answer customer messages sent while the AI is replying

internal/aiagent/worker.go

@@ -234,14 +234,19 @@ func (m *Manager) handle(ctx context.Context, convID int) {
 	if inbound == nil {
 		return
 	}
-	// Only respond to a fresh inbound customer message, never to the assistant's own or automated
-	// replies. A requeued run sees the previous run's just-posted reply as the last message, so it
-	// instead checks for an inbound message the previous run's history never included.
 	m.mu.Lock()
 	prevSeen, hasPrev := m.lastSeen[convID]
 	m.lastSeen[convID] = msgs[len(msgs)-1].ID
 	m.mu.Unlock()
-	if !lastIsInboundContact(msgs) && (!hasPrev || inbound.ID <= prevSeen) {
+	// A requeued run finds the previous run's reply after the customer messages that arrived while it
+	// was being written. Moving the reply above them keeps the history in the order the assistant saw
+	// it and leaves the newest customer message last, which providers require.
+	if hasPrev {
+		msgs = previousReplyFirst(msgs, prevSeen)
+	}
+	// Only respond when the newest message is the customer's, never to the assistant's own, a human's
+	// or automated replies.
+	if !lastIsInboundContact(msgs) {
 		return
 	}
 	// The reply and any identity-scoped tools act as the primary contact. An email thread can carry
@@ -867,3 +872,25 @@ func messageMetaBool(raw json.RawMessage, key string) bool {
 	value, _ := meta[key].(bool)
 	return value
 }
+
+// previousReplyFirst moves AI replies posted after prevSeen above the other messages that arrived since.
+func previousReplyFirst(msgs []cmodels.Message, prevSeen int) []cmodels.Message {
+	out := make([]cmodels.Message, 0, len(msgs))
+	var later []cmodels.Message
+	for _, msg := range msgs {
+		if msg.ID > prevSeen && !isAIReply(msg) {
+			later = append(later, msg)
+			continue
+		}
+		out = append(out, msg)
+	}
+	return append(out, later...)
+}
+
+// isAIReply matches replies from any assistant, so a reassignment mid-run still finds the old reply.
+func isAIReply(msg cmodels.Message) bool {
+	var meta struct {
+		AssistantID int `json:"ai_assistant_id"`
+	}
+	return json.Unmarshal(msg.Meta, &meta) == nil && meta.AssistantID > 0
+}

internal/aiagent/worker_test.go

@@ -1,12 +1,14 @@
 package aiagent
 
 import (
+	"encoding/json"
 	"reflect"
 	"strings"
 	"testing"
 
 	aimodels "github.com/abhinavxd/libredesk/internal/ai/models"
 	"github.com/abhinavxd/libredesk/internal/aiagent/models"
+	cmodels "github.com/abhinavxd/libredesk/internal/conversation/models"
 	"github.com/abhinavxd/libredesk/internal/stringutil"
 )
 
@@ -109,3 +111,33 @@ func TestArticleCitationHTML(t *testing.T) {
 		t.Fatalf("unexpected preview: %q", got)
 	}
 }
+
+func TestPreviousReplyFirst(t *testing.T) {
+	msg := func(id int) cmodels.Message { return cmodels.Message{ID: id} }
+	reply := func(id int) cmodels.Message {
+		return cmodels.Message{ID: id, Meta: json.RawMessage(`{"ai_assistant_id":7}`)}
+	}
+	tests := []struct {
+		name     string
+		msgs     []cmodels.Message
+		prevSeen int
+		want     []int
+	}{
+		{"messages sent while replying", []cmodels.Message{msg(1), msg(2), msg(3), reply(4)}, 1, []int{1, 4, 2, 3}},
+		{"split reply", []cmodels.Message{msg(1), msg(2), reply(3), reply(4)}, 1, []int{1, 3, 4, 2}},
+		{"no new message", []cmodels.Message{msg(1), reply(2)}, 1, []int{1, 2}},
+		{"no reply posted", []cmodels.Message{msg(1), msg(2)}, 1, []int{1, 2}},
+		{"older replies untouched", []cmodels.Message{msg(1), reply(2), msg(3), msg(4), reply(5)}, 3, []int{1, 2, 3, 5, 4}},
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			var got []int
+			for _, m := range previousReplyFirst(tt.msgs, tt.prevSeen) {
+				got = append(got, m.ID)
+			}
+			if !reflect.DeepEqual(got, tt.want) {
+				t.Fatalf("got %v, want %v", got, tt.want)
+			}
+		})
+	}
+}