diff --git a/agent/harness/loop/loop.go b/agent/harness/loop/loop.go
index 3c46446a..e2aa03f9 100644
--- a/agent/harness/loop/loop.go
+++ b/agent/harness/loop/loop.go
@@ -281,12 +281,17 @@ func evaluate(ctx context.Context, evaluators []Evaluator, loopCtx *Context) (Ev
 }
 
 func nextMessages(cfg Config, loopCtx *Context, evaluation Evaluation) (messages []*message.Message, surfaced []*message.Message) {
-	if len(evaluation.Messages) > 0 {
-		cloned := cloneMessages(evaluation.Messages)
-		return cloned, cloned
-	}
 	if cfg.FreshContextPerIteration {
+		// Fresh mode always restarts from the original input (the session is also
+		// reset to a pristine snapshot). Explicit ContinueWithMessages compose
+		// with that fresh context rather than replacing it, so the original input
+		// is not lost.
 		nextMessages := cloneMessages(loopCtx.InitialMessages)
+		if len(evaluation.Messages) > 0 {
+			explicit := cloneMessages(evaluation.Messages)
+			nextMessages = append(nextMessages, explicit...)
+			return nextMessages, explicit
+		}
 		feedbackMessage := aggregatedFeedbackMessage(loopCtx.Feedback, cfg.OnBehalfOfAuthorName)
 		if feedbackMessage == nil {
 			return nextMessages, nil
@@ -294,6 +299,10 @@ func nextMessages(cfg Config, loopCtx *Context, evaluation Evaluation) (messages
 		nextMessages = append(nextMessages, feedbackMessage)
 		return nextMessages, []*message.Message{feedbackMessage}
 	}
+	if len(evaluation.Messages) > 0 {
+		cloned := cloneMessages(evaluation.Messages)
+		return cloned, cloned
+	}
 	if evaluation.Feedback == "" {
 		return nil, nil
 	}
diff --git a/agent/harness/loop/loop_test.go b/agent/harness/loop/loop_test.go
index 119dab69..1aa8488d 100644
--- a/agent/harness/loop/loop_test.go
+++ b/agent/harness/loop/loop_test.go
@@ -559,3 +559,32 @@ func cloneMessages(messages []*message.Message) []*message.Message {
 	}
 	return out
 }
+
+func TestLoop_FreshContextPerIteration_ContinueWithMessagesKeepsInitial(t *testing.T) {
+	capture := newCaptureAgent(func(int, []*message.Message) []*agent.ResponseUpdate {
+		return textUpdates("ack")
+	})
+	a := agent.New(capture.provider(), agent.Config{
+		Middlewares: []agent.Middleware{loop.New(loop.Config{
+			FreshContextPerIteration: true,
+			Evaluators: []loop.Evaluator{loop.EvaluatorFunc(func(_ context.Context, ctx *loop.Context) (loop.Evaluation, error) {
+				if ctx.Iteration == 1 {
+					return loop.ContinueWithMessages([]*message.Message{message.NewText("explicit")}), nil
+				}
+				return loop.Stop(), nil
+			})},
+		})},
+	})
+
+	if _, err := a.RunText(context.Background(), "original").Collect(); err != nil {
+		t.Fatal(err)
+	}
+	secondCall := messageTexts(capture.messagesPerCall[1])
+	// Fresh mode must re-seed the original input; explicit messages compose with it.
+	if len(secondCall) == 0 || secondCall[0] != "original" {
+		t.Fatalf("second call = %v, want the original input preserved in fresh mode", secondCall)
+	}
+	if !slices.Contains(secondCall, "explicit") {
+		t.Fatalf("second call = %v, want the explicit message included", secondCall)
+	}
+}