Merge 5c0f3fccb4 into 1a0f168b6e

go.mod

@@ -34,6 +34,7 @@ require (
 	go.opentelemetry.io/otel v1.31.0
 	go.opentelemetry.io/otel/exporters/otlp/otlptrace/otlptracegrpc v1.31.0
 	go.opentelemetry.io/otel/sdk v1.31.0
+	go.step.sm/crypto v0.45.0
 	go.uber.org/automaxprocs v1.6.0
 	go.uber.org/zap v1.27.0
 	go.uber.org/zap/exp v0.3.0
@@ -145,7 +146,6 @@ require (
 	go.opentelemetry.io/otel/trace v1.31.0
 	go.opentelemetry.io/proto/otlp v1.3.1 // indirect
 	go.step.sm/cli-utils v0.9.0 // indirect
-	go.step.sm/crypto v0.45.0
 	go.step.sm/linkedca v0.20.1 // indirect
 	go.uber.org/multierr v1.11.0 // indirect
 	golang.org/x/mod v0.24.0 // indirect

modules/caddypki/adminapi.go

@@ -222,10 +222,15 @@ func rootAndIntermediatePEM(ca *CA) (root, inter []byte, err error) {
 	if err != nil {
 		return
 	}
-	inter, err = pemEncodeCert(ca.IntermediateCertificate().Raw)
+
-	if err != nil {
+	for _, interCert := range ca.IntermediateCertificateChain() {
-		return
+		pemBytes, err := pemEncodeCert(interCert.Raw)
+		if err != nil {
+			return nil, nil, err
+		}
+		inter = append(inter, pemBytes...)
 	}
+
 	return
 }
 

modules/caddypki/ca.go

@@ -75,10 +75,11 @@ type CA struct {
 	// and module provisioning.
 	ID string `json:"-"`
 
-	storage     certmagic.Storage
+	storage    certmagic.Storage
-	root, inter *x509.Certificate
+	root       *x509.Certificate
-	interKey    any // TODO: should we just store these as crypto.Signer?
+	interChain []*x509.Certificate
-	mu          *sync.RWMutex
+	interKey   any // TODO: should we just store these as crypto.Signer?
+	mu         *sync.RWMutex
 
 	rootCertPath string // mainly used for logging purposes if trusting
 	log          *zap.Logger
@@ -129,14 +130,16 @@ func (ca *CA) Provision(ctx caddy.Context, id string, log *zap.Logger) error {
 	}
 
 	// load the certs and key that will be used for signing
-	var rootCert, interCert *x509.Certificate
+	var rootCert *x509.Certificate
+	var rootCertChain, interCertChain []*x509.Certificate
 	var rootKey, interKey crypto.Signer
 	var err error
 	if ca.Root != nil {
 		if ca.Root.Format == "" || ca.Root.Format == "pem_file" {
 			ca.rootCertPath = ca.Root.Certificate
 		}
-		rootCert, rootKey, err = ca.Root.Load()
+		rootCertChain, rootKey, err = ca.Root.Load()
+		rootCert = rootCertChain[0]
 	} else {
 		ca.rootCertPath = "storage:" + ca.storageKeyRootCert()
 		rootCert, rootKey, err = ca.loadOrGenRoot()
@@ -145,16 +148,16 @@ func (ca *CA) Provision(ctx caddy.Context, id string, log *zap.Logger) error {
 		return err
 	}
 	if ca.Intermediate != nil {
-		interCert, interKey, err = ca.Intermediate.Load()
+		interCertChain, interKey, err = ca.Intermediate.Load()
 	} else {
-		interCert, interKey, err = ca.loadOrGenIntermediate(rootCert, rootKey)
+		interCertChain, interKey, err = ca.loadOrGenIntermediate(rootCert, rootKey)
 	}
 	if err != nil {
 		return err
 	}
 
 	ca.mu.Lock()
-	ca.root, ca.inter, ca.interKey = rootCert, interCert, interKey
+	ca.root, ca.interChain, ca.interKey = rootCert, interCertChain, interKey
 	ca.mu.Unlock()
 
 	return nil
@@ -180,7 +183,15 @@ func (ca CA) RootKey() (any, error) {
 func (ca CA) IntermediateCertificate() *x509.Certificate {
 	ca.mu.RLock()
 	defer ca.mu.RUnlock()
-	return ca.inter
+	return ca.interChain[0]
+}
+
+// IntermediateCertificateChain returns the CA's intermediate
+// certificate chain.
+func (ca CA) IntermediateCertificateChain() []*x509.Certificate {
+	ca.mu.RLock()
+	defer ca.mu.RUnlock()
+	return ca.interChain
 }
 
