feat(pgpainless): add detection for passphrase-less messages (#3069)

* WIP: feat(pgpainless): add detection for passphrase-less messages

* refactor: test keys instead of the message

This makes more logical sense

6 files changed, 51 insertions, 2 deletions

diff --git a/app/src/main/java/app/passwordstore/data/crypto/CryptoRepository.kt b/app/src/main/java/app/passwordstore/data/crypto/CryptoRepository.kt
index 50d7a841..773a355a 100644
--- a/app/src/main/java/app/passwordstore/data/crypto/CryptoRepository.kt
+++ b/app/src/main/java/app/passwordstore/data/crypto/CryptoRepository.kt
@@ -45,6 +45,11 @@ constructor(
     out: ByteArrayOutputStream,
   ) = withContext(dispatcherProvider.io()) { decryptPgp(password, identities, message, out) }
 
+  suspend fun isPasswordProtected(identifiers: List<PGPIdentifier>): Boolean {
+    val keys = identifiers.map { pgpKeyManager.getKeyById(it) }.filterValues()
+    return pgpCryptoHandler.isPassphraseProtected(keys)
+  }
+
   suspend fun encrypt(
     identities: List<PGPIdentifier>,
     content: ByteArrayInputStream,
diff --git a/app/src/main/java/app/passwordstore/ui/autofill/AutofillDecryptActivity.kt b/app/src/main/java/app/passwordstore/ui/autofill/AutofillDecryptActivity.kt
index 1af46a89..4518e62f 100644
--- a/app/src/main/java/app/passwordstore/ui/autofill/AutofillDecryptActivity.kt
+++ b/app/src/main/java/app/passwordstore/ui/autofill/AutofillDecryptActivity.kt
@@ -131,12 +131,16 @@ class AutofillDecryptActivity : BasePGPActivity() {
     }
   }
 
-  private fun askPassphrase(
+  private suspend fun askPassphrase(
     filePath: String,
     identifiers: List<PGPIdentifier>,
     clientState: Bundle,
     action: AutofillAction,
   ) {
+    if (!repository.isPasswordProtected(identifiers)) {
+      decryptWithPassphrase(File(filePath), identifiers, clientState, action, password = "")
+      return
+    }
     val dialog = PasswordDialog()
     dialog.show(supportFragmentManager, "PASSWORD_DIALOG")
     dialog.setFragmentResultListener(PasswordDialog.PASSWORD_RESULT_KEY) { key, bundle ->
diff --git a/app/src/main/java/app/passwordstore/ui/crypto/DecryptActivity.kt b/app/src/main/java/app/passwordstore/ui/crypto/DecryptActivity.kt
index b222f2ea..6f14bdea 100644
--- a/app/src/main/java/app/passwordstore/ui/crypto/DecryptActivity.kt
+++ b/app/src/main/java/app/passwordstore/ui/crypto/DecryptActivity.kt
@@ -179,7 +179,7 @@ class DecryptActivity : BasePGPActivity() {
     }
   }
 
-  private fun askPassphrase(
+  private suspend fun askPassphrase(
     isError: Boolean,
     gpgIdentifiers: List<PGPIdentifier>,
     authResult: BiometricResult,
@@ -189,6 +189,10 @@ class DecryptActivity : BasePGPActivity() {
     } else {
       finish()
     }
+    if (!repository.isPasswordProtected(gpgIdentifiers)) {
+      decryptWithPassphrase(passphrase = "", gpgIdentifiers, authResult)
+      return
+    }
     val dialog = PasswordDialog()
     if (isError) {
       dialog.setError()
diff --git a/crypto/common/src/main/kotlin/app/passwordstore/crypto/CryptoHandler.kt b/crypto/common/src/main/kotlin/app/passwordstore/crypto/CryptoHandler.kt
index 898cf058..c823342b 100644
--- a/crypto/common/src/main/kotlin/app/passwordstore/crypto/CryptoHandler.kt
+++ b/crypto/common/src/main/kotlin/app/passwordstore/crypto/CryptoHandler.kt
@@ -41,4 +41,9 @@ public interface CryptoHandler<Key, EncOpts : CryptoOptions, DecryptOpts : Crypt
 
