diff --git a/internal/memory/indexer.go b/internal/memory/indexer.go
index 9938ff653..b1b511833 100644
--- a/internal/memory/indexer.go
+++ b/internal/memory/indexer.go
@@ -22,6 +22,7 @@ import (
 const (
 	DefaultMinScore          = 0.5
 	DefaultValidDurationDays = 60
+	maxMergeSections         = 3
 )
 
 // MemoryIndex is an in-memory HNSW index for memory chunks.
@@ -407,7 +408,14 @@ func (idx *MemoryIndex) PruneHashes(validHashes map[string]struct{}) int {
 	return pruned
 }
 
-// ParseDailyFile parses a daily markdown file into MemoryEntry chunks.
+
+type rawSection struct {
+	timestamp string
+	userID    string
+	lines     []string
+}
+
+// ParseDailyFile parses a daily markdown file into MemoryEntry chunks and merge if from same user up to maxMergeSections.
 func ParseDailyFile(path string) ([]MemoryEntry, error) {
 	content, err := os.ReadFile(path)
 	if err != nil {
@@ -418,50 +426,88 @@ func ParseDailyFile(path string) ([]MemoryEntry, error) {
 	dateStem := strings.TrimSuffix(base, filepath.Ext(base))
 	datePrefix := "[Date: " + dateStem + "]"
 
-	userTagRe := regexp.MustCompile(`^\[User: (.+)\]$`)
+	sections := parseSections(string(content))
+	if len(sections) == 0 {
+		return nil, nil
+	}
 
 	var chunks []MemoryEntry
-	var currentChunk strings.Builder
-	var currentUserID string
-
-	lines := strings.Split(string(content), "\n")
-	for _, line := range lines {
-		if strings.HasPrefix(line, "## ") && currentChunk.Len() > 0 {
-			text := strings.TrimSpace(currentChunk.String())
-			if text != "" {
-				meta := map[string]string{"source": base}
-				if currentUserID != "" {
-					meta["user_id"] = currentUserID
-				}
-				chunks = append(chunks, MemoryEntry{
-					Text:     datePrefix + "\n" + text,
-					Metadata: meta,
-				})
+	i := 0
+	for i < len(sections) {
+		userID := sections[i].userID
+		start := i
+		for i < len(sections) && sections[i].userID == userID && (i-start) < maxMergeSections {
+			i++
+		}
+		merged := sections[start:i]
+
+		var sb strings.Builder
+		sb.WriteString(datePrefix)
+		sb.WriteString("\n[User: ")
+		sb.WriteString(userID)
+		sb.WriteString("]\n")
+		for _, sec := range merged {
+			for _, line := range sec.lines {
+				fmt.Fprintf(&sb, "[%s] %s\n", sec.timestamp, convertLine(line))
 			}
-			currentChunk.Reset()
-			currentUserID = ""
 		}
-
-		if m := userTagRe.FindStringSubmatch(line); m != nil {
-			currentUserID = strings.ToLower(strings.TrimSpace(m[1]))
+		text := strings.TrimSpace(sb.String())
+		if text != "" {
+			meta := map[string]string{"source": base}
+			if userID != "" {
+				meta["user_id"] = userID
+			}
+			chunks = append(chunks, MemoryEntry{Text: text, Metadata: meta})
 		}
-		currentChunk.WriteString(line)
-		currentChunk.WriteByte('\n')
 	}
+	return chunks, nil
+}
+
+// parseSections splits daily file content into rawSection structs.
+func parseSections(content string) []rawSection {
+	headerRe := regexp.MustCompile(`^## (\d{2}:\d{2}:\d{2})`)
+	userTagRe := regexp.MustCompile(`^\[User: (.+)\]$`)
+
+	var sections []rawSection
+	var cur *rawSection
 
