Add certificate validation and PGP/MIME encryption; rename to pro.thinhha.mailsender

- validation: CertificateValidator checks revocation, expiry, matching
  user ID, a valid communications encryption subkey and the algorithm
  policy; uses the earlier expiry when PGPainless and Bouncy Castle disagree
- crypto: PgpEncryptor (ASCII armor, hidden recipients for Bcc)
- mime: PgpMimeEncryptor builds RFC 3156 multipart/encrypted from the
  whole CRLF-canonical inner entity, keeping envelope headers in the clear
- autoconfigure: validator and encryptor beans
- demo: encrypts when a valid key is found, plaintext otherwise
- rename groupId and Java packages to pro.thinhha.mailsender

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_01G71TQ5jDETVwdUJxGAwaiT

mailsender-demo/pom.xml

@@ -5,7 +5,7 @@
     <modelVersion>4.0.0</modelVersion>
 
     <parent>
-        <groupId>io.github.sneakybugmaster.mailsender</groupId>
+        <groupId>pro.thinhha.mailsender</groupId>
         <artifactId>mailsender-parent</artifactId>
         <version>0.1.0-SNAPSHOT</version>
     </parent>
@@ -15,7 +15,7 @@
 
     <dependencies>
         <dependency>
-            <groupId>io.github.sneakybugmaster.mailsender</groupId>
+            <groupId>pro.thinhha.mailsender</groupId>
             <artifactId>mailsender-pgp-spring-boot-starter</artifactId>
         </dependency>
         <dependency>

mailsender-demo/src/main/java/io/github/sneakybugmaster/mailsender/demo/TestMailRunner.java

@@ -1,76 +0,0 @@
-package io.github.sneakybugmaster.mailsender.demo;
-
-import java.time.OffsetDateTime;
-import java.util.HexFormat;
-import java.util.stream.Collectors;
-
-import org.slf4j.Logger;
-import org.slf4j.LoggerFactory;
-import org.springframework.boot.ApplicationArguments;
-import org.springframework.boot.ApplicationRunner;
-import org.springframework.mail.javamail.JavaMailSender;
-import org.springframework.mail.javamail.MimeMessageHelper;
-import org.springframework.stereotype.Component;
-
-import io.github.sneakybugmaster.mailsender.pgp.discovery.DiscoveryResult;
-import io.github.sneakybugmaster.mailsender.pgp.discovery.KeyDiscovery;
-import jakarta.mail.MessagingException;
-import jakarta.mail.internet.MimeMessage;
-
-/**
- * Looks up the recipient's key via WKD, then sends {@code demo.count} test mails describing what was found.
- * <p>
- * Encryption is not wired in yet (milestones 3–6), so the mails go out in plaintext.
- */
-@Component
-class TestMailRunner implements ApplicationRunner {
-
-    private static final Logger log = LoggerFactory.getLogger(TestMailRunner.class);
-
-    private final DemoProperties properties;
-    private final KeyDiscovery keyDiscovery;
-    private final JavaMailSender mailSender;
-
-    TestMailRunner(DemoProperties properties, KeyDiscovery keyDiscovery, JavaMailSender mailSender) {
-        this.properties = properties;
-        this.keyDiscovery = keyDiscovery;
-        this.mailSender = mailSender;
-    }
-
-    @Override
-    public void run(ApplicationArguments args) throws MessagingException {
-        DiscoveryResult discovery = keyDiscovery.discover(properties.to());
-        String summary = describe(discovery);
-        log.info("Key discovery for {}: {}", properties.to(), summary);
-
-        for (int i = 1; i <= properties.count(); i++) {
-            MimeMessage message = mailSender.createMimeMessage();
-            MimeMessageHelper helper = new MimeMessageHelper(message, "UTF-8");
-            if (properties.from() != null) {
-                helper.setFrom(properties.from());
-            }
-            helper.setTo(properties.to());
-            helper.setSubject("mailsender test %d/%d".formatted(i, properties.count()));
-            helper.setText("""
-                    Test mail %d of %d from the mailsender demo, sent %s.
-
-                    Key discovery for %s: %s
-
-                    This message was sent in plaintext: PGP/MIME encryption is not implemented yet.
-                    """.formatted(i, properties.count(), OffsetDateTime.now(), properties.to(), summary));
-            mailSender.send(message);
-            log.info("Sent test mail {}/{} to {}", i, properties.count(), properties.to());
-        }
-    }
-
-    private static String describe(DiscoveryResult result) {
-        return switch (result) {
-            case DiscoveryResult.Found found -> "found via " + found.source() + ", fingerprint(s) "
-                    + found.certificates().stream()
-                            .map(c -> HexFormat.of().withUpperCase().formatHex(c.getFingerprint()))
-                            .collect(Collectors.joining(", "));
-            case DiscoveryResult.NotFound ignored -> "no key published";
-            case DiscoveryResult.Unreachable u -> "lookup failed (" + u.reason() + ")";
-        };
-    }
-}