 // IntermediateKey returns the CA's intermediate private key.
@@ -218,13 +229,14 @@ func (ca *CA) NewAuthority(authorityConfig AuthorityConfig) (*authority.Authorit
 		// sure it's always fresh, because the intermediate may
 		// renew while Caddy is running (medium lifetime)
 		signerOption = authority.WithX509SignerFunc(func() ([]*x509.Certificate, crypto.Signer, error) {
-			issuerCert := ca.IntermediateCertificate()
+			issuerChain := ca.IntermediateCertificateChain()
+			issuerCert := issuerChain[0]
 			issuerKey := ca.IntermediateKey().(crypto.Signer)
 			ca.log.Debug("using intermediate signer",
 				zap.String("serial", issuerCert.SerialNumber.String()),
 				zap.String("not_before", issuerCert.NotBefore.String()),
 				zap.String("not_after", issuerCert.NotAfter.String()))
-			return []*x509.Certificate{issuerCert}, issuerKey, nil
+			return issuerChain, issuerKey, nil
 		})
 	}
 
@@ -250,7 +262,11 @@ func (ca *CA) NewAuthority(authorityConfig AuthorityConfig) (*authority.Authorit
 
 func (ca CA) loadOrGenRoot() (rootCert *x509.Certificate, rootKey crypto.Signer, err error) {
 	if ca.Root != nil {
-		return ca.Root.Load()
+		rootChain, rootSigner, err := ca.Root.Load()
+		if err != nil {
+			return nil, nil, err
+		}
+		return rootChain[0], rootSigner, nil
 	}
 	rootCertPEM, err := ca.storage.Load(ca.ctx, ca.storageKeyRootCert())
 	if err != nil {
@@ -312,7 +328,8 @@ func (ca CA) genRoot() (rootCert *x509.Certificate, rootKey crypto.Signer, err e
 	return rootCert, rootKey, nil
 }
 
-func (ca CA) loadOrGenIntermediate(rootCert *x509.Certificate, rootKey crypto.Signer) (interCert *x509.Certificate, interKey crypto.Signer, err error) {
+func (ca CA) loadOrGenIntermediate(rootCert *x509.Certificate, rootKey crypto.Signer) (interCertChain []*x509.Certificate, interKey crypto.Signer, err error) {
+	var interCert *x509.Certificate
 	interCertPEM, err := ca.storage.Load(ca.ctx, ca.storageKeyIntermediateCert())
 	if err != nil {
 		if !errors.Is(err, fs.ErrNotExist) {
@@ -324,10 +341,12 @@ func (ca CA) loadOrGenIntermediate(rootCert *x509.Certificate, rootKey crypto.Si
 		if err != nil {
 			return nil, nil, fmt.Errorf("generating new intermediate cert: %v", err)
 		}
+
+		interCertChain = append(interCertChain, interCert)
 	}
 
-	if interCert == nil {
+	if len(interCertChain) == 0 {
-		interCert, err = pemDecodeSingleCert(interCertPEM)
+		interCertChain, err = pemDecodeCertificateChain(interCertPEM)
 		if err != nil {
 			return nil, nil, fmt.Errorf("decoding intermediate certificate PEM: %v", err)
 		}
@@ -344,7 +363,7 @@ func (ca CA) loadOrGenIntermediate(rootCert *x509.Certificate, rootKey crypto.Si
 		}
 	}
 
-	return interCert, interKey, nil
+	return interCertChain, interKey, nil
 }
 
 func (ca CA) genIntermediate(rootCert *x509.Certificate, rootKey crypto.Signer) (interCert *x509.Certificate, interKey crypto.Signer, err error) {

modules/caddypki/crypto.go

@@ -17,12 +17,17 @@ package caddypki
 import (
 	"bytes"
 	"crypto"
+	"crypto/ecdsa"
+	"crypto/ed25519"
+	"crypto/rsa"
 	"crypto/x509"
 	"encoding/pem"
+	"errors"
 	"fmt"
 	"os"
 