-	// Flush last chunk.
-	if text := strings.TrimSpace(currentChunk.String()); text != "" {
-		meta := map[string]string{"source": base}
-		if currentUserID != "" {
-			meta["user_id"] = currentUserID
+	for _, line := range strings.Split(content, "\n") {
+		if m := headerRe.FindStringSubmatch(line); m != nil {
+			if cur != nil && len(cur.lines) > 0 {
+				sections = append(sections, *cur)
+			}
+			cur = &rawSection{timestamp: m[1]}
+			continue
 		}
-		chunks = append(chunks, MemoryEntry{
-			Text:     datePrefix + "\n" + text,
-			Metadata: meta,
-		})
+		if cur == nil {
+			continue
+		}
+		if m := userTagRe.FindStringSubmatch(line); m != nil {
+			cur.userID = strings.ToLower(strings.TrimSpace(m[1]))
+			continue
+		}
+		trimmed := strings.TrimSpace(line)
+		if trimmed != "" {
+			cur.lines = append(cur.lines, trimmed)
+		}
+	}
+	if cur != nil && len(cur.lines) > 0 {
+		sections = append(sections, *cur)
 	}
+	return sections
+}
 
-	return chunks, nil
+func convertLine(line string) string {
+	if after, ok := strings.CutPrefix(line, "- **User**: "); ok {
+		return "User: " + after
+	}
+	if after, ok := strings.CutPrefix(line, "- **Robot**: "); ok {
+		return "Robot: " + after
+	}
+	if after, ok := strings.CutPrefix(line, "- "); ok {
+		return after
+	}
+	return line
 }
 
 // BuildIndex populates the given MemoryIndex from recent daily markdown files.
diff --git a/internal/memory/indexer_test.go b/internal/memory/indexer_test.go
index 13510d6fa..7bb18639f 100644
--- a/internal/memory/indexer_test.go
+++ b/internal/memory/indexer_test.go
@@ -43,14 +43,14 @@ func TestParseDailyFile(t *testing.T) {
 
 	chunks, err := ParseDailyFile(path)
 	require.NoError(t, err)
-	require.Len(t, chunks, 2)
+	require.Len(t, chunks, 2, "different users should produce separate chunks")
 
 	require.Contains(t, chunks[0].Text, "[Date: 2026-06-03]")
-	require.Contains(t, chunks[0].Text, "Hello, how are you?")
+	require.Contains(t, chunks[0].Text, "[14:18:28] User: Hello, how are you?")
 	require.Equal(t, "alice", chunks[0].Metadata["user_id"])
 	require.Equal(t, "2026-06-03.md", chunks[0].Metadata["source"])
 
-	require.Contains(t, chunks[1].Text, "What is your name?")
+	require.Contains(t, chunks[1].Text, "[14:19:00] User: What is your name?")
 	require.Equal(t, "bob", chunks[1].Metadata["user_id"])
 }
 
@@ -79,6 +79,68 @@ func TestParseDailyFile_SingleChunk(t *testing.T) {
 	require.Equal(t, "dave", chunks[0].Metadata["user_id"])
 }
 
+func TestParseDailyFile_SameUserMerge(t *testing.T) {
+	dir := t.TempDir()
+	content := `
+## 14:00:00
+[User: alice]
+- **User**: First message
+
+## 14:01:00
+[User: alice]
+- **User**: Second message
+
+## 14:02:00
+[User: bob]
+- **User**: Bob here
+
+## 14:03:00
+[User: alice]
+- **User**: Alice again
+`
+	path := filepath.Join(dir, "2026-06-05.md")
+	require.NoError(t, os.WriteFile(path, []byte(content), 0o644))
+
+	chunks, err := ParseDailyFile(path)
+	require.NoError(t, err)
+	require.Len(t, chunks, 3, "alice(2) + bob(1) + alice(1) = 3 chunks")
+
+	require.Contains(t, chunks[0].Text, "[14:00:00] User: First message")
+	require.Contains(t, chunks[0].Text, "[14:01:00] User: Second message")
+	require.Equal(t, "alice", chunks[0].Metadata["user_id"])
+
+	require.Equal(t, "bob", chunks[1].Metadata["user_id"])
+
+	require.Contains(t, chunks[2].Text, "[14:03:00] User: Alice again")
+	require.Equal(t, "alice", chunks[2].Metadata["user_id"])
+}
+
+func TestParseDailyFile_WithRobotReply(t *testing.T) {
+	dir := t.TempDir()
+	content := `
+## 14:00:00
+[User: alice]
+- **User**: Hello
+- **Robot**: Hi there!
+
+## 14:01:00
+[User: alice]
+- **User**: What's your name?
+- **Robot**: I'm OM1!
+`
+	path := filepath.Join(dir, "2026-06-06.md")
+	require.NoError(t, os.WriteFile(path, []byte(content), 0o644))
+
+	chunks, err := ParseDailyFile(path)
+	require.NoError(t, err)
+	require.Len(t, chunks, 1, "same user alice → merged into 1 chunk")
+
+	require.Contains(t, chunks[0].Text, "[14:00:00] User: Hello")
+	require.Contains(t, chunks[0].Text, "[14:00:00] Robot: Hi there!")
+	require.Contains(t, chunks[0].Text, "[14:01:00] User: What's your name?")
+	require.Contains(t, chunks[0].Text, "[14:01:00] Robot: I'm OM1!")
+}
+
 func TestMemoryIndex_AddChunkAndSearch(t *testing.T) {
 	idx := NewMemoryIndex(&mockEmbedder{dim: 32}, testLogger())
 