mailsender-demo/src/main/java/pro/thinhha/mailsender/demo/DemoApplication.java

@@ -1,4 +1,4 @@
-package io.github.sneakybugmaster.mailsender.demo;
+package pro.thinhha.mailsender.demo;
 
 import org.springframework.boot.SpringApplication;
 import org.springframework.boot.autoconfigure.SpringBootApplication;

mailsender-demo/src/main/java/pro/thinhha/mailsender/demo/DemoProperties.java

@@ -1,4 +1,4 @@
-package io.github.sneakybugmaster.mailsender.demo;
+package pro.thinhha.mailsender.demo;
 
 import org.springframework.boot.context.properties.ConfigurationProperties;
 import org.springframework.boot.context.properties.bind.DefaultValue;

mailsender-demo/src/main/java/pro/thinhha/mailsender/demo/TestMailRunner.java

@@ -0,0 +1,123 @@
+package pro.thinhha.mailsender.demo;
+
+import java.io.IOException;
+import java.time.OffsetDateTime;
+import java.util.HexFormat;
+import java.util.List;
+import java.util.Optional;
+
+import org.bouncycastle.openpgp.api.OpenPGPCertificate;
+import org.slf4j.Logger;
+import org.slf4j.LoggerFactory;
+import org.springframework.boot.ApplicationArguments;
+import org.springframework.boot.ApplicationRunner;
+import org.springframework.mail.javamail.JavaMailSender;
+import org.springframework.mail.javamail.MimeMessageHelper;
+import org.springframework.stereotype.Component;
+
+import jakarta.mail.MessagingException;
+import jakarta.mail.internet.MimeMessage;
+import pro.thinhha.mailsender.pgp.discovery.DiscoveryResult;
+import pro.thinhha.mailsender.pgp.discovery.KeyDiscovery;
+import pro.thinhha.mailsender.pgp.mime.PgpMimeEncryptor;
+import pro.thinhha.mailsender.pgp.validation.CertificateValidator;
+import pro.thinhha.mailsender.pgp.validation.ValidationResult;
+
+/**
+ * Looks up and validates the recipient's key, then sends {@code demo.count} test mails: PGP/MIME-encrypted when a
+ * valid key was found, otherwise in plaintext (logged as a downgrade).
+ * <p>
+ * This calls the building blocks directly; the policy layer and {@code SecureMailSender} (milestones 5–6) will
+ * replace this wiring.
+ */
+@Component
+class TestMailRunner implements ApplicationRunner {
+
+    private static final Logger log = LoggerFactory.getLogger(TestMailRunner.class);
+
+    private final DemoProperties properties;
+    private final KeyDiscovery keyDiscovery;
+    private final CertificateValidator validator;
+    private final PgpMimeEncryptor mimeEncryptor;
+    private final JavaMailSender mailSender;
+
+    TestMailRunner(DemoProperties properties, KeyDiscovery keyDiscovery, CertificateValidator validator,
+            PgpMimeEncryptor mimeEncryptor, JavaMailSender mailSender) {
+        this.properties = properties;
+        this.keyDiscovery = keyDiscovery;
+        this.validator = validator;
+        this.mimeEncryptor = mimeEncryptor;
+        this.mailSender = mailSender;
+    }
+
+    @Override
+    public void run(ApplicationArguments args) throws MessagingException, IOException {
+        String to = properties.to();
+        DiscoveryResult discovery = keyDiscovery.discover(to);
+        Optional<OpenPGPCertificate> key = usableKey(discovery, to);
+
+        for (int i = 1; i <= properties.count(); i++) {
+            MimeMessage message = compose(i, discovery, key.isPresent());
+            if (key.isPresent()) {
+                message = mimeEncryptor.encrypt(message, List.of(key.get()), List.of(), mailSender::createMimeMessage);
