Preserve recent messages during session compaction

pkg/runtime/event.go

@@ -333,17 +333,19 @@ func SessionTitle(sessionID, title string) Event {
 type SessionSummaryEvent struct {
 	AgentContext
 
-	Type      string `json:"type"`
-	SessionID string `json:"session_id"`
-	Summary   string `json:"summary"`
+	Type           string `json:"type"`
+	SessionID      string `json:"session_id"`
+	Summary        string `json:"summary"`
+	FirstKeptEntry int    `json:"first_kept_entry,omitempty"`
 }
 
-func SessionSummary(sessionID, summary, agentName string) Event {
+func SessionSummary(sessionID, summary, agentName string, firstKeptEntry int) Event {
 	return &SessionSummaryEvent{
-		Type:         "session_summary",
-		SessionID:    sessionID,
-		Summary:      summary,
-		AgentContext: newAgentContext(agentName),
+		Type:           "session_summary",
+		SessionID:      sessionID,
+		Summary:        summary,
+		FirstKeptEntry: firstKeptEntry,
+		AgentContext:   newAgentContext(agentName),
 	}
 }
 

pkg/runtime/persistent_runtime.go

@@ -131,7 +131,7 @@ func (r *PersistentRuntime) handleEvent(ctx context.Context, sess *session.Sessi
 		}
 
 	case *SessionSummaryEvent:
-		if err := r.sessionStore.AddSummary(ctx, e.SessionID, e.Summary); err != nil {
+		if err := r.sessionStore.AddSummary(ctx, e.SessionID, e.Summary, e.FirstKeptEntry); err != nil {
 			slog.Warn("Failed to persist summary", "session_id", e.SessionID, "error", err)
 		}
 

pkg/runtime/remote_runtime.go

@@ -228,7 +228,7 @@ func (r *RemoteRuntime) Resume(ctx context.Context, req ResumeRequest) {
 // Summarize generates a summary for the session
 func (r *RemoteRuntime) Summarize(_ context.Context, sess *session.Session, _ string, events chan Event) {
 	slog.Debug("Summarize not yet implemented for remote runtime", "session_id", r.sessionID)
-	events <- SessionSummary(sess.ID, "Summary generation not yet implemented for remote runtime", r.currentAgent)
+	events <- SessionSummary(sess.ID, "Summary generation not yet implemented for remote runtime", r.currentAgent, 0)
 }
 
 func (r *RemoteRuntime) convertSessionMessages(sess *session.Session) []api.Message {

pkg/runtime/session_compaction.go

@@ -17,6 +17,11 @@ import (
 
 const maxSummaryTokens = 16_000
 
+// maxKeepTokens is the maximum number of tokens to preserve from the end of
+// the conversation during compaction. These recent messages are kept verbatim
+// so the LLM can continue naturally after compaction.
+const maxKeepTokens = 20_000
+
 // doCompact runs compaction on a session and applies the result (events,
 // persistence, token count updates). The agent is used to extract the
 // conversation from the session and to obtain the model for summarization.
@@ -41,8 +46,8 @@ func (r *LocalRuntime) doCompact(ctx context.Context, sess *session.Session, a *
 
 	compactionAgent := agent.New("root", compaction.SystemPrompt, agent.WithModel(summaryModel))
 
-	// Compute the messages to compact.
-	messages := extractMessagesToCompact(sess, compactionAgent, int64(m.Limit.Context), additionalPrompt)
+	// Compute the messages to compact, keeping recent messages aside.
+	messages, firstKeptEntry := extractMessagesToCompact(sess, compactionAgent, int64(m.Limit.Context), additionalPrompt)
 
 	// Run the compaction.
 	compactionSession := session.New(
@@ -72,16 +77,21 @@ func (r *LocalRuntime) doCompact(ctx context.Context, sess *session.Session, a *
 	sess.InputTokens = compactionSession.OutputTokens
 	sess.OutputTokens = 0
 	sess.Messages = append(sess.Messages, session.Item{
-		Summary: summary,
-		Cost:    compactionSession.TotalCost(),
+		Summary:        summary,
+		FirstKeptEntry: firstKeptEntry,
+		Cost:           compactionSession.TotalCost(),
 	})
 	_ = r.sessionStore.UpdateSession(ctx, sess)
 
 	slog.Debug("Generated session summary", "session_id", sess.ID, "summary_length", len(summary))
-	events <- SessionSummary(sess.ID, summary, a.Name())
+	events <- SessionSummary(sess.ID, summary, a.Name(), firstKeptEntry)
 }
 
