secret.GetName())
 	}
 }
+
+func write(t *testing.T, ldr loadertest.FakeLoader, dir string, content string) {
+	err := ldr.AddFile(
+		filepath.Join(dir, constants.KustomizationFileName),
+		[]byte(`
+apiVersion: v1
+kind: Kustomization
+`+content))
+	if err != nil {
+		t.Fatalf("Failed to setup fake loader.")
+	}
+}
+
+func TestIssue596AllowDirectoriesThatAreSubstringsOfEachOther(t *testing.T) {
+	ldr := loadertest.NewFakeLoader(
+		"/app/overlays/aws-sandbox2.us-east-1")
+	write(t, ldr, "/app/base", "")
+	write(t, ldr, "/app/overlays/aws", `
+bases:
+- ../../base
+`)
+	write(t, ldr, "/app/overlays/aws-nonprod", `
+bases:
+- ../aws
+`)
+	write(t, ldr, "/app/overlays/aws-sandbox2.us-east-1", `
+bases:
+- ../aws-nonprod
+`)
+	m, err := makeKustTarget(t, ldr).MakeCustomizedResMap()
+	if err != nil {
+		t.Fatalf("Err: %v", err)
+	}
+	if m == nil {
+		t.Fatalf("Empty map.")
+	}
+}