+                log.info("Sending test mail {}/{} to {} ENCRYPTED to {}", i, properties.count(), to,
+                        fingerprint(key.get()));
+            } else {
+                log.warn("Sending test mail {}/{} to {} in PLAINTEXT: no usable key", i, properties.count(), to);
+            }
+            mailSender.send(message);
+        }
+    }
+
+    private Optional<OpenPGPCertificate> usableKey(DiscoveryResult discovery, String to) {
+        switch (discovery) {
+            case DiscoveryResult.Found found -> {
+                for (OpenPGPCertificate certificate : found.certificates()) {
+                    ValidationResult result = validator.validate(certificate, to);
+                    switch (result) {
+                        case ValidationResult.Valid valid -> {
+                            log.info("Key for {} found via {}: {}", to, found.source(), fingerprint(certificate));
+                            return Optional.of(valid.certificate());
+                        }
+                        case ValidationResult.Rejected rejected -> log.warn("Key {} for {} rejected: {} ({})",
+                                fingerprint(certificate), to, rejected.reason(), rejected.detail());
+                    }
+                }
+            }
+            case DiscoveryResult.NotFound ignored -> log.info("No key published for {}", to);
+            case DiscoveryResult.Unreachable unreachable ->
+                    log.warn("Key lookup for {} failed: {}", to, unreachable.reason());
+        }
+        return Optional.empty();
+    }
+
+    private MimeMessage compose(int index, DiscoveryResult discovery, boolean encrypted) throws MessagingException {
+        MimeMessage message = mailSender.createMimeMessage();
+        MimeMessageHelper helper = new MimeMessageHelper(message, "UTF-8");
+        if (properties.from() != null && !properties.from().isBlank()) {
+            helper.setFrom(properties.from());
+        }
+        helper.setTo(properties.to());
+        helper.setSubject("mailsender test %d/%d".formatted(index, properties.count()));
+        helper.setText("""
+                Test mail %d of %d from the mailsender demo, sent %s.
+
+                Key discovery for %s: %s
+                This message was sent %s.
+                """.formatted(index, properties.count(), OffsetDateTime.now(), properties.to(),
+                describe(discovery), encrypted ? "PGP/MIME-encrypted" : "in plaintext"));
+        return message;
+    }
+
+    private static String describe(DiscoveryResult result) {
+        return switch (result) {
+            case DiscoveryResult.Found found -> "found via " + found.source();
+            case DiscoveryResult.NotFound ignored -> "no key published";
+            case DiscoveryResult.Unreachable u -> "lookup failed (" + u.reason() + ")";
+        };
+    }
+
+    private static String fingerprint(OpenPGPCertificate certificate) {
+        return HexFormat.of().withUpperCase().formatHex(certificate.getFingerprint());
+    }
+}

mailsender-demo/src/main/resources/application.yml

@@ -20,4 +20,4 @@ demo:
 
 logging:
   level:
-    io.github.sneakybugmaster.mailsender: DEBUG
+    pro.thinhha.mailsender: DEBUG

mailsender-demo/src/test/java/pro/thinhha/mailsender/demo/EncryptedTestMailTest.java

