diff --git a/cmd/headscale/headscale.go b/cmd/headscale/headscale.go
index f9dcaa17..776ffb92 100644
--- a/cmd/headscale/headscale.go
+++ b/cmd/headscale/headscale.go
@@ -1,6 +1,7 @@
 package main
 
 import (
+	"errors"
 	"fmt"
 	"io"
 	"log"
@@ -249,7 +250,7 @@ var createPreAuthKeyCmd = &cobra.Command{
 	},
 }
 
-func loadConfig(path string) {
+func loadConfig(path string) error {
 	viper.SetConfigName("config")
 	if path == "" {
 		viper.AddConfigPath("/etc/headscale/")
@@ -266,28 +267,38 @@ func loadConfig(path string) {
 
 	err := viper.ReadInConfig()
 	if err != nil {
-		log.Fatalf("Fatal error config file: %s \n", err)
+		return errors.New(fmt.Sprintf("Fatal error reading config file: %s \n", err))
 	}
 
+	// Collect any validation errors and return them all at once
+	var errorText string
 	if (viper.GetString("tls_letsencrypt_hostname") != "") && ((viper.GetString("tls_cert_path") != "") || (viper.GetString("tls_key_path") != "")) {
-		log.Fatalf("Fatal config error: set either tls_letsencrypt_hostname or tls_cert_path/tls_key_path, not both")
+		errorText += "Fatal config error: set either tls_letsencrypt_hostname or tls_cert_path/tls_key_path, not both\n"
 	}
 
 	if (viper.GetString("tls_letsencrypt_hostname") != "") && (viper.GetString("tls_letsencrypt_challenge_type") == "TLS-ALPN-01") && (!strings.HasSuffix(viper.GetString("listen_addr"), ":443")) {
-		log.Fatalf("Fatal config error: when using tls_letsencrypt_hostname with TLS-ALPN-01 as challenge type, listen_addr must end in :443")
+		errorText += "Fatal config error: when using tls_letsencrypt_hostname with TLS-ALPN-01 as challenge type, listen_addr must end in :443\n"
 	}
 
 	if (viper.GetString("tls_letsencrypt_challenge_type") != "HTTP-01") && (viper.GetString("tls_letsencrypt_challenge_type") != "TLS-ALPN-01") {
-		log.Fatalf("Fatal config error: the only supported values for tls_letsencrypt_challenge_type are HTTP-01 and TLS-ALPN-01")
+		errorText += "Fatal config error: the only supported values for tls_letsencrypt_challenge_type are HTTP-01 and TLS-ALPN-01\n"
 	}
 
 	if !strings.HasPrefix(viper.GetString("server_url"), "http://") && !strings.HasPrefix(viper.GetString("server_url"), "https://") {
-		log.Fatalf("Fatal config error: server_url must start with https:// or http://")
+		errorText += "Fatal config error: server_url must start with https:// or http://\n"
+	}
+	if errorText != "" {
+		return errors.New(strings.TrimSuffix(errorText, "\n"))
+	} else {
+		return nil
 	}
 }
 
 func main() {
-	loadConfig("")
+	err := loadConfig("")
+	if err != nil {
+		log.Fatalf(err.Error())
+	}
 
 	headscaleCmd.AddCommand(versionCmd)
 	headscaleCmd.AddCommand(serveCmd)
diff --git a/cmd/headscale/headscale_test.go b/cmd/headscale/headscale_test.go
index c1fa3c07..a3894f62 100644
--- a/cmd/headscale/headscale_test.go
+++ b/cmd/headscale/headscale_test.go
@@ -1,9 +1,11 @@
 package main
 
 import (
+	"fmt"
 	"io/ioutil"
 	"os"
 	"path/filepath"
+	"strings"
 	"testing"
 
 	"github.com/spf13/viper"
@@ -43,8 +45,9 @@ func (*Suite) TestConfigLoading(c *check.C) {
 		c.Fatal(err)
 	}
 
-	// Load config
-	loadConfig(tmpDir)
+	// Load example config, it should load without validation errors
+	err = loadConfig(tmpDir)
+	c.Assert(err, check.IsNil)
 
 	// Test that config file was interpreted correctly
 	c.Assert(viper.GetString("server_url"), check.Equals, "http://192.168.1.12:8000")
@@ -54,3 +57,42 @@ func (*Suite) TestConfigLoading(c *check.C) {
 	c.Assert(viper.GetString("tls_letsencrypt_hostname"), check.Equals, "")
 	c.Assert(viper.GetString("tls_letsencrypt_challenge_type"), check.Equals, "HTTP-01")
 }
+
+func writeConfig(c *check.C, tmpDir string, configYaml []byte) {
+	// Populate a custom config file
+	configFile := filepath.Join(tmpDir, "config.yaml")
+	err := ioutil.WriteFile(configFile, configYaml, 0644)
+	if err != nil {
+		c.Fatalf("Couldn't write file %s", configFile)
+	}
+}
+
+func (*Suite) TestTLSConfigValidation(c *check.C) {
+	tmpDir, err := ioutil.TempDir("", "headscale")
+	if err != nil {
+		c.Fatal(err)
+	}
+	//defer os.RemoveAll(tmpDir)
+	fmt.Println(tmpDir)
+
+	configYaml := []byte("---\ntls_letsencrypt_hostname: \"example.com\"\ntls_letsencrypt_challenge_type: \"\"\ntls_cert_path: \"abc.pem\"")
+	writeConfig(c, tmpDir, configYaml)
+
+	// Check configuration validation errors (1)
+	err = loadConfig(tmpDir)
+	c.Assert(err, check.NotNil)
+	// check.Matches can not handle multiline strings
+	tmp := strings.ReplaceAll(err.Error(), "\n", "***")
+	c.Assert(tmp, check.Matches, ".*Fatal config error: set either tls_letsencrypt_hostname or tls_cert_path/tls_key_path, not both.*")
+	c.Assert(tmp, check.Matches, ".*Fatal config error: the only supported values for tls_letsencrypt_challenge_type are.*")
+	c.Assert(tmp, check.Matches, ".*Fatal config error: server_url must start with https:// or http://.*")
+	fmt.Println(tmp)
+
+	// Check configuration validation errors (2)
+	configYaml = []byte("---\nserver_url: \"http://192.168.1.12:8000\"\ntls_letsencrypt_hostname: \"example.com\"\ntls_letsencrypt_challenge_type: \"TLS-ALPN-01\"")
+	fmt.Printf(string(configYaml))
+	writeConfig(c, tmpDir, configYaml)
+	err = loadConfig(tmpDir)
+	c.Assert(err, check.NotNil)
+	c.Assert(err, check.ErrorMatches, "Fatal config error: when using tls_letsencrypt_hostname with TLS-ALPN-01 as challenge type, listen_addr must end in :443.*")
+}