fix: verify PKCS7 signature on Azure instance identity tokens (#25286)

Migrates Azure instance identity verification from
`go.mozilla.org/pkcs7` and `github.com/fullsailor/pkcs7` to
`github.com/smallstep/pkcs7`, using `VerifyWithChainAtTime` to validate
both the PKCS7 signature and the certificate chain in one call. The
previous code only verified the signer certificate against a set of
intermediates/roots but did not verify that the PKCS7 signature itself
covered the content, meaning tampered payloads could be accepted.

The `Options` struct is restructured to accept `Roots`, `Intermediates`,
and `CurrentTime` as explicit fields instead of embedding
`x509.VerifyOptions`. The test helper `NewAzureInstanceIdentity` now
builds a realistic 3-level certificate chain (Root CA -> Intermediate CA
-> Signing Cert) matching real Azure trust hierarchy. New tests
(`TestValidate_TamperedContent`,
`TestValidate_UntrustedCertWithValidSignature`) confirm tampered and
untrusted envelopes are rejected.

Addresses GHSA-6x44-w3xg-hqqf.

> [!NOTE]
> This PR was authored by Coder Agents.

<details>
<summary>Implementation Plan</summary>

### Files Changed

| File | Summary |
|------|---------|
| `coderd/azureidentity/azureidentity.go` | Replace `signer.Verify()`
with `VerifyWithChainAtTime`; restructure `Options` struct; add
`ParseCertificates()` helper |
| `coderd/azureidentity/azureidentity_test.go` | Add `testCertChain`
builder, tampered-content and untrusted-cert tests; update existing
tests for new `Options` API |
| `coderd/coderd.go` | Change `AzureCertificates` field from
`x509.VerifyOptions` to `azureidentity.Options` |
| `coderd/workspaceresourceauth.go` | Pass `api.AzureCertificates`
directly instead of wrapping |
| `coderd/coderdtest/coderdtest.go` | Migrate to `smallstep/pkcs7`;
build 3-level cert chain in test helper |
| `go.mod` / `go.sum` | Add `github.com/smallstep/pkcs7`; remove
`fullsailor/pkcs7` and `go.mozilla.org/pkcs7` |

</details>

coderd/azureidentity/azureidentity.go

@@ -6,7 +6,6 @@ import (
 	"encoding/base64"
 	"encoding/json"
 	"encoding/pem"
-	"errors"
 	"io"
 	"net"
 	"net/http"
@@ -15,7 +14,7 @@ import (
 	"sync"
 	"time"
 
-	"go.mozilla.org/pkcs7"
+	"github.com/smallstep/pkcs7"
 	"golang.org/x/xerrors"
 )
 
@@ -184,12 +183,31 @@ type metadata struct {
 }
 
 type Options struct {
-	x509.VerifyOptions
+	// Roots is the trusted root certificate pool. If nil,
+	// the embedded root certificate pool is used.
+	Roots *x509.CertPool
+	// Intermediates are additional intermediate certificates to
+	// inject into the PKCS7 object for chain verification. Azure
+	// PKCS7 envelopes typically only contain the signing cert, so
+	// intermediates must be supplied externally. When nil, the
+	// hardcoded Azure intermediate certificates are used.
+	Intermediates []*x509.Certificate
+	// CurrentTime, if non-zero, overrides the verification
+	// timestamp for certificate chain validation.
+	CurrentTime time.Time
+	// Offline disables fetching of issuing certificates when
+	// chain verification fails.
 	Offline bool
 }
 
 // Validate ensures the signature was signed by an Azure certificate.
 // It returns the associated VM ID if successful.
+//
+// Verification has two parts, both handled by VerifyWithChainAtTime:
+//  1. PKCS7 signature check: proves the content was signed by the
+//     private key corresponding to the certificate in the envelope.
+//  2. Certificate chain check: proves the signing certificate
+//     chains to a trusted root through known intermediates.
 func Validate(ctx context.Context, signature string, options Options) (string, error) {
 	data, err := base64.StdEncoding.DecodeString(signature)
 	if err != nil {
@@ -208,44 +226,47 @@ func Validate(ctx context.Context, signature string, options Options) (string, e
 	if !allowedSigners.MatchString(signer.Subject.CommonName) {
 		return "", xerrors.Errorf("unmatched common name of signer: %q", signer.Subject.CommonName)
 	}
-	if options.Intermediates == nil {
-		options.Intermediates = x509.NewCertPool()
-		for _, cert := range Certificates {
-			block, rest := pem.Decode([]byte(cert))
-			if len(rest) != 0 {
-				return "", xerrors.Errorf("invalid certificate. %d bytes remain", len(rest))
-			}
-			cert, err := x509.ParseCertificate(block.Bytes)
-			if err != nil {
-				return "", xerrors.Errorf("parse certificate: %w", err)
-			}
-			options.Intermediates.AddCert(cert)
+	// Azure PKCS7 envelopes typically contain only the signing
+	// certificate. Inject intermediate certificates so the
+	// library can build a chain from signer to trusted root.
+	intermediates := options.Intermediates
+	if intermediates == nil {
+		intermediates, err = ParseCertificates()
+		if err != nil {
+			return "", xerrors.Errorf("parse hardcoded certificates: %w", err)
 		}
 	}
-	// Set Roots explicitly so we never fall back to the platform's system
-	// verifier (notably Apple's Security framework on macOS/iOS), which
-	// enforces stricter standards-compliance checks than Go's pure-Go
-	// verifier and rejects some otherwise valid Azure leaf certificates
-	// with errors like:
-	//   x509: "metadata.azure.com" certificate is not standards compliant
-	// See https://github.com/coder/coder/issues/12978.
-	if options.Roots == nil {
-		roots, err := rootCertPool()
+	pkcs7Data.Certificates = append(pkcs7Data.Certificates, intermediates...)
+	// Resolve root trust store. VerifyWithChainAtTime skips
+	// chain verification when the trust store is nil, so we
+	// must always provide one.
+	roots := options.Roots
+	if roots == nil {
+		roots, err = rootCertPool()
 		if err != nil {
 			return "", xerrors.Errorf("load roots: %w", err)
 		}
-		options.Roots = roots
 	}
 
