Timestamp command implementation

README.md

@@ -62,6 +62,7 @@ See https://ebourg.github.io/jsign for more information.
 * File list files prefixed with `@` are now supported with the command line tool to sign multiple files
 * Wildcard patterns are now accepted by the command line tool to scan directories for files to sign
 * Jsign now checks if the certificate subject matches the app manifest publisher before signing APPX/MSIX packages (with contributions from Scott Cooper)
+* The `timestamp` command has been added to timestamp the signatures of a file
 * The `tag` command has been added to add unsigned data (such as user identification data) to signed files
 * The `extract` command has been added to extract the signature from a signed file, in DER or PEM format
 * The `remove` command has been added to remove the signature from a signed file

docs/index.html

@@ -521,7 +521,7 @@ <h3 id="cli">Command Line Tool</h3>
   files (CAB), Catalog files (CAT), Windows packages (APPX/MSIX), Microsoft Dynamics
   365 extension packages, NuGet packages and scripts (PowerShell, VBScript, JScript, WSF)
 
-  commands: sign (default), extract, remove, tag
+  commands: sign (default), timestamp, extract, remove, tag
 
   sign:
   -s,--keystore &lt;FILE>       The keystore file, the SunPKCS11 configuration file,
@@ -576,6 +576,15 @@ <h3 id="cli">Command Line Tool</h3>
      --debug                 Print debugging information
   -h,--help                  Print the help
 
+  timestamp:
+  -t,--tsaurl &lt;URL>          The URL of the timestamping authority
+  -m,--tsmode &lt;MODE>         The timestamping mode (RFC3161 or Authenticode)
+  -r,--tsretries &lt;NUMBER>    The number of retries for timestamping
+  -w,--tsretrywait &lt;SECONDS> The number of seconds to wait between timestamping retries
+  -n,--name &lt;NAME>           The name of the application
+  -u,--url &lt;URL>             The URL of the application
+     --replace               Tells if the previous timestamps should be replaced
+
   extract:
      --format &lt;FORMAT>       The output format of the signature (DER or PEM)
 

jsign-cli/src/main/java/net/jsign/JsignCLI.java

@@ -121,6 +121,17 @@ public static void main(String... args) {
 
         this.options.put("sign", options);
 
+        options = new Options();
+        options.addOption(Option.builder("t").hasArg().longOpt(PARAM_TSAURL).argName("URL").desc("The URL of the timestamping authority").build());
+        options.addOption(Option.builder("m").hasArg().longOpt(PARAM_TSMODE).argName("MODE").desc("The timestamping mode (RFC3161 or Authenticode)").build());
+        options.addOption(Option.builder("r").hasArg().longOpt(PARAM_TSRETRIES).argName("NUMBER").desc("The number of retries for timestamping").build());
+        options.addOption(Option.builder("w").hasArg().longOpt(PARAM_TSRETRY_WAIT).argName("SECONDS").desc("The number of seconds to wait between timestamping retries").build());
+        options.addOption(Option.builder("n").hasArg().longOpt(PARAM_NAME).argName("NAME").desc("The name of the application").build());
+        options.addOption(Option.builder("u").hasArg().longOpt(PARAM_URL).argName("URL").desc("The URL of the application").build());
+        options.addOption(Option.builder().longOpt(PARAM_REPLACE).desc("Tells if the previous timestamps should be replaced").build());
+
+        this.options.put("timestamp", options);
+
         options = new Options();
         options.addOption(Option.builder().hasArg().longOpt(PARAM_FORMAT).argName("FORMAT").desc("      The output format of the signature (DER or PEM)").build());
 

jsign-cli/src/test/java/net/jsign/JsignCLITest.java

@@ -629,4 +629,13 @@ public void testTag() throws Exception {
             assertEquals("message", "No signature found in " + targetFile.getPath(), e.getMessage());
         }
     }
+
+    @Test
+    public void testTimestamp() throws Exception {
+        try {
+            cli.execute("timestamp", "" + targetFile);
+        } catch (SignerException e) {
+            assertEquals("message", "No signature found in " + targetFile.getPath(), e.getMessage());
+        }
+    }
 }

