refactor: Change compact to start new conversation with summary (#356)

Changes the /compact command behavior to start a new conversation with a
summary instead of compacting in-place.
Simplifies the ConversationOptimizerService interface by removing
OptimizeMessagesWithModel and consolidating into OptimizeMessages.
Adds GetCurrentConversationTitle method to preserve conversation
context.

## Key changes in this PR:

- `/compact` now creates a new conversation titled "Continued from
[original title]" with optimized messages
- Removed redundant `OptimizeMessagesWithModel` method from interface
- Added `GetCurrentConversationTitle()` to conversation repository
- Updated all callers to use the simplified `OptimizeMessages` method
- Improved error handling when no model is selected

## Files changed:

- `internal/domain/interfaces.go` - Simplified interface, added
GetCurrentConversationTitle method
- `internal/handlers/chat_shortcut_handler.go` - Updated to use new
compact behavior
- `internal/services/agent.go` - Updated to use simplified
OptimizeMessages method
- `internal/services/conversation.go` - Updated to use simplified
OptimizeMessages method
- `internal/services/conversation_optimizer.go` - Implemented new
compact behavior
- `internal/services/conversation_optimizer_test.go` - Updated tests for
new behavior
- `internal/services/persistent_conversation.go` - Updated to use
simplified OptimizeMessages method
- `internal/shortcuts/core.go` - Updated to use simplified
OptimizeMessages method
- `tests/mocks/domain/fake_conversation_repository.go` - Updated mock to
include new method

Author: edenreich

internal/domain/interfaces.go

@@ -103,12 +103,12 @@ type ConversationRepository interface {
 	RemovePendingToolCallByID(toolCallID string)
 	StartNewConversation(title string) error
 	DeleteMessagesAfterIndex(index int) error
+	GetCurrentConversationTitle() string
 }
 
 // ConversationOptimizerService optimizes conversation history to reduce token usage
 type ConversationOptimizerService interface {
-	OptimizeMessages(messages []sdk.Message, force bool) []sdk.Message
-	OptimizeMessagesWithModel(messages []sdk.Message, currentModel string, force bool) []sdk.Message
+	OptimizeMessages(messages []sdk.Message, model string, force bool) []sdk.Message
 }
 
 // ModelService handles model selection and information

internal/handlers/chat_shortcut_handler.go

@@ -507,6 +507,8 @@ func (s *ChatShortcutHandler) performCompactAsync() tea.Cmd {
 
 		logger.Info("Starting conversation compaction", "message_count", len(entries))
 
+		originalTitle := s.handler.conversationRepo.GetCurrentConversationTitle()
+
 		messages := make([]sdk.Message, 0, len(entries))
 		for _, entry := range entries {
 			if entry.Hidden {
@@ -517,14 +519,19 @@ func (s *ChatShortcutHandler) performCompactAsync() tea.Cmd {
 
 		currentModel := s.handler.modelService.GetCurrentModel()
 		if currentModel == "" {
-			logger.Warn("No current model set for compaction - will use basic summary")
+			return domain.SetStatusEvent{
+				Message:    "No model selected - please select a model first",
+				Spinner:    false,
+				StatusType: domain.StatusError,
+			}
 		}
-		logger.Info("About to optimize conversation", "model", currentModel, "message_count", len(messages))
+
+		logger.Info("Optimizing conversation", "model", currentModel, "message_count", len(messages))
 
 		optimizedChan := make(chan []sdk.Message, 1)
 		go func() {
-			result := s.handler.conversationOptimizer.OptimizeMessagesWithModel(messages, currentModel, true)
-			optimizedChan <- result
+			optimized := s.handler.conversationOptimizer.OptimizeMessages(messages, currentModel, true)
+			optimizedChan <- optimized
 		}()
 
 		var optimizedMessages []sdk.Message
@@ -534,7 +541,7 @@ func (s *ChatShortcutHandler) performCompactAsync() tea.Cmd {
 		case <-time.After(70 * time.Second):
 			logger.Error("Optimization timed out after 70 seconds")
 			return domain.SetStatusEvent{
-				Message:    "Conversation compaction timed out - try again or check gateway logs",
+				Message:    "Conversation optimization timed out - try again or check gateway logs",
 				Spinner:    false,
 				StatusType: domain.StatusError,
 			}
@@ -548,10 +555,11 @@ func (s *ChatShortcutHandler) performCompactAsync() tea.Cmd {
 			}
 		}
 