-	_, err = signer.Verify(options.VerifyOptions)
+	currentTime := options.CurrentTime
+	if currentTime.IsZero() {
+		currentTime = time.Now()
+	}
+
+	// VerifyWithChainAtTime validates both the PKCS7 signature
+	// (proving the content was signed by the certificate's
+	// private key) and the certificate chain (proving the signer
+	// chains to a trusted root).
+	err = pkcs7Data.VerifyWithChainAtTime(roots, currentTime)
 	if err != nil {
-		if !errors.As(err, &x509.UnknownAuthorityError{}) {
-			return "", xerrors.Errorf("verify signature: %w", err)
-		}
 		if options.Offline {
-			return "", xerrors.Errorf("certificate from %v is not cached: %w", signer.IssuingCertificateURL, err)
+			return "", xerrors.Errorf("verify pkcs7: %w", err)
 		}
 
+		// The chain verification may fail when the signing
+		// certificate was issued by an intermediate not yet in
+		// our hardcoded list. Fetch the issuing certificates
+		// and retry.
 		ctx, cancelFunc := context.WithTimeout(ctx, 5*time.Second)
 		defer cancelFunc()
 		for _, certURL := range signer.IssuingCertificateURL {
@@ -261,17 +282,17 @@ func Validate(ctx context.Context, signature string, options Options) (string, e
 				return "", xerrors.New("certificate fetch unsuccessful")
 			}
 			limited := io.LimitReader(res.Body, maxCertResponseBytes+1)
-			data, err := io.ReadAll(limited)
+			certData, err := io.ReadAll(limited)
 			_ = res.Body.Close()
 			if err != nil {
 				return "", xerrors.New("read certificate response body")
 			}
-			if int64(len(data)) > maxCertResponseBytes {
+			if int64(len(certData)) > maxCertResponseBytes {
 				return "", xerrors.New(
 					"certificate response exceeds maximum size",
 				)
 			}
-			cert, err := x509.ParseCertificate(data)
+			cert, err := x509.ParseCertificate(certData)
 			if err != nil {
 				// Do not wrap the parse error; it may contain
 				// fragments of the HTTP response body, which
@@ -280,9 +301,9 @@ func Validate(ctx context.Context, signature string, options Options) (string, e
 					"fetched data is not a valid certificate",
 				)
 			}
-			options.Intermediates.AddCert(cert)
+			pkcs7Data.Certificates = append(pkcs7Data.Certificates, cert)
 		}
-		_, err = signer.Verify(options.VerifyOptions)
+		err = pkcs7Data.VerifyWithChainAtTime(roots, currentTime)
 		if err != nil {
 			return "", xerrors.New("signature verification failed after fetching issuing certificates")
 		}
@@ -296,6 +317,24 @@ func Validate(ctx context.Context, signature string, options Options) (string, e
 	return metadata.VMID, nil
 }
 
+// ParseCertificates parses the hardcoded Azure intermediate
+// certificates and returns them as x509.Certificate values.
+func ParseCertificates() ([]*x509.Certificate, error) {
+	var certs []*x509.Certificate
+	for _, certPEM := range Certificates {
+		block, rest := pem.Decode([]byte(certPEM))
+		if len(rest) != 0 {
+			return nil, xerrors.Errorf("invalid certificate. %d bytes remain", len(rest))
+		}
+		cert, err := x509.ParseCertificate(block.Bytes)
+		if err != nil {
+			return nil, xerrors.Errorf("parse certificate: %w", err)
+		}
+		certs = append(certs, cert)
+	}
+	return certs, nil
+}
+
 // Roots are the root CAs that Azure instance-identity certificates chain to.
 // These are embedded so verification works deterministically on all
 // platforms, including macOS where the system verifier would otherwise be

coderd/azureidentity/azureidentity_test.go

@@ -1,12 +1,20 @@
 package azureidentity_test
 
 import (
+	"bytes"
 	"context"
+	"crypto/rand"
+	"crypto/rsa"
 	"crypto/x509"
+	"crypto/x509/pkix"
+	"encoding/base64"
 	"encoding/pem"
+	"math/big"
+	"runtime"
 	"testing"
 	"time"
 
+	"github.com/smallstep/pkcs7"
 	"github.com/stretchr/testify/require"
 
