Add ability to encrypt CA private key at rest (#386)

Fixes #8.

`nebula-cert ca` now supports encrypting the CA's private key with a
passphrase. Pass `-encrypt` in order to be prompted for a passphrase.
Encryption is performed using AES-256-GCM and Argon2id for KDF. KDF
parameters default to RFC recommendations, but can be overridden via CLI
flags `-argon-memory`, `-argon-parallelism`, and `-argon-iterations`.

CHANGELOG.md

@@ -7,6 +7,13 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ## [Unreleased]
 
+### Added
+- `nebula-cert ca` now supports encrypting the CA's private key with a
+  passphrase. Pass `-encrypt` in order to be prompted for a passphrase.
+  Encryption is performed using AES-256-GCM and Argon2id for KDF. KDF
+  parameters default to RFC recommendations, but can be overridden via CLI
+  flags `-argon-memory`, `-argon-parallelism`, and `-argon-iterations`.
+
 ## [1.6.1] - 2022-09-26
 
 ### Fixed

cert/cert.go

@@ -9,7 +9,9 @@ import (
 	"encoding/hex"
 	"encoding/json"
 	"encoding/pem"
+	"errors"
 	"fmt"
+	"math"
 	"net"
 	"time"
 
@@ -21,11 +23,12 @@ import (
 const publicKeyLen = 32
 
 const (
-	CertBanner              = "NEBULA CERTIFICATE"
+	CertBanner                       = "NEBULA CERTIFICATE"
-	X25519PrivateKeyBanner  = "NEBULA X25519 PRIVATE KEY"
+	X25519PrivateKeyBanner           = "NEBULA X25519 PRIVATE KEY"
-	X25519PublicKeyBanner   = "NEBULA X25519 PUBLIC KEY"
+	X25519PublicKeyBanner            = "NEBULA X25519 PUBLIC KEY"
-	Ed25519PrivateKeyBanner = "NEBULA ED25519 PRIVATE KEY"
+	EncryptedEd25519PrivateKeyBanner = "NEBULA ED25519 ENCRYPTED PRIVATE KEY"
-	Ed25519PublicKeyBanner  = "NEBULA ED25519 PUBLIC KEY"
+	Ed25519PrivateKeyBanner          = "NEBULA ED25519 PRIVATE KEY"
+	Ed25519PublicKeyBanner           = "NEBULA ED25519 PUBLIC KEY"
 )
 
 type NebulaCertificate struct {
@@ -48,8 +51,21 @@ type NebulaCertificateDetails struct {
 	InvertedGroups map[string]struct{}
 }
 
+type NebulaEncryptedData struct {
+	EncryptionMetadata NebulaEncryptionMetadata
+	Ciphertext         []byte
+}
+
+type NebulaEncryptionMetadata struct {
+	EncryptionAlgorithm string
+	Argon2Parameters    Argon2Parameters
+}
+
 type m map[string]interface{}
 
+// Returned if we try to unmarshal an encrypted private key without a passphrase
+var ErrPrivateKeyEncrypted = errors.New("private key must be decrypted")
+
 // UnmarshalNebulaCertificate will unmarshal a protobuf byte representation of a nebula cert
 func UnmarshalNebulaCertificate(b []byte) (*NebulaCertificate, error) {
 	if len(b) == 0 {
@@ -144,6 +160,30 @@ func MarshalEd25519PrivateKey(key ed25519.PrivateKey) []byte {
 	return pem.EncodeToMemory(&pem.Block{Type: Ed25519PrivateKeyBanner, Bytes: key})
 }
 
+// EncryptAndMarshalX25519PrivateKey is a simple helper to encrypt and PEM encode an X25519 private key
+func EncryptAndMarshalEd25519PrivateKey(b []byte, passphrase []byte, kdfParams *Argon2Parameters) ([]byte, error) {
+	ciphertext, err := aes256Encrypt(passphrase, kdfParams, b)
+	if err != nil {
+		return nil, err
+	}
+
+	b, err = proto.Marshal(&RawNebulaEncryptedData{
+		EncryptionMetadata: &RawNebulaEncryptionMetadata{
+			EncryptionAlgorithm: "AES-256-GCM",
+			Argon2Parameters: &RawNebulaArgon2Parameters{
+				Version:     kdfParams.version,
+				Memory:      kdfParams.Memory,
+				Parallelism: uint32(kdfParams.Parallelism),
+				Iterations:  kdfParams.Iterations,
+				Salt:        kdfParams.salt,
+			},
+		},
+		Ciphertext: ciphertext,
+	})
+
+	return pem.EncodeToMemory(&pem.Block{Type: EncryptedEd25519PrivateKeyBanner, Bytes: b}), nil
+}
+
 // UnmarshalX25519PrivateKey will try to pem decode an X25519 private key, returning any other bytes b
 // or an error on failure
 func UnmarshalX25519PrivateKey(b []byte) ([]byte, []byte, error) {
@@ -168,9 +208,13 @@ func UnmarshalEd25519PrivateKey(b []byte) (ed25519.PrivateKey, []byte, error) {
 	if k == nil {
 		return nil, r, fmt.Errorf("input did not contain a valid PEM encoded block")
 	}
-	if k.Type != Ed25519PrivateKeyBanner {
+
+	if k.Type == EncryptedEd25519PrivateKeyBanner {
+		return nil, r, ErrPrivateKeyEncrypted
+	} else if k.Type != Ed25519PrivateKeyBanner {
 		return nil, r, fmt.Errorf("bytes did not contain a proper nebula Ed25519 private key banner")
 	}
+
 	if len(k.Bytes) != ed25519.PrivateKeySize {
 		return nil, r, fmt.Errorf("key was not 64 bytes, is invalid ed25519 private key")
 	}
@@ -178,6 +222,101 @@ func UnmarshalEd25519PrivateKey(b []byte) (ed25519.PrivateKey, []byte, error) {
 	return k.Bytes, r, nil
 }
 
+// UnmarshalNebulaCertificate will unmarshal a protobuf byte representation of a nebula cert into its
+// protobuf-generated struct.
+func UnmarshalNebulaEncryptedData(b []byte) (*NebulaEncryptedData, error) {
+	if len(b) == 0 {
+		return nil, fmt.Errorf("nil byte array")
+	}
+	var rned RawNebulaEncryptedData
+	err := proto.Unmarshal(b, &rned)
+	if err != nil {
+		return nil, err
+	}
+
+	if rned.EncryptionMetadata == nil {
+		return nil, fmt.Errorf("encoded EncryptionMetadata was nil")
+	}
+
+	if rned.EncryptionMetadata.Argon2Parameters == nil {
+		return nil, fmt.Errorf("encoded Argon2Parameters was nil")
+	}
+
+	params, err := unmarshalArgon2Parameters(rned.EncryptionMetadata.Argon2Parameters)
+	if err != nil {
+		return nil, err
+	}
+
+	ned := NebulaEncryptedData{
+		EncryptionMetadata: NebulaEncryptionMetadata{
+			EncryptionAlgorithm: rned.EncryptionMetadata.EncryptionAlgorithm,
+			Argon2Parameters:    *params,
+		},
+		Ciphertext: rned.Ciphertext,
+	}
+
+	return &ned, nil
+}
+
+func unmarshalArgon2Parameters(params *RawNebulaArgon2Parameters) (*Argon2Parameters, error) {
+	if params.Version < math.MinInt32 || params.Version > math.MaxInt32 {
+		return nil, fmt.Errorf("Argon2Parameters Version must be at least %d and no more than %d", math.MinInt32, math.MaxInt32)
+	}
+	if params.Memory <= 0 || params.Memory > math.MaxUint32 {
+		return nil, fmt.Errorf("Argon2Parameters Memory must be be greater than 0 and no more than %d KiB", uint32(math.MaxUint32))
+	}
+	if params.Parallelism <= 0 || params.Parallelism > math.MaxUint8 {
+		return nil, fmt.Errorf("Argon2Parameters Parallelism must be be greater than 0 and no more than %d", math.MaxUint8)
+	}
+	if params.Iterations <= 0 || params.Iterations > math.MaxUint32 {
+		return nil, fmt.Errorf("-argon-iterations must be be greater than 0 and no more than %d", uint32(math.MaxUint32))
+	}
+
+	return &Argon2Parameters{
+		version:     rune(params.Version),
+		Memory:      uint32(params.Memory),
+		Parallelism: uint8(params.Parallelism),
+		Iterations:  uint32(params.Iterations),
+		salt:        params.Salt,
+	}, nil
+
+}
+
+// DecryptAndUnmarshalEd25519PrivateKey will try to pem decode and decrypt an Ed25519 private key with
+// the given passphrase, returning any other bytes b or an error on failure
+func DecryptAndUnmarshalEd25519PrivateKey(passphrase, b []byte) (ed25519.PrivateKey, []byte, error) {
+	k, r := pem.Decode(b)
+	if k == nil {
+		return nil, r, fmt.Errorf("input did not contain a valid PEM encoded block")
+	}
+
+	if k.Type != EncryptedEd25519PrivateKeyBanner {
+		return nil, r, fmt.Errorf("bytes did not contain a proper nebula encrypted Ed25519 private key banner")
+	}
+
+	ned, err := UnmarshalNebulaEncryptedData(k.Bytes)
+	if err != nil {
+		return nil, r, err
+	}
+
+	var bytes []byte
+	switch ned.EncryptionMetadata.EncryptionAlgorithm {
+	case "AES-256-GCM":
+		bytes, err = aes256Decrypt(passphrase, &ned.EncryptionMetadata.Argon2Parameters, ned.Ciphertext)
+		if err != nil {
+			return nil, r, err
+		}
+	default:
+		return nil, r, fmt.Errorf("unsupported encryption algorithm: %s", ned.EncryptionMetadata.EncryptionAlgorithm)
+	}
+
+	if len(bytes) != ed25519.PrivateKeySize {
+		return nil, r, fmt.Errorf("key was not 64 bytes, is invalid ed25519 private key")
+	}
+
+	return bytes, r, nil
+}
+
 // MarshalX25519PublicKey is a simple helper to PEM encode an X25519 public key
 func MarshalX25519PublicKey(b []byte) []byte {
 	return pem.EncodeToMemory(&pem.Block{Type: X25519PublicKeyBanner, Bytes: b})