-		if clearErr := s.handler.conversationRepo.Clear(); clearErr != nil {
-			logger.Error("failed to clear conversation during compaction", "error", clearErr)
+		newTitle := fmt.Sprintf("Continued from %s", originalTitle)
+		if err := s.handler.conversationRepo.StartNewConversation(newTitle); err != nil {
+			logger.Error("Failed to start new conversation", "error", err)
 			return domain.SetStatusEvent{
-				Message:    fmt.Sprintf("Failed to compact conversation: %v", clearErr),
+				Message:    fmt.Sprintf("Failed to start new conversation: %v", err),
 				Spinner:    false,
 				StatusType: domain.StatusError,
 			}
@@ -560,29 +568,14 @@ func (s *ChatShortcutHandler) performCompactAsync() tea.Cmd {
 		for _, msg := range optimizedMessages {
 			entry := domain.ConversationEntry{
 				Message: msg,
+				Model:   currentModel,
 				Time:    time.Now(),
 			}
-			if addErr := s.handler.conversationRepo.AddMessage(entry); addErr != nil {
-				logger.Error("failed to add optimized message during compaction", "error", addErr)
+			if err := s.handler.conversationRepo.AddMessage(entry); err != nil {
+				logger.Error("Failed to add optimized message", "error", err)
 			}
 		}
 
-		reduction := len(messages) - len(optimizedMessages)
-		reductionPercent := (float64(reduction) / float64(len(messages))) * 100
-
-		infoEntry := domain.ConversationEntry{
-			Message: sdk.Message{
-				Role:    sdk.Assistant,
-				Content: sdk.NewMessageContent(fmt.Sprintf("Conversation compacted successfully! Reduced from %d to %d messages (%.1f%% reduction).", len(messages), len(optimizedMessages), reductionPercent)),
-			},
-			Model: "",
-			Time:  time.Now(),
-		}
-
-		if addErr := s.handler.conversationRepo.AddMessage(infoEntry); addErr != nil {
-			logger.Error("failed to add compact info message", "error", addErr)
-		}
-
 		return tea.Batch(
 			func() tea.Msg {
 				return domain.UpdateHistoryEvent{
@@ -591,7 +584,7 @@ func (s *ChatShortcutHandler) performCompactAsync() tea.Cmd {
 			},
 			func() tea.Msg {
 				return domain.SetStatusEvent{
-					Message:    fmt.Sprintf("Conversation compacted: %d messages reduced to %d", len(messages), len(optimizedMessages)),
+					Message:    fmt.Sprintf("• Started new conversation with summary (%d messages preserved)", len(messages)),
 					Spinner:    false,
 					StatusType: domain.StatusDefault,
 				}

internal/infra/adapters/persistent_conversation_adapter.go

@@ -71,7 +71,6 @@ func (a *PersistentConversationAdapter) GetCurrentConversationMetadata() shortcu
 		CostStats: metadata.CostStats,
 		Model:     metadata.Model,
 		Tags:      metadata.Tags,
-		Summary:   metadata.Summary,
 	}
 }
 

internal/infra/storage/interfaces.go

@@ -36,21 +36,19 @@ type ConversationStorage interface {
 
 // ConversationMetadata contains metadata about a conversation
 type ConversationMetadata struct {
-	ID                  string                     `json:"id"`
-	Title               string                     `json:"title"`
-	CreatedAt           time.Time                  `json:"created_at"`
-	UpdatedAt           time.Time                  `json:"updated_at"`
-	MessageCount        int                        `json:"message_count"`
-	TokenStats          domain.SessionTokenStats   `json:"token_stats"`
-	CostStats           domain.SessionCostStats    `json:"cost_stats,omitempty"`
-	Model               string                     `json:"model,omitempty"`
-	Tags                []string                   `json:"tags,omitempty"`
-	Summary             string                     `json:"summary,omitempty"`
-	OptimizedMessages   []domain.ConversationEntry `json:"optimized_messages,omitempty"`
-	TitleGenerated      bool                       `json:"title_generated,omitempty"`
-	TitleInvalidated    bool                       `json:"title_invalidated,omitempty"`
-	TitleGenerationTime *time.Time                 `json:"title_generation_time,omitempty"`
-	ContextID           string                     `json:"context_id,omitempty"`
+	ID                  string                   `json:"id"`
+	Title               string                   `json:"title"`
+	CreatedAt           time.Time                `json:"created_at"`
+	UpdatedAt           time.Time                `json:"updated_at"`
+	MessageCount        int                      `json:"message_count"`
+	TokenStats          domain.SessionTokenStats `json:"token_stats"`
+	CostStats           domain.SessionCostStats  `json:"cost_stats,omitempty"`
+	Model               string                   `json:"model,omitempty"`
+	Tags                []string                 `json:"tags,omitempty"`
+	TitleGenerated      bool                     `json:"title_generated,omitempty"`
+	TitleInvalidated    bool                     `json:"title_invalidated,omitempty"`
+	TitleGenerationTime *time.Time               `json:"title_generation_time,omitempty"`
+	ContextID           string                   `json:"context_id,omitempty"`
 }
 