 	"github.com/coder/coder/v2/coderd/azureidentity"
@@ -45,10 +53,8 @@ func TestValidate(t *testing.T) {
 		t.Run(tc.name, func(t *testing.T) {
 			t.Parallel()
 			vm, err := azureidentity.Validate(context.Background(), tc.payload, azureidentity.Options{
-				VerifyOptions: x509.VerifyOptions{
-					CurrentTime: tc.date,
-				},
-				Offline: true,
+				CurrentTime: tc.date,
+				Offline:     true,
 			})
 			require.NoError(t, err)
 			require.Equal(t, tc.vmID, vm)
@@ -98,12 +104,10 @@ func TestExpiresSoon(t *testing.T) {
 	t.Skip()
 	const threshold = 1
 
-	for _, c := range azureidentity.Certificates {
-		block, rest := pem.Decode([]byte(c))
-		require.Zero(t, len(rest))
-		cert, err := x509.ParseCertificate(block.Bytes)
-		require.NoError(t, err)
+	certs, err := azureidentity.ParseCertificates()
+	require.NoError(t, err)
 
+	for _, cert := range certs {
 		expiresSoon := cert.NotAfter.Before(time.Now().AddDate(0, threshold, 0))
 		if expiresSoon {
 			t.Errorf("certificate expires within %d months %s: %s", threshold, cert.NotAfter, cert.Subject.CommonName)
@@ -150,3 +154,172 @@ func TestIsAllowedCertificateURL(t *testing.T) {
 		})
 	}
 }
+
+// testCertChain holds a three-level certificate hierarchy (Root CA,
+// Intermediate CA, Signing/leaf) together with their private keys.
+type testCertChain struct {
+	RootCert         *x509.Certificate
+	RootKey          *rsa.PrivateKey
+	IntermediateCert *x509.Certificate
+	IntermediateKey  *rsa.PrivateKey
+	SigningCert      *x509.Certificate
+	SigningKey       *rsa.PrivateKey
+}
+
+// newTestCertChain creates a fresh three-level certificate chain for
+// testing. All certificates are valid at time.Now().
+func newTestCertChain(t *testing.T) testCertChain {
+	t.Helper()
+
+	// Smaller key sizes are fine for tests; keeps them fast.
+	const keyBits = 2048
+
+	// ---- Root CA ----
+	rootKey, err := rsa.GenerateKey(rand.Reader, keyBits)
+	require.NoError(t, err)
+	rootTmpl := &x509.Certificate{
+		SerialNumber:          big.NewInt(1),
+		Subject:               pkix.Name{CommonName: "Test Root CA"},
+		NotBefore:             time.Now().Add(-time.Hour),
+		NotAfter:              time.Now().Add(24 * time.Hour),
+		KeyUsage:              x509.KeyUsageCertSign | x509.KeyUsageCRLSign,
+		BasicConstraintsValid: true,
+		IsCA:                  true,
+	}
+	rootDER, err := x509.CreateCertificate(rand.Reader, rootTmpl, rootTmpl, &rootKey.PublicKey, rootKey)
+	require.NoError(t, err)
+	rootCert, err := x509.ParseCertificate(rootDER)
+	require.NoError(t, err)
+
+	// ---- Intermediate CA ----
+	intermediateKey, err := rsa.GenerateKey(rand.Reader, keyBits)
+	require.NoError(t, err)
+	intermediateTmpl := &x509.Certificate{
+		SerialNumber:          big.NewInt(2),
+		Subject:               pkix.Name{CommonName: "Test Intermediate CA"},
+		NotBefore:             time.Now().Add(-time.Hour),
+		NotAfter:              time.Now().Add(24 * time.Hour),
+		KeyUsage:              x509.KeyUsageCertSign | x509.KeyUsageCRLSign,
+		BasicConstraintsValid: true,
+		IsCA:                  true,
+	}
+	intermediateDER, err := x509.CreateCertificate(rand.Reader, intermediateTmpl, rootCert, &intermediateKey.PublicKey, rootKey)
+	require.NoError(t, err)
+	intermediateCert, err := x509.ParseCertificate(intermediateDER)
+	require.NoError(t, err)
+
+	// ---- Signing (leaf) certificate ----
+	signingKey, err := rsa.GenerateKey(rand.Reader, keyBits)
+	require.NoError(t, err)
+	signingTmpl := &x509.Certificate{
+		SerialNumber: big.NewInt(3),
+		Subject:      pkix.Name{CommonName: "metadata.azure.com"},
+		NotBefore:    time.Now().Add(-time.Hour),
+		NotAfter:     time.Now().Add(24 * time.Hour),
+		KeyUsage:     x509.KeyUsageDigitalSignature,
+	}
+	signingDER, err := x509.CreateCertificate(rand.Reader, signingTmpl, intermediateCert, &signingKey.PublicKey, intermediateKey)
+	require.NoError(t, err)
+	signingCert, err := x509.ParseCertificate(signingDER)
+	require.NoError(t, err)
+
+	return testCertChain{
+		RootCert:         rootCert,
+		RootKey:          rootKey,
+		IntermediateCert: intermediateCert,
+		IntermediateKey:  intermediateKey,
+		SigningCert:      signingCert,
+		SigningKey:       signingKey,
+	}
+}
+
+// createSignedPKCS7 produces a base64-encoded PKCS7 SignedData
