Ed25519 and Ed448 keys support

ebourg · May 10, 2024 · c723528 · c723528
1 parent 6003001
commit c723528
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Showing 10 changed files with 217 additions and 2 deletions.
diff --git a/README.md b/README.md
@@ -60,6 +60,7 @@ See https://ebourg.github.io/jsign for more information.
 * The `remove` command has been added to remove the signature from a signed file
 * The JCA provider now works with [apksigner](https://developer.android.com/tools/apksigner) for signing Android applications
 * RSA 4096 keys are supported with the `PIV` storetype (for Yubikeys with firmware version 5.7 or higher)
+* Certificates using an Ed25519 or Ed448 key are now supported (experimental)
 * The APPX/MSIX bundles are now signed with the correct Authenticode UUID
 * The error message displayed when the password of a PKCS#12 keystore is missing has been fixed
 * The log4j configuration warning displayed when signing a MSI file has been fixed (contributed by Pascal Davoust)

diff --git a/jsign-core/src/main/java/net/jsign/AuthenticodeSigner.java b/jsign-core/src/main/java/net/jsign/AuthenticodeSigner.java
@@ -29,6 +29,8 @@
 import java.security.cert.CertificateEncodingException;
 import java.security.cert.X509Certificate;
 import java.util.ArrayList;
+import java.util.Arrays;
+import java.util.Collection;
 import java.util.List;
 
 import org.bouncycastle.asn1.ASN1Encodable;
@@ -300,9 +302,18 @@ private String getSignatureAlgorithm() {
             return signatureAlgorithm;
         } else if ("EC".equals(privateKey.getAlgorithm())) {
             return digestAlgorithm + "withECDSA";
-        } else {
-            return digestAlgorithm + "with" + privateKey.getAlgorithm();
+        } else if ("EdDSA".equals(privateKey.getAlgorithm())) {
+            X509Certificate certificate = (X509Certificate) chain[0];
+            PublicKey publicKey = certificate.getPublicKey();
+            if (publicKey.toString().contains("Ed25519")) {
+                return "Ed25519";
+            } else if (publicKey.toString().contains("Ed448")) {
+                return "Ed448";
+            }
+            // return ((EdECKey) publicKey).getParams().getName(); // todo with Java 15+
         }
+
+        return digestAlgorithm + "with" + privateKey.getAlgorithm();
     }
 
     /**
@@ -574,6 +585,11 @@ protected CMSSignedData addNestedSignature(CMSSignedData primary, CMSSignedData
      * @return an AlgorithmIdentifier for the digestAlgorithm and including parameters
      */
     protected AlgorithmIdentifier createContentDigestAlgorithmIdentifier(AlgorithmIdentifier signatureAlgorithm) {
+        if ("1.3.101.112".equals(signatureAlgorithm.getAlgorithm().getId()) // Ed25519
+            || "1.3.101.113".equals(signatureAlgorithm.getAlgorithm().getId())) { // Ed448
+            return new AlgorithmIdentifier(digestAlgorithm.oid, DERNull.INSTANCE);
+        }
+
         AlgorithmIdentifier ai = new DefaultDigestAlgorithmIdentifierFinder().find(signatureAlgorithm);
         if (ai.getParameters() == null) {
             // Always include parameters to align with what signtool does

diff --git a/jsign-core/src/test/java/net/jsign/PESignerTest.java b/jsign-core/src/test/java/net/jsign/PESignerTest.java
@@ -28,6 +28,8 @@
 import java.util.HashSet;
 
 import org.apache.commons.io.FileUtils;
+import org.apache.commons.lang3.JavaVersion;
+import org.apache.commons.lang3.SystemUtils;
 import org.bouncycastle.asn1.DERNull;
 import org.bouncycastle.asn1.cms.CMSAttributes;
 import org.bouncycastle.asn1.nist.NISTObjectIdentifiers;
@@ -547,6 +549,46 @@ public void testSignWithECKey() throws Exception {
         }
     }
 