 // ConversationSummary contains summary information about a conversation

internal/infra/storage/jsonl.go

@@ -208,7 +208,6 @@ func (s *JsonlStorage) ListConversations(ctx context.Context, limit, offset int)
 					CostStats:           metadataWrapper.Metadata.CostStats,
 					Model:               metadataWrapper.Metadata.Model,
 					Tags:                metadataWrapper.Metadata.Tags,
-					Summary:             metadataWrapper.Metadata.Summary,
 					TitleGenerated:      metadataWrapper.Metadata.TitleGenerated,
 					TitleInvalidated:    metadataWrapper.Metadata.TitleInvalidated,
 					TitleGenerationTime: metadataWrapper.Metadata.TitleGenerationTime,

internal/infra/storage/memory.go

@@ -81,7 +81,6 @@ func (m *MemoryStorage) ListConversations(ctx context.Context, limit, offset int
 			TokenStats:          data.metadata.TokenStats,
 			Model:               data.metadata.Model,
 			Tags:                data.metadata.Tags,
-			Summary:             data.metadata.Summary,
 			TitleGenerated:      data.metadata.TitleGenerated,
 			TitleInvalidated:    data.metadata.TitleInvalidated,
 			TitleGenerationTime: data.metadata.TitleGenerationTime,

internal/infra/storage/migrations/postgres_migrations.go

@@ -15,8 +15,6 @@ func GetPostgresMigrations() []Migration {
 					message_count INTEGER NOT NULL DEFAULT 0,
 					model VARCHAR(255),
 					tags JSONB,
-					summary TEXT,
-					optimized_messages JSONB,
 					token_stats JSONB,
 					cost_stats JSONB,
 					title_generated BOOLEAN DEFAULT FALSE,

internal/infra/storage/migrations/sqlite_migrations.go

@@ -12,14 +12,12 @@ func GetSQLiteMigrations() []Migration {
 					title TEXT NOT NULL,
 					count INTEGER NOT NULL DEFAULT 0,
 					messages TEXT NOT NULL,
-					optimized_messages TEXT,
 					total_input_tokens INTEGER NOT NULL DEFAULT 0,
 					total_output_tokens INTEGER NOT NULL DEFAULT 0,
 					request_count INTEGER NOT NULL DEFAULT 0,
 					cost_stats TEXT DEFAULT '{}',
 					models TEXT DEFAULT '[]',
 					tags TEXT DEFAULT '[]',
-					summary TEXT DEFAULT '',
 					title_generated BOOLEAN DEFAULT FALSE,
 					title_invalidated BOOLEAN DEFAULT FALSE,
 					title_generation_time DATETIME,

internal/infra/storage/postgres.go

@@ -130,31 +130,21 @@ func (s *PostgresStorage) SaveConversation(ctx context.Context, conversationID s
 		return fmt.Errorf("failed to marshal cost stats: %w", err)
 	}
 