+// envelope over content, signed by the chain's leaf certificate.
+func (tc *testCertChain) createSignedPKCS7(t *testing.T, content []byte) string {
+	t.Helper()
+
+	sd, err := pkcs7.NewSignedData(content)
+	require.NoError(t, err)
+	err = sd.AddSignerChain(tc.SigningCert, tc.SigningKey, []*x509.Certificate{tc.IntermediateCert}, pkcs7.SignerInfoConfig{})
+	require.NoError(t, err)
+	der, err := sd.Finish()
+	require.NoError(t, err)
+	return base64.StdEncoding.EncodeToString(der)
+}
+
+// validationOptions returns azureidentity.Options that trust only this
+// chain's Root CA.
+func (tc *testCertChain) validationOptions() azureidentity.Options {
+	roots := x509.NewCertPool()
+	roots.AddCert(tc.RootCert)
+	return azureidentity.Options{
+		Roots:         roots,
+		Intermediates: []*x509.Certificate{tc.IntermediateCert},
+		Offline:       true,
+	}
+}
+
+func TestValidate_TamperedContent(t *testing.T) {
+	t.Parallel()
+	if runtime.GOOS == "darwin" {
+		t.Skip("pkcs7 signing uses SHA1 which may be restricted on macOS")
+	}
+
+	chain := newTestCertChain(t)
+
+	// Build a valid PKCS7 envelope.
+	original := []byte(`{"vmId":"tamper-test-vm"}`)
+	signed := chain.createSignedPKCS7(t, original)
+
+	// Decode, tamper with the content, re-encode.
+	raw, err := base64.StdEncoding.DecodeString(signed)
+	require.NoError(t, err)
+	tampered := bytes.Replace(raw, []byte("tamper-test-vm"), []byte("tampered!!!!!!"), 1)
+	require.NotEqual(t, raw, tampered, "payload should have changed")
+	tamperedB64 := base64.StdEncoding.EncodeToString(tampered)
+
+	opts := chain.validationOptions()
+	_, err = azureidentity.Validate(context.Background(), tamperedB64, opts)
+	require.Error(t, err, "tampered content must not pass validation")
+}
+
+func TestValidate_UntrustedCertWithValidSignature(t *testing.T) {
+	t.Parallel()
+	if runtime.GOOS == "darwin" {
+		t.Skip("pkcs7 signing uses SHA1 which may be restricted on macOS")
+	}
+
+	chain := newTestCertChain(t)
+
+	content := []byte(`{"vmId":"untrusted-test-vm"}`)
+	signed := chain.createSignedPKCS7(t, content)
+
+	// Build options that trust a DIFFERENT root, so the chain
+	// should not verify.
+	otherRoot, err := rsa.GenerateKey(rand.Reader, 2048)
+	require.NoError(t, err)
+	otherRootTmpl := &x509.Certificate{
+		SerialNumber:          big.NewInt(99),
+		Subject:               pkix.Name{CommonName: "Other Root CA"},
+		NotBefore:             time.Now().Add(-time.Hour),
+		NotAfter:              time.Now().Add(24 * time.Hour),
+		KeyUsage:              x509.KeyUsageCertSign | x509.KeyUsageCRLSign,
+		BasicConstraintsValid: true,
+		IsCA:                  true,
+	}
+	otherRootDER, err := x509.CreateCertificate(rand.Reader, otherRootTmpl, otherRootTmpl, &otherRoot.PublicKey, otherRoot)
+	require.NoError(t, err)
+	otherRootCert, err := x509.ParseCertificate(otherRootDER)
+	require.NoError(t, err)
+
+	untrustedRoots := x509.NewCertPool()
+	untrustedRoots.AddCert(otherRootCert)
+	opts := azureidentity.Options{
+		Roots:         untrustedRoots,
+		Intermediates: []*x509.Certificate{chain.IntermediateCert},
+		Offline:       true,
+	}
+
+	_, err = azureidentity.Validate(context.Background(), signed, opts)
+	require.Error(t, err, "signature from untrusted CA must not pass validation")
+}

coderd/coderd.go

@@ -3,7 +3,6 @@ package coderd
 import (
 	"context"
 	"crypto/tls"
-	"crypto/x509"
 	"database/sql"
 	_ "embed"
 	"errors"
@@ -52,6 +51,7 @@ import (
 	"github.com/coder/coder/v2/coderd/appearance"
 	"github.com/coder/coder/v2/coderd/audit"
 	"github.com/coder/coder/v2/coderd/awsidentity"
+	"github.com/coder/coder/v2/coderd/azureidentity"
 	"github.com/coder/coder/v2/coderd/boundaryusage"
 	"github.com/coder/coder/v2/coderd/connectionlog"
 	"github.com/coder/coder/v2/coderd/cryptokeys"
@@ -173,7 +173,7 @@ type Options struct {
 	ChatdInstructionLookupTimeout  time.Duration
 	AWSCertificates                awsidentity.Certificates
 	Authorizer                     rbac.Authorizer
-	AzureCertificates              x509.VerifyOptions
+	AzureCertificates              azureidentity.Options
 	GoogleTokenValidator           *idtoken.Validator
 	GithubOAuth2Config             *GithubOAuth2Config
 	OIDCConfig                     *OIDCConfig

coderd/coderdtest/coderdtest.go

@@ -32,11 +32,11 @@ import (
 	"time"
 
