diff --git a/cmd/root.go b/cmd/root.go
index a99feff..095d700 100644
--- a/cmd/root.go
+++ b/cmd/root.go
@@ -1,3 +1,4 @@
+//go:build !desktop
 // +build !desktop
 
 package cmd
@@ -9,6 +10,7 @@ import (
 	"time"
 
 	"github.com/loophole/cli/config"
+	"github.com/loophole/cli/internal/app/loophole/models"
 	"github.com/loophole/cli/internal/pkg/cache"
 	"github.com/mattn/go-colorable"
 	"github.com/rs/zerolog"
@@ -33,6 +35,10 @@ func init() {
 }
 
 func initLogger() {
+	stdlogWriter := models.LevelWriter{
+		Level:         zerolog.InfoLevel,
+		MessagePrefix: "[sys]",
+	}
 	logLocation := cache.GetLocalStorageFile(fmt.Sprintf("%s.log", time.Now().Format("2006-01-02--15-04-05")), "logs")
 
 	f, err := os.Create(logLocation)
@@ -50,7 +56,7 @@ func initLogger() {
 	}
 
 	stdlog.SetFlags(0)
-	stdlog.SetOutput(log.Logger)
+	stdlog.SetOutput(stdlogWriter)
 }
 
 // Execute runs command parsing chain
diff --git a/internal/app/loophole/loophole.go b/internal/app/loophole/loophole.go
index 332cb6a..7a4321c 100644
--- a/internal/app/loophole/loophole.go
+++ b/internal/app/loophole/loophole.go
@@ -358,7 +358,7 @@ func forward(remoteEndpointSpecs lm.RemoteEndpointSpecs,
 		_, err := netClient.Get(urlmaker.GetSiteURL("https", remoteEndpointSpecs.SiteID, remoteEndpointSpecs.Domain))
 
 		if err != nil {
-			communication.TunnelError(remoteEndpointSpecs.TunnelID, "TLS Certificate failed to provision. Will be obtained with first request made by any client, therefore first execution may be slower")
+			communication.TunnelDebug(remoteEndpointSpecs.TunnelID, "TLS Certificate failed to provision. Will be obtained with first request made by any client, therefore first execution may be slower")
 		} else {
 			communication.TunnelInfo(remoteEndpointSpecs.TunnelID, "TLS Certificate successfully provisioned")
 		}
diff --git a/internal/app/loophole/models/LevelWriter.go b/internal/app/loophole/models/LevelWriter.go
new file mode 100644
index 0000000..a28e99d
--- /dev/null
+++ b/internal/app/loophole/models/LevelWriter.go
@@ -0,0 +1,20 @@
+package models
+
+import (
+	"fmt"
+
+	"github.com/rs/zerolog"
+	"github.com/rs/zerolog/log"
+)
+
+//Implementation of io.Writer which writes to zerolog with a configurable level
+//and identifying prefix to prevent "???" level messages
+type LevelWriter struct {
+	Level         zerolog.Level
+	MessagePrefix string
+}
+
+func (l LevelWriter) Write(p []byte) (n int, err error) {
+	log.WithLevel(l.Level).Msg(fmt.Sprintf("%s %s", l.MessagePrefix, string(p)))
+	return len(p), nil
+}