+    @Test
+    public void testSignWithEd25519Key() throws Exception {
+        Assume.assumeTrue("EdDSA requires Java 15 or higher", SystemUtils.isJavaVersionAtLeast(JavaVersion.JAVA_15));
+
+        KeyStore keystore = new KeyStoreBuilder().keystore("target/test-classes/keystores/keystore-ed25519.p12").storepass("password").build();
+
+        File sourceFile = new File("target/test-classes/wineyes.exe");
+        File targetFile = new File("target/test-classes/wineyes-signed-ed25519.exe");
+
+        FileUtils.copyFile(sourceFile, targetFile);
+
+        AuthenticodeSigner signer = new AuthenticodeSigner(keystore, ALIAS, PRIVATE_KEY_PASSWORD).withTimestamping(false);
+
+        try (PEFile peFile = new PEFile(targetFile)) {
+            signer.sign(peFile);
+
+            SignatureAssert.assertSigned(peFile, SHA256);
+        }
+    }
+
+    @Test
+    public void testSignWithEd448Key() throws Exception {
+        Assume.assumeTrue("EdDSA requires Java 15 or higher", SystemUtils.isJavaVersionAtLeast(JavaVersion.JAVA_15));
+
+        KeyStore keystore = new KeyStoreBuilder().keystore("target/test-classes/keystores/keystore-ed448.p12").storepass("password").build();
+
+        File sourceFile = new File("target/test-classes/wineyes.exe");
+        File targetFile = new File("target/test-classes/wineyes-signed-ed448.exe");
+
+        FileUtils.copyFile(sourceFile, targetFile);
+
+        AuthenticodeSigner signer = new AuthenticodeSigner(keystore, ALIAS, PRIVATE_KEY_PASSWORD).withTimestamping(false);
+
+        try (PEFile peFile = new PEFile(targetFile)) {
+            signer.sign(peFile);
+
+            SignatureAssert.assertSigned(peFile, SHA256);
+        }
+    }
+
     @Test
     public void testContentDigestAlgorithmIdentifier() throws Exception {
         // ensure the algorithm identifier has a DER NULL optional parameters field to match the signtool output

diff --git a/jsign-core/src/test/resources/keystores/generate-certificate-chain.sh b/jsign-core/src/test/resources/keystores/generate-certificate-chain.sh
@@ -52,6 +52,14 @@ openssl req -new -key privatekey-ec-p384.pkcs1.pem -subj "/CN=Jsign Code Signing
 openssl x509 -req -in jsign-test-certificate-ec.csr -CA jsign-code-signing-ca.pem -CAkey jsign-code-signing-ca.key -CAcreateserial \
              -out jsign-test-certificate-ec.pem $CERT_OPTS -extfile extensions.cnf -extensions final
 
+openssl req -new -key privatekey-ed25519.pem -subj "/CN=Jsign Code Signing Test Certificate $YEAR (Ed25519)" -out jsign-test-certificate-ed25519.csr
+openssl x509 -req -in jsign-test-certificate-ed25519.csr -CA jsign-code-signing-ca.pem -CAkey jsign-code-signing-ca.key -CAcreateserial \
+             -out jsign-test-certificate-ed25519.pem $CERT_OPTS -extfile extensions.cnf -extensions final
+
+openssl req -new -key privatekey-ed448.pem -subj "/CN=Jsign Code Signing Test Certificate $YEAR (Ed448)" -out jsign-test-certificate-ed448.csr
+openssl x509 -req -in jsign-test-certificate-ed448.csr -CA jsign-code-signing-ca.pem -CAkey jsign-code-signing-ca.key -CAcreateserial \
+             -out jsign-test-certificate-ed448.pem $CERT_OPTS -extfile extensions.cnf -extensions final
+
 # Generate the certificate chains
 cat jsign-root-ca.pem jsign-code-signing-ca.pem jsign-test-certificate.pem > jsign-test-certificate-full-chain-reversed.pem
 cat jsign-test-certificate.pem jsign-code-signing-ca.pem jsign-root-ca.pem > jsign-test-certificate-full-chain.pem
@@ -70,6 +78,12 @@ openssl pkcs12 $OPENSSL_OPTS -in jsign-test-certificate.pem            -out keys
 OPENSSL_OPTS="-export -inkey privatekey-ec-p384.pkcs1.pem -name test -passout pass:password"
 openssl pkcs12 $OPENSSL_OPTS -in jsign-test-certificate-ec.pem         -out keystore-ec.p12
 
+OPENSSL_OPTS="-export -inkey privatekey-ed25519.pem -name test -passout pass:password"
+openssl pkcs12 $OPENSSL_OPTS -in jsign-test-certificate-ed25519.pem    -out keystore-ed25519.p12
+
+OPENSSL_OPTS="-export -inkey privatekey-ed448.pem -name test -passout pass:password"
+openssl pkcs12 $OPENSSL_OPTS -in jsign-test-certificate-ed448.pem      -out keystore-ed448.p12
+
 # Generate the Java keystores
 KEYTOOL_OPTS="-importkeystore -srcstoretype pkcs12 -srcstorepass password -srcalias test -deststoretype jks -deststorepass password -destalias test"
 keytool $KEYTOOL_OPTS -srckeystore keystore.p12          -destkeystore keystore.jks