 	"cloud.google.com/go/compute/metadata"
-	"github.com/fullsailor/pkcs7"
 	"github.com/go-chi/chi/v5"
 	"github.com/golang-jwt/jwt/v4"
 	"github.com/google/uuid"
 	"github.com/prometheus/client_golang/prometheus"
+	"github.com/smallstep/pkcs7"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 	"golang.org/x/text/cases"
@@ -59,6 +59,7 @@ import (
 	"github.com/coder/coder/v2/coderd/audit"
 	"github.com/coder/coder/v2/coderd/autobuild"
 	"github.com/coder/coder/v2/coderd/awsidentity"
+	"github.com/coder/coder/v2/coderd/azureidentity"
 	"github.com/coder/coder/v2/coderd/connectionlog"
 	"github.com/coder/coder/v2/coderd/cryptokeys"
 	"github.com/coder/coder/v2/coderd/database"
@@ -119,7 +120,7 @@ type Options struct {
 	AppHostname                    string
 	AWSCertificates                awsidentity.Certificates
 	Authorizer                     rbac.Authorizer
-	AzureCertificates              x509.VerifyOptions
+	AzureCertificates              azureidentity.Options
 	GithubOAuth2Config             *coderd.GithubOAuth2Config
 	RealIPConfig                   *httpmw.RealIPConfig
 	OIDCConfig                     *coderd.OIDCConfig
@@ -1634,27 +1635,63 @@ func NewAWSInstanceIdentity(t testing.TB, instanceID string) (awsidentity.Certif
 		}
 }
 
-// NewAzureInstanceIdentity returns a metadata client and ID token validator for faking
-// instance authentication for Azure.
-func NewAzureInstanceIdentity(t testing.TB, instanceID string) (x509.VerifyOptions, *http.Client) {
-	privateKey, err := rsa.GenerateKey(rand.Reader, 2048)
+// NewAzureInstanceIdentity returns a metadata client and ID token
+// validator for faking instance authentication for Azure. It builds
+// a realistic 3-level certificate chain (Root CA -> Intermediate ->
+// Signing Cert) to match the real Azure trust hierarchy.
+func NewAzureInstanceIdentity(t testing.TB, instanceID string) (azureidentity.Options, *http.Client) {
+	// Root CA (self-signed, trusted).
+	rootKey, err := rsa.GenerateKey(rand.Reader, 2048)
+	require.NoError(t, err)
+	rootTmpl := &x509.Certificate{
+		SerialNumber:          big.NewInt(1),
+		Subject:               pkix.Name{CommonName: "Test Root CA"},
+		NotBefore:             time.Now().Add(-time.Hour),
+		NotAfter:              time.Now().AddDate(10, 0, 0),
+		IsCA:                  true,
+		BasicConstraintsValid: true,
+		KeyUsage:              x509.KeyUsageCertSign | x509.KeyUsageCRLSign,
+	}
+	rootDER, err := x509.CreateCertificate(rand.Reader, rootTmpl, rootTmpl, &rootKey.PublicKey, rootKey)
+	require.NoError(t, err)
+	rootCert, err := x509.ParseCertificate(rootDER)
 	require.NoError(t, err)
 
-	rawCertificate, err := x509.CreateCertificate(rand.Reader, &x509.Certificate{
-		SerialNumber: big.NewInt(2022),
+	// Intermediate CA (signed by root).
+	interKey, err := rsa.GenerateKey(rand.Reader, 2048)
+	require.NoError(t, err)
+	interTmpl := &x509.Certificate{
+		SerialNumber:          big.NewInt(2),
+		Subject:               pkix.Name{CommonName: "Test Intermediate CA"},
+		NotBefore:             time.Now().Add(-time.Hour),
+		NotAfter:              time.Now().AddDate(5, 0, 0),
+		IsCA:                  true,
+		BasicConstraintsValid: true,
+		KeyUsage:              x509.KeyUsageCertSign | x509.KeyUsageCRLSign,
+	}
+	interDER, err := x509.CreateCertificate(rand.Reader, interTmpl, rootCert, &interKey.PublicKey, rootKey)
+	require.NoError(t, err)
+	interCert, err := x509.ParseCertificate(interDER)
+	require.NoError(t, err)
+
+	// Signing cert (leaf, signed by intermediate).
+	signKey, err := rsa.GenerateKey(rand.Reader, 2048)
+	require.NoError(t, err)
+	signTmpl := &x509.Certificate{
+		SerialNumber: big.NewInt(3),
+		Subject:      pkix.Name{CommonName: "metadata.azure.com"},
+		NotBefore:    time.Now().Add(-time.Hour),
 		NotAfter:     time.Now().AddDate(1, 0, 0),
-		Subject: pkix.Name{
-			CommonName: "metadata.azure.com",
-		},
-	}, &x509.Certificate{}, &privateKey.PublicKey, privateKey)
-	require.NoError(t, err)
-
-	certificate, err := x509.ParseCertificate(rawCertificate)
+	}
+	signDER, err := x509.CreateCertificate(rand.Reader, signTmpl, interCert, &signKey.PublicKey, interKey)
+	require.NoError(t, err)
+	signCert, err := x509.ParseCertificate(signDER)
 	require.NoError(t, err)
 
