diff --git a/config/setup/errors.go b/config/setup/errors.go
index 58f22dfa5..9221ee92c 100644
--- a/config/setup/errors.go
+++ b/config/setup/errors.go
@@ -11,6 +11,7 @@ import (
 	"github.com/hashicorp/go-syslog"
 	"github.com/mholt/caddy/middleware"
 	"github.com/mholt/caddy/middleware/errors"
+	"gopkg.in/natefinch/lumberjack.v2"
 )
 
 // Errors configures a new gzip middleware instance.
@@ -35,10 +36,15 @@ func Errors(c *Controller) (middleware.Middleware, error) {
 				return err
 			}
 		} else if handler.LogFile != "" {
-			file, err = os.OpenFile(handler.LogFile, os.O_RDWR|os.O_CREATE|os.O_APPEND, 0644)
+			_, err = os.OpenFile(handler.LogFile, os.O_RDWR|os.O_CREATE|os.O_APPEND, 0644)
 			if err != nil {
 				return err
 			}
+			file = &lumberjack.Logger{
+				Filename:   handler.LogFile,
+				MaxSize:    20,
+				MaxBackups: 10,
+			}
 		}
 
 		handler.Log = log.New(file, "", 0)
diff --git a/config/setup/log.go b/config/setup/log.go
index 0c15c3d0f..6bf9f3120 100644
--- a/config/setup/log.go
+++ b/config/setup/log.go
@@ -9,6 +9,7 @@ import (
 	"github.com/mholt/caddy/middleware"
 	caddylog "github.com/mholt/caddy/middleware/log"
 	"github.com/mholt/caddy/server"
+	"gopkg.in/natefinch/lumberjack.v2"
 )
 
 // Log sets up the logging middleware.
@@ -34,10 +35,15 @@ func Log(c *Controller) (middleware.Middleware, error) {
 					return err
 				}
 			} else {
-				file, err = os.OpenFile(rules[i].OutputFile, os.O_RDWR|os.O_CREATE|os.O_APPEND, 0644)
+				_, err = os.OpenFile(rules[i].OutputFile, os.O_RDWR|os.O_CREATE|os.O_APPEND, 0644)
 				if err != nil {
 					return err
 				}
+				file = &lumberjack.Logger{
+					Filename:   rules[i].OutputFile,
+					MaxSize:    20,
+					MaxBackups: 10,
+				}
 			}
 
 			rules[i].Log = log.New(file, "", 0)