diff --git a/RELEASE-NOTES.md b/RELEASE-NOTES.md
index 84883aa08..29c3bc02e 100644
--- a/RELEASE-NOTES.md
+++ b/RELEASE-NOTES.md
@@ -22,17 +22,17 @@ Artifacts in this release are signed by Remko Popma (6601 E5C0 8DCC BB96).
 `PropertiesDefaultProvider` now tries to load properties from the classpath if the file cannot be found  in the user.home directory.
 
 
-
 ## <a name="4.7.6-fixes"></a> Fixed issues
 
 * [#2102][#2107] Enhancement: `PropertiesDefaultProvider` should try to load properties from classpath (last). Thanks to [Lumír Návrat](https://github.com/rimuln) for the pull request.
 * [#2202] Enhancement: Change log level from WARN to INFO when bean not found in ApplicationContext. Thanks to [Desmond Kirrane](https://github.com/dkirrane) for raising this.
 * [#2248] Enhancement: Don't show hidden commands in JLine3 command description. Thanks to [Reinhard Handler](https://github.com/rehand) for the pull request.
+* [#2170] Enhancement: Use `...` vararg instead of array parameter to match overridden method signature. Thanks to [Michael Vorburger](https://github.com/vorburger) for the pull request.
 * [#2058] Bugfix: `defaultValue` should not be applied in addition to user-specified value for options with a custom `IParameterConsumer`. Thanks to [Staffan Arvidsson McShane](https://github.com/StaffanArvidsson) for raising this.
 * [#2148] Bugfix: Fix NPE in jline3 `Example.jar` as `ConfigurationPath` cannot be `null` anymore. Thanks to [llzen44](https://github.com/llzen44) for the pull request.
 * [#2232] Bugfix: fix bug for `Optional<T>` arguments with initial value. Thanks to [hq6](https://github.com/hq6) for raising this.
 * [#2149] Bugfix: `@Option`-annotated setter method not invoked with default value when used in mixin for both command and subcommand. Thanks to [Zhonghao Wang](https://github.com/JBWKZsf) for raising this.
-* [#2170] Enhancement: Use `...` vararg instead of array parameter to match overridden method signature. Thanks to [Michael Vorburger](https://github.com/vorburger) for the pull request.
+* [#2270] Bugfix: Custom type converter for primitive `boolean` options should not be ignored. Thanks to [Sven Kammerer](https://codeberg.org/sven.k) for raising this.
 * [#2234] BUILD: fix errorprone `TruthSelfEquals` warnings
 * [#2172] BUILD: Fix broken build. Thanks to [Michael Vorburger](https://github.com/vorburger) for the pull request.
 * [#2174] BUILD: Fix .gitattributes related CR/LF problems. Thanks to [Michael Vorburger](https://github.com/vorburger) for the pull request.
diff --git a/picocli-tests-java8/build.gradle b/picocli-tests-java8/build.gradle
index 123e5d83c..565d5eb7f 100644
--- a/picocli-tests-java8/build.gradle
+++ b/picocli-tests-java8/build.gradle
@@ -16,9 +16,8 @@ test {
 
 dependencies {
     api rootProject
-    testImplementation supportDependencies.junit5Api
-    testRuntimeOnly    supportDependencies.junit5Engine
-    testImplementation supportDependencies.systemLambda
+    testImplementation supportDependencies.junit
+    testImplementation supportDependencies.hamcrestCore
 }
 
 jar {
diff --git a/picocli-tests-java8/src/test/java/picocli/Issue2270.java b/picocli-tests-java8/src/test/java/picocli/Issue2270.java
new file mode 100644
index 000000000..5d087330f
--- /dev/null
+++ b/picocli-tests-java8/src/test/java/picocli/Issue2270.java
@@ -0,0 +1,78 @@
+package picocli;
+
+import org.junit.After;
+import org.junit.Before;
+import org.junit.Test;
+import picocli.CommandLine.ITypeConverter;
+import picocli.CommandLine.Option;
+
+import java.util.ArrayList;
+import java.util.Arrays;
+import java.util.Base64;
+import java.util.List;
+
+import static org.hamcrest.MatcherAssert.assertThat;
+import static org.hamcrest.Matchers.greaterThanOrEqualTo;
+import static org.junit.Assert.*;
+
+public class Issue2270 {
+    static class CmdObjectBoolean {
+        @Option(names = "--test-Boolean", defaultValue = "dHJ1ZQ==" /* base64-encoded 'true' */)
+        Boolean testBoolean;
+    }
+    static class CmdPrimitiveBoolean {
+        @Option(names = "--test-boolean", defaultValue = "dHJ1ZQ==" /* base64-encoded 'true' */)
+        boolean testboolean;
+    }
+
+    static class Base64BooleanTypeConverter implements ITypeConverter<Boolean> {
+
+        static List<String> invocations = new ArrayList<>();
+
+        public Boolean convert(String value) {
+            invocations.add(value);
+            System.out.printf("converter invocation %s: called with value %s%n",
+                    invocations.size(), value);
+            if (Boolean.parseBoolean(value)) {
+                return true;
+            }
+            return Boolean.parseBoolean(new String(Base64.getDecoder().decode(value)));
+        }
+    }
+
+    @Before
+    public void beforeTests() {
+        CommandLine.tracer().setLevel(CommandLine.TraceLevel.DEBUG);
+    }
+
+    @After
+    public void afterTests() {
+        CommandLine.tracer().setLevel(CommandLine.TraceLevel.WARN);
+    }
+
+    @Test
+    public void testObjectBoolean() {
+        Base64BooleanTypeConverter.invocations.clear();
+        CmdObjectBoolean cmd = new CmdObjectBoolean();
+        new CommandLine(cmd)
+            .registerConverter(Boolean.class, new Base64BooleanTypeConverter())
+            .parseArgs();
+        assertThat(Base64BooleanTypeConverter.invocations.size(), greaterThanOrEqualTo(1));
+        assertEquals(Arrays.asList("dHJ1ZQ==", "true"), Base64BooleanTypeConverter.invocations);
+
+        assertTrue(cmd.testBoolean);
+    }
+
+    @Test
+    public void testPrimitiveBoolean() {
+        Base64BooleanTypeConverter.invocations.clear();
+        CmdPrimitiveBoolean cmd = new CmdPrimitiveBoolean();
+        new CommandLine(cmd)
+            .registerConverter(Boolean.TYPE, new Base64BooleanTypeConverter())
+            .parseArgs();
+        assertThat(Base64BooleanTypeConverter.invocations.size(), greaterThanOrEqualTo(1));
+        assertEquals(Arrays.asList("dHJ1ZQ==", "true"), Base64BooleanTypeConverter.invocations);
+
+        assertTrue(cmd.testboolean);
+    }
+}
diff --git a/src/main/java/picocli/CommandLine.java b/src/main/java/picocli/CommandLine.java
index 46953013a..d1910f0d5 100644
--- a/src/main/java/picocli/CommandLine.java
+++ b/src/main/java/picocli/CommandLine.java
@@ -14910,7 +14910,7 @@ private boolean booleanValue(ArgSpec argSpec, Object value) {
             }
             String stringValue = String.valueOf(value);
             if (empty(stringValue) || "null".equals(stringValue) || "Optional.empty".equals(value)) { return false; }
-            ITypeConverter<?> converter = getTypeConverter(new Class<?>[]{Boolean.class}, argSpec, 0);
+            ITypeConverter<?> converter = getTypeConverter(argSpec.auxiliaryTypes(), argSpec, 0);
             return (Boolean) tryConvert(argSpec, -1, converter, stringValue, 0);
         }