-func extractMessagesToCompact(sess *session.Session, compactionAgent *agent.Agent, contextLimit int64, additionalPrompt string) []chat.Message {
+// extractMessagesToCompact returns the messages to send to the compaction model
+// and the index (into sess.Messages) of the first message that was kept aside.
+// Recent messages (up to maxKeepTokens) are excluded from compaction so they
+// can be preserved verbatim in the session after summarization.
+func extractMessagesToCompact(sess *session.Session, compactionAgent *agent.Agent, contextLimit int64, additionalPrompt string) ([]chat.Message, int) {
 	// Add all the existing messages.
 	var messages []chat.Message
 	for _, msg := range sess.GetMessages(compactionAgent) {
@@ -95,6 +105,17 @@ func extractMessagesToCompact(sess *session.Session, compactionAgent *agent.Agen
 		messages = append(messages, msg)
 	}
 
+	// Split: keep the last N tokens of messages aside so the LLM retains
+	// recent context after compaction.
+	splitIdx := splitIndexForKeep(messages, maxKeepTokens)
+	messagesToCompact := messages[:splitIdx]
+	// Compute firstKeptEntry: index into sess.Messages of the first kept message.
+	// The kept messages start at splitIdx in the non-system filtered list. We
+	// need to map this back to the original sess.Messages index.
+	firstKeptEntry := mapToSessionIndex(sess, splitIdx)
+
+	messages = messagesToCompact
+
 	// Prepare the first (system) message.
 	systemPromptMessage := chat.Message{
 		Role:      chat.MessageRoleSystem,
@@ -131,7 +152,49 @@ func extractMessagesToCompact(sess *session.Session, compactionAgent *agent.Agen
 	// Append the last (user) message.
 	messages = append(messages, userPromptMessage)
 
-	return messages
+	return messages, firstKeptEntry
+}
+
+// splitIndexForKeep returns the index that splits messages into [0:idx] (to
+// compact) and [idx:] (to keep). It walks backwards accumulating tokens up to
+// maxTokens, snapping to user/assistant boundaries.
+func splitIndexForKeep(messages []chat.Message, maxTokens int64) int {
+	if len(messages) == 0 {
+		return 0
+	}
+
+	var tokens int64
+	// Walk from the end; find the earliest index whose suffix fits in maxTokens.
+	lastValidBoundary := len(messages)
+	for i := len(messages) - 1; i >= 0; i-- {
+		tokens += compaction.EstimateMessageTokens(&messages[i])
+		if tokens > maxTokens {
+			return lastValidBoundary
+		}
+		role := messages[i].Role
+		if role == chat.MessageRoleUser || role == chat.MessageRoleAssistant {
+			lastValidBoundary = i
+		}
+	}
+	// All messages fit within maxTokens — don't keep any aside (compact everything).
+	return len(messages)
+}
+
+// mapToSessionIndex maps an index in the non-system-filtered message list back
+// to the corresponding index in sess.Messages. It counts only message items
+// that are not system messages.
+func mapToSessionIndex(sess *session.Session, filteredIdx int) int {
+	count := 0
+	for i, item := range sess.Messages {
+		if item.IsMessage() && item.Message.Message.Role != chat.MessageRoleSystem {
+			if count == filteredIdx {
+				return i
+			}
+			count++
+		}
+	}
+	// filteredIdx is past the end — no messages to keep.
+	return len(sess.Messages)
 }
 
 func firstMessageToKeep(messages []chat.Message, contextLimit int64) int {

pkg/runtime/session_compaction_test.go

@@ -1,9 +1,11 @@
 package runtime
 
 import (
+	"strings"
 	"testing"
 