-	var optimizedMessagesJSON []byte
-	if len(metadata.OptimizedMessages) > 0 {
-		optimizedMessagesJSON, err = json.Marshal(metadata.OptimizedMessages)
-		if err != nil {
-			return fmt.Errorf("failed to marshal optimized messages: %w", err)
-		}
-	}
-
 	_, err = tx.ExecContext(ctx, `
-		INSERT INTO conversations (id, title, created_at, updated_at, message_count, model, tags, summary, optimized_messages, token_stats, cost_stats, title_generated, title_invalidated, title_generation_time)
-		VALUES ($1, $2, $3, $4, $5, $6, $7, $8, $9, $10, $11, $12, $13, $14)
+		INSERT INTO conversations (id, title, created_at, updated_at, message_count, model, tags, token_stats, cost_stats, title_generated, title_invalidated, title_generation_time)
+		VALUES ($1, $2, $3, $4, $5, $6, $7, $8, $9, $10, $11, $12)
 		ON CONFLICT(id) DO UPDATE SET
 			title = EXCLUDED.title,
 			updated_at = EXCLUDED.updated_at,
 			message_count = EXCLUDED.message_count,
 			model = EXCLUDED.model,
 			tags = EXCLUDED.tags,
-			summary = EXCLUDED.summary,
-			optimized_messages = EXCLUDED.optimized_messages,
 			token_stats = EXCLUDED.token_stats,
 			cost_stats = EXCLUDED.cost_stats,
 			title_generated = EXCLUDED.title_generated,
 			title_invalidated = EXCLUDED.title_invalidated,
 			title_generation_time = EXCLUDED.title_generation_time
-	`, conversationID, metadata.Title, metadata.CreatedAt, metadata.UpdatedAt, len(entries), metadata.Model, string(tagsJSON), metadata.Summary, optimizedMessagesJSON, string(tokenStatsJSON), string(costStatsJSON), metadata.TitleGenerated, metadata.TitleInvalidated, metadata.TitleGenerationTime)
+	`, conversationID, metadata.Title, metadata.CreatedAt, metadata.UpdatedAt, len(entries), metadata.Model, string(tagsJSON), string(tokenStatsJSON), string(costStatsJSON), metadata.TitleGenerated, metadata.TitleInvalidated, metadata.TitleGenerationTime)
 	if err != nil {
 		return fmt.Errorf("failed to save conversation metadata: %w", err)
 	}
@@ -186,15 +176,14 @@ func (s *PostgresStorage) SaveConversation(ctx context.Context, conversationID s
 func (s *PostgresStorage) LoadConversation(ctx context.Context, conversationID string) ([]domain.ConversationEntry, ConversationMetadata, error) {
 	var metadata ConversationMetadata
 	var tokenStatsJSON, tagsJSON, costStatsJSON string
-	var optimizedMessagesJSON sql.NullString
 
 	err := s.db.QueryRowContext(ctx, `
-		SELECT id, title, created_at, updated_at, message_count, model, tags, summary, optimized_messages, token_stats, COALESCE(cost_stats, '{}'),
+		SELECT id, title, created_at, updated_at, message_count, model, tags, token_stats, COALESCE(cost_stats, '{}'),
 			   COALESCE(title_generated, FALSE), COALESCE(title_invalidated, FALSE), title_generation_time
 		FROM conversations WHERE id = $1
 	`, conversationID).Scan(
 		&metadata.ID, &metadata.Title, &metadata.CreatedAt, &metadata.UpdatedAt,
-		&metadata.MessageCount, &metadata.Model, &tagsJSON, &metadata.Summary, &optimizedMessagesJSON, &tokenStatsJSON, &costStatsJSON,
+		&metadata.MessageCount, &metadata.Model, &tagsJSON, &tokenStatsJSON, &costStatsJSON,
 		&metadata.TitleGenerated, &metadata.TitleInvalidated, &metadata.TitleGenerationTime,
 	)
 	if err != nil {
@@ -218,12 +207,6 @@ func (s *PostgresStorage) LoadConversation(ctx context.Context, conversationID s
 		return nil, metadata, fmt.Errorf("failed to unmarshal tags: %w", err)
 	}
 
-	if optimizedMessagesJSON.Valid && optimizedMessagesJSON.String != "" {
-		if err := json.Unmarshal([]byte(optimizedMessagesJSON.String), &metadata.OptimizedMessages); err != nil {
-			return nil, metadata, fmt.Errorf("failed to unmarshal optimized messages: %w", err)
-		}
-	}
-
 	rows, err := s.db.QueryContext(ctx, `
 		SELECT entry_data FROM conversation_entries
 		WHERE conversation_id = $1
@@ -273,7 +256,7 @@ func (s *PostgresStorage) ListConversations(ctx context.Context, limit, offset i
 
 		err := rows.Scan(
 			&summary.ID, &summary.Title, &summary.CreatedAt, &summary.UpdatedAt,
-			&summary.MessageCount, &summary.Model, &tagsJSON, &summary.Summary, &tokenStatsJSON, &costStatsJSON,
+			&summary.MessageCount, &summary.Model, &tagsJSON, &tokenStatsJSON, &costStatsJSON,
 			&summary.TitleGenerated, &summary.TitleInvalidated, &summary.TitleGenerationTime,
 		)
 		if err != nil {
@@ -323,7 +306,7 @@ func (s *PostgresStorage) ListConversationsNeedingTitles(ctx context.Context, li
 