   /** Given a [fileName], return whether this instance can handle it. */
   public fun canHandle(fileName: String): Boolean
+
+  /**
+   * Inspects the given [keys] and returns `false` if none of them require a passphrase to decrypt.
+   */
+  public fun isPassphraseProtected(keys: List<Key>): Boolean
 }
diff --git a/crypto/pgpainless/src/main/kotlin/app/passwordstore/crypto/PGPainlessCryptoHandler.kt b/crypto/pgpainless/src/main/kotlin/app/passwordstore/crypto/PGPainlessCryptoHandler.kt
index 1aabe54f..b3f2a64b 100644
--- a/crypto/pgpainless/src/main/kotlin/app/passwordstore/crypto/PGPainlessCryptoHandler.kt
+++ b/crypto/pgpainless/src/main/kotlin/app/passwordstore/crypto/PGPainlessCryptoHandler.kt
@@ -11,6 +11,7 @@ import app.passwordstore.crypto.errors.NoKeysProvidedException
 import app.passwordstore.crypto.errors.NonStandardAEAD
 import app.passwordstore.crypto.errors.UnknownError
 import com.github.michaelbull.result.Result
+import com.github.michaelbull.result.mapBoth
 import com.github.michaelbull.result.mapError
 import com.github.michaelbull.result.runCatching
 import java.io.InputStream
@@ -140,4 +141,14 @@ public class PGPainlessCryptoHandler @Inject constructor() :
   public override fun canHandle(fileName: String): Boolean {
     return fileName.substringAfterLast('.', "") == "gpg"
   }
+
+  public override fun isPassphraseProtected(keys: List<PGPKey>): Boolean =
+    keys
+      .mapNotNull { key -> PGPainless.readKeyRing().secretKeyRing(key.contents) }
+      .map(::keyringHasPassphrase)
+      .all { it }
+
+  internal fun keyringHasPassphrase(keyRing: PGPSecretKeyRing) =
+    runCatching { keyRing.secretKey.extractPrivateKey(null) }
+      .mapBoth(success = { false }, failure = { true })
 }
diff --git a/crypto/pgpainless/src/test/kotlin/app/passwordstore/crypto/PGPainlessCryptoHandlerTest.kt b/crypto/pgpainless/src/test/kotlin/app/passwordstore/crypto/PGPainlessCryptoHandlerTest.kt
index 5de2bf4f..600cc39d 100644
--- a/crypto/pgpainless/src/test/kotlin/app/passwordstore/crypto/PGPainlessCryptoHandlerTest.kt
+++ b/crypto/pgpainless/src/test/kotlin/app/passwordstore/crypto/PGPainlessCryptoHandlerTest.kt
@@ -156,6 +156,26 @@ class PGPainlessCryptoHandlerTest {
   }
 
   @Test
+  fun detectsKeysWithPassphrase() {
+    assertTrue(cryptoHandler.isPassphraseProtected(listOf(PGPKey(TestUtils.getArmoredSecretKey()))))
+    assertTrue(
+      cryptoHandler.isPassphraseProtected(
+        listOf(PGPKey(TestUtils.getArmoredSecretKeyWithMultipleIdentities()))
+      )
+    )
+  }
+
+  @Test
+  fun detectsKeysWithoutPassphrase() {
+    // Uses the internal method instead of the public API because GnuPG seems to have made it
+    // impossible to generate a key without a passphrase and I can't care to find a magical
+    // incantation to convince it I am smarter than whatever they are protecting against.
+    assertFalse(
+      cryptoHandler.keyringHasPassphrase(PGPainless.generateKeyRing().modernKeyRing("John Doe"))
+    )
+  }
+
+  @Test
   fun canHandleFiltersFormats() {
     assertFalse { cryptoHandler.canHandle("example.com") }
     assertTrue { cryptoHandler.canHandle("example.com.gpg") }