cert/cert.pb.go

@@ -1,7 +1,7 @@
 // Code generated by protoc-gen-go. DO NOT EDIT.
 // versions:
 // 	protoc-gen-go v1.28.0
-// 	protoc        v3.20.0
+// 	protoc        v3.19.4
 // source: cert.proto
 
 package cert
@@ -188,6 +188,195 @@ func (x *RawNebulaCertificateDetails) GetIssuer() []byte {
 	return nil
 }
 
+type RawNebulaEncryptedData struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+
+	EncryptionMetadata *RawNebulaEncryptionMetadata `protobuf:"bytes,1,opt,name=EncryptionMetadata,proto3" json:"EncryptionMetadata,omitempty"`
+	Ciphertext         []byte                       `protobuf:"bytes,2,opt,name=Ciphertext,proto3" json:"Ciphertext,omitempty"`
+}
+
+func (x *RawNebulaEncryptedData) Reset() {
+	*x = RawNebulaEncryptedData{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_cert_proto_msgTypes[2]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *RawNebulaEncryptedData) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*RawNebulaEncryptedData) ProtoMessage() {}
+
+func (x *RawNebulaEncryptedData) ProtoReflect() protoreflect.Message {
+	mi := &file_cert_proto_msgTypes[2]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use RawNebulaEncryptedData.ProtoReflect.Descriptor instead.
+func (*RawNebulaEncryptedData) Descriptor() ([]byte, []int) {
+	return file_cert_proto_rawDescGZIP(), []int{2}
+}
+
+func (x *RawNebulaEncryptedData) GetEncryptionMetadata() *RawNebulaEncryptionMetadata {
+	if x != nil {
+		return x.EncryptionMetadata
+	}
+	return nil
+}
+
+func (x *RawNebulaEncryptedData) GetCiphertext() []byte {
+	if x != nil {
+		return x.Ciphertext
+	}
+	return nil
+}
+
+type RawNebulaEncryptionMetadata struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+
+	EncryptionAlgorithm string                     `protobuf:"bytes,1,opt,name=EncryptionAlgorithm,proto3" json:"EncryptionAlgorithm,omitempty"`
+	Argon2Parameters    *RawNebulaArgon2Parameters `protobuf:"bytes,2,opt,name=Argon2Parameters,proto3" json:"Argon2Parameters,omitempty"`
+}
+
+func (x *RawNebulaEncryptionMetadata) Reset() {
+	*x = RawNebulaEncryptionMetadata{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_cert_proto_msgTypes[3]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *RawNebulaEncryptionMetadata) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*RawNebulaEncryptionMetadata) ProtoMessage() {}
+
+func (x *RawNebulaEncryptionMetadata) ProtoReflect() protoreflect.Message {
+	mi := &file_cert_proto_msgTypes[3]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use RawNebulaEncryptionMetadata.ProtoReflect.Descriptor instead.
+func (*RawNebulaEncryptionMetadata) Descriptor() ([]byte, []int) {
+	return file_cert_proto_rawDescGZIP(), []int{3}
+}
+
+func (x *RawNebulaEncryptionMetadata) GetEncryptionAlgorithm() string {
+	if x != nil {
+		return x.EncryptionAlgorithm
+	}
+	return ""
+}
+
+func (x *RawNebulaEncryptionMetadata) GetArgon2Parameters() *RawNebulaArgon2Parameters {
+	if x != nil {
+		return x.Argon2Parameters
+	}
+	return nil
+}
+
+type RawNebulaArgon2Parameters struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+
+	Version     int32  `protobuf:"varint,1,opt,name=version,proto3" json:"version,omitempty"` // rune in Go
+	Memory      uint32 `protobuf:"varint,2,opt,name=memory,proto3" json:"memory,omitempty"`
+	Parallelism uint32 `protobuf:"varint,4,opt,name=parallelism,proto3" json:"parallelism,omitempty"` // uint8 in Go
+	Iterations  uint32 `protobuf:"varint,3,opt,name=iterations,proto3" json:"iterations,omitempty"`
+	Salt        []byte `protobuf:"bytes,5,opt,name=salt,proto3" json:"salt,omitempty"`
+}
+
+func (x *RawNebulaArgon2Parameters) Reset() {
+	*x = RawNebulaArgon2Parameters{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_cert_proto_msgTypes[4]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *RawNebulaArgon2Parameters) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*RawNebulaArgon2Parameters) ProtoMessage() {}
+
+func (x *RawNebulaArgon2Parameters) ProtoReflect() protoreflect.Message {
+	mi := &file_cert_proto_msgTypes[4]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use RawNebulaArgon2Parameters.ProtoReflect.Descriptor instead.
+func (*RawNebulaArgon2Parameters) Descriptor() ([]byte, []int) {
+	return file_cert_proto_rawDescGZIP(), []int{4}
+}
+
+func (x *RawNebulaArgon2Parameters) GetVersion() int32 {
+	if x != nil {
+		return x.Version
+	}
+	return 0
+}
+
+func (x *RawNebulaArgon2Parameters) GetMemory() uint32 {
+	if x != nil {
+		return x.Memory
+	}
+	return 0
+}
+
+func (x *RawNebulaArgon2Parameters) GetParallelism() uint32 {
+	if x != nil {
+		return x.Parallelism
+	}
+	return 0
+}
+
+func (x *RawNebulaArgon2Parameters) GetIterations() uint32 {
+	if x != nil {
+		return x.Iterations
+	}
+	return 0
+}
+
+func (x *RawNebulaArgon2Parameters) GetSalt() []byte {
+	if x != nil {
+		return x.Salt
+	}
+	return nil
+}
+
 var File_cert_proto protoreflect.FileDescriptor
 
 var file_cert_proto_rawDesc = []byte{
@@ -215,9 +404,38 @@ var file_cert_proto_rawDesc = []byte{
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+	0x61, 0x2f, 0x63, 0x65, 0x72, 0x74, 0x62, 0x06, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x33,
 }
 
 var (
@@ -232,18 +450,23 @@ func file_cert_proto_rawDescGZIP() []byte {
 	return file_cert_proto_rawDescData
 }
 