diff --git a/jsign-core/src/test/resources/keystores/jsign-test-certificate-ed25519.pem b/jsign-core/src/test/resources/keystores/jsign-test-certificate-ed25519.pem
@@ -0,0 +1,67 @@
+Certificate:
+    Data:
+        Version: 3 (0x2)
+        Serial Number:
+            23:2a:e7:47:43:b0:ae:4d:a7:4b:ea:e1:53:87:64:4a:f6:ca:7a:05
+        Signature Algorithm: sha256WithRSAEncryption
+        Issuer: CN = Jsign Code Signing CA 2024
+        Validity
+            Not Before: May 10 13:08:21 2024 GMT
+            Not After : May 10 13:08:21 2044 GMT
+        Subject: CN = Jsign Code Signing Test Certificate 2024 (Ed25519)
+        Subject Public Key Info:
+            Public Key Algorithm: ED25519
+                ED25519 Public-Key:
+                pub:
+                    23:f7:02:37:90:f2:31:ff:7a:a1:24:99:a2:48:77:
+                    91:cc:ba:4c:44:bd:6b:c8:7c:cf:b3:ab:68:1e:2d:
+                    2f:30
+        X509v3 extensions:
+            X509v3 Basic Constraints: 
+                CA:FALSE
+            X509v3 Key Usage: 
+                Digital Signature
+            X509v3 Extended Key Usage: 
+                Code Signing
+            X509v3 Subject Key Identifier: 
+                09:4F:86:91:81:F8:C1:BD:C4:B6:FE:C5:66:7E:19:A9:17:44:21:4A
+            X509v3 Authority Key Identifier: 
+                E2:71:4A:A3:53:E9:58:2A:7B:94:44:3D:3B:AE:8A:01:D4:E5:04:FD
+            Authority Information Access: 
+                CA Issuers - URI:http://raw.githubusercontent.com/ebourg/jsign/master/jsign-core/src/test/resources/keystores/jsign-code-signing-ca.cer
+    Signature Algorithm: sha256WithRSAEncryption
+    Signature Value:
+        0d:e8:75:5a:94:4c:0c:a1:b0:c6:8b:0d:98:c7:31:3b:5e:a8:
+        c6:7f:6d:c4:11:bf:27:5c:93:9f:28:9d:97:40:1d:63:83:c2:
+        bf:ff:f4:e1:fd:b6:43:fd:5d:6e:99:b9:e2:82:aa:c1:3c:b2:
+        c3:86:c4:bf:d1:ec:dd:23:d5:8e:1d:48:e6:10:d7:46:eb:fc:
+        a8:20:49:23:9c:1c:0d:83:22:54:92:ed:02:57:f7:22:20:a9:
+        5d:12:fb:ec:36:6c:85:b4:38:27:e4:b2:d8:26:7c:c1:a3:83:
+        22:25:58:ac:12:84:b6:7e:c6:17:1c:57:8e:bf:70:15:1b:67:
+        1d:a6:fe:9d:de:0a:e4:dc:92:f4:8c:c0:6f:a4:ef:2f:96:89:
+        05:23:c0:20:f9:4a:52:62:8c:cc:b6:8d:fb:f8:0c:5d:4f:11:
+        85:1a:5b:57:08:98:e8:01:7e:19:9a:c8:f8:6a:0f:b4:4b:d2:
+        9f:84:a5:bb:ce:c4:5d:1f:96:4d:b8:cb:d2:26:4a:df:66:45:
+        32:a1:10:d2:e3:c3:9d:57:45:9e:55:b8:d7:5f:a9:56:2a:2f:
+        e6:df:b4:5f:8a:9c:40:e8:8f:ee:2f:d7:bb:0c:d9:3e:94:dd:
+        57:fb:aa:55:18:2e:3a:f3:91:a3:42:a3:85:a5:46:a3:88:5f:
+        ae:ec:79:ad
+-----BEGIN CERTIFICATE-----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+-----END CERTIFICATE-----
diff --git a/jsign-core/src/test/resources/keystores/jsign-test-certificate-ed448.pem b/jsign-core/src/test/resources/keystores/jsign-test-certificate-ed448.pem
@@ -0,0 +1,68 @@
+Certificate:
+    Data:
+        Version: 3 (0x2)
+        Serial Number:
+            23:2a:e7:47:43:b0:ae:4d:a7:4b:ea:e1:53:87:64:4a:f6:ca:7a:06
+        Signature Algorithm: sha256WithRSAEncryption
+        Issuer: CN = Jsign Code Signing CA 2024
+        Validity
+            Not Before: May 10 13:08:21 2024 GMT