@@ -0,0 +1,85 @@
+package pro.thinhha.mailsender.demo;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+import java.io.ByteArrayInputStream;
+import java.io.ByteArrayOutputStream;
+import java.nio.file.Files;
+import java.nio.file.Path;
+
+import org.bouncycastle.openpgp.api.OpenPGPKey;
+import org.junit.jupiter.api.AfterAll;
+import org.junit.jupiter.api.BeforeAll;
+import org.junit.jupiter.api.Test;
+import org.pgpainless.PGPainless;
+import org.pgpainless.decryption_verification.ConsumerOptions;
+import org.pgpainless.decryption_verification.DecryptionStream;
+import org.springframework.boot.test.context.SpringBootTest;
+import org.springframework.test.context.DynamicPropertyRegistry;
+import org.springframework.test.context.DynamicPropertySource;
+
+import com.icegreen.greenmail.util.GreenMail;
+import com.icegreen.greenmail.util.ServerSetupTest;
+
+import jakarta.mail.Multipart;
+import jakarta.mail.internet.ContentType;
+import jakarta.mail.internet.MimeBodyPart;
+import jakarta.mail.internet.MimeMessage;
+
+/** The recipient has a (pinned) key, so the demo must deliver a decryptable PGP/MIME message. */
+@SpringBootTest(properties = {
+        "spring.mail.properties.mail.smtp.auth=false",
+        "spring.mail.properties.mail.smtp.starttls.enable=false",
+        "spring.mail.properties.mail.smtp.starttls.required=false",
+        "spring.mail.username=",
+        "demo.from=demo@mailsender.test",
+        "mail.pgp.wkd.enabled=false"
+})
+class EncryptedTestMailTest {
+
+    static final PGPainless API = PGPainless.getInstance();
+    static final OpenPGPKey RECIPIENT = API.generateKey().modernKeyRing("Test Account <test@thinhha.pro>");
+    static GreenMail greenMail;
+    static Path keyFile;
+
+    @BeforeAll
+    static void start() throws Exception {
+        keyFile = Files.createTempFile("recipient", ".asc");
+        Files.writeString(keyFile, RECIPIENT.toCertificate().toAsciiArmoredString());
+        greenMail = new GreenMail(ServerSetupTest.SMTP.dynamicPort());
+        greenMail.start();
+    }
+
+    @AfterAll
+    static void stop() throws Exception {
+        greenMail.stop();
+        Files.deleteIfExists(keyFile);
+    }
+
+    @DynamicPropertySource
+    static void properties(DynamicPropertyRegistry registry) {
+        registry.add("spring.mail.host", () -> "127.0.0.1");
+        registry.add("spring.mail.port", () -> greenMail.getSmtp().getPort());
+        registry.add("mail.pgp.static-keys[test@thinhha.pro]", () -> "file:" + keyFile);
+    }
+
+    @Test
+    void deliversDecryptablePgpMime() throws Exception {
+        MimeMessage[] received = greenMail.getReceivedMessages();
+        assertThat(received).hasSize(1);
+        MimeMessage message = received[0];
+
+        assertThat(new ContentType(message.getContentType()).getBaseType()).isEqualTo("multipart/encrypted");
+        assertThat(message.getSubject()).isEqualTo("mailsender test 1/1");
+        Multipart parts = (Multipart) message.getContent();
+        byte[] armored = parts.getBodyPart(1).getInputStream().readAllBytes();
+
+        ByteArrayOutputStream inner = new ByteArrayOutputStream();
+        try (DecryptionStream in = API.processMessage().onInputStream(new ByteArrayInputStream(armored))
+                .withOptions(ConsumerOptions.get(API).addDecryptionKey(RECIPIENT))) {
+            in.transferTo(inner);
+        }
+        MimeBodyPart entity = new MimeBodyPart(new ByteArrayInputStream(inner.toByteArray()));
+        assertThat(entity.getContent().toString()).contains("found via STATIC", "PGP/MIME-encrypted");
+    }
+}

mailsender-demo/src/test/java/pro/thinhha/mailsender/demo/PlaintextTestMailTest.java

@@ -1,4 +1,4 @@
-package io.github.sneakybugmaster.mailsender.demo;
+package pro.thinhha.mailsender.demo;
 
 import static org.assertj.core.api.Assertions.assertThat;
 
@@ -25,7 +25,7 @@ import jakarta.mail.internet.MimeMessage;
         // keep the test offline: no real WKD lookup
         "mail.pgp.wkd.enabled=false"
 })
-class TestMailRunnerTest {
+class PlaintextTestMailTest {
 
     // Started before the Spring context, because the runner sends while the context starts.
     static GreenMail greenMail;
@@ -54,6 +54,6 @@ class TestMailRunnerTest {
         assertThat(received).hasSize(2);
         assertThat(received[0].getAllRecipients()).extracting(Object::toString).containsExactly("test@thinhha.pro");
         assertThat(received[0].getSubject()).isEqualTo("mailsender test 1/2");
-        assertThat(GreenMailUtil.getBody(received[0])).contains("no key published");
+        assertThat(GreenMailUtil.getBody(received[0])).contains("no key published", "in plaintext");
     }
 }