diff --git a/internal/memory/manager.go b/internal/memory/manager.go
index 20f05d62f..73b8e0516 100644
--- a/internal/memory/manager.go
+++ b/internal/memory/manager.go
@@ -84,22 +84,27 @@ func (m *Manager) SearchAndFormat(ctx context.Context, query string, uuid string
 	return m.reader.FormatContext(results, 0, uuid)
 }
 
-// RecordInteraction writes the user message to the daily log and hot-updates the index.
-func (m *Manager) RecordInteraction(ctx context.Context, voiceInput, uuid, name string) {
+// RecordInteraction writes the user message and robot reply to the daily log and hot-updates the index.
+func (m *Manager) RecordInteraction(ctx context.Context, voiceInput, robotReply, uuid, name string) {
 	if m.writer == nil {
 		return
 	}
-	m.writer.AppendInteraction(voiceInput, uuid, name)
+	m.writer.AppendInteraction(voiceInput, robotReply, uuid, name)
 	if m.reader.IndexReady() {
-		m.writer.AppendToIndex(ctx, m.reader.Index(), voiceInput, uuid)
+		m.writer.AppendToIndex(ctx, m.reader.Index(), voiceInput, robotReply, uuid)
 	}
 }
 
-// MaybeSummarize triggers background summarization.
+// MaybeSummarize triggers background summarization
 func (m *Manager) Summarize(ctx context.Context) {
 	if m.summarizer != nil && m.summarizer.CheckEligibility() {
 		go func() {
 			m.summarizer.Run(ctx)
+			if err := m.reader.RebuildIndex(ctx); err != nil {
+				m.log.Warn("index rebuild failed, keeping old index", zap.Error(err))
+				return
+			}
+			m.log.Info("index rebuilt after summarization", zap.Int("chunks", m.reader.Index().Size()))
 			if err := m.reader.Index().SaveToDisk(m.indexDir); err != nil {
 				m.log.Warn("failed to persist index", zap.Error(err))
 			}
diff --git a/internal/memory/reader.go b/internal/memory/reader.go
index 033234063..d30402bb8 100644
--- a/internal/memory/reader.go
+++ b/internal/memory/reader.go
@@ -68,6 +68,17 @@ func (r *Reader) IndexReady() bool {
 	return r.indexReady
 }
 