-var file_cert_proto_msgTypes = make([]protoimpl.MessageInfo, 2)
+var file_cert_proto_msgTypes = make([]protoimpl.MessageInfo, 5)
 var file_cert_proto_goTypes = []interface{}{
 	(*RawNebulaCertificate)(nil),        // 0: cert.RawNebulaCertificate
 	(*RawNebulaCertificateDetails)(nil), // 1: cert.RawNebulaCertificateDetails
+	(*RawNebulaEncryptedData)(nil),      // 2: cert.RawNebulaEncryptedData
+	(*RawNebulaEncryptionMetadata)(nil), // 3: cert.RawNebulaEncryptionMetadata
+	(*RawNebulaArgon2Parameters)(nil),   // 4: cert.RawNebulaArgon2Parameters
 }
 var file_cert_proto_depIdxs = []int32{
 	1, // 0: cert.RawNebulaCertificate.Details:type_name -> cert.RawNebulaCertificateDetails
-	1, // [1:1] is the sub-list for method output_type
+	3, // 1: cert.RawNebulaEncryptedData.EncryptionMetadata:type_name -> cert.RawNebulaEncryptionMetadata
-	1, // [1:1] is the sub-list for method input_type
+	4, // 2: cert.RawNebulaEncryptionMetadata.Argon2Parameters:type_name -> cert.RawNebulaArgon2Parameters
-	1, // [1:1] is the sub-list for extension type_name
+	3, // [3:3] is the sub-list for method output_type
-	1, // [1:1] is the sub-list for extension extendee
+	3, // [3:3] is the sub-list for method input_type
-	0, // [0:1] is the sub-list for field type_name
+	3, // [3:3] is the sub-list for extension type_name
+	3, // [3:3] is the sub-list for extension extendee
+	0, // [0:3] is the sub-list for field type_name
 }
 
 func init() { file_cert_proto_init() }
@@ -276,6 +499,42 @@ func file_cert_proto_init() {
 				return nil
 			}
 		}
+		file_cert_proto_msgTypes[2].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*RawNebulaEncryptedData); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+		file_cert_proto_msgTypes[3].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*RawNebulaEncryptionMetadata); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+		file_cert_proto_msgTypes[4].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*RawNebulaArgon2Parameters); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
 	}
 	type x struct{}
 	out := protoimpl.TypeBuilder{
@@ -283,7 +542,7 @@ func file_cert_proto_init() {
 			GoPackagePath: reflect.TypeOf(x{}).PkgPath(),
 			RawDescriptor: file_cert_proto_rawDesc,
 			NumEnums:      0,
-			NumMessages:   2,
+			NumMessages:   5,
 			NumExtensions: 0,
 			NumServices:   0,
 		},

cert/cert.proto

@@ -26,4 +26,22 @@ message RawNebulaCertificateDetails {
 
     // sha-256 of the issuer certificate, if this field is blank the cert is self-signed
     bytes Issuer = 9;
-}
+}
+
+message RawNebulaEncryptedData {
+	RawNebulaEncryptionMetadata EncryptionMetadata = 1;
+	bytes Ciphertext = 2;
+}
+
+message RawNebulaEncryptionMetadata {
+	string EncryptionAlgorithm = 1;
+	RawNebulaArgon2Parameters Argon2Parameters = 2;
+}
+
+message RawNebulaArgon2Parameters {
+	int32 version = 1; // rune in Go
+	uint32 memory = 2;
+	uint32 parallelism = 4; // uint8 in Go
+	uint32 iterations = 3;
+	bytes salt = 5;
+}

cert/cert_test.go

@@ -578,6 +578,91 @@ AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA
 	assert.EqualError(t, err, "input did not contain a valid PEM encoded block")
 }
 
+func TestDecryptAndUnmarshalEd25519PrivateKey(t *testing.T) {
+	passphrase := []byte("DO NOT USE THIS KEY")
+	privKey := []byte(`# A good key
+-----BEGIN NEBULA ED25519 ENCRYPTED PRIVATE KEY-----
+CjwKC0FFUy0yNTYtR0NNEi0IExCAgIABGAEgBCognnjujd67Vsv99p22wfAjQaDT
+oCMW1mdjkU3gACKNW4MSXOWR9Sts4C81yk1RUku2gvGKs3TB9LYoklLsIizSYOLl
++Vs//O1T0I1Xbml2XBAROsb/VSoDln/6LMqR4B6fn6B3GOsLBBqRI8daDl9lRMPB
+qrlJ69wer3ZUHFXA
+-----END NEBULA ED25519 ENCRYPTED PRIVATE KEY-----
+`)
+	shortKey := []byte(`# A key which, once decrypted, is too short
+-----BEGIN NEBULA ED25519 ENCRYPTED PRIVATE KEY-----
+CjwKC0FFUy0yNTYtR0NNEi0IExCAgIABGAEgBCoga5h8owMEBWRSMMJKzuUvWce7
+k0qlBkQmCxiuLh80MuASW70YcKt8jeEIS2axo2V6zAKA9TSMcCsJW1kDDXEtL/xe
+GLF5T7sDl5COp4LU3pGxpV+KoeQ/S3gQCAAcnaOtnJQX+aSDnbO3jCHyP7U9CHbs
+rQr3bdH3Oy/WiYU=
+-----END NEBULA ED25519 ENCRYPTED PRIVATE KEY-----
+`)
+	invalidBanner := []byte(`# Invalid banner (not encrypted)
+-----BEGIN NEBULA ED25519 PRIVATE KEY-----
+bWRp2CTVFhW9HD/qCd28ltDgK3w8VXSeaEYczDWos8sMUBqDb9jP3+NYwcS4lURG
+XgLvodMXZJuaFPssp+WwtA==
+-----END NEBULA ED25519 PRIVATE KEY-----
+`)
+	invalidPem := []byte(`# Not a valid PEM format
+-BEGIN NEBULA ED25519 ENCRYPTED PRIVATE KEY-----
+CjwKC0FFUy0yNTYtR0NNEi0IExCAgIABGAEgBCognnjujd67Vsv99p22wfAjQaDT
+oCMW1mdjkU3gACKNW4MSXOWR9Sts4C81yk1RUku2gvGKs3TB9LYoklLsIizSYOLl
++Vs//O1T0I1Xbml2XBAROsb/VSoDln/6LMqR4B6fn6B3GOsLBBqRI8daDl9lRMPB
+qrlJ69wer3ZUHFXA
+-END NEBULA ED25519 ENCRYPTED PRIVATE KEY-----
+`)
+
+	keyBundle := appendByteSlices(privKey, shortKey, invalidBanner, invalidPem)
+
+	// Success test case
+	k, rest, err := DecryptAndUnmarshalEd25519PrivateKey(passphrase, keyBundle)
+	assert.Nil(t, err)
+	assert.Len(t, k, 64)
+	assert.Equal(t, rest, appendByteSlices(shortKey, invalidBanner, invalidPem))
+
+	// Fail due to short key
+	k, rest, err = DecryptAndUnmarshalEd25519PrivateKey(passphrase, rest)
+	assert.EqualError(t, err, "key was not 64 bytes, is invalid ed25519 private key")
+	assert.Nil(t, k)
+	assert.Equal(t, rest, appendByteSlices(invalidBanner, invalidPem))
+
+	// Fail due to invalid banner
+	k, rest, err = DecryptAndUnmarshalEd25519PrivateKey(passphrase, rest)
+	assert.EqualError(t, err, "bytes did not contain a proper nebula encrypted Ed25519 private key banner")
+	assert.Nil(t, k)
+	assert.Equal(t, rest, invalidPem)
+
+	// Fail due to ivalid PEM format, because
+	// it's missing the requisite pre-encapsulation boundary.
+	k, rest, err = DecryptAndUnmarshalEd25519PrivateKey(passphrase, rest)
+	assert.EqualError(t, err, "input did not contain a valid PEM encoded block")
+	assert.Nil(t, k)
+	assert.Equal(t, rest, invalidPem)
+
+	// Fail due to invalid passphrase
+	k, rest, err = DecryptAndUnmarshalEd25519PrivateKey([]byte("invalid passphrase"), privKey)
+	assert.EqualError(t, err, "invalid passphrase or corrupt private key")
+	assert.Nil(t, k)
+	assert.Equal(t, rest, []byte{})
+}
+
+func TestEncryptAndMarshalEd25519PrivateKey(t *testing.T) {
+	// Having proved that decryption works correctly above, we can test the
+	// encryption function produces a value which can be decrypted
+	passphrase := []byte("passphrase")
+	bytes := []byte("AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA")
+	kdfParams := NewArgon2Parameters(64*1024, 4, 3)
+	key, err := EncryptAndMarshalEd25519PrivateKey(bytes, passphrase, kdfParams)
+	assert.Nil(t, err)
+
+	// Verify the "key" can be decrypted successfully
+	k, rest, err := DecryptAndUnmarshalEd25519PrivateKey(passphrase, key)
+	assert.Len(t, k, 64)
+	assert.Equal(t, rest, []byte{})
+	assert.Nil(t, err)
+
+	// EncryptAndMarshalEd25519PrivateKey does not create any errors itself
+}
+
 func TestUnmarshalX25519PrivateKey(t *testing.T) {
 	privKey := []byte(`# A good key
 -----BEGIN NEBULA X25519 PRIVATE KEY-----