 	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
 
 	"github.com/docker/docker-agent/pkg/agent"
 	"github.com/docker/docker-agent/pkg/chat"
@@ -96,7 +98,7 @@ func TestExtractMessagesToCompact(t *testing.T) {
 			sess := session.New(session.WithMessages(tt.messages))
 
 			a := agent.New("test", "test prompt")
-			result := extractMessagesToCompact(sess, a, tt.contextLimit, tt.additionalPrompt)
+			result, _ := extractMessagesToCompact(sess, a, tt.contextLimit, tt.additionalPrompt)
 
 			assert.GreaterOrEqual(t, len(result), tt.wantConversationMsgCount+2)
 			assert.Equal(t, chat.MessageRoleSystem, result[0].Role)
@@ -121,3 +123,169 @@ func TestExtractMessagesToCompact(t *testing.T) {
 		})
 	}
 }
+
+func TestSplitIndexForKeep(t *testing.T) {
+	msg := func(role chat.MessageRole, content string) chat.Message {
+		return chat.Message{Role: role, Content: content}
+	}
+
+	tests := []struct {
+		name      string
+		messages  []chat.Message
+		maxTokens int64
+		wantSplit int // expected split index
+	}{
+		{
+			name:      "empty messages",
+			messages:  nil,
+			maxTokens: 1000,
+			wantSplit: 0,
+		},
+		{
+			name: "all messages fit in keep budget - compact everything",
+			messages: []chat.Message{
+				msg(chat.MessageRoleUser, "short"),
+				msg(chat.MessageRoleAssistant, "short"),
+			},
+			maxTokens: 100_000,
+			wantSplit: 2, // all fit → compact everything
+		},
+		{
+			name: "recent messages kept, older ones compacted",
+			messages: []chat.Message{
+				msg(chat.MessageRoleUser, strings.Repeat("a", 40000)),      // ~10005 tokens
+				msg(chat.MessageRoleAssistant, strings.Repeat("b", 40000)), // ~10005 tokens
+				msg(chat.MessageRoleUser, strings.Repeat("c", 40000)),      // ~10005 tokens
+				msg(chat.MessageRoleAssistant, strings.Repeat("d", 40000)), // ~10005 tokens
+				msg(chat.MessageRoleUser, strings.Repeat("e", 40000)),      // ~10005 tokens
+				msg(chat.MessageRoleAssistant, strings.Repeat("f", 40000)), // ~10005 tokens
+			},
+			maxTokens: 20_100, // enough for exactly 2 messages
+			wantSplit: 4,      // last 2 messages are kept
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			got := splitIndexForKeep(tt.messages, tt.maxTokens)
+			assert.Equal(t, tt.wantSplit, got)
+		})
+	}
+}
+
+func TestExtractMessagesToCompact_KeepsRecentMessages(t *testing.T) {
+	// Create a session with many messages, some large enough that the last
+	// ~20k tokens are kept aside.
+	var items []session.Item
+	for range 10 {
+		items = append(items, session.NewMessageItem(&session.Message{
+			Message: chat.Message{
+				Role:    chat.MessageRoleUser,
+				Content: strings.Repeat("x", 20000), // ~5k tokens each
+			},
+		}), session.NewMessageItem(&session.Message{
+			Message: chat.Message{
+				Role:    chat.MessageRoleAssistant,
+				Content: strings.Repeat("y", 20000), // ~5k tokens each
+			},
+		}))
+	}
+
+	sess := session.New(session.WithMessages(items))
+	a := agent.New("test", "test prompt")
+
+	result, firstKeptEntry := extractMessagesToCompact(sess, a, 200_000, "")
+
+	// The kept messages should not appear in the compaction result
+	// (only system + compacted messages + user prompt).
+	// Total: 20 messages × ~5k tokens = ~100k tokens.
+	// Keep budget: 20k tokens → ~4 messages kept.
+	// So compacted messages should be 20 - 4 = 16.
+	compactedMsgCount := len(result) - 2 // minus system and user prompt
+	assert.Less(t, compactedMsgCount, 20, "some messages should have been kept aside")
+	assert.Positive(t, compactedMsgCount, "some messages should be compacted")
+
+	// firstKeptEntry should point into sess.Messages