+// RebuildIndex rebuilds the index from daily files. On failure the old index is kept.
+func (r *Reader) RebuildIndex(ctx context.Context) error {
+	newIdx := NewMemoryIndex(r.index.embedder, r.log)
+	if err := BuildIndex(ctx, newIdx, r.dailyDir, DefaultValidDurationDays); err != nil {
+		return err
+	}
+	r.index = newIdx
+	r.indexReady = true
+	return nil
+}
+
 // SearchDaily searches daily logs using hybrid retrieval (embedding + BM25).
 func (r *Reader) SearchDaily(ctx context.Context, queryText string, topK int, userID string) ([]MemoryEntry, error) {
 	if strings.TrimSpace(queryText) == "" {
diff --git a/internal/memory/writer.go b/internal/memory/writer.go
index 320a42c85..e3e7f0ae3 100644
--- a/internal/memory/writer.go
+++ b/internal/memory/writer.go
@@ -56,7 +56,7 @@ func NewWriter(memoryRoot string, log *zap.Logger) (*Writer, error) {
 }
 
 // AppendInteraction writes a user message to today's daily log.
-func (w *Writer) AppendInteraction(userMsg, uuid, name string) {
+func (w *Writer) AppendInteraction(userMsg, robotReply, uuid, name string) {
 	if strings.TrimSpace(userMsg) == "" {
 		return
 	}
@@ -74,7 +74,11 @@ func (w *Writer) AppendInteraction(userMsg, uuid, name string) {
 		tag = uuid
 	}
 
-	entry := fmt.Sprintf("\n## %s\n[User: %s]\n- **User**: %s\n", ts, tag, strings.TrimSpace(userMsg))
+	var sb strings.Builder
+	fmt.Fprintf(&sb, "\n## %s\n[User: %s]\n- **User**: %s\n", ts, tag, strings.TrimSpace(userMsg))
+	if reply := strings.TrimSpace(robotReply); reply != "" {
+		fmt.Fprintf(&sb, "- **Robot**: %s\n", reply)
+	}
 
 	f, err := os.OpenFile(dailyPath, os.O_APPEND|os.O_CREATE|os.O_WRONLY, 0o644)
 	if err != nil {
@@ -83,13 +87,13 @@ func (w *Writer) AppendInteraction(userMsg, uuid, name string) {
 	}
 	defer func() { _ = f.Close() }()
 
-	if _, err := f.WriteString(entry); err != nil {
+	if _, err := f.WriteString(sb.String()); err != nil {
 		w.log.Error("failed to write interaction", zap.Error(err))
 	}
 }
 
 // AppendToIndex embeds and inserts a new user message into the given index.
-func (w *Writer) AppendToIndex(ctx context.Context, idx *MemoryIndex, userMsg, uuid string) {
+func (w *Writer) AppendToIndex(ctx context.Context, idx *MemoryIndex, userMsg, robotReply, uuid string) {
 	if strings.TrimSpace(userMsg) == "" || idx == nil {
 		return
 	}
@@ -101,14 +105,16 @@ func (w *Writer) AppendToIndex(ctx context.Context, idx *MemoryIndex, userMsg, u
 	if uuid != "" {
 		tag = uuid
 	}
-	userTag := fmt.Sprintf("[User: %s]\n", tag)
 
-	text := fmt.Sprintf("[Date: %s]\n## %s\n%s- **User**: %s",
-		dateStr, ts, userTag, strings.TrimSpace(userMsg))
+	var sb strings.Builder
+	fmt.Fprintf(&sb, "[Date: %s]\n[User: %s]\n[%s] User: %s", dateStr, tag, ts, strings.TrimSpace(userMsg))
+	if reply := strings.TrimSpace(robotReply); reply != "" {
+		fmt.Fprintf(&sb, "\n[%s] Robot: %s", ts, reply)
+	}
 
 	meta := map[string]string{"source": dateStr + ".md", "user_id": uuid}
 
-	if _, err := idx.AddChunk(ctx, MemoryEntry{Text: text, Metadata: meta}); err != nil {
+	if _, err := idx.AddChunk(ctx, MemoryEntry{Text: sb.String(), Metadata: meta}); err != nil {
 		w.log.Warn("write-through index failed", zap.Error(err))
 	}
 }
diff --git a/internal/memory/writer_test.go b/internal/memory/writer_test.go
index b29002674..4da481817 100644
--- a/internal/memory/writer_test.go
+++ b/internal/memory/writer_test.go
@@ -19,8 +19,8 @@ func TestWriter_AppendInteraction(t *testing.T) {
 	w, err := NewWriter(dir, log)
 	require.NoError(t, err)
 