cert/crypto.go

@@ -0,0 +1,140 @@
+package cert
+
+import (
+	"crypto/aes"
+	"crypto/cipher"
+	"crypto/rand"
+	"fmt"
+	"io"
+
+	"golang.org/x/crypto/argon2"
+)
+
+// KDF factors
+type Argon2Parameters struct {
+	version     rune
+	Memory      uint32 // KiB
+	Parallelism uint8
+	Iterations  uint32
+	salt        []byte
+}
+
+// Returns a new Argon2Parameters object with current version set
+func NewArgon2Parameters(memory uint32, parallelism uint8, iterations uint32) *Argon2Parameters {
+	return &Argon2Parameters{
+		version:     argon2.Version,
+		Memory:      memory, // KiB
+		Parallelism: parallelism,
+		Iterations:  iterations,
+	}
+}
+
+// Encrypts data using AES-256-GCM and the Argon2id key derivation function
+func aes256Encrypt(passphrase []byte, kdfParams *Argon2Parameters, data []byte) ([]byte, error) {
+	key, err := aes256DeriveKey(passphrase, kdfParams)
+	if err != nil {
+		return nil, err
+	}
+
+	// this should never happen, but since this dictates how our calls into the
+	// aes package behave and could be catastraphic, let's sanity check this
+	if len(key) != 32 {
+		return nil, fmt.Errorf("invalid AES-256 key length (%d) - cowardly refusing to encrypt", len(key))
+	}
+
+	block, err := aes.NewCipher(key)
+	if err != nil {
+		return nil, err
+	}
+
+	gcm, err := cipher.NewGCM(block)
+	if err != nil {
+		return nil, err
+	}
+
+	nonce := make([]byte, gcm.NonceSize())
+	if _, err := io.ReadFull(rand.Reader, nonce); err != nil {
+		return nil, err
+	}
+
+	ciphertext := gcm.Seal(nil, nonce, data, nil)
+	blob := joinNonceCiphertext(nonce, ciphertext)
+
+	return blob, nil
+}
+
+// Decrypts data using AES-256-GCM and the Argon2id key derivation function
+// Expects the data to include an Argon2id parameter string before the encrypted data
+func aes256Decrypt(passphrase []byte, kdfParams *Argon2Parameters, data []byte) ([]byte, error) {
+	key, err := aes256DeriveKey(passphrase, kdfParams)
+	if err != nil {
+		return nil, err
+	}
+
+	block, err := aes.NewCipher(key)
+	if err != nil {
+		return nil, err
+	}
+
+	gcm, err := cipher.NewGCM(block)
+
+	nonce, ciphertext, err := splitNonceCiphertext(data, gcm.NonceSize())
+	if err != nil {
+		return nil, err
+	}
+
+	plaintext, err := gcm.Open(nil, nonce, ciphertext, nil)
+	if err != nil {
+		return nil, fmt.Errorf("invalid passphrase or corrupt private key")
+	}
+
+	return plaintext, nil
+}
+
+func aes256DeriveKey(passphrase []byte, params *Argon2Parameters) ([]byte, error) {
+	if params.salt == nil {
+		params.salt = make([]byte, 32)
+		if _, err := rand.Read(params.salt); err != nil {
+			return nil, err
+		}
+	}
+
+	// keySize of 32 bytes will result in AES-256 encryption
+	key, err := deriveKey(passphrase, 32, params)
+	if err != nil {
+		return nil, err
+	}
+
+	return key, nil
+}
+
+// Derives a key from a passphrase using Argon2id
+func deriveKey(passphrase []byte, keySize uint32, params *Argon2Parameters) ([]byte, error) {
+	if params.version != argon2.Version {
+		return nil, fmt.Errorf("incompatible Argon2 version: %d", params.version)
+	}
+
+	if params.salt == nil {
+		return nil, fmt.Errorf("salt must be set in argon2Parameters")
+	} else if len(params.salt) < 16 {
+		return nil, fmt.Errorf("salt must be at least 128  bits")
+	}
+
+	key := argon2.IDKey(passphrase, params.salt, params.Iterations, params.Memory, params.Parallelism, keySize)
+
+	return key, nil
+}
+
+// Prepends nonce to ciphertext
+func joinNonceCiphertext(nonce []byte, ciphertext []byte) []byte {
+	return append(nonce, ciphertext...)
+}
+
+// Splits nonce from ciphertext
+func splitNonceCiphertext(blob []byte, nonceSize int) ([]byte, []byte, error) {
+	if len(blob) <= nonceSize {
+		return nil, nil, fmt.Errorf("invalid ciphertext blob - blob shorter than nonce length")
+	}
+
+	return blob[:nonceSize], blob[nonceSize:], nil
+}

cert/crypto_test.go

@@ -0,0 +1,25 @@
+package cert
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"golang.org/x/crypto/argon2"
+)
+
+func TestNewArgon2Parameters(t *testing.T) {
+	p := NewArgon2Parameters(64*1024, 4, 3)
+	assert.EqualValues(t, &Argon2Parameters{
+		version:     argon2.Version,
+		Memory:      64 * 1024,
+		Parallelism: 4,
+		Iterations:  3,
+	}, p)
+	p = NewArgon2Parameters(2*1024*1024, 2, 1)
+	assert.EqualValues(t, &Argon2Parameters{
+		version:     argon2.Version,
+		Memory:      2 * 1024 * 1024,
+		Parallelism: 2,
+		Iterations:  1,
+	}, p)
+}

cmd/nebula-cert/ca.go

@@ -6,6 +6,7 @@ import (
 	"fmt"
 	"io"
 	"io/ioutil"
+	"math"
 	"net"
 	"os"
 	"strings"
@@ -17,15 +18,19 @@ import (
 )
 
 type caFlags struct {
-	set         *flag.FlagSet
+	set              *flag.FlagSet
-	name        *string
+	name             *string
-	duration    *time.Duration
+	duration         *time.Duration
-	outKeyPath  *string
+	outKeyPath       *string
-	outCertPath *string
+	outCertPath      *string
-	outQRPath   *string
+	outQRPath        *string
-	groups      *string
+	groups           *string
-	ips         *string
+	ips              *string
-	subnets     *string
+	subnets          *string
+	argonMemory      *uint
+	argonIterations  *uint
+	argonParallelism *uint
+	encryption       *bool
 }
 
 func newCaFlags() *caFlags {
@@ -39,10 +44,28 @@ func newCaFlags() *caFlags {
 	cf.groups = cf.set.String("groups", "", "Optional: comma separated list of groups. This will limit which groups subordinate certs can use")
 	cf.ips = cf.set.String("ips", "", "Optional: comma separated list of ipv4 address and network in CIDR notation. This will limit which ipv4 addresses and networks subordinate certs can use for ip addresses")
 	cf.subnets = cf.set.String("subnets", "", "Optional: comma separated list of ipv4 address and network in CIDR notation. This will limit which ipv4 addresses and networks subordinate certs can use in subnets")
+	cf.argonMemory = cf.set.Uint("argon-memory", 2*1024*1024, "Optional: Argon2 memory parameter (in KiB) used for encrypted private key passphrase")
+	cf.argonParallelism = cf.set.Uint("argon-parallelism", 4, "Optional: Argon2 parallelism parameter used for encrypted private key passphrase")
+	cf.argonIterations = cf.set.Uint("argon-iterations", 1, "Optional: Argon2 iterations parameter used for encrypted private key passphrase")
+	cf.encryption = cf.set.Bool("encrypt", false, "Optional: prompt for passphrase and write out-key in an encrypted format")
 	return &cf
 }
 
-func ca(args []string, out io.Writer, errOut io.Writer) error {
+func parseArgonParameters(memory uint, parallelism uint, iterations uint) (*cert.Argon2Parameters, error) {
+	if memory <= 0 || memory > math.MaxUint32 {
+		return nil, newHelpErrorf("-argon-memory must be be greater than 0 and no more than %d KiB", uint32(math.MaxUint32))
+	}
+	if parallelism <= 0 || parallelism > math.MaxUint8 {
+		return nil, newHelpErrorf("-argon-parallelism must be be greater than 0 and no more than %d", math.MaxUint8)
+	}
+	if iterations <= 0 || iterations > math.MaxUint32 {
+		return nil, newHelpErrorf("-argon-iterations must be be greater than 0 and no more than %d", uint32(math.MaxUint32))
+	}
+
+	return cert.NewArgon2Parameters(uint32(memory), uint8(parallelism), uint32(iterations)), nil
+}
+
+func ca(args []string, out io.Writer, errOut io.Writer, pr PasswordReader) error {
 	cf := newCaFlags()
 	err := cf.set.Parse(args)
 	if err != nil {
@@ -58,6 +81,12 @@ func ca(args []string, out io.Writer, errOut io.Writer) error {
 	if err := mustFlagString("out-crt", cf.outCertPath); err != nil {
 		return err
 	}
+	var kdfParams *cert.Argon2Parameters
+	if *cf.encryption {
+		if kdfParams, err = parseArgonParameters(*cf.argonMemory, *cf.argonParallelism, *cf.argonIterations); err != nil {
+			return err
+		}
+	}
 
 	if *cf.duration <= 0 {
 		return &helpError{"-duration must be greater than 0"}
@@ -109,6 +138,28 @@ func ca(args []string, out io.Writer, errOut io.Writer) error {
 		}
 	}
 
