diff --git a/server/contexts/ctxerr/ctxerr.go b/server/contexts/ctxerr/ctxerr.go
index e4733ec843..6a14d0823f 100644
--- a/server/contexts/ctxerr/ctxerr.go
+++ b/server/contexts/ctxerr/ctxerr.go
@@ -18,6 +18,9 @@ import (
 	"fmt"
 	"strings"
 	"time"
+
+	"github.com/fleetdm/fleet/v4/server/contexts/host"
+	"github.com/fleetdm/fleet/v4/server/contexts/viewer"
 )
 
 type key int
@@ -76,8 +79,25 @@ func setMetadata(ctx context.Context, data map[string]interface{}) map[string]in
 		data = map[string]interface{}{}
 	}
 
-	// TODO: add more metadata from ctx
 	data["timestamp"] = nowFn().Format(time.RFC3339)
+
+	if h, ok := host.FromContext(ctx); ok {
+		data["host"] = map[string]interface{}{
+			"platform":        h.Platform,
+			"osquery_version": h.OsqueryVersion,
+		}
+	}
+
+	if v, ok := viewer.FromContext(ctx); ok {
+		vdata := map[string]interface{}{}
+		data["viewer"] = vdata
+		vdata["is_logged_in"] = v.IsLoggedIn()
+
+		if v.User != nil {
+			vdata["sso_enabled"] = v.User.SSOEnabled
+		}
+	}
+
 	return data
 }
 
diff --git a/server/contexts/ctxerr/ctxerr_test.go b/server/contexts/ctxerr/ctxerr_test.go
index 066273639e..ada98fc1de 100644
--- a/server/contexts/ctxerr/ctxerr_test.go
+++ b/server/contexts/ctxerr/ctxerr_test.go
@@ -10,6 +10,9 @@ import (
 	"testing"
 	"time"
 
+	"github.com/fleetdm/fleet/v4/server/contexts/host"
+	"github.com/fleetdm/fleet/v4/server/contexts/viewer"
+	"github.com/fleetdm/fleet/v4/server/fleet"
 	pkgerrors "github.com/pkg/errors" //nolint:depguard
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
@@ -341,3 +344,23 @@ func TestHandle(t *testing.T) {
 		Handle(ctx, err)
 	})
 }
+
+func TestAdditionalMetadata(t *testing.T) {
+	t.Run("saves additional data about the host if present", func(t *testing.T) {
+		ctx, cleanup := setup()
+		defer cleanup()
+		hctx := host.NewContext(ctx, &fleet.Host{Platform: "test_platform", OsqueryVersion: "5.0"})
+		err := New(hctx, "with host context").(*FleetError)
+
+		require.JSONEq(t, string(err.data), `{"host":{"osquery_version":"5.0","platform":"test_platform"},"timestamp":"1969-06-19T21:44:05Z"}`)
+	})
+
+	t.Run("saves additional data about the viewer if present", func(t *testing.T) {
+		ctx, cleanup := setup()
+		defer cleanup()
+		vctx := viewer.NewContext(ctx, viewer.Viewer{Session: &fleet.Session{ID: 1}, User: &fleet.User{SSOEnabled: true}})
+		err := New(vctx, "with host context").(*FleetError)
+
+		require.JSONEq(t, string(err.data), `{"viewer":{"is_logged_in":true,"sso_enabled":true},"timestamp":"1969-06-19T21:44:05Z"}`)
+	})
+}