diff --git a/appsec/appsec.go b/appsec/appsec.go
index 33286cdc17..5d0c1ec8f9 100644
--- a/appsec/appsec.go
+++ b/appsec/appsec.go
@@ -50,6 +50,10 @@ func MonitorParsedHTTPBody(ctx context.Context, body any) error {
 // APM tracer middleware on use according to your blocking configuration.
 // This function always returns nil when appsec is disabled and doesn't block users.
 func SetUser(ctx context.Context, id string, opts ...tracer.UserMonitoringOption) error {
+	return setUser(ctx, id, usersec.UserSet, opts)
+}
+
+func setUser(ctx context.Context, id string, userEventType usersec.UserEventType, opts []tracer.UserMonitoringOption) error {
 	s, ok := tracer.SpanFromContext(ctx)
 	if !ok {
 		log.Debug("appsec: could not retrieve span from context. User ID tag won't be set")
@@ -61,11 +65,10 @@ func SetUser(ctx context.Context, id string, opts ...tracer.UserMonitoringOption
 		return nil
 	}
 
-	op, errPtr := usersec.StartUserLoginOperation(ctx, usersec.UserLoginOperationArgs{})
+	op, errPtr := usersec.StartUserLoginOperation(ctx, userEventType, usersec.UserLoginOperationArgs{})
 	op.Finish(usersec.UserLoginOperationRes{
 		UserID:    id,
 		SessionID: getSessionID(opts...),
-		Success:   true,
 	})
 
 	return *errPtr
@@ -85,7 +88,7 @@ func SetUser(ctx context.Context, id string, opts ...tracer.UserMonitoringOption
 // associated to them.
 func TrackUserLoginSuccessEvent(ctx context.Context, uid string, md map[string]string, opts ...tracer.UserMonitoringOption) error {
 	TrackCustomEvent(ctx, "users.login.success", md)
-	return SetUser(ctx, uid, opts...)
+	return setUser(ctx, uid, usersec.UserLoginSuccess, opts)
 }
 
 // TrackUserLoginFailureEvent sets a failed user login event, with the given
@@ -111,8 +114,8 @@ func TrackUserLoginFailureEvent(ctx context.Context, uid string, exists bool, md
 
 	TrackCustomEvent(ctx, "users.login.failure", md)
 
-	op, _ := usersec.StartUserLoginOperation(ctx, usersec.UserLoginOperationArgs{})
-	op.Finish(usersec.UserLoginOperationRes{UserID: uid, Success: false})
+	op, _ := usersec.StartUserLoginOperation(ctx, usersec.UserLoginFailure, usersec.UserLoginOperationArgs{})
+	op.Finish(usersec.UserLoginOperationRes{UserID: uid})
 }
 
 // TrackCustomEvent sets a custom event as service entry span tags. This span is
diff --git a/internal/appsec/emitter/usersec/user.go b/internal/appsec/emitter/usersec/user.go
index 50a4352e6d..235da876bb 100644
--- a/internal/appsec/emitter/usersec/user.go
+++ b/internal/appsec/emitter/usersec/user.go
@@ -7,36 +7,58 @@ package usersec
 
 import (
 	"context"
+	"sync"
 
 	"gopkg.in/DataDog/dd-trace-go.v1/appsec/events"
 	"gopkg.in/DataDog/dd-trace-go.v1/internal/appsec/dyngo"
+	"gopkg.in/DataDog/dd-trace-go.v1/internal/log"
 )
 
 const errorLog = `
 appsec: user login monitoring ignored: could not find the http handler instrumentation metadata in the request context:
-	the request handler is not being monitored by a middleware function or the provided context is not the expected request context
+	the request handler is not being monitored by a middleware function or the provided context is not the expected request context.
+	If the user has been blocked using remote rules, blocking will still be enforced but it will not be reported.
 `
 
+var errorLogOnce sync.Once
+
 type (
+	// UserEventType is the type of user event, such as a successful login or a failed login or any other authenticated request.
+	UserEventType int
+
 	// UserLoginOperation type representing a call to appsec.SetUser(). It gets both created and destroyed in a single
 	// call to ExecuteUserIDOperation
 	UserLoginOperation struct {
 		dyngo.Operation
+		EventType UserEventType
 	}
 	// UserLoginOperationArgs is the user ID operation arguments.
-	UserLoginOperationArgs struct{}
+	UserLoginOperationArgs struct {
+	}
 
 	// UserLoginOperationRes is the user ID operation results.
 	UserLoginOperationRes struct {
 		UserID    string
 		SessionID string
-		Success   bool
 	}
 )
 
-func StartUserLoginOperation(ctx context.Context, args UserLoginOperationArgs) (*UserLoginOperation, *error) {
-	parent, _ := dyngo.FromContext(ctx)
-	op := &UserLoginOperation{Operation: dyngo.NewOperation(parent)}
+const (
+	// UserLoginSuccess is the event type for a successful user login, when a new session or JWT is created.
+	UserLoginSuccess UserEventType = iota
+	// UserLoginFailure is the event type for a failed user login, when the user ID is not found or the password is incorrect.
+	UserLoginFailure
+	// UserSet is the event type for a user ID operation that is not a login, such as any authenticated request made by the user.
+	UserSet
+)
+
+func StartUserLoginOperation(ctx context.Context, eventType UserEventType, args UserLoginOperationArgs) (*UserLoginOperation, *error) {
+	parent, ok := dyngo.FromContext(ctx)
+	if !ok { // Nothing will be reported in this case, but we can still block so we don't return
+		errorLogOnce.Do(func() { log.Error(errorLog) })
+	}
+
+	op := &UserLoginOperation{Operation: dyngo.NewOperation(parent), EventType: eventType}
 	var err error
 	dyngo.OnData(op, func(e *events.BlockingSecurityEvent) { err = e })
 	dyngo.StartOperation(op, args)
diff --git a/internal/appsec/listener/usersec/usec.go b/internal/appsec/listener/usersec/usec.go
index c8a6458019..5989604578 100644
--- a/internal/appsec/listener/usersec/usec.go
+++ b/internal/appsec/listener/usersec/usec.go
@@ -37,14 +37,19 @@ func NewUserSecFeature(cfg *config.Config, rootOp dyngo.Operation) (listener.Fea
 }
 
 func (*Feature) OnFinish(op *usersec.UserLoginOperation, res usersec.UserLoginOperationRes) {
-	builder := addresses.NewAddressesBuilder().
-		WithUserID(res.UserID).
-		WithUserSessionID(res.SessionID)
-
-	if res.Success {
-		builder = builder.WithUserLoginSuccess()
-	} else {
-		builder = builder.WithUserLoginFailure()
+	builder := addresses.NewAddressesBuilder()
+
+	switch op.EventType {
+	case usersec.UserLoginSuccess:
+		builder = builder.WithUserLoginSuccess().
+			WithUserID(res.UserID).
+			WithUserSessionID(res.SessionID)
+	case usersec.UserLoginFailure:
+		builder = builder.WithUserLoginFailure().
+			WithUserID(res.UserID)
+	case usersec.UserSet:
+		builder = builder.WithUserID(res.UserID).
+			WithUserSessionID(res.SessionID)
 	}
 
 	dyngo.EmitData(op, waf.RunEvent{