diff --git a/gateway/service/src/main/java/org/eclipse/ditto/gateway/service/security/authentication/jwt/JwtPlaceholder.java b/gateway/service/src/main/java/org/eclipse/ditto/gateway/service/security/authentication/jwt/JwtPlaceholder.java
index 586fa7a78d..dbe7b0ec69 100644
--- a/gateway/service/src/main/java/org/eclipse/ditto/gateway/service/security/authentication/jwt/JwtPlaceholder.java
+++ b/gateway/service/src/main/java/org/eclipse/ditto/gateway/service/security/authentication/jwt/JwtPlaceholder.java
@@ -15,10 +15,10 @@
 import static org.eclipse.ditto.base.model.common.ConditionChecker.argumentNotEmpty;
 import static org.eclipse.ditto.base.model.common.ConditionChecker.checkNotNull;
 
-import java.util.Collections;
 import java.util.List;
-import java.util.Optional;
+import java.util.stream.Stream;
 
+import org.eclipse.ditto.json.JsonPointer;
 import org.eclipse.ditto.json.JsonValue;
 import org.eclipse.ditto.jwt.model.JsonWebToken;
 import org.eclipse.ditto.placeholders.Placeholder;
@@ -63,15 +63,23 @@ public boolean supports(final String name) {
     public List<String> resolveValues(final JsonWebToken jwt, final String placeholder) {
         argumentNotEmpty(placeholder, "placeholder");
         checkNotNull(jwt, "jwt");
-        final Optional<JsonValue> value = jwt.getBody().getValue(placeholder);
-        return value.filter(JsonValue::isArray)
-                .map(JsonValue::asArray)
-                .map(array -> array.stream()
-                        .map(JsonValue::formatAsString)
-                        .toList())
-                .or(() -> value.map(JsonValue::formatAsString)
-                        .map(Collections::singletonList))
-                .orElseGet(Collections::emptyList);
+        return resolveValues(jwt.getBody(), JsonPointer.of(placeholder))
+                .distinct()
+                .toList();
+    }
+
+    private static Stream<String> resolveValues(final JsonValue jsonValue, final JsonPointer jsonPointer) {
+        return jsonPointer.getRoot()
+                .<Stream<String>>map(root -> jsonValue.isArray()
+                        ? jsonValue.asArray().stream().flatMap(item -> resolveValues(item, jsonPointer))
+                        : (jsonValue.isObject()
+                                ? jsonValue.asObject().getValue(root)
+                                        .map(v -> resolveValues(v, jsonPointer.nextLevel()))
+                                        .orElseGet(Stream::empty)
+                                : Stream.empty()))
+                .orElseGet(() -> jsonValue.isArray()
+                    ? jsonValue.asArray().stream().map(JsonValue::formatAsString)
+                    : Stream.of(jsonValue.formatAsString()));
     }
 