 	"github.com/caddyserver/certmagic"
+	"go.step.sm/crypto/pemutil"
 )
 
 func pemDecodeSingleCert(pemDER []byte) (*x509.Certificate, error) {
@@ -39,6 +44,15 @@ func pemDecodeSingleCert(pemDER []byte) (*x509.Certificate, error) {
 	return x509.ParseCertificate(pemBlock.Bytes)
 }
 
+func pemDecodeCertificateChain(pemDER []byte) ([]*x509.Certificate, error) {
+	chain, err := pemutil.ParseCertificateBundle(pemDER)
+	if err != nil {
+		return nil, fmt.Errorf("failed parsing certificate chain: %w", err)
+	}
+
+	return chain, nil
+}
+
 func pemEncodeCert(der []byte) ([]byte, error) {
 	return pemEncode("CERTIFICATE", der)
 }
@@ -71,14 +85,14 @@ type KeyPair struct {
 }
 
 // Load loads the certificate and key.
-func (kp KeyPair) Load() (*x509.Certificate, crypto.Signer, error) {
+func (kp KeyPair) Load() ([]*x509.Certificate, crypto.Signer, error) {
 	switch kp.Format {
 	case "", "pem_file":
 		certData, err := os.ReadFile(kp.Certificate)
 		if err != nil {
 			return nil, nil, err
 		}
-		cert, err := pemDecodeSingleCert(certData)
+		chain, err := pemDecodeCertificateChain(certData)
 		if err != nil {
 			return nil, nil, err
 		}
@@ -93,11 +107,49 @@ func (kp KeyPair) Load() (*x509.Certificate, crypto.Signer, error) {
 			if err != nil {
 				return nil, nil, err
 			}
+			if err := verifyKeysMatch(chain[0], key); err != nil {
+				return nil, nil, err
+			}
 		}
 
-		return cert, key, nil
+		return chain, key, nil
 
 	default:
 		return nil, nil, fmt.Errorf("unsupported format: %s", kp.Format)
 	}
 }
+
+// verifyKeysMatch verifies that the public key in the [x509.Certificate] matches
+// the public key of the [crypto.Signer].
+func verifyKeysMatch(crt *x509.Certificate, signer crypto.Signer) error {
+	switch pub := crt.PublicKey.(type) {
+	case *rsa.PublicKey:
+		pk, ok := signer.Public().(*rsa.PublicKey)
+		if !ok {
+			return fmt.Errorf("private key type %T does not match issuer public key type %T", signer.Public(), pub)
+		}
+		if !pub.Equal(pk) {
+			return errors.New("private key does not match issuer public key")
+		}
+	case *ecdsa.PublicKey:
+		pk, ok := signer.Public().(*ecdsa.PublicKey)
+		if !ok {
+			return fmt.Errorf("private key type %T does not match issuer public key type %T", signer.Public(), pub)
+		}
+		if !pub.Equal(pk) {
+			return errors.New("private key does not match issuer public key")
+		}
+	case ed25519.PublicKey:
+		pk, ok := signer.Public().(ed25519.PublicKey)
+		if !ok {
+			return fmt.Errorf("private key type %T does not match issuer public key type %T", signer.Public(), pub)
+		}
+		if !pub.Equal(pk) {
+			return errors.New("private key does not match issuer public key")
+		}
+	default:
+		return fmt.Errorf("unsupported key type: %T", pub)
+	}
+
+	return nil
+}

