diff --git a/pgpainless-core/src/test/java/org/pgpainless/key/modification/FixUserIdDoesNotBreakEncryptionCapabilityTest.java b/pgpainless-core/src/test/java/org/pgpainless/key/modification/FixUserIdDoesNotBreakEncryptionCapabilityTest.java
new file mode 100644
index 00000000..1995b8bf
--- /dev/null
+++ b/pgpainless-core/src/test/java/org/pgpainless/key/modification/FixUserIdDoesNotBreakEncryptionCapabilityTest.java
@@ -0,0 +1,84 @@
+// SPDX-FileCopyrightText: 2022 Paul Schaub <vanitasvitae@fsfe.org>
+//
+// SPDX-License-Identifier: Apache-2.0
+
+package org.pgpainless.key.modification;
+
+import org.bouncycastle.openpgp.PGPException;
+import org.bouncycastle.openpgp.PGPSecretKeyRing;
+import org.junit.jupiter.api.Test;
+import org.pgpainless.PGPainless;
+import org.pgpainless.key.info.KeyRingInfo;
+import org.pgpainless.key.protection.SecretKeyRingProtector;
+import org.pgpainless.signature.subpackets.SelfSignatureSubpackets;
+
+import java.io.IOException;
+
+import static org.junit.jupiter.api.Assertions.assertFalse;
+import static org.junit.jupiter.api.Assertions.assertTrue;
+
+/**
+ * Test for #298.
+ */
+public class FixUserIdDoesNotBreakEncryptionCapabilityTest {
+
+    private static final String SECRET_KEY = "-----BEGIN PGP PRIVATE KEY BLOCK-----\n" +
+            "\n" +
+            "lFgEYsyc4hYJKwYBBAHaRw8BAQdAjm3bQ61H2E6/xzjjHjl6G+mNl72r7fwdux9f\n" +
+            "CXQrCpoAAQDwY5Vblm+7Dq8NfP5gqThyv+23aMBYLr3UgJAZyAgu/RDBtCQoQilv\n" +
+            "YiAoSilvaG5zb24gPGJqQGV2YWx1YXRpb24udGVzdD6IkAQTFggAOBYhBI70BlHo\n" +
+            "XvYV3ufIc8MDl+w8xmx4BQJizJziAhsjBQsJCAcCBhUKCQgLAgQWAgMBAh4BAheA\n" +
+            "AAoJEMMDl+w8xmx4ZAMBAIZsBqoClMlwymvNWIENCAZMQSy9NpBABk3jDyEjbhgs\n" +
+            "AP9sGI7URQNUDXiV+sIzvastNX/nOZ7fkwp6Xrx+74WxC5xdBGLMnOISCisGAQQB\n" +
+            "l1UBBQEBB0CGU2EGdS4mvy0apuPukStWSqEDH16AFSGEeTt2GyN1IQMBCAcAAP9J\n" +
+            "nrIGndqzxxIUHVsoImYIu9SFl9Z1tCSia6mADTtbsA88iHgEGBYIACAWIQSO9AZR\n" +
+            "6F72Fd7nyHPDA5fsPMZseAUCYsyc4gIbDAAKCRDDA5fsPMZseACnAQDIR7QwBTIs\n" +
+            "Hfu4XIpZTyipOy6ZOEKlY3akyb9TtOq1wAD8Da+0Insssuf0J5WPqShJ/wMX3+xk\n" +
+            "gqeRV2HyogQ7aAE=\n" +
+            "=6zZo\n" +
+            "-----END PGP PRIVATE KEY BLOCK-----\n";
+    private static final String CERTIFICATE = "-----BEGIN PGP PUBLIC KEY BLOCK-----\n" +
+            "\n" +
+            "mDMEYsyc4hYJKwYBBAHaRw8BAQdAjm3bQ61H2E6/xzjjHjl6G+mNl72r7fwdux9f\n" +
+            "CXQrCpq0JChCKW9iIChKKW9obnNvbiA8YmpAZXZhbHVhdGlvbi50ZXN0PoiQBBMW\n" +
+            "CAA4FiEEjvQGUehe9hXe58hzwwOX7DzGbHgFAmLMnOICGyMFCwkIBwIGFQoJCAsC\n" +
+            "BBYCAwECHgECF4AACgkQwwOX7DzGbHhkAwEAhmwGqgKUyXDKa81YgQ0IBkxBLL02\n" +
+            "kEAGTeMPISNuGCwA/2wYjtRFA1QNeJX6wjO9qy01f+c5nt+TCnpevH7vhbELuDgE\n" +
+            "Ysyc4hIKKwYBBAGXVQEFAQEHQIZTYQZ1Lia/LRqm4+6RK1ZKoQMfXoAVIYR5O3Yb\n" +
+            "I3UhAwEIB4h4BBgWCAAgFiEEjvQGUehe9hXe58hzwwOX7DzGbHgFAmLMnOICGwwA\n" +
+            "CgkQwwOX7DzGbHgApwEAyEe0MAUyLB37uFyKWU8oqTsumThCpWN2pMm/U7TqtcAA\n" +
+            "/A2vtCJ7LLLn9CeVj6koSf8DF9/sZIKnkVdh8qIEO2gB\n" +
+            "=3sNT\n" +
+            "-----END PGP PUBLIC KEY BLOCK-----";
+
+    private static final String userIdBefore = "(B)ob (J)ohnson <bj@evaluation.test>";
+    private static final String userIdAfter = "\"(B)ob (J)ohnson\" <bj@evaluation.test>";
+
+    @Test
+    public void replaceUserIdWithFixedVersionDoesNotHinderEncryptionCapability() throws IOException, PGPException {
+        PGPSecretKeyRing secretKeys = PGPainless.readKeyRing().secretKeyRing(SECRET_KEY);
+        SecretKeyRingProtector protector = SecretKeyRingProtector.unprotectedKeys();
+        PGPSecretKeyRing modified = PGPainless.modifyKeyRing(secretKeys)
+                .addUserId(userIdAfter, new SelfSignatureSubpackets.Callback() {
+                    @Override
+                    public void modifyHashedSubpackets(SelfSignatureSubpackets hashedSubpackets) {
+                        hashedSubpackets.setPrimaryUserId();
+                    }
+                }, protector)
+                .removeUserId(userIdBefore, protector)
+                .done();
+
+        KeyRingInfo before = PGPainless.inspectKeyRing(secretKeys);
+        KeyRingInfo after = PGPainless.inspectKeyRing(modified);
+
+        assertTrue(before.isUsableForEncryption());
+        assertTrue(before.isUsableForSigning());
+        assertTrue(before.isUserIdValid(userIdBefore));
+        assertFalse(before.isUserIdValid(userIdAfter));
+
+        assertTrue(after.isUsableForEncryption());
+        assertTrue(after.isUsableForSigning());
+        assertFalse(after.isUserIdValid(userIdBefore));
+        assertTrue(after.isUserIdValid(userIdAfter));
+    }
+}