diff --git a/subprojects/signing/src/main/groovy/org/gradle/plugins/signing/signatory/pgp/PgpSignatoryFactory.groovy b/subprojects/signing/src/main/groovy/org/gradle/plugins/signing/signatory/pgp/PgpSignatoryFactory.groovy
index e77f20c5e4df..3b60fed20f5a 100644
--- a/subprojects/signing/src/main/groovy/org/gradle/plugins/signing/signatory/pgp/PgpSignatoryFactory.groovy
+++ b/subprojects/signing/src/main/groovy/org/gradle/plugins/signing/signatory/pgp/PgpSignatoryFactory.groovy
@@ -72,11 +72,22 @@ class PgpSignatoryFactory {
     }
         
     PGPSecretKey readSecretKey(String keyId, File file) {
+        if (!file.exists()) {
+            throw new InvalidUserDataException("Unable to retrieve secret key from key ring file '$file' as it does not exist")
+        }
+        
         file.withInputStream { readSecretKey(it, keyId, "file: $file.absolutePath") }
     }
     
     protected PGPSecretKey readSecretKey(InputStream input, String keyId, String sourceDescription) {
-        readSecretKey(new PGPSecretKeyRingCollection(input), normalizeKeyId(keyId), sourceDescription)
+        def keyRingCollection
+        try {
+            keyRingCollection = new PGPSecretKeyRingCollection(input)
+        } catch (Exception e) {
+            throw new InvalidUserDataException("Unable to read secret key from $sourceDescription (it may not be a PGP secret key ring)", e)
+        }
+        
+        readSecretKey(keyRingCollection, normalizeKeyId(keyId), sourceDescription)
     }
     
     protected PGPSecretKey readSecretKey(PGPSecretKeyRingCollection keyRings, PgpKeyId keyId, String sourceDescription) {
diff --git a/subprojects/signing/src/test/groovy/org/gradle/plugins/signing/SignatoriesConfigurationSpec.groovy b/subprojects/signing/src/test/groovy/org/gradle/plugins/signing/SignatoriesConfigurationSpec.groovy
index c672784912d5..0bde32f4f1b1 100644
--- a/subprojects/signing/src/test/groovy/org/gradle/plugins/signing/SignatoriesConfigurationSpec.groovy
+++ b/subprojects/signing/src/test/groovy/org/gradle/plugins/signing/SignatoriesConfigurationSpec.groovy
@@ -15,6 +15,8 @@
  */
 package org.gradle.plugins.signing
 
+import org.gradle.api.InvalidUserDataException
+
 class SignatoriesConfigurationSpec extends SigningProjectSpec {
     
     def setup() {
@@ -65,5 +67,31 @@ class SignatoriesConfigurationSpec extends SigningProjectSpec {
         signing.signatories.custom != null
         signing.signatories.custom.keyId.asHex == properties.keyId
     }
+ 
+    def "trying to read non existent file produces reasonable error message"() {
+        when:
+        setProperty("signing.keyId", "aaaaaaaa")
+        setProperty("signing.secretKeyRingFile", "i/dont/exist")
+        setProperty("signing.password", "anything")
+        
+        and:
+        signing.signatory
+        
+        then:
+        def e = thrown(InvalidUserDataException)
+        e.message.contains "it does not exist"
+    }
+    
+    def "trying to use an invalid key ring file produces a reasonable error message"() {
+        given:
+        addSigningProperties(set: "invalid-key-ring")
+        
+        when:
+        signing.signatory
+        
+        then:
+        def e = thrown(InvalidUserDataException)
+        e.message.contains "Unable to read secret key from"
+    }
     
 }
\ No newline at end of file
diff --git a/subprojects/signing/src/test/resources/keys/invalid-key-ring/keyId.txt b/subprojects/signing/src/test/resources/keys/invalid-key-ring/keyId.txt
new file mode 100644
index 000000000000..ee028cc4cadb
--- /dev/null
+++ b/subprojects/signing/src/test/resources/keys/invalid-key-ring/keyId.txt
@@ -0,0 +1 @@
+24875D73
diff --git a/subprojects/signing/src/test/resources/keys/invalid-key-ring/password.txt b/subprojects/signing/src/test/resources/keys/invalid-key-ring/password.txt
new file mode 100644
index 000000000000..82be7ae0c7cb
--- /dev/null
+++ b/subprojects/signing/src/test/resources/keys/invalid-key-ring/password.txt
@@ -0,0 +1 @@
+gradle
\ No newline at end of file
diff --git a/subprojects/signing/src/test/resources/keys/invalid-key-ring/secring.gpg b/subprojects/signing/src/test/resources/keys/invalid-key-ring/secring.gpg
new file mode 100644
index 000000000000..c74084ef4c51
--- /dev/null
+++ b/subprojects/signing/src/test/resources/keys/invalid-key-ring/secring.gpg
@@ -0,0 +1 @@
+not a valid key ring file
\ No newline at end of file