modules/caddypki/crypto_test.go

@@ -0,0 +1,170 @@
+// Copyright 2015 Matthew Holt and The Caddy Authors
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+package caddypki
+
+import (
+	"crypto/rand"
+	"crypto/x509"
+	"crypto/x509/pkix"
+	"encoding/pem"
+	"os"
+	"path/filepath"
+	"testing"
+	"time"
+
+	"go.step.sm/crypto/keyutil"
+	"go.step.sm/crypto/pemutil"
+)
+
+func TestKeyPair_Load(t *testing.T) {
+	rootSigner, err := keyutil.GenerateDefaultSigner()
+	if err != nil {
+		t.Fatalf("Failed creating signer: %v", err)
+	}
+
+	tmpl := &x509.Certificate{
+		Subject:    pkix.Name{CommonName: "test-root"},
+		IsCA:       true,
+		MaxPathLen: 3,
+	}
+	rootBytes, err := x509.CreateCertificate(rand.Reader, tmpl, tmpl, rootSigner.Public(), rootSigner)
+	if err != nil {
+		t.Fatalf("Creating root certificate failed: %v", err)
+	}
+
+	root, err := x509.ParseCertificate(rootBytes)
+	if err != nil {
+		t.Fatalf("Parsing root certificate failed: %v", err)
+	}
+
+	intermediateSigner, err := keyutil.GenerateDefaultSigner()
+	if err != nil {
+		t.Fatalf("Creating intermedaite signer failed: %v", err)
+	}
+
+	intermediateBytes, err := x509.CreateCertificate(rand.Reader, &x509.Certificate{
+		Subject:    pkix.Name{CommonName: "test-first-intermediate"},
+		IsCA:       true,
+		MaxPathLen: 2,
+		NotAfter:   time.Now().Add(time.Hour),
+	}, root, intermediateSigner.Public(), rootSigner)
+	if err != nil {
+		t.Fatalf("Creating intermediate certificate failed: %v", err)
+	}
+
+	intermediate, err := x509.ParseCertificate(intermediateBytes)
+	if err != nil {
+		t.Fatalf("Parsing intermediate certificate failed: %v", err)
+	}
+
+	var chainContents []byte
+	chain := []*x509.Certificate{intermediate, root}
+	for _, cert := range chain {
+		b, err := pemutil.Serialize(cert)
+		if err != nil {
+			t.Fatalf("Failed serializing intermediate certificate: %v", err)
+		}
+		chainContents = append(chainContents, pem.EncodeToMemory(b)...)
+	}
+
+	dir := t.TempDir()
+	rootCertFile := filepath.Join(dir, "root.pem")
+	if _, err = pemutil.Serialize(root, pemutil.WithFilename(rootCertFile)); err != nil {
+		t.Fatalf("Failed serializing root certificate: %v", err)
+	}
+	rootKeyFile := filepath.Join(dir, "root.key")
+	if _, err = pemutil.Serialize(rootSigner, pemutil.WithFilename(rootKeyFile)); err != nil {
+		t.Fatalf("Failed serializing root key: %v", err)
+	}
+	intermediateCertFile := filepath.Join(dir, "intermediate.pem")
+	if _, err = pemutil.Serialize(intermediate, pemutil.WithFilename(intermediateCertFile)); err != nil {
+		t.Fatalf("Failed serializing intermediate certificate: %v", err)
+	}
+	intermediateKeyFile := filepath.Join(dir, "intermediate.key")
+	if _, err = pemutil.Serialize(intermediateSigner, pemutil.WithFilename(intermediateKeyFile)); err != nil {
+		t.Fatalf("Failed serializing intermediate key: %v", err)
+	}
+	chainFile := filepath.Join(dir, "chain.pem")
+	if err := os.WriteFile(chainFile, chainContents, 0644); err != nil {
+		t.Fatalf("Failed writing intermediate chain: %v", err)
+	}
+
+	t.Run("ok/single-certificate-without-signer", func(t *testing.T) {
+		kp := KeyPair{
+			Certificate: rootCertFile,
+		}
+		chain, signer, err := kp.Load()
+		if err != nil {
+			t.Fatalf("Failed loading KeyPair: %v", err)
+		}
+		if len(chain) != 1 {
+			t.Errorf("Expected 1 certificate in chain; got %d", len(chain))
+		}
+		if signer != nil {
+			t.Error("Expected no signer to be returned")
+		}
+	})
+
+	t.Run("ok/single-certificate-with-signer", func(t *testing.T) {
+		kp := KeyPair{
+			Certificate: rootCertFile,
+			PrivateKey:  rootKeyFile,
+		}
+		chain, signer, err := kp.Load()
+		if err != nil {
+			t.Fatalf("Failed loading KeyPair: %v", err)
+		}
+		if len(chain) != 1 {
+			t.Errorf("Expected 1 certificate in chain; got %d", len(chain))
+		}
+		if signer == nil {
+			t.Error("Expected signer to be returned")
+		}
+	})
+
+	t.Run("ok/multiple-certificates-with-signer", func(t *testing.T) {
+		kp := KeyPair{
+			Certificate: chainFile,
+			PrivateKey:  intermediateKeyFile,
+		}
+		chain, signer, err := kp.Load()
+		if err != nil {
+			t.Fatalf("Failed loading KeyPair: %v", err)
+		}
+		if len(chain) != 2 {
+			t.Errorf("Expected 1 certificate in chain; got %d", len(chain))
+		}
+		if signer == nil {
+			t.Error("Expected signer to be returned")
+		}
+	})
+
+	t.Run("fail/non-matching-public-key", func(t *testing.T) {
+		kp := KeyPair{
+			Certificate: intermediateCertFile,
+			PrivateKey:  rootKeyFile,
+		}
+		chain, signer, err := kp.Load()
+		if err == nil {
+			t.Error("Expected loading KeyPair to return an error")
+		}
+		if chain != nil {
+			t.Error("Expected no chain to be returned")
+		}
+		if signer != nil {
+			t.Error("Expected no signer to be returned")
+		}
+	})
+}

