diff --git a/app.go b/app.go
index 126ed861..0ad33605 100644
--- a/app.go
+++ b/app.go
@@ -120,9 +120,10 @@ type DERPConfig struct {
 }
 
 type CLIConfig struct {
-	Address string
-	APIKey  string
-	Timeout time.Duration
+	Address  string
+	APIKey   string
+	Timeout  time.Duration
+	Insecure bool
 }
 
 // Headscale represents the base app of the service.
diff --git a/cmd/headscale/cli/utils.go b/cmd/headscale/cli/utils.go
index 072e3040..84ff977b 100644
--- a/cmd/headscale/cli/utils.go
+++ b/cmd/headscale/cli/utils.go
@@ -2,6 +2,7 @@ package cli
 
 import (
 	"context"
+	"crypto/tls"
 	"encoding/json"
 	"errors"
 	"fmt"
@@ -60,6 +61,7 @@ func LoadConfig(path string) error {
 	viper.SetDefault("grpc_listen_addr", ":50443")
 
 	viper.SetDefault("cli.timeout", "5s")
+	viper.SetDefault("cli.insecure", false)
 
 	if err := viper.ReadInConfig(); err != nil {
 		return fmt.Errorf("fatal error reading config file: %w", err)
@@ -325,9 +327,10 @@ func getHeadscaleConfig() headscale.Config {
 		},
 
 		CLI: headscale.CLIConfig{
-			Address: viper.GetString("cli.address"),
-			APIKey:  viper.GetString("cli.api_key"),
-			Timeout: viper.GetDuration("cli.timeout"),
+			Address:  viper.GetString("cli.address"),
+			APIKey:   viper.GetString("cli.api_key"),
+			Timeout:  viper.GetDuration("cli.timeout"),
+			Insecure: viper.GetBool("cli.insecure"),
 		},
 	}
 }
@@ -411,8 +414,22 @@ func getHeadscaleCLIClient() (context.Context, v1.HeadscaleServiceClient, *grpc.
 			grpc.WithPerRPCCredentials(tokenAuth{
 				token: apiKey,
 			}),
-			grpc.WithTransportCredentials(credentials.NewClientTLSFromCert(nil, "")),
 		)
+
+		if cfg.CLI.Insecure {
+			tlsConfig := &tls.Config{
+				InsecureSkipVerify: true,
+			}
+
+			grpcOptions = append(grpcOptions,
+				grpc.WithTransportCredentials(credentials.NewTLS(tlsConfig)),
+			)
+
+		} else {
+			grpcOptions = append(grpcOptions,
+				grpc.WithTransportCredentials(credentials.NewClientTLSFromCert(nil, "")),
+			)
+		}
 	}
 
 	log.Trace().Caller().Str("address", address).Msg("Connecting via gRPC")
diff --git a/docs/remote-cli.md b/docs/remote-cli.md
index 5ff2f4a0..5ba27ee0 100644
--- a/docs/remote-cli.md
+++ b/docs/remote-cli.md
@@ -5,7 +5,7 @@
 - A workstation to run `headscale` (could be Linux, macOS, other supported platforms)
 - A `headscale` server (version `0.13.0` or newer)
 - Access to create API keys (local access to the `headscale` server)
-- `headscale` _must_ be served over TLS/HTTPS with a _trusted_ certificate
+- `headscale` _must_ be served over TLS/HTTPS
   - Remote access does _not_ support unencrypted traffic.
 - Port `50443` must be open in the firewall (or port overriden by `grpc_listen_addr` option)
 
@@ -89,4 +89,5 @@ 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 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.
+  - 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 or
+  - Set `HEADSCALE_CLI_INSECURE` to 0 in your environement