diff --git a/jvm/src/main/kotlin/app/cash/trifle/SignedData.kt b/jvm/src/main/kotlin/app/cash/trifle/SignedData.kt
index 4b2486d..c4a1a5d 100644
--- a/jvm/src/main/kotlin/app/cash/trifle/SignedData.kt
+++ b/jvm/src/main/kotlin/app/cash/trifle/SignedData.kt
@@ -22,11 +22,7 @@ data class SignedData internal constructor(
 ) {
   fun verify(certAnchor: Certificate): Boolean {
     val validator = CertChainValidatorFactory.get(certAnchor)
-    try {
-      if (!validator.validate(certificates)) return false
-    } catch (e: Exception) {
-      return false
-    }
+    if (!validator.validate(certificates)) return false
 
     val contentVerifier = JCAContentVerifierProvider(certificates.first())
       .get(envelopedData.signingAlgorithm)
diff --git a/jvm/src/main/kotlin/app/cash/trifle/TrifleErrors.kt b/jvm/src/main/kotlin/app/cash/trifle/TrifleErrors.kt
new file mode 100644
index 0000000..b736aee
--- /dev/null
+++ b/jvm/src/main/kotlin/app/cash/trifle/TrifleErrors.kt
@@ -0,0 +1,6 @@
+package app.cash.trifle
+
+class NoTrustAnchorException(message: String? = null, cause: Throwable? = null) : Exception(message, cause)
+class ExpiredCertificateException(message: String? = null, cause: Throwable? = null) : Exception(message, cause)
+class IncorrectSignatureException(message: String? = null, cause: Throwable? = null) : Exception(message, cause)
+class UnSpecifiedFailureException(message: String? = null, cause: Throwable? = null) : Exception(message, cause)
diff --git a/jvm/src/main/kotlin/app/cash/trifle/internal/validators/X509CertChainValidator.kt b/jvm/src/main/kotlin/app/cash/trifle/internal/validators/X509CertChainValidator.kt
index 48375b8..4eeec24 100644
--- a/jvm/src/main/kotlin/app/cash/trifle/internal/validators/X509CertChainValidator.kt
+++ b/jvm/src/main/kotlin/app/cash/trifle/internal/validators/X509CertChainValidator.kt
@@ -1,10 +1,11 @@
 package app.cash.trifle.internal.validators
 
-import app.cash.trifle.Certificate
+import app.cash.trifle.*
 import java.security.cert.CertPathValidatorException
 import java.security.cert.CertPathValidatorException.BasicReason
 import java.security.cert.CertificateFactory
 import java.security.cert.PKIXParameters
+import java.security.cert.PKIXReason
 import java.security.cert.TrustAnchor
 import java.security.cert.X509Certificate
 import java.util.Date
@@ -43,7 +44,21 @@ internal class X509CertChainValidator(certAnchor: Certificate, date: Date? = nul
       return false
     }
 
-    PATH_VALIDATOR.validate(X509FACTORY.generateCertPath(x509Certs), pkixParams)
+    try {
+      PATH_VALIDATOR.validate(X509FACTORY.generateCertPath(x509Certs), pkixParams)
+    } catch (e: CertPathValidatorException) {
+      val reason = e.reason
+      // https://docs.oracle.com/javase/8/docs/api/java/security/cert/PKIXReason.html
+      // https://docs.oracle.com/javase/8/docs/api/java/security/cert/CertPathValidatorException.BasicReason.html
+      when (reason) {
+          BasicReason.EXPIRED -> throw ExpiredCertificateException("Expired Trifle certificate", e)
+          BasicReason.INVALID_SIGNATURE -> throw IncorrectSignatureException("Invalid Trifle signature", e)
+          PKIXReason.NO_TRUST_ANCHOR -> throw NoTrustAnchorException("No acceptable Trifle trust anchor found", e)
+          else -> throw UnSpecifiedFailureException("Unspecified Trifle verification failure", e)
+      }
+    } catch (e: Exception) {
+      throw UnSpecifiedFailureException("Unspecified Trifle verification failure", e)
+    }
     return true
   }
 
diff --git a/jvm/src/test/kotlin/app/cash/trifle/TrifleTest.kt b/jvm/src/test/kotlin/app/cash/trifle/TrifleTest.kt
index 002aa53..285c08f 100644
--- a/jvm/src/test/kotlin/app/cash/trifle/TrifleTest.kt
+++ b/jvm/src/test/kotlin/app/cash/trifle/TrifleTest.kt
@@ -205,7 +205,9 @@ internal class TrifleTest {
 
     @Test
     fun `test no data extracted with bad verification`() {
-      assertNull(signedData.verifyAndExtract(TestCertificateAuthority().rootCertificate))
+      assertThrows<NoTrustAnchorException> {
+        signedData.verifyAndExtract(TestCertificateAuthority().rootCertificate)
+      }
     }
   }