+            Not After : May 10 13:08:21 2044 GMT
+        Subject: CN = Jsign Code Signing Test Certificate 2024 (Ed448)
+        Subject Public Key Info:
+            Public Key Algorithm: ED448
+                ED448 Public-Key:
+                pub:
+                    78:06:56:5e:32:f1:1a:7e:b2:cf:70:b1:15:52:32:
+                    d4:5d:f9:cb:48:ec:08:72:cf:e6:25:7a:19:fa:c4:
+                    85:7d:2d:51:ab:3b:ee:fe:70:c6:a8:96:bc:37:01:
+                    d1:59:72:d2:bb:f1:44:7e:d9:17:65:00
+        X509v3 extensions:
+            X509v3 Basic Constraints: 
+                CA:FALSE
+            X509v3 Key Usage: 
+                Digital Signature
+            X509v3 Extended Key Usage: 
+                Code Signing
+            X509v3 Subject Key Identifier: 
+                3A:BD:FC:B1:93:A6:62:8D:23:A7:C5:65:AB:91:8E:76:1A:88:92:77
+            X509v3 Authority Key Identifier: 
+                E2:71:4A:A3:53:E9:58:2A:7B:94:44:3D:3B:AE:8A:01:D4:E5:04:FD
+            Authority Information Access: 
+                CA Issuers - URI:http://raw.githubusercontent.com/ebourg/jsign/master/jsign-core/src/test/resources/keystores/jsign-code-signing-ca.cer
+    Signature Algorithm: sha256WithRSAEncryption
+    Signature Value:
+        53:39:73:2c:fa:bb:45:cc:bc:7d:ea:43:f4:c6:59:54:58:fe:
+        87:4e:c7:c8:9c:cc:a9:55:ac:a0:da:57:88:7c:f5:51:07:f5:
+        67:21:f5:eb:33:ac:70:7f:a9:9a:d7:d4:eb:0d:91:10:d8:8b:
+        f8:5a:df:5d:74:3a:d8:df:2f:0e:9e:ac:c6:d5:95:b4:13:35:
+        34:64:07:c9:fa:36:57:99:49:1b:73:ae:02:63:3b:af:f9:bf:
+        6d:03:ec:3b:cc:2d:76:70:82:d6:47:5c:75:ae:cd:79:26:7e:
+        87:57:25:a5:93:23:c0:f9:a0:b7:84:49:27:b6:6d:0b:f2:a6:
+        aa:be:de:46:ea:d8:0b:6a:81:69:ea:f2:59:75:37:90:d1:86:
+        5b:f1:4e:50:7c:fb:83:fb:a5:36:1c:ef:d1:dc:99:76:12:cf:
+        8a:28:9e:13:cf:bb:ae:ab:7e:9e:27:f3:db:d9:17:17:f8:33:
+        c8:02:d6:6e:54:98:94:69:0c:bd:73:05:50:7d:fb:61:57:f9:
+        db:5e:2b:de:02:1c:a3:a1:70:96:29:60:0c:5a:92:7b:24:e9:
+        cf:01:76:17:2d:de:63:e2:84:0d:ce:50:39:f2:8a:f3:b7:1e:
+        8e:62:b2:94:d5:32:0d:81:15:ce:01:e4:8a:07:ec:64:a6:e4:
+        c0:5e:01:52
+-----BEGIN CERTIFICATE-----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+-----END CERTIFICATE-----
diff --git a/jsign-core/src/test/resources/keystores/keystore-ed25519.p12 b/jsign-core/src/test/resources/keystores/keystore-ed25519.p12
diff --git a/jsign-core/src/test/resources/keystores/keystore-ed448.p12 b/jsign-core/src/test/resources/keystores/keystore-ed448.p12
diff --git a/jsign-core/src/test/resources/keystores/privatekey-ed25519.pem b/jsign-core/src/test/resources/keystores/privatekey-ed25519.pem
@@ -0,0 +1,3 @@
+-----BEGIN PRIVATE KEY-----
+MC4CAQAwBQYDK2VwBCIEIPct5Gzf9mxFpSHqEqgdRfq9bc2UAddOZSKcFfT5px7Z
+-----END PRIVATE KEY-----
diff --git a/jsign-core/src/test/resources/keystores/privatekey-ed448.pem b/jsign-core/src/test/resources/keystores/privatekey-ed448.pem
@@ -0,0 +1,4 @@
+-----BEGIN PRIVATE KEY-----
+MEcCAQAwBQYDK2VxBDsEOawzggKYvvx3TrGySJ3cBEpaj+I8Mq/3HV2U+6aTKDll
+GbhxK885+vSC5scbnsiqEWNjUwy84JoVPg==
+-----END PRIVATE KEY-----