diff --git a/Makefile b/Makefile
index 565418a9a..06f7d77c7 100644
--- a/Makefile
+++ b/Makefile
@@ -3,7 +3,7 @@ SHELL := /bin/bash
 GIT_VERSION         ?= v0.1.0
 GIT_MODULE          ?= opendev.org/airship/airshipctl/pkg/version
 
-GO_FLAGS            := -ldflags '-extldflags "-static"' -tags=netgo
+GO_FLAGS            := -ldflags '-extldflags "-static"' -tags=netgo -trimpath
 GO_FLAGS            += -ldflags "-X ${GIT_MODULE}.gitVersion=${GIT_VERSION}"
 
 BINDIR              := bin
diff --git a/pkg/log/log.go b/pkg/log/log.go
index e0322d3cd..0ecda2a24 100644
--- a/pkg/log/log.go
+++ b/pkg/log/log.go
@@ -15,6 +15,7 @@
 package log
 
 import (
+	"fmt"
 	"io"
 	"log"
 	"os"
@@ -28,31 +29,34 @@ var (
 // Init initializes settings related to logging
 func Init(debugFlag bool, out io.Writer) {
 	debug = debugFlag
+	if debug {
+		airshipLog.SetFlags(log.LstdFlags | log.Llongfile)
+	}
 	airshipLog.SetOutput(out)
 }
 
 // Debug is a wrapper for log.Debug
 func Debug(v ...interface{}) {
 	if debug {
-		airshipLog.Print(v...)
+		writeLog(v...)
 	}
 }
 
 // Debugf is a wrapper for log.Debugf
 func Debugf(format string, v ...interface{}) {
 	if debug {
-		airshipLog.Printf(format, v...)
+		writeLog(fmt.Sprintf(format, v...))
 	}
 }
 
 // Print is a wrapper for log.Print
 func Print(v ...interface{}) {
-	airshipLog.Print(v...)
+	writeLog(v...)
 }
 
 // Printf is a wrapper for log.Printf
 func Printf(format string, v ...interface{}) {
-	airshipLog.Printf(format, v...)
+	writeLog(fmt.Sprintf(format, v...))
 }
 
 // Fatal is a wrapper for log.Fatal
@@ -69,3 +73,15 @@ func Fatalf(format string, v ...interface{}) {
 func Writer() io.Writer {
 	return airshipLog.Writer()
 }
+
+func writeLog(v ...interface{}) {
+	if debug {
+		err := airshipLog.Output(3, fmt.Sprint(v...))
+		if err != nil {
+			log.Print(v...)
+			log.Print(err)
+		}
+	} else {
+		airshipLog.Print(v...)
+	}
+}
diff --git a/pkg/log/log_test.go b/pkg/log/log_test.go
index cb134eec9..3bf4d8561 100644
--- a/pkg/log/log_test.go
+++ b/pkg/log/log_test.go
@@ -17,6 +17,7 @@ package log_test
 import (
 	"bytes"
 	"regexp"
+	"strings"
 	"testing"
 
 	"github.com/stretchr/testify/assert"
@@ -73,7 +74,8 @@ func TestLoggingDebug(t *testing.T) {
 
 		expected := "DebugTrue args 5\n"
 		require.Regexp(logFormatRegex, actual)
-		actual = actual[prefixLength:]
+		lastIndex := strings.LastIndex(actual, ":")
+		actual = actual[lastIndex+2:]
 		assert.Equal(expected, actual)
 	})
 
@@ -86,7 +88,8 @@ func TestLoggingDebug(t *testing.T) {
 
 		expected := "DebugfTrue args 5\n"
 		require.Regexp(logFormatRegex, actual)
-		actual = actual[prefixLength:]
+		lastIndex := strings.LastIndex(actual, ":")
+		actual = actual[lastIndex+2:]
 		assert.Equal(expected, actual)
 	})