+	assert.Positive(t, firstKeptEntry, "firstKeptEntry should be > 0")
+	assert.Less(t, firstKeptEntry, len(sess.Messages), "firstKeptEntry should be within bounds")
+}
+
+func TestSessionGetMessages_WithFirstKeptEntry(t *testing.T) {
+	// Build a session with some messages, then add a summary with FirstKeptEntry.
+	items := []session.Item{
+		session.NewMessageItem(&session.Message{
+			Message: chat.Message{Role: chat.MessageRoleUser, Content: "m1"},
+		}),
+		session.NewMessageItem(&session.Message{
+			Message: chat.Message{Role: chat.MessageRoleAssistant, Content: "m2"},
+		}),
+		session.NewMessageItem(&session.Message{
+			Message: chat.Message{Role: chat.MessageRoleUser, Content: "m3"},
+		}),
+		session.NewMessageItem(&session.Message{
+			Message: chat.Message{Role: chat.MessageRoleAssistant, Content: "m4"},
+		}),
+		session.NewMessageItem(&session.Message{
+			Message: chat.Message{Role: chat.MessageRoleUser, Content: "m5"},
+		}),
+	}
+
+	// Add summary that says "first kept entry is index 3" (m4).
+	// So we expect: [system...] + [summary] + [m4, m5]
+	items = append(items, session.Item{
+		Summary:        "This is a summary of m1-m3",
+		FirstKeptEntry: 3, // index of m4 in the Messages slice
+	})
+
+	sess := session.New(session.WithMessages(items))
+	a := agent.New("test", "test instruction")
+
+	messages := sess.GetMessages(a)
+
+	// Extract just the non-system messages
+	var conversationMessages []chat.Message
+	for _, msg := range messages {
+		if msg.Role != chat.MessageRoleSystem {
+			conversationMessages = append(conversationMessages, msg)
+		}
+	}
+
+	// Should have: summary (as user message), m4, m5
+	require.Len(t, conversationMessages, 3, "expected summary + 2 kept messages")
+	assert.Contains(t, conversationMessages[0].Content, "Session Summary:")
+	assert.Equal(t, "m4", conversationMessages[1].Content)
+	assert.Equal(t, "m5", conversationMessages[2].Content)
+}
+
+func TestSessionGetMessages_SummaryWithoutFirstKeptEntry(t *testing.T) {
+	// Backward compatibility: summary without FirstKeptEntry should work as before.
+	items := []session.Item{
+		session.NewMessageItem(&session.Message{
+			Message: chat.Message{Role: chat.MessageRoleUser, Content: "m1"},
+		}),
+		session.NewMessageItem(&session.Message{
+			Message: chat.Message{Role: chat.MessageRoleAssistant, Content: "m2"},
+		}),
+		{Summary: "This is a summary"},
+		session.NewMessageItem(&session.Message{
+			Message: chat.Message{Role: chat.MessageRoleUser, Content: "m3"},
+		}),
+	}
+
+	sess := session.New(session.WithMessages(items))
+	a := agent.New("test", "test instruction")
+
+	messages := sess.GetMessages(a)
+
+	var conversationMessages []chat.Message
+	for _, msg := range messages {
+		if msg.Role != chat.MessageRoleSystem {
+			conversationMessages = append(conversationMessages, msg)
+		}
+	}
+
+	// Should have: summary + m3 (messages after the summary)
+	require.Len(t, conversationMessages, 2)
+	assert.Contains(t, conversationMessages[0].Content, "Session Summary:")
+	assert.Equal(t, "m3", conversationMessages[1].Content)
+}

pkg/session/migrations.go

@@ -350,6 +350,12 @@ func getAllMigrations() []Migration {
 			Description: "Drop the legacy messages JSON column now that all data lives in session_items",
 			UpSQL:       `ALTER TABLE sessions DROP COLUMN messages`,
 		},
+		{
+			ID:          21,
+			Name:        "021_add_first_kept_entry_column",
+			Description: "Add first_kept_entry column to session_items for compaction-preserved messages",
+			UpSQL:       `ALTER TABLE session_items ADD COLUMN first_kept_entry INTEGER DEFAULT 0`,
+		},
 	}
 }