 }
diff --git a/gateway/service/src/test/java/org/eclipse/ditto/gateway/service/security/authentication/jwt/JwtPlaceholderTest.java b/gateway/service/src/test/java/org/eclipse/ditto/gateway/service/security/authentication/jwt/JwtPlaceholderTest.java
new file mode 100644
index 0000000000..01fe39611a
--- /dev/null
+++ b/gateway/service/src/test/java/org/eclipse/ditto/gateway/service/security/authentication/jwt/JwtPlaceholderTest.java
@@ -0,0 +1,179 @@
+/*
+ * Copyright (c) 2024 Contributors to the Eclipse Foundation
+ *
+ * See the NOTICE file(s) distributed with this work for additional
+ * information regarding copyright ownership.
+ *
+ * This program and the accompanying materials are made available under the
+ * terms of the Eclipse Public License 2.0 which is available at
+ * http://www.eclipse.org/legal/epl-2.0
+ *
+ * SPDX-License-Identifier: EPL-2.0
+ */
+package org.eclipse.ditto.gateway.service.security.authentication.jwt;
+
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.mockito.Mockito.mock;
+import static org.mockito.Mockito.when;
+
+import org.eclipse.ditto.json.JsonObject;
+import org.eclipse.ditto.jwt.model.JsonWebToken;
+import org.junit.Test;
+
+import nl.jqno.equalsverifier.EqualsVerifier;
+import nl.jqno.equalsverifier.Warning;
+
+/**
+ * Tests {@link JwtPlaceholder}.
+ */
+public final class JwtPlaceholderTest {
+
+    private static final JwtPlaceholder UNDER_TEST = new JwtPlaceholder();
+
+    @Test
+    public void testHashCodeAndEquals() {
+        EqualsVerifier.forClass(JwtPlaceholder.class)
+                .suppress(Warning.INHERITED_DIRECTLY_FROM_OBJECT)
+                .usingGetClass()
+                .verify();
+    }
+
+    @Test
+    public void testResolveRootProperty() {
+        final JsonWebToken jwt = createToken("""
+                {
+                    "sub": "jwt-subject"
+                }
+                """);
+        assertThat(UNDER_TEST.resolveValues(jwt, "sub"))
+                .containsExactlyInAnyOrder("jwt-subject");
+    }
+
+    @Test
+    public void testResolveObjectProperty() {
+        final JsonWebToken jwt = createToken("""
+                {
+                    "authorization": {
+                        "isFull": true
+                    }
+                }
+                """);
+        assertThat(UNDER_TEST.resolveValues(jwt, "authorization"))
+                .containsExactlyInAnyOrder("{\"isFull\":true}");
+    }
+
+    @Test
+    public void testResolveNestedSimpleProperty() {
+        final JsonWebToken jwt = createToken("""
+                {
+                    "authorization": {
+                        "isFull": true
+                    }
+                }
+                """);
+        assertThat(UNDER_TEST.resolveValues(jwt, "authorization/isFull"))
+                .containsExactlyInAnyOrder("true");
+    }
+
+    @Test
+    public void testResolveArrayProperty() {
+        final JsonWebToken jwt = createToken("""
+                {
+                    "authorization": {
+                        "roles": ["user", "admin"]
+                    }
+                }
+                """);
+        assertThat(UNDER_TEST.resolveValues(jwt, "authorization/roles"))
+                .containsExactlyInAnyOrder("user", "admin");
+    }
+
+    @Test
+    public void testResolveSimplePropertyInArray() {
+        final JsonWebToken jwt = createToken("""
+                {
+                    "authorization": {
+                        "roles": [
+                            { "name": "user" },
+                            { "name": "admin" }
+                        ]
+                    }
+                }
+                """);
+        assertThat(UNDER_TEST.resolveValues(jwt, "authorization/roles/name"))
+                .containsExactlyInAnyOrder("user", "admin");
+    }
+
+    @Test
+    public void testResolveObjectPropertyInArray() {
+        final JsonWebToken jwt = createToken("""
+                {
+                    "authorization": {
+                        "roles": [
+                            {
+                                "info": { "name": "user" }
+                            },
+                            {
+                                "info": { "name": "admin" }
+                            }
+                        ]
+                    }
+                }
+                """);
+        assertThat(UNDER_TEST.resolveValues(jwt, "authorization/roles/info"))
+                .containsExactlyInAnyOrder("{\"name\":\"user\"}", "{\"name\":\"admin\"}");
+    }
+
+    @Test
+    public void testResolveArrayPropertyInArray() {
+        final JsonWebToken jwt = createToken("""
+                {
+                    "authorization": {
+                        "roles": [
+                            {
+                                "name": "user",
+                                "claims": [ "read" ]
+                            },
+                            {
+                                "name": "admin",
+                                "claims": [ "read", "write" ]
+                            }
+                        ]
+                    }
+                }
+                """);
+        assertThat(UNDER_TEST.resolveValues(jwt, "authorization/roles/claims"))
+                .containsExactlyInAnyOrder("read", "write");
+    }
+
+    @Test
+    public void testResolveNestedPropertyOnSimpleValue() {
+        final JsonWebToken jwt = createToken("""
+                {
+                    "authorization": {
+                        "roles": [ "user", "admin" ]
+                    }
+                }
+                """);
+        assertThat(UNDER_TEST.resolveValues(jwt, "authorization/roles/name"))
+                .isEmpty();
+    }
+
+    @Test
+    public void testResolveNestedPropertyOnMissingValue() {
+        final JsonWebToken jwt = createToken("""
+                {
+                    "authorization": {}
+                }
+                """);
+        assertThat(UNDER_TEST.resolveValues(jwt, "authorization/roles"))
+                .isEmpty();
+    }
+
+    private static JsonWebToken createToken(final String body) {
+        final JsonWebToken jsonWebToken = mock(JsonWebToken.class);
+        when(jsonWebToken.getBody()).thenReturn(JsonObject.of(body));
+        return jsonWebToken;
+    }
+
+}