diff --git a/cmd/commandfuncs.go b/cmd/commandfuncs.go
index cc5666bb1..77a4cdf4a 100644
--- a/cmd/commandfuncs.go
+++ b/cmd/commandfuncs.go
@@ -208,6 +208,16 @@ func cmdRun(fl Flags) (int, error) {
 		}
 	}
 
+	// create pidfile now, in case loading config takes a while (issue #5477)
+	if runCmdPidfileFlag != "" {
+		err := caddy.PIDFile(runCmdPidfileFlag)
+		if err != nil {
+			caddy.Log().Error("unable to write PID file",
+				zap.String("pidfile", runCmdPidfileFlag),
+				zap.Error(err))
+		}
+	}
+
 	// run the initial config
 	err = caddy.Load(config, true)
 	if err != nil {
@@ -242,16 +252,6 @@ func cmdRun(fl Flags) (int, error) {
 		go watchConfigFile(configFile, runCmdConfigAdapterFlag)
 	}
 
-	// create pidfile
-	if runCmdPidfileFlag != "" {
-		err := caddy.PIDFile(runCmdPidfileFlag)
-		if err != nil {
-			caddy.Log().Error("unable to write PID file",
-				zap.String("pidfile", runCmdPidfileFlag),
-				zap.Error(err))
-		}
-	}
-
 	// warn if the environment does not provide enough information about the disk
 	hasXDG := os.Getenv("XDG_DATA_HOME") != "" &&
 		os.Getenv("XDG_CONFIG_HOME") != "" &&