modules/caddypki/maintain.go

@@ -66,16 +66,16 @@ func (p *PKI) renewCertsForCA(ca *CA) error {
 		if needsRenewal(ca.root) {
 			// TODO: implement root renewal (use same key)
 			log.Warn("root certificate expiring soon (FIXME: ROOT RENEWAL NOT YET IMPLEMENTED)",
-				zap.Duration("time_remaining", time.Until(ca.inter.NotAfter)),
+				zap.Duration("time_remaining", time.Until(ca.interChain[0].NotAfter)),
 			)
 		}
 	}
 
 	// only maintain the intermediate if it's not manually provided in the config
 	if ca.Intermediate == nil {
-		if needsRenewal(ca.inter) {
+		if needsRenewal(ca.interChain[0]) {
 			log.Info("intermediate expires soon; renewing",
-				zap.Duration("time_remaining", time.Until(ca.inter.NotAfter)),
+				zap.Duration("time_remaining", time.Until(ca.interChain[0].NotAfter)),
 			)
 
 			rootCert, rootKey, err := ca.loadOrGenRoot()
@@ -86,10 +86,10 @@ func (p *PKI) renewCertsForCA(ca *CA) error {
 			if err != nil {
 				return fmt.Errorf("generating new certificate: %v", err)
 			}
-			ca.inter, ca.interKey = interCert, interKey
+			ca.interChain, ca.interKey = []*x509.Certificate{interCert}, interKey
 
 			log.Info("renewed intermediate",
-				zap.Time("new_expiration", ca.inter.NotAfter),
+				zap.Time("new_expiration", ca.interChain[0].NotAfter),
 			)
 		}
 	}

modules/caddytls/capools.go

@@ -257,7 +257,7 @@ func (PKIIntermediateCAPool) CaddyModule() caddy.ModuleInfo {
 	}
 }
 
-// Loads the PKI app and load the intermediate certificates into the certificate pool
+// Loads the PKI app and loads the intermediate certificates into the certificate pool
 func (p *PKIIntermediateCAPool) Provision(ctx caddy.Context) error {
 	pkiApp, err := ctx.AppIfConfigured("pki")
 	if err != nil {
@@ -274,7 +274,9 @@ func (p *PKIIntermediateCAPool) Provision(ctx caddy.Context) error {
 
 	caPool := x509.NewCertPool()
 	for _, ca := range p.ca {
-		caPool.AddCert(ca.IntermediateCertificate())
+		for _, c := range ca.IntermediateCertificateChain() {
+			caPool.AddCert(c)
+		}
 	}
 	p.pool = caPool
 	return nil

