diff --git a/dd-java-agent/instrumentation/spring/spring-security/spring-security-5.0/src/main/java/datadog/trace/instrumentation/springsecurity5/SpringSecurityUserEventDecorator.java b/dd-java-agent/instrumentation/spring/spring-security/spring-security-5.0/src/main/java/datadog/trace/instrumentation/springsecurity5/SpringSecurityUserEventDecorator.java
index d7285e7f976..7bfb63e06a1 100644
--- a/dd-java-agent/instrumentation/spring/spring-security/spring-security-5.0/src/main/java/datadog/trace/instrumentation/springsecurity5/SpringSecurityUserEventDecorator.java
+++ b/dd-java-agent/instrumentation/spring/spring-security/spring-security-5.0/src/main/java/datadog/trace/instrumentation/springsecurity5/SpringSecurityUserEventDecorator.java
@@ -43,6 +43,10 @@ public void onUserNotFound() {
     tracker.onUserNotFound(UserIdCollectionMode.get());
   }
 
+  public void onUserNotFound(final String username) {
+    onUserNotFound();
+  }
+
   public void onSignup(UserDetails user, Throwable throwable) {
     // skip failures while signing up a user, later on, we might want to generate a separate event
     // for this case
diff --git a/dd-java-agent/instrumentation/spring/spring-security/spring-security-5.0/src/main/java/datadog/trace/instrumentation/springsecurity5/UsernameNotFoundExceptionFactoryInstrumentation.java b/dd-java-agent/instrumentation/spring/spring-security/spring-security-5.0/src/main/java/datadog/trace/instrumentation/springsecurity5/UsernameNotFoundExceptionFactoryInstrumentation.java
new file mode 100644
index 00000000000..e531fef6b25
--- /dev/null
+++ b/dd-java-agent/instrumentation/spring/spring-security/spring-security-5.0/src/main/java/datadog/trace/instrumentation/springsecurity5/UsernameNotFoundExceptionFactoryInstrumentation.java
@@ -0,0 +1,54 @@
+package datadog.trace.instrumentation.springsecurity5;
+
+import static datadog.trace.agent.tooling.bytebuddy.matcher.NameMatchers.named;
+import static net.bytebuddy.matcher.ElementMatchers.isMethod;
+import static net.bytebuddy.matcher.ElementMatchers.isPublic;
+import static net.bytebuddy.matcher.ElementMatchers.isStatic;
+
+import com.google.auto.service.AutoService;
+import datadog.trace.agent.tooling.Instrumenter;
+import datadog.trace.agent.tooling.InstrumenterModule;
+import net.bytebuddy.asm.Advice;
+
+/**
+ * Hooks the static factory method {@code UsernameNotFoundException.fromUsername(String)} added in
+ * Spring Security 7. In Spring Security 7, {@code UserDetailsService} implementations (notably
+ * {@code InMemoryUserDetailsManager}) construct {@code UsernameNotFoundException} via this factory
+ * rather than the public constructor, so the sibling {@link UsernameNotFoundExceptionInstrumentation}
+ * (constructor-based) no longer fires on that path.
+ */
+@AutoService(InstrumenterModule.class)
+public class UsernameNotFoundExceptionFactoryInstrumentation extends InstrumenterModule.AppSec
+    implements Instrumenter.ForSingleType, Instrumenter.HasMethodAdvice {
+
+  public UsernameNotFoundExceptionFactoryInstrumentation() {
+    super("spring-security");
+  }
+
+  @Override
+  public String instrumentedType() {
+    return "org.springframework.security.core.userdetails.UsernameNotFoundException";
+  }
+
+  @Override
+  public String[] helperClassNames() {
+    return new String[] {
+      "datadog.trace.instrumentation.springsecurity5.SpringSecurityUserEventDecorator"
+    };
+  }
+
+  @Override
+  public void methodAdvice(MethodTransformer transformer) {
+    transformer.applyAdvice(
+        isMethod().and(named("fromUsername")).and(isStatic()).and(isPublic()),
+        getClass().getName() + "$FromUsernameAdvice");
+  }
+
+  public static class FromUsernameAdvice {
+
+    @Advice.OnMethodEnter(suppress = Throwable.class)
+    public static void onEnter(@Advice.Argument(0) final String username) {
+      SpringSecurityUserEventDecorator.DECORATE.onUserNotFound(username);
+    }
+  }
+}
diff --git a/dd-java-agent/instrumentation/spring/spring-security/spring-security-6.0/build.gradle b/dd-java-agent/instrumentation/spring/spring-security/spring-security-6.0/build.gradle
index e271c5ad55c..83968e41118 100644
--- a/dd-java-agent/instrumentation/spring/spring-security/spring-security-6.0/build.gradle
+++ b/dd-java-agent/instrumentation/spring/spring-security/spring-security-6.0/build.gradle
@@ -24,9 +24,9 @@ dependencies {
   testImplementation group: 'org.springframework.boot', name: 'spring-boot-starter-web', version: springBootVersion
   testImplementation group: 'org.springframework.boot', name: 'spring-boot-starter-security', version: springBootVersion
 
