diff --git a/pgpainless-core/src/main/java/org/pgpainless/key/protection/CallbackBasedKeyringProtector.java b/pgpainless-core/src/main/java/org/pgpainless/key/protection/CallbackBasedKeyringProtector.java
index 6da9856d..9e37eb32 100644
--- a/pgpainless-core/src/main/java/org/pgpainless/key/protection/CallbackBasedKeyringProtector.java
+++ b/pgpainless-core/src/main/java/org/pgpainless/key/protection/CallbackBasedKeyringProtector.java
@@ -50,7 +50,7 @@ public class CallbackBasedKeyringProtector implements SecretKeyRingProtector2 {
     @Override
     public PBESecretKeyEncryptor getEncryptor(PGPSecretKey key) throws PGPException {
         Passphrase passphrase = lookupPassphraseInCache(key);
-        if (passphrase != null) {
+        if (passphrase == null) {
             passphrase = callback.getPassphraseFor(key);
             passphraseCache.put(key.getKeyID(), passphrase);
         }