jsign-core/src/main/java/net/jsign/AuthenticodeSigner.java

@@ -34,7 +34,6 @@
 import java.util.List;
 
 import org.bouncycastle.asn1.ASN1Encodable;
-import org.bouncycastle.asn1.ASN1EncodableVector;
 import org.bouncycastle.asn1.DERNull;
 import org.bouncycastle.asn1.DERSet;
 import org.bouncycastle.asn1.cms.Attribute;
@@ -54,8 +53,6 @@
 import org.bouncycastle.cms.DefaultSignedAttributeTableGenerator;
 import org.bouncycastle.cms.SignerInfoGenerator;
 import org.bouncycastle.cms.SignerInfoGeneratorBuilder;
-import org.bouncycastle.cms.SignerInformation;
-import org.bouncycastle.cms.SignerInformationStore;
 import org.bouncycastle.cms.SignerInformationVerifier;
 import org.bouncycastle.cms.jcajce.JcaSignerInfoVerifierBuilder;
 import org.bouncycastle.operator.ContentSigner;
@@ -376,7 +373,7 @@ public void sign(Signable file) throws Exception {
             List<CMSSignedData> signatures = file.getSignatures();
             if (!signatures.isEmpty()) {
                 // append the nested signature
-                sigData = addNestedSignature(signatures.get(0), sigData);
+                sigData = SignatureUtils.addNestedSignature(signatures.get(0), false, sigData);
             }
         }
 
@@ -516,42 +513,6 @@ private AttributeTable createAuthenticatedAttributes() {
         return new AttributeTable(new DERSet(attributes.toArray(new ASN1Encodable[0])));
     }
 
-    /**
-     * Embed a signature as an unsigned attribute of an existing signature.
-     * 
-     * @param primary   the root signature hosting the nested secondary signature
-     * @param secondary the additional signature to nest inside the primary one
-     * @return the signature combining the specified signatures
-     */
-    protected CMSSignedData addNestedSignature(CMSSignedData primary, CMSSignedData secondary) {
-        SignerInformation signerInformation = primary.getSignerInfos().getSigners().iterator().next();
-
-        AttributeTable unsignedAttributes = signerInformation.getUnsignedAttributes();
-        if (unsignedAttributes == null) {
-            unsignedAttributes = new AttributeTable(new DERSet());
-        }
-        Attribute nestedSignaturesAttribute = unsignedAttributes.get(AuthenticodeObjectIdentifiers.SPC_NESTED_SIGNATURE_OBJID);
-        if (nestedSignaturesAttribute == null) {
-            // first nested signature
-            unsignedAttributes = unsignedAttributes.add(AuthenticodeObjectIdentifiers.SPC_NESTED_SIGNATURE_OBJID, secondary.toASN1Structure());
-        } else {
-            // append the signature to the previous nested signatures
-            ASN1EncodableVector nestedSignatures = new ASN1EncodableVector();
-            for (ASN1Encodable nestedSignature : nestedSignaturesAttribute.getAttrValues()) {
-                nestedSignatures.add(nestedSignature);
-            }
-            nestedSignatures.add(secondary.toASN1Structure());
-
-            ASN1EncodableVector attributes = unsignedAttributes.remove(AuthenticodeObjectIdentifiers.SPC_NESTED_SIGNATURE_OBJID).toASN1EncodableVector();
-            attributes.add(new Attribute(AuthenticodeObjectIdentifiers.SPC_NESTED_SIGNATURE_OBJID, new DERSet(nestedSignatures)));
-
-            unsignedAttributes = new AttributeTable(attributes);
-        }
-
-        signerInformation = SignerInformation.replaceUnsignedAttributes(signerInformation, unsignedAttributes);
-        return CMSSignedData.replaceSigners(primary, new SignerInformationStore(signerInformation));
-    }
-
     /**
      * Create the digest algorithm identifier to use as content digest.
      * By default looks up the default identifier but also makes sure it includes