 		err := rows.Scan(
 			&summary.ID, &summary.Title, &summary.CreatedAt, &summary.UpdatedAt,
-			&summary.MessageCount, &summary.Model, &tagsJSON, &summary.Summary, &tokenStatsJSON, &costStatsJSON,
+			&summary.MessageCount, &summary.Model, &tagsJSON, &tokenStatsJSON, &costStatsJSON,
 			&summary.TitleGenerated, &summary.TitleInvalidated, &summary.TitleGenerationTime,
 		)
 		if err != nil {
@@ -388,10 +371,10 @@ func (s *PostgresStorage) UpdateConversationMetadata(ctx context.Context, conver
 
 	result, err := s.db.ExecContext(ctx, `
 		UPDATE conversations
-		SET title = $1, updated_at = $2, model = $3, tags = $4, summary = $5, token_stats = $6, cost_stats = $7,
-		    title_generated = $8, title_invalidated = $9, title_generation_time = $10
-		WHERE id = $11
-	`, metadata.Title, metadata.UpdatedAt, metadata.Model, string(tagsJSON), metadata.Summary, string(tokenStatsJSON), string(costStatsJSON), metadata.TitleGenerated, metadata.TitleInvalidated, metadata.TitleGenerationTime, conversationID)
+		SET title = $1, updated_at = $2, model = $3, tags = $4, token_stats = $5, cost_stats = $6,
+		    title_generated = $7, title_invalidated = $8, title_generation_time = $9
+		WHERE id = $10
+	`, metadata.Title, metadata.UpdatedAt, metadata.Model, string(tagsJSON), string(tokenStatsJSON), string(costStatsJSON), metadata.TitleGenerated, metadata.TitleInvalidated, metadata.TitleGenerationTime, conversationID)
 	if err != nil {
 		return fmt.Errorf("failed to update conversation metadata: %w", err)
 	}

internal/infra/storage/redis.go

@@ -221,15 +221,15 @@ func (s *RedisStorage) ListConversations(ctx context.Context, limit, offset int)
 		}
 
 		summary := ConversationSummary{
-			ID:                  metadata.ID,
-			Title:               metadata.Title,
-			CreatedAt:           metadata.CreatedAt,
-			UpdatedAt:           metadata.UpdatedAt,
-			MessageCount:        metadata.MessageCount,
-			TokenStats:          metadata.TokenStats,
-			Model:               metadata.Model,
-			Tags:                metadata.Tags,
-			Summary:             metadata.Summary,
+			ID:           metadata.ID,
+			Title:        metadata.Title,
+			CreatedAt:    metadata.CreatedAt,
+			UpdatedAt:    metadata.UpdatedAt,
+			MessageCount: metadata.MessageCount,
+			TokenStats:   metadata.TokenStats,
+			Model:        metadata.Model,
+			Tags:         metadata.Tags,
+
 			TitleGenerated:      metadata.TitleGenerated,
 			TitleInvalidated:    metadata.TitleInvalidated,
 			TitleGenerationTime: metadata.TitleGenerationTime,
@@ -288,15 +288,15 @@ func (s *RedisStorage) ListConversationsNeedingTitles(ctx context.Context, limit
 
 		if (!metadata.TitleGenerated || metadata.TitleInvalidated) && metadata.MessageCount > 0 {
 			summary := ConversationSummary{
-				ID:                  metadata.ID,
-				Title:               metadata.Title,
-				CreatedAt:           metadata.CreatedAt,
-				UpdatedAt:           metadata.UpdatedAt,
-				MessageCount:        metadata.MessageCount,
-				TokenStats:          metadata.TokenStats,
-				Model:               metadata.Model,
-				Tags:                metadata.Tags,
-				Summary:             metadata.Summary,
+				ID:           metadata.ID,
+				Title:        metadata.Title,
+				CreatedAt:    metadata.CreatedAt,
+				UpdatedAt:    metadata.UpdatedAt,
+				MessageCount: metadata.MessageCount,
+				TokenStats:   metadata.TokenStats,
+				Model:        metadata.Model,
+				Tags:         metadata.Tags,
+
 				TitleGenerated:      metadata.TitleGenerated,
 				TitleInvalidated:    metadata.TitleInvalidated,
 				TitleGenerationTime: metadata.TitleGenerationTime,