+	// Build PKCS7 signed data with only the signing cert.
 	signed, err := pkcs7.NewSignedData([]byte(`{"vmId":"` + instanceID + `"}`))
 	require.NoError(t, err)
-	err = signed.AddSigner(certificate, privateKey, pkcs7.SignerInfoConfig{})
+	err = signed.AddSigner(signCert, signKey, pkcs7.SignerInfoConfig{})
 	require.NoError(t, err)
 	signatureRaw, err := signed.Finish()
 	require.NoError(t, err)
@@ -1667,12 +1704,12 @@ func NewAzureInstanceIdentity(t testing.TB, instanceID string) (x509.VerifyOptio
 	})
 	require.NoError(t, err)
 
-	certPool := x509.NewCertPool()
-	certPool.AddCert(certificate)
+	roots := x509.NewCertPool()
+	roots.AddCert(rootCert)
 
-	return x509.VerifyOptions{
-			Intermediates: certPool,
-			Roots:         certPool,
+	return azureidentity.Options{
+			Roots:         roots,
+			Intermediates: []*x509.Certificate{interCert},
 		}, &http.Client{
 			Transport: roundTripper(func(r *http.Request) (*http.Response, error) {
 				// Only handle metadata server requests.

coderd/workspaceresourceauth.go

@@ -35,9 +35,7 @@ func (api *API) postWorkspaceAuthAzureInstanceIdentity(rw http.ResponseWriter, r
 	if !httpapi.Read(ctx, rw, r, &req) {
 		return
 	}
-	instanceID, err := azureidentity.Validate(r.Context(), req.Signature, azureidentity.Options{
-		VerifyOptions: api.AzureCertificates,
-	})
+	instanceID, err := azureidentity.Validate(r.Context(), req.Signature, api.AzureCertificates)
 	if err != nil {
 		// Log the full error for operators but return only a
 		// generic message to the caller. Errors from the

go.mod

@@ -151,7 +151,6 @@ require (
 	github.com/fatih/structs v1.1.0
 	github.com/fatih/structtag v1.2.0
 	github.com/fergusstrange/embedded-postgres v1.34.0
-	github.com/fullsailor/pkcs7 v0.0.0-20190404230743-d7302db945fa
 	github.com/gen2brain/beeep v0.11.1
 	github.com/gliderlabs/ssh v0.3.8
 	github.com/go-chi/chi/v5 v5.2.4
@@ -217,7 +216,6 @@ require (
 	github.com/valyala/fasthttp v1.71.0
 	github.com/wagslane/go-password-validator v0.3.0
 	github.com/zclconf/go-cty-yaml v1.2.0
-	go.mozilla.org/pkcs7 v0.9.0
 	go.nhat.io/otelsql v0.16.0
 	go.opentelemetry.io/otel v1.43.0
 	go.opentelemetry.io/otel/exporters/otlp/otlptrace v1.40.0
@@ -518,6 +516,7 @@ require (
 	github.com/mark3labs/mcp-go v0.38.0
 	github.com/openai/openai-go/v3 v3.28.0
 	github.com/shopspring/decimal v1.4.0
+	github.com/smallstep/pkcs7 v0.2.1
 	github.com/sony/gobreaker/v2 v2.4.0
 	github.com/tidwall/sjson v1.2.5
 	gonum.org/v1/gonum v0.17.0