jsign-core/src/main/java/net/jsign/SignatureUtils.java

@@ -22,16 +22,21 @@
 import java.util.NoSuchElementException;
 
 import org.bouncycastle.asn1.ASN1Encodable;
+import org.bouncycastle.asn1.ASN1EncodableVector;
 import org.bouncycastle.asn1.ASN1InputStream;
+import org.bouncycastle.asn1.DERSet;
 import org.bouncycastle.asn1.cms.Attribute;
 import org.bouncycastle.asn1.cms.AttributeTable;
+import org.bouncycastle.asn1.cms.CMSAttributes;
 import org.bouncycastle.asn1.cms.ContentInfo;
+import org.bouncycastle.asn1.pkcs.PKCSObjectIdentifiers;
 import org.bouncycastle.cms.CMSException;
 import org.bouncycastle.cms.CMSProcessable;
 import org.bouncycastle.cms.CMSSignedData;
 import org.bouncycastle.cms.SignerInformation;
+import org.bouncycastle.cms.SignerInformationStore;
 
-import net.jsign.asn1.authenticode.AuthenticodeObjectIdentifiers;
+import static net.jsign.asn1.authenticode.AuthenticodeObjectIdentifiers.*;
 
 /**
  * Helper class for working with signatures.
@@ -67,10 +72,10 @@ public static List<CMSSignedData> getSignatures(CMSSignedData signature) throws
                 signatures.add(signature);
 
                 // look for nested signatures
-                SignerInformation signerInformation = signature.getSignerInfos().getSigners().iterator().next();
+                SignerInformation signerInformation = signature.getSignerInfos().iterator().next();
                 AttributeTable unsignedAttributes = signerInformation.getUnsignedAttributes();
                 if (unsignedAttributes != null) {
-                    Attribute nestedSignatures = unsignedAttributes.get(AuthenticodeObjectIdentifiers.SPC_NESTED_SIGNATURE_OBJID);
+                    Attribute nestedSignatures = unsignedAttributes.get(SPC_NESTED_SIGNATURE_OBJID);
                     if (nestedSignatures != null) {
                         for (ASN1Encodable nestedSignature : nestedSignatures.getAttrValues()) {
                             signatures.add(new CMSSignedData((CMSProcessable) null, ContentInfo.getInstance(nestedSignature)));
@@ -84,4 +89,85 @@ public static List<CMSSignedData> getSignatures(CMSSignedData signature) throws
 
