diff --git a/cmd/lil-rag/main.go b/cmd/lil-rag/main.go
index 0a99a9b..0e916a2 100644
--- a/cmd/lil-rag/main.go
+++ b/cmd/lil-rag/main.go
@@ -648,7 +648,6 @@ func handleChat(ctx context.Context, rag *lilrag.LilRag, profileConfig *config.P
 					i++
 				}
 			}
-			break
 		}
 	}
 
@@ -826,17 +825,23 @@ func handleDelete(ctx context.Context, rag *lilrag.LilRag, args []string) error
 
 func handleReindex(ctx context.Context, rag *lilrag.LilRag, args []string) error {
 	if len(args) > 0 && (args[0] == "--help" || args[0] == "-h") {
-		fmt.Println("Usage: lil-rag reindex [--force]")
+		fmt.Println("Usage: lil-rag reindex [--force] [--chunking=STRATEGY]")
 		fmt.Println("")
-		fmt.Println("Reprocess all documents with the current recursive chunking configuration.")
+		fmt.Println("Reprocess all documents with the specified chunking configuration.")
 		fmt.Println("This will:")
-		fmt.Println("  • Re-chunk all documents using the latest algorithm")
+		fmt.Println("  • Re-chunk all documents using the specified algorithm")
 		fmt.Println("  • Regenerate embeddings for all chunks")
 		fmt.Println("  • Update chunk boundaries and overlap")
 		fmt.Println("  • Preserve original document content and metadata")
 		fmt.Println("")
 		fmt.Println("Options:")
-		fmt.Println("  --force    Skip confirmation prompt")
+		fmt.Println("  --force              Skip confirmation prompt")
+		fmt.Println("  --chunking=STRATEGY  Chunking strategy to use (default: recursive)")
+		fmt.Println("")
+		fmt.Println("Available chunking strategies:")
+		fmt.Println("  recursive   Hierarchical text splitting with semantic boundaries (default)")
+		fmt.Println("  semantic    Adaptive chunking focused on semantic coherence")
+		fmt.Println("  simple      Basic word-based chunking")
 		fmt.Println("")
 		fmt.Println("Note: This operation can take several minutes depending on the number")
 		fmt.Println("of documents and their size. The system will remain accessible during")
@@ -844,14 +849,30 @@ func handleReindex(ctx context.Context, rag *lilrag.LilRag, args []string) error
 		return nil
 	}
 
-	// Check if --force flag is provided
+	// Parse flags
 	force := false
+	chunkingStrategy := "recursive" // default strategy
 	for _, arg := range args {
 		if arg == forceFlag {
 			force = true
+		} else if strings.HasPrefix(arg, "--chunking=") {
+			chunkingStrategy = strings.TrimPrefix(arg, "--chunking=")
+		}
+	}
+
+	// Validate chunking strategy
+	validStrategies := []string{"recursive", "semantic", "simple"}
+	isValid := false
+	for _, valid := range validStrategies {
+		if chunkingStrategy == valid {
+			isValid = true
 			break
 		}
 	}
+	if !isValid {
+		return fmt.Errorf("invalid chunking strategy '%s'. Valid strategies: %s",
+			chunkingStrategy, strings.Join(validStrategies, ", "))
+	}
 
 	// Get document count for confirmation
 	documents, err := rag.ListDocuments(ctx)
@@ -864,9 +885,9 @@ func handleReindex(ctx context.Context, rag *lilrag.LilRag, args []string) error
 		return nil
 	}
 
-	fmt.Printf("This will reindex %d documents with recursive chunking.\n", len(documents))
+	fmt.Printf("This will reindex %d documents with %s chunking.\n", len(documents), chunkingStrategy)
 	fmt.Println("The process will:")
-	fmt.Println("  • Re-chunk all documents using the latest algorithm")
+	fmt.Println("  • Re-chunk all documents using the specified algorithm")
 	fmt.Println("  • Regenerate embeddings for improved search performance")
 	fmt.Println("  • Update chunk boundaries for better semantic coherence")
 	fmt.Printf("\nEstimated time: %d-%d minutes (depending on document size and Ollama performance)\n",
@@ -887,11 +908,11 @@ func handleReindex(ctx context.Context, rag *lilrag.LilRag, args []string) error
 		}
 	}
 
-	fmt.Println("\n🔄 Starting reindex with recursive chunking...")
+	fmt.Printf("\n🔄 Starting reindex with %s chunking...\n", chunkingStrategy)
 	fmt.Println("This may take several minutes. Please do not interrupt the process.")
 