modules/caddytls/internalissuer_test.go

@@ -0,0 +1,258 @@
+// Copyright 2015 Matthew Holt and The Caddy Authors
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+package caddytls
+
+import (
+	"crypto/rand"
+	"crypto/x509"
+	"crypto/x509/pkix"
+	"encoding/pem"
+	"fmt"
+	"os"
+	"path/filepath"
+	"testing"
+	"time"
+
+	"github.com/caddyserver/caddy/v2"
+	"github.com/caddyserver/caddy/v2/modules/caddypki"
+	"go.uber.org/zap"
+
+	"go.step.sm/crypto/keyutil"
+	"go.step.sm/crypto/pemutil"
+)
+
+func TestInternalIssuer_Issue(t *testing.T) {
+	rootSigner, err := keyutil.GenerateDefaultSigner()
+	if err != nil {
+		t.Fatalf("Creating root signer failed: %v", err)
+	}
+
+	tmpl := &x509.Certificate{
+		Subject:    pkix.Name{CommonName: "test-root"},
+		IsCA:       true,
+		MaxPathLen: 3,
+	}
+	rootBytes, err := x509.CreateCertificate(rand.Reader, tmpl, tmpl, rootSigner.Public(), rootSigner)
+	if err != nil {
+		t.Fatalf("Creating root certificate failed: %v", err)
+	}
+
+	root, err := x509.ParseCertificate(rootBytes)
+	if err != nil {
+		t.Fatalf("Parsing root certificate failed: %v", err)
+	}
+
+	firstIntermediateSigner, err := keyutil.GenerateDefaultSigner()
+	if err != nil {
+		t.Fatalf("Creating intermedaite signer failed: %v", err)
+	}
+
+	firstIntermediateBytes, err := x509.CreateCertificate(rand.Reader, &x509.Certificate{
+		Subject:    pkix.Name{CommonName: "test-first-intermediate"},
+		IsCA:       true,
+		MaxPathLen: 2,
+		NotAfter:   time.Now().Add(time.Hour),
+	}, root, firstIntermediateSigner.Public(), rootSigner)
+	if err != nil {
+		t.Fatalf("Creating intermediate certificate failed: %v", err)
+	}
+
+	firstIntermediate, err := x509.ParseCertificate(firstIntermediateBytes)
+	if err != nil {
+		t.Fatalf("Parsing intermediate certificate failed: %v", err)
+	}
+
+	secondIntermediateSigner, err := keyutil.GenerateDefaultSigner()
+	if err != nil {
+		t.Fatalf("Creating second intermedaite signer failed: %v", err)
+	}
+
+	secondIntermediateBytes, err := x509.CreateCertificate(rand.Reader, &x509.Certificate{
+		Subject:    pkix.Name{CommonName: "test-second-intermediate"},
+		IsCA:       true,
+		MaxPathLen: 2,
+		NotAfter:   time.Now().Add(time.Hour),
+	}, firstIntermediate, secondIntermediateSigner.Public(), firstIntermediateSigner)
+	if err != nil {
+		t.Fatalf("Creating second intermediate certificate failed: %v", err)
+	}
+
+	secondIntermediate, err := x509.ParseCertificate(secondIntermediateBytes)
+	if err != nil {
+		t.Fatalf("Parsing second intermediate certificate failed: %v", err)
+	}
+
+	dir := t.TempDir()
+	storageDir := filepath.Join(dir, "certmagic")
+	rootCertFile := filepath.Join(dir, "root.pem")
+	if _, err = pemutil.Serialize(root, pemutil.WithFilename(rootCertFile)); err != nil {
+		t.Fatalf("Failed serializing root certificate: %v", err)
+	}
+	intermediateCertFile := filepath.Join(dir, "intermediate.pem")
+	if _, err = pemutil.Serialize(firstIntermediate, pemutil.WithFilename(intermediateCertFile)); err != nil {
+		t.Fatalf("Failed serializing intermediate certificate: %v", err)
+	}
+	intermediateKeyFile := filepath.Join(dir, "intermediate.key")
+	if _, err = pemutil.Serialize(firstIntermediateSigner, pemutil.WithFilename(intermediateKeyFile)); err != nil {
+		t.Fatalf("Failed serializing intermediate key: %v", err)
+	}
+
+	var intermediateChainContents []byte
+	intermediateChain := []*x509.Certificate{secondIntermediate, firstIntermediate}
+	for _, cert := range intermediateChain {
+		b, err := pemutil.Serialize(cert)
+		if err != nil {
+			t.Fatalf("Failed serializing intermediate certificate: %v", err)
+		}
+		intermediateChainContents = append(intermediateChainContents, pem.EncodeToMemory(b)...)
+	}
+	intermediateChainFile := filepath.Join(dir, "intermediates.pem")
+	if err := os.WriteFile(intermediateChainFile, intermediateChainContents, 0644); err != nil {
