diff --git a/app.go b/app.go
index aad8156b..4922fba8 100644
--- a/app.go
+++ b/app.go
@@ -119,10 +119,9 @@ type DERPConfig struct {
 }
 
 type CLIConfig struct {
-	Address  string
-	APIKey   string
-	Insecure bool
-	Timeout  time.Duration
+	Address string
+	APIKey  string
+	Timeout time.Duration
 }
 
 // Headscale represents the base app of the service.
diff --git a/cmd/headscale/cli/utils.go b/cmd/headscale/cli/utils.go
index 6a95e271..072e3040 100644
--- a/cmd/headscale/cli/utils.go
+++ b/cmd/headscale/cli/utils.go
@@ -59,7 +59,6 @@ func LoadConfig(path string) error {
 
 	viper.SetDefault("grpc_listen_addr", ":50443")
 
-	viper.SetDefault("cli.insecure", false)
 	viper.SetDefault("cli.timeout", "5s")
 
 	if err := viper.ReadInConfig(); err != nil {
@@ -326,10 +325,9 @@ func getHeadscaleConfig() headscale.Config {
 		},
 
 		CLI: headscale.CLIConfig{
-			Address:  viper.GetString("cli.address"),
-			APIKey:   viper.GetString("cli.api_key"),
-			Insecure: viper.GetBool("cli.insecure"),
-			Timeout:  viper.GetDuration("cli.timeout"),
+			Address: viper.GetString("cli.address"),
+			APIKey:  viper.GetString("cli.api_key"),
+			Timeout: viper.GetDuration("cli.timeout"),
 		},
 	}
 }
@@ -413,17 +411,8 @@ func getHeadscaleCLIClient() (context.Context, v1.HeadscaleServiceClient, *grpc.
 			grpc.WithPerRPCCredentials(tokenAuth{
 				token: apiKey,
 			}),
+			grpc.WithTransportCredentials(credentials.NewClientTLSFromCert(nil, "")),
 		)
-
-		if cfg.CLI.Insecure {
-			grpcOptions = append(grpcOptions,
-				grpc.WithTransportCredentials(insecure.NewCredentials()),
-			)
-		} else {
-			grpcOptions = append(grpcOptions,
-				grpc.WithTransportCredentials(credentials.NewClientTLSFromCert(nil, "")),
-			)
-		}
 	}
 
 	log.Trace().Caller().Str("address", address).Msg("Connecting via gRPC")
@@ -500,7 +489,7 @@ func (t tokenAuth) GetRequestMetadata(
 }
 
 func (tokenAuth) RequireTransportSecurity() bool {
-	return false
+	return true
 }
 
 // loadOIDCMatchMap is a wrapper around viper to verifies that the keys in
diff --git a/docs/remote-cli.md b/docs/remote-cli.md
index 1a1dc1de..adcced78 100644
--- a/docs/remote-cli.md
+++ b/docs/remote-cli.md
@@ -88,5 +88,5 @@ Checklist:
 
 - Make sure you have the _same_ `headscale` version on your server and workstation
 - Make sure you use version `0.13.0` or newer.
-- Verify that your TLS certificate is valid
-  - If it is not valid, set the environment variable `HEADSCALE_CLI_INSECURE=true` to allow insecure certs.
+- Verify that your TLS certificate is valid and trusted
+  - If you do not have access to a trusted certificate (e.g. from Let's Encrypt), add your self signed certificate to the trust store of your OS.