diff --git a/components/inspectit-ocelot-configurationserver/src/main/java/rocks/inspectit/ocelot/agentconfiguration/AgentConfigurationManager.java b/components/inspectit-ocelot-configurationserver/src/main/java/rocks/inspectit/ocelot/agentconfiguration/AgentConfigurationManager.java
index 8108076886..e0cb7ed1b9 100644
--- a/components/inspectit-ocelot-configurationserver/src/main/java/rocks/inspectit/ocelot/agentconfiguration/AgentConfigurationManager.java
+++ b/components/inspectit-ocelot-configurationserver/src/main/java/rocks/inspectit/ocelot/agentconfiguration/AgentConfigurationManager.java
@@ -100,7 +100,7 @@ private synchronized void replaceConfigurations(List<AgentConfiguration> newConf
                     @Override
                     public AgentConfiguration load(Map<String, String> agentAttributes) {
                         return newConfigurations.stream()
-                                .filter(config -> config.getMapping().matchesAttributes(agentAttributes))
+                                .filter(configuration -> configuration.getMapping().matchesAttributes(agentAttributes))
                                 .findFirst()
                                 .orElse(NO_MATCHING_MAPPING);
                     }
diff --git a/components/inspectit-ocelot-configurationserver/src/main/java/rocks/inspectit/ocelot/mappings/model/AgentMapping.java b/components/inspectit-ocelot-configurationserver/src/main/java/rocks/inspectit/ocelot/mappings/model/AgentMapping.java
index 6c0549f628..f0c24020b1 100644
--- a/components/inspectit-ocelot-configurationserver/src/main/java/rocks/inspectit/ocelot/mappings/model/AgentMapping.java
+++ b/components/inspectit-ocelot-configurationserver/src/main/java/rocks/inspectit/ocelot/mappings/model/AgentMapping.java
@@ -6,6 +6,7 @@
 import lombok.Builder;
 import lombok.Singular;
 import lombok.Value;
+import org.apache.commons.lang3.StringUtils;
 import rocks.inspectit.ocelot.security.audit.AuditDetail;
 import rocks.inspectit.ocelot.security.audit.Auditable;
 
@@ -13,6 +14,7 @@
 import java.util.Collections;
 import java.util.List;
 import java.util.Map;
+import java.util.regex.Pattern;
 
 /**
  * The model of the agent mappings.
@@ -54,8 +56,13 @@ public AgentMapping(@JsonProperty("name") String name, @JsonProperty("sources")
      */
     public boolean matchesAttributes(Map<String, String> agentAttributes) {
         for (Map.Entry<String, String> pair : attributes.entrySet()) {
+            String pattern = pair.getValue();
             String value = agentAttributes.getOrDefault(pair.getKey(), "");
-            if (!value.matches(pair.getValue())) {
+
+            boolean matches = Pattern.compile(pattern, Pattern.CASE_INSENSITIVE)
+                    .matcher(value)
+                    .matches();
+            if (!matches) {
                 return false;
             }
         }
diff --git a/components/inspectit-ocelot-configurationserver/src/test/java/rocks/inspectit/ocelot/mappings/model/AgentMappingTest.java b/components/inspectit-ocelot-configurationserver/src/test/java/rocks/inspectit/ocelot/mappings/model/AgentMappingTest.java
new file mode 100644
index 0000000000..2aa484cb44
--- /dev/null
+++ b/components/inspectit-ocelot-configurationserver/src/test/java/rocks/inspectit/ocelot/mappings/model/AgentMappingTest.java
@@ -0,0 +1,81 @@
+package rocks.inspectit.ocelot.mappings.model;
+
+import com.google.common.collect.ImmutableMap;
+import org.junit.jupiter.api.BeforeEach;
+import org.junit.jupiter.api.Nested;
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.extension.ExtendWith;
+import org.mockito.junit.jupiter.MockitoExtension;
+
+import java.util.*;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+@ExtendWith(MockitoExtension.class)
+class AgentMappingTest {
+
+    private AgentMapping mapping;
+
+    @BeforeEach
+    public void beforeEach() {
+        Map<String, String> attributes = new HashMap<>();
+        attributes.put("first", "01234");
+        attributes.put("second", "AnAttribute");
+        attributes.put("third", "\\d+");
+        List<String> sources = new ArrayList<>();
+        sources.add("/one");
+        sources.add("/two/a.yml");
+        sources.add("/two/b.yml");
+        mapping = new AgentMapping("test-mapping", sources, attributes);
+    }
+
+    @Nested
+    class MatchesAttributes {
+
+        @Test
+        public void sameAttributes() {
+            Map<String, String> attributes = ImmutableMap.of("first", "01234", "second", "AnAttribute", "third", "0");
+
+            boolean result = mapping.matchesAttributes(attributes);
+
+            assertThat(result).isTrue();
+        }
+
+        @Test
+        public void differentCasing() {
+            Map<String, String> attributes = ImmutableMap.of("first", "01234", "second", "anaTTribute", "third", "0");
+
+            boolean result = mapping.matchesAttributes(attributes);
+
+            assertThat(result).isTrue();
+        }
+
+        @Test
+        public void differentAttributes() {
+            Map<String, String> attributes = ImmutableMap.of("first", "00000", "second", "AnAttribute", "third", "0");
+
+            boolean result = mapping.matchesAttributes(attributes);
+
+            assertThat(result).isFalse();
+        }
+
+        @Test
+        public void emptyAttributes() {
+            Map<String, String> attributes = Collections.emptyMap();
+
+            boolean result = mapping.matchesAttributes(attributes);
+
+            assertThat(result).isFalse();
+        }
+
+        @Test
+        public void wrongRegexAttribute() {
+            Map<String, String> attributes = ImmutableMap.of("first", "01234", "second", "AnAttribute", "third", "");
+
+            boolean result = mapping.matchesAttributes(attributes);
+
+            assertThat(result).isFalse();
+        }
+    }
+
+}
\ No newline at end of file