diff --git a/logging/logging.go b/logging/logging.go
index a49db0b8b..3cf0dad97 100644
--- a/logging/logging.go
+++ b/logging/logging.go
@@ -6,6 +6,7 @@ package logging
 import (
 	"math"
 	"os"
+	"path/filepath"
 	"sync"
 	"time"
 
@@ -29,9 +30,10 @@ var Logger *OCLogger
 // Setup configures our custom logging destinations.
 func Setup(enableDebugOptions bool, enableVerboseLogging bool) {
 	// Create the logging directory if needed
-	if !utils.DoesFileExists(getLogFilePath()) {
-		if err := os.Mkdir(getLogFilePath(), 0700); err != nil {
-			logger.Errorln("unable to create directory", getLogFilePath(), err)
+	loggingDirectory := filepath.Dir(getLogFilePath())
+	if !utils.DoesFileExists(loggingDirectory) {
+		if err := os.Mkdir(loggingDirectory, 0700); err != nil {
+			logger.Errorln("unable to create logs directory", loggingDirectory, err)
 		}
 	}
 
diff --git a/main.go b/main.go
index 1ef788a82..b9dcc5bcb 100644
--- a/main.go
+++ b/main.go
@@ -38,7 +38,6 @@ func main() {
 		config.LogDirectory = *logDirectory
 	}
 
-	configureLogging(*enableDebugOptions, *enableVerboseLogging)
 	log.Infoln(config.GetReleaseString())
 
 	if *backupDirectory != "" {
@@ -52,6 +51,8 @@ func main() {
 		}
 	}
 
+	configureLogging(*enableDebugOptions, *enableVerboseLogging)
+
 	// Allows a user to restore a specific database backup
 	if *restoreDatabaseFile != "" {
 		databaseFile := config.DatabaseFilePath