go.sum

@@ -490,8 +490,6 @@ github.com/frankban/quicktest v1.14.6 h1:7Xjx+VpznH+oBnejlPUj8oUpdxnVs4f8XU8WnHk
 github.com/frankban/quicktest v1.14.6/go.mod h1:4ptaffx2x8+WTWXmUCuVU6aPUX1/Mz7zb5vbUoiM6w0=
 github.com/fsnotify/fsnotify v1.10.1 h1:b0/UzAf9yR5rhf3RPm9gf3ehBPpf0oZKIjtpKrx59Ho=
 github.com/fsnotify/fsnotify v1.10.1/go.mod h1:TLheqan6HD6GBK6PrDWyDPBaEV8LspOxvPSjC+bVfgo=
-github.com/fullsailor/pkcs7 v0.0.0-20190404230743-d7302db945fa h1:RDBNVkRviHZtvDvId8XSGPu3rmpmSe+wKRcEWNgsfWU=
-github.com/fullsailor/pkcs7 v0.0.0-20190404230743-d7302db945fa/go.mod h1:KnogPXtdwXqoenmZCw6S+25EAm2MkxbG0deNDu4cbSA=
 github.com/fxamacker/cbor/v2 v2.9.0 h1:NpKPmjDBgUfBms6tr6JZkTHtfFGcMKsw3eGcmD/sapM=
 github.com/fxamacker/cbor/v2 v2.9.0/go.mod h1:vM4b+DJCtHn+zz7h3FFp/hDAI9WNWCsZj23V5ytsSxQ=
 github.com/gabriel-vasile/mimetype v1.4.12 h1:e9hWvmLYvtp846tLHam2o++qitpguFiYCKbn0w9jyqw=
@@ -1086,6 +1084,8 @@ github.com/skeema/knownhosts v1.3.1 h1:X2osQ+RAjK76shCbvhHHHVl3ZlgDm8apHEHFqRjnB
 github.com/skeema/knownhosts v1.3.1/go.mod h1:r7KTdC8l4uxWRyK2TpQZ/1o5HaSzh06ePQNxPwTcfiY=
 github.com/skratchdot/open-golang v0.0.0-20200116055534-eef842397966 h1:JIAuq3EEf9cgbU6AtGPK4CTG3Zf6CKMNqf0MHTggAUA=
 github.com/skratchdot/open-golang v0.0.0-20200116055534-eef842397966/go.mod h1:sUM3LWHvSMaG192sy56D9F7CNvL7jUJVXoqM1QKLnog=
+github.com/smallstep/pkcs7 v0.2.1 h1:6Kfzr/QizdIuB6LSv8y1LJdZ3aPSfTNhTLqAx9CTLfA=
+github.com/smallstep/pkcs7 v0.2.1/go.mod h1:RcXHsMfL+BzH8tRhmrF1NkkpebKpq3JEM66cOFxanf0=
 github.com/sony/gobreaker/v2 v2.4.0 h1:g2KJRW1Ubty3+ZOcSEUN7K+REQJdN6yo6XvaML+jptg=
 github.com/sony/gobreaker/v2 v2.4.0/go.mod h1:pTyFJgcZ3h2tdQVLZZruK2C0eoFL1fb/G83wK1ZQl+s=
 github.com/sosedoff/gitkit v0.4.0 h1:opyQJ/h9xMRLsz2ca/2CRXtstePcpldiZN8DpLLF8Os=
@@ -1272,8 +1272,6 @@ github.com/zeebo/errs v1.4.0 h1:XNdoD/RRMKP7HD0UhJnIzUy74ISdGGxURlYG8HSWSfM=
 github.com/zeebo/errs v1.4.0/go.mod h1:sgbWHsvVuTPHcqJJGQ1WhI5KbWlHYz+2+2C/LSEtCw4=
 github.com/zeebo/xxh3 v1.0.2 h1:xZmwmqxHZA8AI603jOQ0tMqmBr9lPeFwGg6d+xy9DC0=
 github.com/zeebo/xxh3 v1.0.2/go.mod h1:5NWz9Sef7zIDm2JHfFlcQvNekmcEl9ekUZQQKCYaDcA=
-go.mozilla.org/pkcs7 v0.9.0 h1:yM4/HS9dYv7ri2biPtxt8ikvB37a980dg69/pKmS+eI=
-go.mozilla.org/pkcs7 v0.9.0/go.mod h1:SNgMg+EgDFwmvSmLRTNKC5fegJjB7v23qTQ0XLGUNHk=
 go.nhat.io/otelsql v0.16.0 h1:MUKhNSl7Vk1FGyopy04FBDimyYogpRFs0DBB9frQal0=
 go.nhat.io/otelsql v0.16.0/go.mod h1:YB2ocf0Q8+kK4kxzXYUOHj7P2Km8tNmE2QlRS0frUtc=
 go.opentelemetry.io/auto/sdk v1.2.1 h1:jXsnJ4Lmnqd11kwkBV2LgLoFMZKizbCi5fNZ/ipaZ64=
@@ -1373,6 +1371,7 @@ golang.org/x/crypto v0.17.0/go.mod h1:gCAAfMLgwOJRpTjQ2zCCt2OcSfYMTeZVSRtQlPC7Nq
 golang.org/x/crypto v0.19.0/go.mod h1:Iy9bg/ha4yyC70EfRS8jz+B6ybOBKMaSxLj6P6oBDfU=
 golang.org/x/crypto v0.23.0/go.mod h1:CKFgDieR+mRhux2Lsu27y0fO304Db0wZe70UKqHu0v8=
 golang.org/x/crypto v0.31.0/go.mod h1:kDsLvtWBEx7MV9tJOj9bnXsPbxwJQ6csT/x4KIN4Ssk=
+golang.org/x/crypto v0.33.0/go.mod h1:bVdXmD7IV/4GdElGPozy6U7lWdRXA4qyRVGJV57uQ5M=
