diff --git a/repo/history.go b/repo/history.go
index 21b7abc..de4eea5 100644
--- a/repo/history.go
+++ b/repo/history.go
@@ -1,13 +1,13 @@
 package repo
 
 import (
-	"fmt"
 	"io/ioutil"
 	"os"
 	"path"
 	"sort"
 	"strings"
 	"time"
+	"github.com/pkg/errors"
 )
 
 const historyRepoJSONPrefix = "contentserver-repo-"
@@ -50,26 +50,42 @@ func (h *history) getHistory() (files []string, err error) {
 			}
 		}
 	}
-	sort.Strings(files)
+	sort.Sort(sort.Reverse(sort.StringSlice(files)))
 	return
 }
 
 func (h *history) cleanup() error {
-	files, err := h.getHistory()
+	files, err := h.getFilesForCleanup(maxHistoryVersions)
 	if err != nil {
 		return err
 	}
-	if len(files) > maxHistoryVersions {
-		for i := maxHistoryVersions; i < len(files); i++ {
-			err := os.Remove(files[i])
-			if err != nil {
-				return fmt.Errorf("could not remove file %q got %q", files[i], err)
-			}
+	for _, f := range files {
+		err := os.Remove(f)
+		if err != nil {
+			return errors.Wrapf(err, "could not remove file %q", f)
 		}
 	}
+
 	return nil
 }
 
+func (h *history) getFilesForCleanup(historyVersions int) (files []string, err error) {
+	contentFiles, err := h.getHistory()
+	if err != nil {
+		return nil, errors.Wrap(err, "could not generate file cleanup list")
+	}
+	if len(contentFiles) > historyVersions {
+		for i := historyVersions; i < len(contentFiles); i++ {
+			// ignore current repository file to fall back on
+			if contentFiles[i] == h.getCurrentFilename() {
+				continue
+			}
+			files = append(files, contentFiles[i])
+		}
+	}
+	return files, nil
+}
+
 func (h *history) getCurrentFilename() string {
 	return path.Join(h.varDir, historyRepoJSONPrefix+"current"+historyRepoJSONSuffix)
 }
diff --git a/repo/history_test.go b/repo/history_test.go
index 77dbe05..756c496 100644
--- a/repo/history_test.go
+++ b/repo/history_test.go
@@ -7,6 +7,7 @@ import (
 	"os"
 	"testing"
 	"time"
+	"github.com/stretchr/testify/assert"
 )
 
 func testHistory() *history {
@@ -45,3 +46,29 @@ func TestHistoryCleanup(t *testing.T) {
 		t.Fatal("history too long", len(files), "instead of", maxHistoryVersions)
 	}
 }
+
+func TestHistoryOrder(t *testing.T) {
+	h := testHistory()
+	h.varDir = "testdata/order"
+
+	files, err := h.getHistory()
+
+	assert.NoError(t, err)
+	assert.Len(t, files, 4)
+	assert.Equal(t, "testdata/order/contentserver-repo-current.json", files[0])
+	assert.Equal(t, "testdata/order/contentserver-repo-2017-10-23.json", files[1])
+	assert.Equal(t, "testdata/order/contentserver-repo-2017-10-22.json", files[2])
+	assert.Equal(t, "testdata/order/contentserver-repo-2017-10-21.json", files[3])
+}
+
+func TestGetFilesForCleanup(t *testing.T) {
+	h := testHistory()
+	h.varDir = "testdata/order"
+
+	files, err := h.getFilesForCleanup(2)
+
+	assert.NoError(t,err)
+	assert.Len(t, files, 2)
+	assert.Equal(t, "testdata/order/contentserver-repo-2017-10-22.json", files[0])
+	assert.Equal(t, "testdata/order/contentserver-repo-2017-10-21.json", files[1])
+}
diff --git a/repo/testdata/order/contentserver-repo-2017-10-21.json b/repo/testdata/order/contentserver-repo-2017-10-21.json
new file mode 100644
index 0000000..e69de29
diff --git a/repo/testdata/order/contentserver-repo-2017-10-22.json b/repo/testdata/order/contentserver-repo-2017-10-22.json
new file mode 100644
index 0000000..e69de29
diff --git a/repo/testdata/order/contentserver-repo-2017-10-23.json b/repo/testdata/order/contentserver-repo-2017-10-23.json
new file mode 100644
index 0000000..e69de29
diff --git a/repo/testdata/order/contentserver-repo-current.json b/repo/testdata/order/contentserver-repo-current.json
new file mode 100644
index 0000000..e69de29