-	w.AppendInteraction("Hello robot", testUUID, "alice")
-	w.AppendInteraction("What is your name?", testUUID, "alice")
+	w.AppendInteraction("Hello robot", "", testUUID, "alice")
+	w.AppendInteraction("What is your name?", "", testUUID, "alice")
 
 	dailyPath := w.dailyPath()
 	content, err := os.ReadFile(dailyPath)
@@ -35,8 +35,8 @@ func TestWriter_AppendInteraction_EmptyMessage(t *testing.T) {
 	w, err := NewWriter(dir, testLogger())
 	require.NoError(t, err)
 
-	w.AppendInteraction("", testUUID, "alice")
-	w.AppendInteraction("   ", testUUID, "alice")
+	w.AppendInteraction("", "", testUUID, "alice")
+	w.AppendInteraction("   ", "", testUUID, "alice")
 
 	dailyPath := w.dailyPath()
 	_, err = os.Stat(dailyPath)
@@ -48,7 +48,7 @@ func TestWriter_AppendInteraction_UnknownUser(t *testing.T) {
 	w, err := NewWriter(dir, testLogger())
 	require.NoError(t, err)
 
-	w.AppendInteraction("Hello", "", "")
+	w.AppendInteraction("Hello", "", "", "")
 
 	content, err := os.ReadFile(w.dailyPath())
 	require.NoError(t, err)
@@ -60,7 +60,7 @@ func TestWriter_EnsureUserDir(t *testing.T) {
 	w, err := NewWriter(dir, testLogger())
 	require.NoError(t, err)
 
-	w.AppendInteraction("Hi", testUUID, "bob")
+	w.AppendInteraction("Hi", "", testUUID, "bob")
 
 	// Profile should be created with UUID.
 	profilePath := filepath.Join(dir, "users", testUUID, "profile.json")
@@ -88,8 +88,8 @@ func TestWriter_UpdateUserProfile_VisitCount(t *testing.T) {
 	require.NoError(t, err)
 
 	// Multiple interactions in same session = 1 visit.
-	w.AppendInteraction("Hi", testUUID, "carol")
-	w.AppendInteraction("Bye", testUUID, "carol")
+	w.AppendInteraction("Hi", "", testUUID, "carol")
+	w.AppendInteraction("Bye", "", testUUID, "carol")
 
 	profilePath := filepath.Join(dir, "users", testUUID, "profile.json")
 	raw, err := os.ReadFile(profilePath)
@@ -106,8 +106,8 @@ func TestWriter_MultipleNames(t *testing.T) {
 	w, err := NewWriter(dir, testLogger())
 	require.NoError(t, err)
 
-	w.AppendInteraction("Hi", testUUID, "anon_73d0a4")
-	w.AppendInteraction("Hi again", testUUID, "sean")
+	w.AppendInteraction("Hi", "", testUUID, "anon_73d0a4")
+	w.AppendInteraction("Hi again", "", testUUID, "sean")
 
 	profilePath := filepath.Join(dir, "users", testUUID, "profile.json")
 	raw, err := os.ReadFile(profilePath)
diff --git a/internal/runtime/runtime.go b/internal/runtime/runtime.go
index b4bdd76f9..a1be87396 100644
--- a/internal/runtime/runtime.go
+++ b/internal/runtime/runtime.go
@@ -502,7 +502,7 @@ func (rt *Runtime) tick(ctx context.Context, current *modeState, tickStart time.
 		if voice != nil && voice.Input != "" && voice.Tick == rt.ioProvider.TickCounter() {
 			uuid, _ := rt.ioProvider.GetDynamicVar("current_user_id")
 			name, _ := rt.ioProvider.GetDynamicVar("current_user_name")
-			current.memory.RecordInteraction(ctx, strings.TrimSpace(voice.Input), uuid, name)
+			current.memory.RecordInteraction(ctx, strings.TrimSpace(voice.Input), response.TextContent, uuid, name)
 		}
 		current.memory.Summarize(ctx)
 	}