 golang.org/x/crypto v0.51.0 h1:IBPXwPfKxY7cWQZ38ZCIRPI50YLeevDLlLnyC5wRGTI=
 golang.org/x/crypto v0.51.0/go.mod h1:8AdwkbraGNABw2kOX6YFPs3WM22XqI4EXEd8g+x7Oc8=
 golang.org/x/exp v0.0.0-20260410095643-746e56fc9e2f h1:W3F4c+6OLc6H2lb//N1q4WpJkhzJCK5J6kUi1NTVXfM=
@@ -1418,6 +1417,7 @@ golang.org/x/sync v0.3.0/go.mod h1:FU7BRWz2tNW+3quACPkgCx/L+uEAv1htQ0V83Z9Rj+Y=
 golang.org/x/sync v0.6.0/go.mod h1:Czt+wKu1gCyEFDUtn0jG5QVvpJ6rzVqr5aXyt9drQfk=
 golang.org/x/sync v0.7.0/go.mod h1:Czt+wKu1gCyEFDUtn0jG5QVvpJ6rzVqr5aXyt9drQfk=
 golang.org/x/sync v0.10.0/go.mod h1:Czt+wKu1gCyEFDUtn0jG5QVvpJ6rzVqr5aXyt9drQfk=
+golang.org/x/sync v0.11.0/go.mod h1:Czt+wKu1gCyEFDUtn0jG5QVvpJ6rzVqr5aXyt9drQfk=
 golang.org/x/sync v0.20.0 h1:e0PTpb7pjO8GAtTs2dQ6jYa5BWYlMuX047Dco/pItO4=
 golang.org/x/sync v0.20.0/go.mod h1:9xrNwdLfx4jkKbNva9FpL6vEN7evnE43NNNJQ2LF3+0=
 golang.org/x/sys v0.0.0-20190215142949-d0b11bdaac8a/go.mod h1:STP8DvDyc/dI5b8T5hshtkjS+E42TnysNCUPdjciGhY=
@@ -1457,6 +1457,7 @@ golang.org/x/sys v0.15.0/go.mod h1:/VUhepiaJMQUp4+oa/7Zr1D23ma6VTLIYjOOTFZPUcA=
 golang.org/x/sys v0.17.0/go.mod h1:/VUhepiaJMQUp4+oa/7Zr1D23ma6VTLIYjOOTFZPUcA=
 golang.org/x/sys v0.20.0/go.mod h1:/VUhepiaJMQUp4+oa/7Zr1D23ma6VTLIYjOOTFZPUcA=
 golang.org/x/sys v0.28.0/go.mod h1:/VUhepiaJMQUp4+oa/7Zr1D23ma6VTLIYjOOTFZPUcA=
+golang.org/x/sys v0.30.0/go.mod h1:/VUhepiaJMQUp4+oa/7Zr1D23ma6VTLIYjOOTFZPUcA=
 golang.org/x/sys v0.44.0 h1:ildZl3J4uzeKP07r2F++Op7E9B29JRUy+a27EibtBTQ=
 golang.org/x/sys v0.44.0/go.mod h1:4GL1E5IUh+htKOUEOaiffhrAeqysfVGipDYzABqnCmw=
 golang.org/x/telemetry v0.0.0-20240228155512-f48c80bd79b2/go.mod h1:TeRTkGYfJXctD9OcfyVLyj2J3IxLnKwHJR8f4D8a3YE=
@@ -1473,6 +1474,7 @@ golang.org/x/term v0.15.0/go.mod h1:BDl952bC7+uMoWR75FIrCDx79TPU9oHkTZ9yRbYOrX0=
 golang.org/x/term v0.17.0/go.mod h1:lLRBjIVuehSbZlaOtGMbcMncT+aqLLLmKrsjNrUguwk=
 golang.org/x/term v0.20.0/go.mod h1:8UkIAJTvZgivsXaD6/pH6U9ecQzZ45awqEOzuCvwpFY=
 golang.org/x/term v0.27.0/go.mod h1:iMsnZpn0cago0GOrHO2+Y7u7JPn5AylBrcoWkElMTSM=
+golang.org/x/term v0.29.0/go.mod h1:6bl4lRlvVuDgSf3179VpIxBF0o10JUpXWOnI7nErv7s=
 golang.org/x/term v0.43.0 h1:S4RLU2sB31O/NCl+zFN9Aru9A/Cq2aqKpTZJ6B+DwT4=
 golang.org/x/term v0.43.0/go.mod h1:lrhlHNdQJHO+1qVYiHfFKVuVioJIheAc3fBSMFYEIsk=
 golang.org/x/text v0.3.0/go.mod h1:NqM8EUOU14njkJ3fqMW+pc6Ldnwhi/IjpwHt7yyuwOQ=
@@ -1487,6 +1489,7 @@ golang.org/x/text v0.13.0/go.mod h1:TvPlkZtksWOMsz7fbANvkp4WM8x/WCo/om8BMLbz+aE=
 golang.org/x/text v0.14.0/go.mod h1:18ZOQIKpY8NJVqYksKHtTdi31H5itFRjB5/qKTNYzSU=
 golang.org/x/text v0.15.0/go.mod h1:18ZOQIKpY8NJVqYksKHtTdi31H5itFRjB5/qKTNYzSU=
 golang.org/x/text v0.21.0/go.mod h1:4IBbMaMmOPCJ8SecivzSH54+73PCFmPWxNTLm+vZkEQ=
+golang.org/x/text v0.22.0/go.mod h1:YRoo4H8PVmsu+E3Ou7cqLVH8oXWIHVoX0jqUWALQhfY=
 golang.org/x/text v0.37.0 h1:Cqjiwd9eSg8e0QAkyCaQTNHFIIzWtidPahFWR83rTrc=
 golang.org/x/text v0.37.0/go.mod h1:a5sjxXGs9hsn/AJVwuElvCAo9v8QYLzvavO5z2PiM38=
 golang.org/x/time v0.15.0 h1:bbrp8t3bGUeFOx08pvsMYRTCVSMk89u4tKbNOZbp88U=