+		t.Fatalf("Failed writing intermediate chain: %v", err)
+	}
+	intermediateChainKeyFile := filepath.Join(dir, "intermediates.key")
+	if _, err = pemutil.Serialize(secondIntermediateSigner, pemutil.WithFilename(intermediateChainKeyFile)); err != nil {
+		t.Fatalf("Failed serializing intermediate key: %v", err)
+	}
+
+	signer, err := keyutil.GenerateDefaultSigner()
+	if err != nil {
+		t.Fatalf("Failed creating signer: %v", err)
+	}
+
+	csrBytes, err := x509.CreateCertificateRequest(rand.Reader, &x509.CertificateRequest{
+		Subject: pkix.Name{CommonName: "test"},
+	}, signer)
+	if err != nil {
+		t.Fatalf("Failed creating CSR: %v", err)
+	}
+
+	csr, err := x509.ParseCertificateRequest(csrBytes)
+	if err != nil {
+		t.Fatalf("Failed parsing CSR: %v", err)
+	}
+
+	t.Run("generated-with-defaults", func(t *testing.T) {
+		caddyCtx, cancel := caddy.NewContext(caddy.Context{Context: t.Context()})
+		t.Cleanup(cancel)
+		logger := zap.NewNop()
+
+		ca := &caddypki.CA{
+			StorageRaw: []byte(fmt.Sprintf(`{"module": "file_system", "root": %q}`, storageDir)),
+		}
+		if err := ca.Provision(caddyCtx, "local-test-generated", logger); err != nil {
+			t.Fatalf("Failed provisioning CA: %v", err)
+		}
+
+		iss := InternalIssuer{
+			SignWithRoot: false,
+			ca:           ca,
+			logger:       logger,
+		}
+
+		c, err := iss.Issue(t.Context(), csr)
+		if err != nil {
+			t.Fatalf("Failed issuing certificate: %v", err)
+		}
+
+		chain, err := pemutil.ParseCertificateBundle(c.Certificate)
+		if err != nil {
+			t.Errorf("Failed issuing certificate: %v", err)
+		}
+		if len(chain) != 2 {
+			t.Errorf("Expected 2 certificates in chain; got %d", len(chain))
+		}
+	})
+
+	t.Run("single-intermediate-from-disk", func(t *testing.T) {
+		caddyCtx, cancel := caddy.NewContext(caddy.Context{Context: t.Context()})
+		t.Cleanup(cancel)
+		logger := zap.NewNop()
+
+		ca := &caddypki.CA{
+			Root: &caddypki.KeyPair{
+				Certificate: rootCertFile,
+			},
+			Intermediate: &caddypki.KeyPair{
+				Certificate: intermediateCertFile,
+				PrivateKey:  intermediateKeyFile,
+			},
+			StorageRaw: []byte(fmt.Sprintf(`{"module": "file_system", "root": %q}`, storageDir)),
+		}
+
+		if err := ca.Provision(caddyCtx, "local-test-single-intermediate", logger); err != nil {
+			t.Fatalf("Failed provisioning CA: %v", err)
+		}
+
+		iss := InternalIssuer{
+			ca:           ca,
+			SignWithRoot: false,
+			logger:       logger,
+		}
+
+		c, err := iss.Issue(t.Context(), csr)
+		if err != nil {
+			t.Fatalf("Failed issuing certificate: %v", err)
+		}
+
+		chain, err := pemutil.ParseCertificateBundle(c.Certificate)
+		if err != nil {
+			t.Errorf("Failed issuing certificate: %v", err)
+		}
+		if len(chain) != 2 {
+			t.Errorf("Expected 2 certificates in chain; got %d", len(chain))
+		}
+	})
+
+	t.Run("multiple-intermediates-from-disk", func(t *testing.T) {
+		caddyCtx, cancel := caddy.NewContext(caddy.Context{Context: t.Context()})
+		t.Cleanup(cancel)
+		logger := zap.NewNop()
+
+		ca := &caddypki.CA{
+			Root: &caddypki.KeyPair{
+				Certificate: rootCertFile,
+			},
+			Intermediate: &caddypki.KeyPair{
+				Certificate: intermediateChainFile,
+				PrivateKey:  intermediateChainKeyFile,
+			},
+			StorageRaw: []byte(fmt.Sprintf(`{"module": "file_system", "root": %q}`, storageDir)),
+		}
+
+		if err := ca.Provision(caddyCtx, "local-test", zap.NewNop()); err != nil {
+			t.Fatalf("Failed provisioning CA: %v", err)
+		}
+
+		iss := InternalIssuer{
+			ca:           ca,
+			SignWithRoot: false,
+			logger:       logger,
+		}
+
+		c, err := iss.Issue(t.Context(), csr)
+		if err != nil {
+			t.Fatalf("Failed issuing certificate: %v", err)
+		}
+
+		chain, err := pemutil.ParseCertificateBundle(c.Certificate)
+		if err != nil {
+			t.Errorf("Failed issuing certificate: %v", err)
+		}
+		if len(chain) != 3 {
+			t.Errorf("Expected 3 certificates in chain; got %d", len(chain))
+		}
+	})
+}