+	var passphrase []byte
+	if *cf.encryption {
+		for i := 0; i < 5; i++ {
+			out.Write([]byte("Enter passphrase: "))
+			passphrase, err = pr.ReadPassword()
+
+			if err == ErrNoTerminal {
+				return fmt.Errorf("out-key must be encrypted interactively")
+			} else if err != nil {
+				return fmt.Errorf("error reading passphrase: %s", err)
+			}
+
+			if len(passphrase) > 0 {
+				break
+			}
+		}
+
+		if len(passphrase) == 0 {
+			return fmt.Errorf("no passphrase specified, remove -encrypt flag to write out-key in plaintext")
+		}
+	}
+
 	pub, rawPriv, err := ed25519.GenerateKey(rand.Reader)
 	if err != nil {
 		return fmt.Errorf("error while generating ed25519 keys: %s", err)
@@ -140,7 +191,17 @@ func ca(args []string, out io.Writer, errOut io.Writer) error {
 		return fmt.Errorf("error while signing: %s", err)
 	}
 
-	err = ioutil.WriteFile(*cf.outKeyPath, cert.MarshalEd25519PrivateKey(rawPriv), 0600)
+	if *cf.encryption {
+		b, err := cert.EncryptAndMarshalEd25519PrivateKey(rawPriv, passphrase, kdfParams)
+		if err != nil {
+			return fmt.Errorf("error while encrypting out-key: %s", err)
+		}
+
+		err = ioutil.WriteFile(*cf.outKeyPath, b, 0600)
+	} else {
+		err = ioutil.WriteFile(*cf.outKeyPath, cert.MarshalEd25519PrivateKey(rawPriv), 0600)
+	}
+
 	if err != nil {
 		return fmt.Errorf("error while writing out-key: %s", err)
 	}

cmd/nebula-cert/ca_test.go

@@ -5,8 +5,11 @@ package main
 
 import (
 	"bytes"
+	"encoding/pem"
+	"errors"
 	"io/ioutil"
 	"os"
+	"strings"
 	"testing"
 	"time"
 
@@ -26,8 +29,16 @@ func Test_caHelp(t *testing.T) {
 	assert.Equal(
 		t,
 		"Usage of "+os.Args[0]+" ca <flags>: create a self signed certificate authority\n"+
+			"  -argon-iterations uint\n"+
+			"    \tOptional: Argon2 iterations parameter used for encrypted private key passphrase (default 1)\n"+
+			"  -argon-memory uint\n"+
+			"    \tOptional: Argon2 memory parameter (in KiB) used for encrypted private key passphrase (default 2097152)\n"+
+			"  -argon-parallelism uint\n"+
+			"    \tOptional: Argon2 parallelism parameter used for encrypted private key passphrase (default 4)\n"+
 			"  -duration duration\n"+
 			"    \tOptional: amount of time the certificate should be valid for. Valid time units are seconds: \"s\", minutes: \"m\", hours: \"h\" (default 8760h0m0s)\n"+
+			"  -encrypt\n"+
+			"    \tOptional: prompt for passphrase and write out-key in an encrypted format\n"+
 			"  -groups string\n"+
 			"    \tOptional: comma separated list of groups. This will limit which groups subordinate certs can use\n"+
 			"  -ips string\n"+
@@ -50,18 +61,38 @@ func Test_ca(t *testing.T) {
 	ob := &bytes.Buffer{}
 	eb := &bytes.Buffer{}
 
+	nopw := &StubPasswordReader{
+		password: []byte(""),
+		err:      nil,
+	}
+
+	errpw := &StubPasswordReader{
+		password: []byte(""),
+		err:      errors.New("stub error"),
+	}
+
+	passphrase := []byte("DO NOT USE THIS KEY")
+	testpw := &StubPasswordReader{
+		password: passphrase,
+		err:      nil,
+	}
+
+	pwPromptOb := "Enter passphrase: "
+
 	// required args
-	assertHelpError(t, ca([]string{"-out-key", "nope", "-out-crt", "nope", "duration", "100m"}, ob, eb), "-name is required")
+	assertHelpError(t, ca(
+		[]string{"-out-key", "nope", "-out-crt", "nope", "duration", "100m"}, ob, eb, nopw,
+	), "-name is required")
 	assert.Equal(t, "", ob.String())
 	assert.Equal(t, "", eb.String())
 
 	// ipv4 only ips
-	assertHelpError(t, ca([]string{"-name", "ipv6", "-ips", "100::100/100"}, ob, eb), "invalid ip definition: can only be ipv4, have 100::100/100")
+	assertHelpError(t, ca([]string{"-name", "ipv6", "-ips", "100::100/100"}, ob, eb, nopw), "invalid ip definition: can only be ipv4, have 100::100/100")
 	assert.Equal(t, "", ob.String())
 	assert.Equal(t, "", eb.String())
 
 	// ipv4 only subnets
-	assertHelpError(t, ca([]string{"-name", "ipv6", "-subnets", "100::100/100"}, ob, eb), "invalid subnet definition: can only be ipv4, have 100::100/100")
+	assertHelpError(t, ca([]string{"-name", "ipv6", "-subnets", "100::100/100"}, ob, eb, nopw), "invalid subnet definition: can only be ipv4, have 100::100/100")
 	assert.Equal(t, "", ob.String())
 	assert.Equal(t, "", eb.String())
 
@@ -69,7 +100,7 @@ func Test_ca(t *testing.T) {
 	ob.Reset()
 	eb.Reset()
 	args := []string{"-name", "test", "-duration", "100m", "-out-crt", "/do/not/write/pleasecrt", "-out-key", "/do/not/write/pleasekey"}
-	assert.EqualError(t, ca(args, ob, eb), "error while writing out-key: open /do/not/write/pleasekey: "+NoSuchDirError)
+	assert.EqualError(t, ca(args, ob, eb, nopw), "error while writing out-key: open /do/not/write/pleasekey: "+NoSuchDirError)
 	assert.Equal(t, "", ob.String())
 	assert.Equal(t, "", eb.String())
 
@@ -82,7 +113,7 @@ func Test_ca(t *testing.T) {
 	ob.Reset()
 	eb.Reset()
 	args = []string{"-name", "test", "-duration", "100m", "-out-crt", "/do/not/write/pleasecrt", "-out-key", keyF.Name()}
-	assert.EqualError(t, ca(args, ob, eb), "error while writing out-crt: open /do/not/write/pleasecrt: "+NoSuchDirError)
+	assert.EqualError(t, ca(args, ob, eb, nopw), "error while writing out-crt: open /do/not/write/pleasecrt: "+NoSuchDirError)
 	assert.Equal(t, "", ob.String())
 	assert.Equal(t, "", eb.String())
 
@@ -96,7 +127,7 @@ func Test_ca(t *testing.T) {
 	ob.Reset()
 	eb.Reset()
 	args = []string{"-name", "test", "-duration", "100m", "-groups", "1,,   2    ,        ,,,3,4,5", "-out-crt", crtF.Name(), "-out-key", keyF.Name()}
-	assert.Nil(t, ca(args, ob, eb))
+	assert.Nil(t, ca(args, ob, eb, nopw))
 	assert.Equal(t, "", ob.String())
 	assert.Equal(t, "", eb.String())
 
@@ -122,19 +153,65 @@ func Test_ca(t *testing.T) {
 	assert.Equal(t, "", lCrt.Details.Issuer)
 	assert.True(t, lCrt.CheckSignature(lCrt.Details.PublicKey))
 
+	// test encrypted key
+	os.Remove(keyF.Name())
+	os.Remove(crtF.Name())
+	ob.Reset()
+	eb.Reset()
+	args = []string{"-encrypt", "-name", "test", "-duration", "100m", "-groups", "1,2,3,4,5", "-out-crt", crtF.Name(), "-out-key", keyF.Name()}
+	assert.Nil(t, ca(args, ob, eb, testpw))
+	assert.Equal(t, pwPromptOb, ob.String())
+	assert.Equal(t, "", eb.String())
+
+	// read encrypted key file and verify default params
+	rb, _ = ioutil.ReadFile(keyF.Name())
+	k, _ := pem.Decode(rb)
+	ned, err := cert.UnmarshalNebulaEncryptedData(k.Bytes)
+	assert.Nil(t, err)
+	// we won't know salt in advance, so just check start of string
+	assert.Equal(t, uint32(2*1024*1024), ned.EncryptionMetadata.Argon2Parameters.Memory)
+	assert.Equal(t, uint8(4), ned.EncryptionMetadata.Argon2Parameters.Parallelism)
+	assert.Equal(t, uint32(1), ned.EncryptionMetadata.Argon2Parameters.Iterations)
+
+	// verify the key is valid and decrypt-able
+	lKey, b, err = cert.DecryptAndUnmarshalEd25519PrivateKey(passphrase, rb)
+	assert.Nil(t, err)
+	assert.Len(t, b, 0)
+	assert.Len(t, lKey, 64)
+
+	// test when reading passsword results in an error
+	os.Remove(keyF.Name())
+	os.Remove(crtF.Name())
+	ob.Reset()
+	eb.Reset()
+	args = []string{"-encrypt", "-name", "test", "-duration", "100m", "-groups", "1,2,3,4,5", "-out-crt", crtF.Name(), "-out-key", keyF.Name()}
+	assert.Error(t, ca(args, ob, eb, errpw))
+	assert.Equal(t, pwPromptOb, ob.String())
+	assert.Equal(t, "", eb.String())
+
+	// test when user fails to enter a password
+	os.Remove(keyF.Name())
+	os.Remove(crtF.Name())
+	ob.Reset()
+	eb.Reset()
+	args = []string{"-encrypt", "-name", "test", "-duration", "100m", "-groups", "1,2,3,4,5", "-out-crt", crtF.Name(), "-out-key", keyF.Name()}
+	assert.EqualError(t, ca(args, ob, eb, nopw), "no passphrase specified, remove -encrypt flag to write out-key in plaintext")
+	assert.Equal(t, strings.Repeat(pwPromptOb, 5), ob.String()) // prompts 5 times before giving up
+	assert.Equal(t, "", eb.String())
+
 	// create valid cert/key for overwrite tests
 	os.Remove(keyF.Name())
 	os.Remove(crtF.Name())
 	ob.Reset()
 	eb.Reset()
 	args = []string{"-name", "test", "-duration", "100m", "-groups", "1,,   2    ,        ,,,3,4,5", "-out-crt", crtF.Name(), "-out-key", keyF.Name()}
-	assert.Nil(t, ca(args, ob, eb))
+	assert.Nil(t, ca(args, ob, eb, nopw))
 