         return signatures;
     }
+
+    /**
+     * Embed a signature as an unsigned attribute of an existing signature.
+     *
+     * @param parent    the root signature hosting the nested secondary signature
+     * @param children  the additional signature to nest inside the root signature
+     * @return the signature combining the specified signatures
+     */
+    static CMSSignedData addNestedSignature(CMSSignedData parent, boolean replace, CMSSignedData... children) {
+        SignerInformation signerInformation = parent.getSignerInfos().iterator().next();
+
+        AttributeTable unsignedAttributes = signerInformation.getUnsignedAttributes();
+        if (unsignedAttributes == null) {
+            unsignedAttributes = new AttributeTable(new DERSet());
+        }
+
+        Attribute nestedSignaturesAttribute = unsignedAttributes.get(SPC_NESTED_SIGNATURE_OBJID);
+        ASN1EncodableVector nestedSignatures = new ASN1EncodableVector();
+        if (nestedSignaturesAttribute != null && !replace) {
+            // keep the previous nested signatures
+            for (ASN1Encodable nestedSignature : nestedSignaturesAttribute.getAttrValues()) {
+                nestedSignatures.add(nestedSignature);
+            }
+        }
+
+        // append the new signatures
+        for (CMSSignedData nestedSignature : children) {
+            nestedSignatures.add(nestedSignature.toASN1Structure());
+        }
+
+        // replace the nested signatures attribute
+        ASN1EncodableVector attributes = unsignedAttributes.remove(SPC_NESTED_SIGNATURE_OBJID).toASN1EncodableVector();
+        attributes.add(new Attribute(SPC_NESTED_SIGNATURE_OBJID, new DERSet(nestedSignatures)));
+
+        unsignedAttributes = new AttributeTable(attributes);
+
+        signerInformation = SignerInformation.replaceUnsignedAttributes(signerInformation, unsignedAttributes);
+        return CMSSignedData.replaceSigners(parent, new SignerInformationStore(signerInformation));
+    }
+
+    /**
+     * Tells if the specified signature is timestamped.
+     *
+     * @param signature the signature to check
+     */
+    static boolean isTimestamped(CMSSignedData signature) {
+        SignerInformation signerInformation = signature.getSignerInfos().iterator().next();
+
+        AttributeTable unsignedAttributes = signerInformation.getUnsignedAttributes();
+        if (unsignedAttributes == null) {
+            return false;
+        }
+
+        boolean authenticode = isAuthenticode(signature.getSignedContentTypeOID());
+        Attribute authenticodeTimestampAttribute = unsignedAttributes.get(CMSAttributes.counterSignature);
+        Attribute rfc3161TimestampAttribute = unsignedAttributes.get(authenticode ? SPC_RFC3161_OBJID : PKCSObjectIdentifiers.id_aa_signatureTimeStampToken);
+        return authenticodeTimestampAttribute != null || rfc3161TimestampAttribute != null;
+    }
+
+    /**
+     * Removes the timestamp from the specified signature.
+     *
+     * @param signature the signature to modify
+     */
+    static CMSSignedData removeTimestamp(CMSSignedData signature) {
+        SignerInformation signerInformation = signature.getSignerInfos().iterator().next();
+
+        AttributeTable unsignedAttributes = signerInformation.getUnsignedAttributes();
+        if (unsignedAttributes == null) {
+            return signature;
+        }
+
+        unsignedAttributes = unsignedAttributes.remove(CMSAttributes.counterSignature);
+        unsignedAttributes = unsignedAttributes.remove(PKCSObjectIdentifiers.id_aa_signatureTimeStampToken);
+        unsignedAttributes = unsignedAttributes.remove(SPC_RFC3161_OBJID);
+
+        // todo remove the TSA certificates from the certificate store
+
+        signerInformation = SignerInformation.replaceUnsignedAttributes(signerInformation, unsignedAttributes);
+        return CMSSignedData.replaceSigners(signature, new SignerInformationStore(signerInformation));
+    }
 }

jsign-core/src/main/java/net/jsign/SignerHelper.java

@@ -36,9 +36,11 @@
 import java.security.PrivateKey;
 import java.security.Provider;
 import java.security.cert.Certificate;
+import java.util.ArrayList;
 import java.util.Base64;
 import java.util.Collection;
 import java.util.Collections;
+import java.util.Date;
 import java.util.LinkedHashSet;
 import java.util.List;
 import java.util.Set;
@@ -55,14 +57,19 @@
 import org.bouncycastle.asn1.DERUTF8String;
 import org.bouncycastle.asn1.cms.AttributeTable;
 import org.bouncycastle.asn1.cms.ContentInfo;
+import org.bouncycastle.asn1.x509.AlgorithmIdentifier;
+import org.bouncycastle.cert.X509CertificateHolder;
 import org.bouncycastle.cms.CMSException;
 import org.bouncycastle.cms.CMSProcessable;
 import org.bouncycastle.cms.CMSSignedData;
+import org.bouncycastle.cms.SignerId;
 import org.bouncycastle.cms.SignerInformation;
 import org.bouncycastle.cms.SignerInformationStore;
+import org.bouncycastle.operator.DefaultAlgorithmNameFinder;
 import org.bouncycastle.util.encoders.Hex;
 
 import net.jsign.asn1.authenticode.AuthenticodeObjectIdentifiers;
+import net.jsign.timestamp.Timestamper;
 import net.jsign.timestamp.TimestampingMode;
 