-  latestDepTestImplementation group: 'org.springframework.boot', name: 'spring-boot-starter-test', version: '3.+'
-  latestDepTestImplementation group: 'org.springframework.boot', name: 'spring-boot-starter-web', version: '3.+'
-  latestDepTestImplementation group: 'org.springframework.boot', name: 'spring-boot-starter-security', version: '3.+'
+  latestDepTestImplementation group: 'org.springframework.boot', name: 'spring-boot-starter-test', version: '4.+'
+  latestDepTestImplementation group: 'org.springframework.boot', name: 'spring-boot-starter-web', version: '4.+'
+  latestDepTestImplementation group: 'org.springframework.boot', name: 'spring-boot-starter-security', version: '4.+'
 
   testRuntimeOnly project(':dd-java-agent:instrumentation:tomcat:tomcat-appsec:tomcat-appsec-6.0')
   testRuntimeOnly project(':dd-java-agent:instrumentation:tomcat:tomcat-5.5')
diff --git a/dd-java-agent/instrumentation/spring/spring-security/spring-security-6.0/src/test/java/datadog/trace/instrumentation/springsecurity6/UsernameNotFoundFromUsernameTest.java b/dd-java-agent/instrumentation/spring/spring-security/spring-security-6.0/src/test/java/datadog/trace/instrumentation/springsecurity6/UsernameNotFoundFromUsernameTest.java
new file mode 100644
index 00000000000..d2e949c0182
--- /dev/null
+++ b/dd-java-agent/instrumentation/spring/spring-security/spring-security-6.0/src/test/java/datadog/trace/instrumentation/springsecurity6/UsernameNotFoundFromUsernameTest.java
@@ -0,0 +1,40 @@
+package datadog.trace.instrumentation.springsecurity6;
+
+import static org.junit.jupiter.api.Assertions.assertDoesNotThrow;
+import static org.junit.jupiter.api.Assertions.assertEquals;
+
+import datadog.trace.instrumentation.springsecurity5.SpringSecurityUserEventDecorator;
+import datadog.trace.instrumentation.springsecurity5.UsernameNotFoundExceptionFactoryInstrumentation;
+import org.junit.jupiter.api.Test;
+
+/**
+ * Unit-level checks for the Spring Security 7 {@code UsernameNotFoundException.fromUsername}
+ * factory hook.
+ *
+ * <p>The end-to-end AppSec event assertion lives in the existing {@code SpringBootBasedTest}
+ * Groovy spec; when {@code latestDepTest} resolves Spring Boot 4 (Spring Security 7) the
+ * "test failed login with non existing user" case exercises the {@code fromUsername} factory
+ * path through {@code InMemoryUserDetailsManager} and verifies the AppSec login-failure tags
+ * are emitted. This Java test pins the contract pieces that aren't covered there: the new
+ * instrumentation targets the exact {@code UsernameNotFoundException} type, and the decorator
+ * overload that the advice invokes is callable without throwing.
+ */
+class UsernameNotFoundFromUsernameTest {
+
+  @Test
+  void instrumentationTargetsUsernameNotFoundException() {
+    final UsernameNotFoundExceptionFactoryInstrumentation instrumentation =
+        new UsernameNotFoundExceptionFactoryInstrumentation();
+    assertEquals(
+        "org.springframework.security.core.userdetails.UsernameNotFoundException",
+        instrumentation.instrumentedType());
+  }
+
+  @Test
+  void decoratorAcceptsUsernameOverload() {
+    // The advice forwards Argument(0) into this overload; ensure it is callable in isolation
+    // (no AppSec tracker is registered in this unit test, so the decorator must no-op cleanly).
+    assertDoesNotThrow(() -> SpringSecurityUserEventDecorator.DECORATE.onUserNotFound("alice"));
+    assertDoesNotThrow(() -> SpringSecurityUserEventDecorator.DECORATE.onUserNotFound(null));
+  }
+}