 	// test that we won't overwrite existing certificate file
 	ob.Reset()
 	eb.Reset()
 	args = []string{"-name", "test", "-duration", "100m", "-groups", "1,,   2    ,        ,,,3,4,5", "-out-crt", crtF.Name(), "-out-key", keyF.Name()}
-	assert.EqualError(t, ca(args, ob, eb), "refusing to overwrite existing CA key: "+keyF.Name())
+	assert.EqualError(t, ca(args, ob, eb, nopw), "refusing to overwrite existing CA key: "+keyF.Name())
 	assert.Equal(t, "", ob.String())
 	assert.Equal(t, "", eb.String())
 
@@ -143,7 +220,7 @@ func Test_ca(t *testing.T) {
 	ob.Reset()
 	eb.Reset()
 	args = []string{"-name", "test", "-duration", "100m", "-groups", "1,,   2    ,        ,,,3,4,5", "-out-crt", crtF.Name(), "-out-key", keyF.Name()}
-	assert.EqualError(t, ca(args, ob, eb), "refusing to overwrite existing CA cert: "+crtF.Name())
+	assert.EqualError(t, ca(args, ob, eb, nopw), "refusing to overwrite existing CA cert: "+crtF.Name())
 	assert.Equal(t, "", ob.String())
 	assert.Equal(t, "", eb.String())
 	os.Remove(keyF.Name())

cmd/nebula-cert/main.go

@@ -62,11 +62,11 @@ func main() {
 
 	switch args[0] {
 	case "ca":
-		err = ca(args[1:], os.Stdout, os.Stderr)
+		err = ca(args[1:], os.Stdout, os.Stderr, StdinPasswordReader{})
 	case "keygen":
 		err = keygen(args[1:], os.Stdout, os.Stderr)
 	case "sign":
-		err = signCert(args[1:], os.Stdout, os.Stderr)
+		err = signCert(args[1:], os.Stdout, os.Stderr, StdinPasswordReader{})
 	case "print":
 		err = printCert(args[1:], os.Stdout, os.Stderr)
 	case "verify":

cmd/nebula-cert/passwords.go

@@ -0,0 +1,28 @@
+package main
+
+import (
+	"errors"
+	"fmt"
+	"os"
+
+	"golang.org/x/term"
+)
+
+var ErrNoTerminal = errors.New("cannot read password from nonexistent terminal")
+
+type PasswordReader interface {
+	ReadPassword() ([]byte, error)
+}
+
+type StdinPasswordReader struct{}
+
+func (pr StdinPasswordReader) ReadPassword() ([]byte, error) {
+	if !term.IsTerminal(int(os.Stdin.Fd())) {
+		return nil, ErrNoTerminal
+	}
+
+	password, err := term.ReadPassword(int(os.Stdin.Fd()))
+	fmt.Println()
+
+	return password, err
+}

cmd/nebula-cert/passwords_test.go

@@ -0,0 +1,10 @@
+package main
+
+type StubPasswordReader struct {
+	password []byte
+	err      error
+}
+
+func (pr *StubPasswordReader) ReadPassword() ([]byte, error) {
+	return pr.password, pr.err
+}

cmd/nebula-cert/sign.go

@@ -1,6 +1,7 @@
 package main
 
 import (
+	"crypto/ed25519"
 	"crypto/rand"
 	"flag"
 	"fmt"
@@ -49,7 +50,7 @@ func newSignFlags() *signFlags {
 
 }
 
-func signCert(args []string, out io.Writer, errOut io.Writer) error {
+func signCert(args []string, out io.Writer, errOut io.Writer, pr PasswordReader) error {
 	sf := newSignFlags()
 	err := sf.set.Parse(args)
 	if err != nil {
@@ -77,8 +78,36 @@ func signCert(args []string, out io.Writer, errOut io.Writer) error {
 		return fmt.Errorf("error while reading ca-key: %s", err)
 	}
 
-	caKey, _, err := cert.UnmarshalEd25519PrivateKey(rawCAKey)
+	var caKey ed25519.PrivateKey
-	if err != nil {
+
+	// naively attempt to decode the private key as though it is not encrypted
+	caKey, _, err = cert.UnmarshalEd25519PrivateKey(rawCAKey)
+	if err == cert.ErrPrivateKeyEncrypted {
+		// ask for a passphrase until we get one
+		var passphrase []byte
+		for i := 0; i < 5; i++ {
+			out.Write([]byte("Enter passphrase: "))
+			passphrase, err = pr.ReadPassword()
+
+			if err == ErrNoTerminal {
+				return fmt.Errorf("ca-key is encrypted and must be decrypted interactively")
+			} else if err != nil {
+				return fmt.Errorf("error reading password: %s", err)
+			}
+
+			if len(passphrase) > 0 {
+				break
+			}
+		}
+		if len(passphrase) == 0 {
+			return fmt.Errorf("cannot open encrypted ca-key without passphrase")
+		}
+
+		caKey, _, err = cert.DecryptAndUnmarshalEd25519PrivateKey(passphrase, rawCAKey)
+		if err != nil {
+			return fmt.Errorf("error while parsing encrypted ca-key: %s", err)
+		}
+	} else if err != nil {
 		return fmt.Errorf("error while parsing ca-key: %s", err)
 	}
 

cmd/nebula-cert/sign_test.go

@@ -6,6 +6,7 @@ package main
 import (
 	"bytes"
 	"crypto/rand"
+	"errors"
 	"io/ioutil"
 	"os"
 	"testing"
@@ -58,17 +59,39 @@ func Test_signCert(t *testing.T) {
 	ob := &bytes.Buffer{}
 	eb := &bytes.Buffer{}
 
+	nopw := &StubPasswordReader{
+		password: []byte(""),
+		err:      nil,
+	}
+
+	errpw := &StubPasswordReader{
+		password: []byte(""),
+		err:      errors.New("stub error"),
+	}
+
+	passphrase := []byte("DO NOT USE THIS KEY")
+	testpw := &StubPasswordReader{
+		password: passphrase,
+		err:      nil,
+	}
+
 	// required args
-	assertHelpError(t, signCert([]string{"-ca-crt", "./nope", "-ca-key", "./nope", "-ip", "1.1.1.1/24", "-out-key", "nope", "-out-crt", "nope"}, ob, eb), "-name is required")
+	assertHelpError(t, signCert(
+		[]string{"-ca-crt", "./nope", "-ca-key", "./nope", "-ip", "1.1.1.1/24", "-out-key", "nope", "-out-crt", "nope"}, ob, eb, nopw,
+	), "-name is required")
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 
-	assertHelpError(t, signCert([]string{"-ca-crt", "./nope", "-ca-key", "./nope", "-name", "test", "-out-key", "nope", "-out-crt", "nope"}, ob, eb), "-ip is required")
+	assertHelpError(t, signCert(
+		[]string{"-ca-crt", "./nope", "-ca-key", "./nope", "-name", "test", "-out-key", "nope", "-out-crt", "nope"}, ob, eb, nopw,
+	), "-ip is required")
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 
 	// cannot set -in-pub and -out-key
-	assertHelpError(t, signCert([]string{"-ca-crt", "./nope", "-ca-key", "./nope", "-name", "test", "-in-pub", "nope", "-ip", "1.1.1.1/24", "-out-crt", "nope", "-out-key", "nope"}, ob, eb), "cannot set both -in-pub and -out-key")
+	assertHelpError(t, signCert(
+		[]string{"-ca-crt", "./nope", "-ca-key", "./nope", "-name", "test", "-in-pub", "nope", "-ip", "1.1.1.1/24", "-out-crt", "nope", "-out-key", "nope"}, ob, eb, nopw,
+	), "cannot set both -in-pub and -out-key")
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 
@@ -76,7 +99,7 @@ func Test_signCert(t *testing.T) {
 	ob.Reset()
 	eb.Reset()
 	args := []string{"-ca-crt", "./nope", "-ca-key", "./nope", "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", "nope", "-out-key", "nope", "-duration", "100m"}
-	assert.EqualError(t, signCert(args, ob, eb), "error while reading ca-key: open ./nope: "+NoSuchFileError)
+	assert.EqualError(t, signCert(args, ob, eb, nopw), "error while reading ca-key: open ./nope: "+NoSuchFileError)
 
