diff --git a/internal/bootstraptoken/bootstraptoken.go b/internal/bootstraptoken/bootstraptoken.go
index 1dfefbfd..abf4c5d1 100644
--- a/internal/bootstraptoken/bootstraptoken.go
+++ b/internal/bootstraptoken/bootstraptoken.go
@@ -88,11 +88,18 @@ func NewFromString(rawBootstrapToken string) (*BootstrapToken, error) {
 		return nil, fmt.Errorf("%w: failed to decode service account name: %v",
 			ErrInvalidBootstrapTokenFormat, err)
 	}
+	if len(serviceAccountName) == 0 {
+		return nil, fmt.Errorf("%w: empty service account name", ErrInvalidBootstrapTokenFormat)
+	}
+
 	serviceAccountToken, err := encoding.DecodeString(splits[2])
 	if err != nil {
 		return nil, fmt.Errorf("%w: failed to decode service account token: %v",
 			ErrInvalidBootstrapTokenFormat, err)
 	}
+	if len(serviceAccountToken) == 0 {
+		return nil, fmt.Errorf("%w: empty service account token", ErrInvalidBootstrapTokenFormat)
+	}
 
 	// Optionally parse the certificate
 	var certificate *x509.Certificate
@@ -106,11 +113,15 @@ func NewFromString(rawBootstrapToken string) (*BootstrapToken, error) {
 		}
 
 		block, _ := pem.Decode(rawCertificate)
+		if block == nil {
+			return nil, fmt.Errorf("%w: failed to parse certificate: expected a PEM format",
+				ErrInvalidBootstrapTokenFormat)
+		}
 
 		certificate, err = x509.ParseCertificate(block.Bytes)
 		if err != nil {
 			return nil, fmt.Errorf("%w: failed to parse certificate: %v",
-				ErrFailedToCreateBootstrapToken, err)
+				ErrInvalidBootstrapTokenFormat, err)
 		}
 	}
 
diff --git a/internal/bootstraptoken/bootstraptoken_test.go b/internal/bootstraptoken/bootstraptoken_test.go
index 9458e3e4..bdc747b5 100644
--- a/internal/bootstraptoken/bootstraptoken_test.go
+++ b/internal/bootstraptoken/bootstraptoken_test.go
@@ -1,12 +1,14 @@
 package bootstraptoken_test
 
 import (
+	"encoding/base64"
 	"encoding/pem"
+	"testing"
+
 	"github.com/cirruslabs/orchard/internal/bootstraptoken"
 	controllercmd "github.com/cirruslabs/orchard/internal/command/controller"
 	"github.com/google/uuid"
 	"github.com/stretchr/testify/require"
-	"testing"
 )
 
 func TestBootstrapTokenTwoWay(t *testing.T) {
@@ -28,6 +30,7 @@ func TestBootstrapTokenTwoWay(t *testing.T) {
 	require.Equal(t, bootstrapTokenOld.ServiceAccountName(), bootstrapTokenNew.ServiceAccountName())
 	require.Equal(t, bootstrapTokenOld.ServiceAccountToken(), bootstrapTokenNew.ServiceAccountToken())
 	require.Equal(t, bootstrapTokenOld.Certificate(), bootstrapTokenNew.Certificate())
+	require.Equal(t, bootstrapTokenOld.String(), bootstrapTokenNew.String())
 }
 
 func TestBootstrapTokenTwoWayEmptyCertificate(t *testing.T) {
@@ -41,3 +44,49 @@ func TestBootstrapTokenTwoWayEmptyCertificate(t *testing.T) {
 	require.Equal(t, bootstrapTokenOld.ServiceAccountToken(), bootstrapTokenNew.ServiceAccountToken())
 	require.Equal(t, bootstrapTokenOld.Certificate(), bootstrapTokenNew.Certificate())
 }
+
+func TestNewFromStringNonPEMCertificate(t *testing.T) {
+	rawBootstrapToken := "orchard-bootstrap-token-v0." +
+		encodeTokenPart("name") + "." +
+		encodeTokenPart("token") + "." +
+		encodeTokenPart("not pem")
+
+	_, err := bootstraptoken.NewFromString(rawBootstrapToken)
+
+	require.ErrorIs(t, err, bootstraptoken.ErrInvalidBootstrapTokenFormat)
+}
+
+func TestNewFromStringInvalidCertificate(t *testing.T) {
+	block := &pem.Block{
+		Type:  "CERTIFICATE",
+		Bytes: []byte("not der"),
+	}
+	rawBootstrapToken := "orchard-bootstrap-token-v0." +
+		encodeTokenPart("name") + "." +
+		encodeTokenPart("token") + "." +
+		encodeTokenPart(string(pem.EncodeToMemory(block)))
+
+	_, err := bootstraptoken.NewFromString(rawBootstrapToken)
+
+	require.ErrorIs(t, err, bootstraptoken.ErrInvalidBootstrapTokenFormat)
+}
+
+func TestNewFromStringEmptyServiceAccountName(t *testing.T) {
+	rawBootstrapToken := "orchard-bootstrap-token-v0.." + encodeTokenPart("token")
+
+	_, err := bootstraptoken.NewFromString(rawBootstrapToken)
+
+	require.ErrorIs(t, err, bootstraptoken.ErrInvalidBootstrapTokenFormat)
+}
+
+func TestNewFromStringEmptyServiceAccountToken(t *testing.T) {
+	rawBootstrapToken := "orchard-bootstrap-token-v0." + encodeTokenPart("name") + "."
+
+	_, err := bootstraptoken.NewFromString(rawBootstrapToken)
+
+	require.ErrorIs(t, err, bootstraptoken.ErrInvalidBootstrapTokenFormat)
+}
+
+func encodeTokenPart(s string) string {
+	return base64.RawURLEncoding.EncodeToString([]byte(s))
+}