 /**
@@ -102,7 +109,9 @@ class SignerHelper {
     /** The name used to refer to a configuration parameter */
     private final String parameterName;
 
+    /** The command to execute */
     private String command = "sign";
+
     private final KeyStoreBuilder ksparams;
     private String alias;
     private String tsaurl;
@@ -300,6 +309,9 @@ public void execute(File file) throws SignerException {
             case "sign":
                 sign(file);
                 break;
+            case "timestamp":
+                timestamp(file);
+                break;
             case "extract":
                 extract(file);
                 break;
@@ -634,6 +646,71 @@ private ASN1Encodable getTagValue() throws IOException {
         }
     }
 
+    private void timestamp(File file) throws SignerException {
+        if (!file.exists()) {
+            throw new SignerException("Couldn't find " + file);
+        }
+
+        try {
+            initializeProxy(proxyUrl, proxyUser, proxyPass);
+        } catch (Exception e) {
+            throw new SignerException("Couldn't initialize proxy", e);
+        }
+
+        try (Signable signable = Signable.of(file)) {
+            if (signable.getSignatures().isEmpty()) {
+                throw new SignerException("No signature found in " + file);
+            }
+
+            Timestamper timestamper = Timestamper.create(tsmode != null ? TimestampingMode.of(tsmode) : TimestampingMode.AUTHENTICODE);
+            timestamper.setRetries(tsretries);
+            timestamper.setRetryWait(tsretrywait);
+            if (tsaurl != null) {
+                timestamper.setURLs(tsaurl.split(","));
+            }
+            DigestAlgorithm digestAlgorithm = alg != null ? DigestAlgorithm.of(alg) : DigestAlgorithm.getDefault();
+
+            List<CMSSignedData> signatures = new ArrayList<>();
+            for (CMSSignedData signature : signable.getSignatures()) {
+                SignerInformation signerInformation = signature.getSignerInfos().iterator().next();
+                SignerId signerId = signerInformation.getSID();
+                X509CertificateHolder certificate = (X509CertificateHolder) signature.getCertificates().getMatches(signerId).iterator().next();
+
+                String digestAlgorithmName = new DefaultAlgorithmNameFinder().getAlgorithmName(signerInformation.getDigestAlgorithmID()); 
+                String keyAlgorithmName = new DefaultAlgorithmNameFinder().getAlgorithmName(new ASN1ObjectIdentifier(signerInformation.getEncryptionAlgOID()));
+                String name = digestAlgorithmName + "/" + keyAlgorithmName + " signature from '" + certificate.getSubject() + "'";
+
+                if (SignatureUtils.isTimestamped(signature) && !replace) {
+                    log.fine(name + " already timestamped");
+                    signatures.add(signature);
+                    continue;
+                }
+
+                boolean expired = certificate.getNotAfter().before(new Date());
+                if (expired) {
+                    log.fine(name + " is expired, skipping");
+                    signatures.add(signature);
+                    continue;
+                }
+
+                log.info("Adding timestamp to " + name);
+                signature = SignatureUtils.removeTimestamp(signature);
+                signature = timestamper.timestamp(digestAlgorithm, signature);
+
+                signatures.add(signature);
+            }
+
+            CMSSignedData signature = signatures.get(0);
+            if (signatures.size() > 1) {
+                Collection<CMSSignedData> nestedSignatures = signatures.subList(1, signatures.size());
+                signature = SignatureUtils.addNestedSignature(signature, true, nestedSignatures.toArray(new CMSSignedData[0]));
+            }
+            signable.setSignature(signature);
+        } catch (IOException | CMSException e) {
+            throw new SignerException("Couldn't timestamp " + file, e);
+        }
+    }
+
     /**
      * Initializes the proxy.
      *