 	// failed to unmarshal key
 	ob.Reset()
@@ -86,7 +109,7 @@ func Test_signCert(t *testing.T) {
 	defer os.Remove(caKeyF.Name())
 
 	args = []string{"-ca-crt", "./nope", "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", "nope", "-out-key", "nope", "-duration", "100m"}
-	assert.EqualError(t, signCert(args, ob, eb), "error while parsing ca-key: input did not contain a valid PEM encoded block")
+	assert.EqualError(t, signCert(args, ob, eb, nopw), "error while parsing ca-key: input did not contain a valid PEM encoded block")
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 
@@ -98,7 +121,7 @@ func Test_signCert(t *testing.T) {
 
 	// failed to read cert
 	args = []string{"-ca-crt", "./nope", "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", "nope", "-out-key", "nope", "-duration", "100m"}
-	assert.EqualError(t, signCert(args, ob, eb), "error while reading ca-crt: open ./nope: "+NoSuchFileError)
+	assert.EqualError(t, signCert(args, ob, eb, nopw), "error while reading ca-crt: open ./nope: "+NoSuchFileError)
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 
@@ -110,7 +133,7 @@ func Test_signCert(t *testing.T) {
 	defer os.Remove(caCrtF.Name())
 
 	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", "nope", "-out-key", "nope", "-duration", "100m"}
-	assert.EqualError(t, signCert(args, ob, eb), "error while parsing ca-crt: input did not contain a valid PEM encoded block")
+	assert.EqualError(t, signCert(args, ob, eb, nopw), "error while parsing ca-crt: input did not contain a valid PEM encoded block")
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 
@@ -129,7 +152,7 @@ func Test_signCert(t *testing.T) {
 
 	// failed to read pub
 	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", "nope", "-in-pub", "./nope", "-duration", "100m"}
-	assert.EqualError(t, signCert(args, ob, eb), "error while reading in-pub: open ./nope: "+NoSuchFileError)
+	assert.EqualError(t, signCert(args, ob, eb, nopw), "error while reading in-pub: open ./nope: "+NoSuchFileError)
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 
@@ -141,7 +164,7 @@ func Test_signCert(t *testing.T) {
 	defer os.Remove(inPubF.Name())
 
 	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", "nope", "-in-pub", inPubF.Name(), "-duration", "100m"}
-	assert.EqualError(t, signCert(args, ob, eb), "error while parsing in-pub: input did not contain a valid PEM encoded block")
+	assert.EqualError(t, signCert(args, ob, eb, nopw), "error while parsing in-pub: input did not contain a valid PEM encoded block")
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 
@@ -155,14 +178,14 @@ func Test_signCert(t *testing.T) {
 	ob.Reset()
 	eb.Reset()
 	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "a1.1.1.1/24", "-out-crt", "nope", "-out-key", "nope", "-duration", "100m"}
-	assertHelpError(t, signCert(args, ob, eb), "invalid ip definition: invalid CIDR address: a1.1.1.1/24")
+	assertHelpError(t, signCert(args, ob, eb, nopw), "invalid ip definition: invalid CIDR address: a1.1.1.1/24")
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 
 	ob.Reset()
 	eb.Reset()
 	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "100::100/100", "-out-crt", "nope", "-out-key", "nope", "-duration", "100m"}
-	assertHelpError(t, signCert(args, ob, eb), "invalid ip definition: can only be ipv4, have 100::100/100")
+	assertHelpError(t, signCert(args, ob, eb, nopw), "invalid ip definition: can only be ipv4, have 100::100/100")
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 
@@ -170,14 +193,14 @@ func Test_signCert(t *testing.T) {
 	ob.Reset()
 	eb.Reset()
 	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", "nope", "-out-key", "nope", "-duration", "100m", "-subnets", "a"}
-	assertHelpError(t, signCert(args, ob, eb), "invalid subnet definition: invalid CIDR address: a")
+	assertHelpError(t, signCert(args, ob, eb, nopw), "invalid subnet definition: invalid CIDR address: a")
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 
 	ob.Reset()
 	eb.Reset()
 	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", "nope", "-out-key", "nope", "-duration", "100m", "-subnets", "100::100/100"}
-	assertHelpError(t, signCert(args, ob, eb), "invalid subnet definition: can only be ipv4, have 100::100/100")
+	assertHelpError(t, signCert(args, ob, eb, nopw), "invalid subnet definition: can only be ipv4, have 100::100/100")
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 
@@ -191,7 +214,7 @@ func Test_signCert(t *testing.T) {
 	ob.Reset()
 	eb.Reset()
 	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF2.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", "nope", "-out-key", "nope", "-duration", "100m", "-subnets", "a"}
-	assert.EqualError(t, signCert(args, ob, eb), "refusing to sign, root certificate does not match private key")
+	assert.EqualError(t, signCert(args, ob, eb, nopw), "refusing to sign, root certificate does not match private key")
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 
@@ -199,7 +222,7 @@ func Test_signCert(t *testing.T) {
 	ob.Reset()
 	eb.Reset()
 	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", "/do/not/write/pleasecrt", "-out-key", "/do/not/write/pleasekey", "-duration", "100m", "-subnets", "10.1.1.1/32"}
-	assert.EqualError(t, signCert(args, ob, eb), "error while writing out-key: open /do/not/write/pleasekey: "+NoSuchDirError)
+	assert.EqualError(t, signCert(args, ob, eb, nopw), "error while writing out-key: open /do/not/write/pleasekey: "+NoSuchDirError)
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 
@@ -212,7 +235,7 @@ func Test_signCert(t *testing.T) {
 	ob.Reset()
 	eb.Reset()
 	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", "/do/not/write/pleasecrt", "-out-key", keyF.Name(), "-duration", "100m", "-subnets", "10.1.1.1/32"}
-	assert.EqualError(t, signCert(args, ob, eb), "error while writing out-crt: open /do/not/write/pleasecrt: "+NoSuchDirError)
+	assert.EqualError(t, signCert(args, ob, eb, nopw), "error while writing out-crt: open /do/not/write/pleasecrt: "+NoSuchDirError)
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 	os.Remove(keyF.Name())
@@ -226,7 +249,7 @@ func Test_signCert(t *testing.T) {
 	ob.Reset()
 	eb.Reset()
 	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", crtF.Name(), "-out-key", keyF.Name(), "-duration", "100m", "-subnets", "10.1.1.1/32, ,   10.2.2.2/32   ,   ,  ,, 10.5.5.5/32", "-groups", "1,,   2    ,        ,,,3,4,5"}
-	assert.Nil(t, signCert(args, ob, eb))
+	assert.Nil(t, signCert(args, ob, eb, nopw))
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 
@@ -268,7 +291,7 @@ func Test_signCert(t *testing.T) {
 	ob.Reset()
 	eb.Reset()
 	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", crtF.Name(), "-in-pub", inPubF.Name(), "-duration", "100m", "-groups", "1"}
-	assert.Nil(t, signCert(args, ob, eb))
+	assert.Nil(t, signCert(args, ob, eb, nopw))
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 
@@ -283,7 +306,7 @@ func Test_signCert(t *testing.T) {
 	ob.Reset()
 	eb.Reset()
 	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", crtF.Name(), "-out-key", keyF.Name(), "-duration", "1000m", "-subnets", "10.1.1.1/32, ,   10.2.2.2/32   ,   ,  ,, 10.5.5.5/32", "-groups", "1,,   2    ,        ,,,3,4,5"}
-	assert.EqualError(t, signCert(args, ob, eb), "refusing to sign, root certificate constraints violated: certificate expires after signing certificate")
+	assert.EqualError(t, signCert(args, ob, eb, nopw), "refusing to sign, root certificate constraints violated: certificate expires after signing certificate")
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 
@@ -291,14 +314,14 @@ func Test_signCert(t *testing.T) {
 	os.Remove(keyF.Name())
 	os.Remove(crtF.Name())
 	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", crtF.Name(), "-out-key", keyF.Name(), "-duration", "100m", "-subnets", "10.1.1.1/32, ,   10.2.2.2/32   ,   ,  ,, 10.5.5.5/32", "-groups", "1,,   2    ,        ,,,3,4,5"}
-	assert.Nil(t, signCert(args, ob, eb))
+	assert.Nil(t, signCert(args, ob, eb, nopw))
 
