diff --git a/pkg/hub/handlers_agent_messaging.go b/pkg/hub/handlers_agent_messaging.go
index 67edec9a8..af860d8b9 100644
--- a/pkg/hub/handlers_agent_messaging.go
+++ b/pkg/hub/handlers_agent_messaging.go
@@ -22,6 +22,7 @@ import (
 	"net/http"
 	"strings"
 	"time"
+	"unicode/utf8"
 
 	"github.com/GoogleCloudPlatform/scion/pkg/agent/state"
 	"github.com/GoogleCloudPlatform/scion/pkg/api"
@@ -68,6 +69,10 @@ func (s *Server) handleAgentOutboundMessage(w http.ResponseWriter, r *http.Reque
 		ValidationError(w, "msg is required", nil)
 		return
 	}
+	if msgLen := utf8.RuneCountInString(req.Msg); msgLen > messages.MaxMessageLength {
+		ValidationError(w, fmt.Sprintf("message exceeds %d character limit (current: %d chars). Consider splitting into multiple messages using multiple scion message invocations", messages.MaxMessageLength, msgLen), nil)
+		return
+	}
 	if req.Type == "" {
 		req.Type = "input-needed"
 	}
diff --git a/pkg/messages/types.go b/pkg/messages/types.go
index 962593325..e4508dfde 100644
--- a/pkg/messages/types.go
+++ b/pkg/messages/types.go
@@ -24,6 +24,9 @@ import (
 // Schema version for the structured message format.
 const Version = 1
 
+// Maximum length of the Msg field in characters for outbound messages.
+const MaxMessageLength = 2000
+
 // Maximum size of the Msg field in bytes.
 const MaxMsgSize = 64 * 1024 // 64KB
 
@@ -127,6 +130,9 @@ func (m *StructuredMessage) Validate() error {
 	if m.Msg == "" {
 		return fmt.Errorf("msg field is required")
 	}
+	if len([]rune(m.Msg)) > MaxMessageLength {
+		return fmt.Errorf("message exceeds %d character limit (current: %d chars). Consider splitting into multiple messages using multiple scion message invocations", MaxMessageLength, len([]rune(m.Msg)))
+	}
 	if len(m.Msg) > MaxMsgSize {
 		return fmt.Errorf("msg exceeds maximum size of %d bytes", MaxMsgSize)
 	}
diff --git a/pkg/messages/types_test.go b/pkg/messages/types_test.go
index 0c19ce0cb..b14aa098b 100644
--- a/pkg/messages/types_test.go
+++ b/pkg/messages/types_test.go
@@ -76,6 +76,25 @@ func TestStructuredMessage_Validate(t *testing.T) {
 		}
 	})
 
+	t.Run("msg exceeds character limit", func(t *testing.T) {
+		m := validMsg()
+		m.Msg = strings.Repeat("x", MaxMessageLength+1)
+		err := m.Validate()
+		if err == nil {
+			t.Error("expected error for msg exceeding character limit")
+		} else if !strings.Contains(err.Error(), "character limit") {
+			t.Errorf("error should mention character limit, got: %v", err)
+		}
+	})
+
+	t.Run("msg at character limit", func(t *testing.T) {
+		m := validMsg()
+		m.Msg = strings.Repeat("x", MaxMessageLength)
+		if err := m.Validate(); err != nil {
+			t.Errorf("unexpected error for msg at character limit: %v", err)
+		}
+	})
+
 	t.Run("msg too large", func(t *testing.T) {
 		m := validMsg()
 		m.Msg = strings.Repeat("x", MaxMsgSize+1)