 	// test that we won't overwrite existing key file
 	os.Remove(crtF.Name())
 	ob.Reset()
 	eb.Reset()
 	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", crtF.Name(), "-out-key", keyF.Name(), "-duration", "100m", "-subnets", "10.1.1.1/32, ,   10.2.2.2/32   ,   ,  ,, 10.5.5.5/32", "-groups", "1,,   2    ,        ,,,3,4,5"}
-	assert.EqualError(t, signCert(args, ob, eb), "refusing to overwrite existing key: "+keyF.Name())
+	assert.EqualError(t, signCert(args, ob, eb, nopw), "refusing to overwrite existing key: "+keyF.Name())
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
 
@@ -306,14 +329,83 @@ func Test_signCert(t *testing.T) {
 	os.Remove(keyF.Name())
 	os.Remove(crtF.Name())
 	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", crtF.Name(), "-out-key", keyF.Name(), "-duration", "100m", "-subnets", "10.1.1.1/32, ,   10.2.2.2/32   ,   ,  ,, 10.5.5.5/32", "-groups", "1,,   2    ,        ,,,3,4,5"}
-	assert.Nil(t, signCert(args, ob, eb))
+	assert.Nil(t, signCert(args, ob, eb, nopw))
 
 	// test that we won't overwrite existing certificate file
 	os.Remove(keyF.Name())
 	ob.Reset()
 	eb.Reset()
 	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", crtF.Name(), "-out-key", keyF.Name(), "-duration", "100m", "-subnets", "10.1.1.1/32, ,   10.2.2.2/32   ,   ,  ,, 10.5.5.5/32", "-groups", "1,,   2    ,        ,,,3,4,5"}
-	assert.EqualError(t, signCert(args, ob, eb), "refusing to overwrite existing cert: "+crtF.Name())
+	assert.EqualError(t, signCert(args, ob, eb, nopw), "refusing to overwrite existing cert: "+crtF.Name())
 	assert.Empty(t, ob.String())
 	assert.Empty(t, eb.String())
+
+	// create valid cert/key using encrypted CA key
+	os.Remove(caKeyF.Name())
+	os.Remove(caCrtF.Name())
+	os.Remove(keyF.Name())
+	os.Remove(crtF.Name())
+	ob.Reset()
+	eb.Reset()
+
+	caKeyF, err = ioutil.TempFile("", "sign-cert.key")
+	assert.Nil(t, err)
+	defer os.Remove(caKeyF.Name())
+
+	caCrtF, err = ioutil.TempFile("", "sign-cert.crt")
+	assert.Nil(t, err)
+	defer os.Remove(caCrtF.Name())
+
+	// generate the encrypted key
+	caPub, caPriv, _ = ed25519.GenerateKey(rand.Reader)
+	kdfParams := cert.NewArgon2Parameters(64*1024, 4, 3)
+	b, _ = cert.EncryptAndMarshalEd25519PrivateKey(caPriv, passphrase, kdfParams)
+	caKeyF.Write(b)
+
+	ca = cert.NebulaCertificate{
+		Details: cert.NebulaCertificateDetails{
+			Name:      "ca",
+			NotBefore: time.Now(),
+			NotAfter:  time.Now().Add(time.Minute * 200),
+			PublicKey: caPub,
+			IsCA:      true,
+		},
+	}
+	b, _ = ca.MarshalToPEM()
+	caCrtF.Write(b)
+
+	// test with the proper password
+	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", crtF.Name(), "-out-key", keyF.Name(), "-duration", "100m", "-subnets", "10.1.1.1/32, ,   10.2.2.2/32   ,   ,  ,, 10.5.5.5/32", "-groups", "1,,   2    ,        ,,,3,4,5"}
+	assert.Nil(t, signCert(args, ob, eb, testpw))
+	assert.Equal(t, "Enter passphrase: ", ob.String())
+	assert.Empty(t, eb.String())
+
+	// test with the wrong password
+	ob.Reset()
+	eb.Reset()
+
+	testpw.password = []byte("invalid password")
+	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", crtF.Name(), "-out-key", keyF.Name(), "-duration", "100m", "-subnets", "10.1.1.1/32, ,   10.2.2.2/32   ,   ,  ,, 10.5.5.5/32", "-groups", "1,,   2    ,        ,,,3,4,5"}
+	assert.Error(t, signCert(args, ob, eb, testpw))
+	assert.Equal(t, "Enter passphrase: ", ob.String())
+	assert.Empty(t, eb.String())
+
+	// test with the user not entering a password
+	ob.Reset()
+	eb.Reset()
+
+	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", crtF.Name(), "-out-key", keyF.Name(), "-duration", "100m", "-subnets", "10.1.1.1/32, ,   10.2.2.2/32   ,   ,  ,, 10.5.5.5/32", "-groups", "1,,   2    ,        ,,,3,4,5"}
+	assert.Error(t, signCert(args, ob, eb, nopw))
+	// normally the user hitting enter on the prompt would add newlines between these
+	assert.Equal(t, "Enter passphrase: Enter passphrase: Enter passphrase: Enter passphrase: Enter passphrase: ", ob.String())
+	assert.Empty(t, eb.String())
+
+	// test an error condition
+	ob.Reset()
+	eb.Reset()
+
+	args = []string{"-ca-crt", caCrtF.Name(), "-ca-key", caKeyF.Name(), "-name", "test", "-ip", "1.1.1.1/24", "-out-crt", crtF.Name(), "-out-key", keyF.Name(), "-duration", "100m", "-subnets", "10.1.1.1/32, ,   10.2.2.2/32   ,   ,  ,, 10.5.5.5/32", "-groups", "1,,   2    ,        ,,,3,4,5"}
+	assert.Error(t, signCert(args, ob, eb, errpw))
+	assert.Equal(t, "Enter passphrase: ", ob.String())
+	assert.Empty(t, eb.String())
 }

go.mod

@@ -24,6 +24,7 @@ require (
 	golang.org/x/exp v0.0.0-20230310171629-522b1b587ee0
 	golang.org/x/net v0.8.0
 	golang.org/x/sys v0.6.0
+	golang.org/x/term v0.6.0
 	golang.zx2c4.com/wintun v0.0.0-20230126152724-0fa3db229ce2
 	golang.zx2c4.com/wireguard/windows v0.5.3
 	google.golang.org/protobuf v1.29.0
@@ -42,7 +43,6 @@ require (
 	github.com/prometheus/procfs v0.9.0 // indirect
 	github.com/vishvananda/netns v0.0.4 // indirect
 	golang.org/x/mod v0.9.0 // indirect
-	golang.org/x/term v0.6.0 // indirect
 	golang.org/x/tools v0.7.0 // indirect
 	gopkg.in/yaml.v3 v3.0.1 // indirect
 )

go.sum

@@ -153,8 +153,6 @@ golang.org/x/crypto v0.0.0-20200622213623-75b288015ac9/go.mod h1:LzIPMQfyMNhhGPh
 golang.org/x/crypto v0.0.0-20210322153248-0c34fe9e7dc2/go.mod h1:T9bdIzuCu7OtxOm1hfPfRQxPLYneinmdGuTeoZ9dtd4=
 golang.org/x/crypto v0.7.0 h1:AvwMYaRytfdeVt3u6mLaxYtErKYjxA2OXjJ1HHq6t3A=
 golang.org/x/crypto v0.7.0/go.mod h1:pYwdfH91IfpZVANVyUOhSIPZaFoJGxTFbZhFTx+dXZU=
-golang.org/x/exp v0.0.0-20230224173230-c95f2b4c22f2 h1:Jvc7gsqn21cJHCmAWx0LiimpP18LZmUxkT5Mp7EZ1mI=
-golang.org/x/exp v0.0.0-20230224173230-c95f2b4c22f2/go.mod h1:CxIveKay+FTh1D0yPZemJVgC/95VzuuOLq5Qi4xnoYc=
 golang.org/x/exp v0.0.0-20230310171629-522b1b587ee0 h1:LGJsf5LRplCck6jUCH3dBL2dmycNruWNF5xugkSlfXw=
 golang.org/x/exp v0.0.0-20230310171629-522b1b587ee0/go.mod h1:CxIveKay+FTh1D0yPZemJVgC/95VzuuOLq5Qi4xnoYc=
 golang.org/x/lint v0.0.0-20200302205851-738671d3881b/go.mod h1:3xt1FjdF8hUf6vQPIChWIBhFzV8gjjsPE/fR3IyQdNY=