 	startTime := time.Now()
-	err = rag.ReindexAllDocuments(ctx)
+	err = rag.ReindexAllDocumentsWithStrategy(ctx, chunkingStrategy)
 	duration := time.Since(startTime)
 
 	if err != nil {
@@ -900,7 +921,7 @@ func handleReindex(ctx context.Context, rag *lilrag.LilRag, args []string) error
 	}
 
 	fmt.Printf("\n✅ Reindex completed successfully in %v\n", duration)
-	fmt.Printf("All %d documents have been reprocessed with recursive chunking.\n", len(documents))
+	fmt.Printf("All %d documents have been reprocessed with %s chunking.\n", len(documents), chunkingStrategy)
 	fmt.Println("Your RAG system now uses improved chunk boundaries for better search performance.")
 
 	return nil
@@ -1058,7 +1079,7 @@ func printUsage() {
 	fmt.Println("      --list-sessions         List all chat sessions")
 	fmt.Println("  documents                    List all indexed documents")
 	fmt.Println("  delete <id> [--force]        Delete a document by ID")
-	fmt.Println("  reindex [--force]            Reprocess all documents with recursive chunking")
+	fmt.Println("  reindex [--force] [--chunking=STRATEGY]  Reprocess all documents with specified chunking")
 	fmt.Println("  health                       Check system health status")
 	fmt.Println("  config <init|show|set>       Manage user profile configuration")
 	fmt.Println("  reset [--force]              Delete database and all indexed data")
@@ -1114,8 +1135,9 @@ func printUsage() {
 	fmt.Println("  lil-rag chat --list-sessions             # List all chat sessions")
 	fmt.Println("  lil-rag documents               # List all documents")
 	fmt.Println("  lil-rag delete doc1 --force     # Delete document")
-	fmt.Println("  lil-rag reindex                 # Reindex all documents with recursive chunking")
+	fmt.Println("  lil-rag reindex                 # Reindex all documents with recursive chunking (default)")
 	fmt.Println("  lil-rag reindex --force         # Reindex without confirmation")
+	fmt.Println("  lil-rag reindex --chunking=simple # Reindex with simple chunking strategy")
 	fmt.Println("  lil-rag health                  # Check system health")
 	fmt.Println("  lil-rag auth add alice password123  # Add user with username and password")
 	fmt.Println("  lil-rag auth list               # List all users")
diff --git a/main b/main
deleted file mode 100755
index 8d60f44..0000000
Binary files a/main and /dev/null differ
diff --git a/pkg/lilrag/chunker.go b/pkg/lilrag/chunker.go
index 45f12a9..e5a348e 100644
--- a/pkg/lilrag/chunker.go
+++ b/pkg/lilrag/chunker.go
@@ -89,6 +89,30 @@ func (tc *TextChunker) ChunkText(text string) []Chunk {
 	return semanticChunks
 }
 
+// ChunkTextWithStrategy applies the specified chunking strategy
+func (tc *TextChunker) ChunkTextWithStrategy(text, strategy string) []Chunk {
+	text = strings.TrimSpace(text)
+	if text == "" {
+		return nil
+	}
+
+	contentType := tc.detectContentType(text)
+
+	switch strategy {
+	case "simple":
+		return tc.fallbackChunk(text, contentType)
+	case "semantic":
+		// Semantic chunking focuses on content-aware boundaries
+		return tc.adaptiveChunk(text, contentType)
+	case "recursive":
+		// Default recursive chunking (same as current ChunkText behavior)
+		return tc.ChunkText(text)
+	default:
+		// Default recursive chunking (same as current ChunkText behavior)
+		return tc.ChunkText(text)
+	}
+}
+
 // detectContentType analyzes text to determine optimal chunking strategy
 func (tc *TextChunker) detectContentType(text string) string {
 	codeIndicators := []string{"function", "class", "def ", "```", "import ", "#include", "var ", "let ", "const "}
diff --git a/pkg/lilrag/lilrag.go b/pkg/lilrag/lilrag.go
index 94c9f90..efd0708 100644
--- a/pkg/lilrag/lilrag.go
+++ b/pkg/lilrag/lilrag.go
@@ -740,6 +740,52 @@ func (m *LilRag) ReindexAllDocuments(ctx context.Context) error {
 	return nil
 }
 
+// ReindexAllDocumentsWithStrategy reprocesses all documents with the specified chunking strategy
+func (m *LilRag) ReindexAllDocumentsWithStrategy(ctx context.Context, strategy string) error {
+	if m.storage == nil || m.chunker == nil || m.embedder == nil || m.documentHandler == nil {
+		return fmt.Errorf("LilRag not properly initialized")
+	}
+
+	// Get all documents
+	documents, err := m.storage.ListDocuments(ctx)
+	if err != nil {
+		return fmt.Errorf("failed to list documents: %w", err)
+	}
+
+	if len(documents) == 0 {
+		fmt.Println("No documents found to reindex")
+		return nil
+	}
+
+	fmt.Printf("Starting reindex of %d documents with %s chunking...\n", len(documents), strategy)
+
+	processed := 0
+	failed := 0
+
+	for i, doc := range documents {
+		fmt.Printf("Reindexing document %d/%d: %s\n", i+1, len(documents), doc.ID)
+
+		err := m.reindexDocumentWithStrategy(ctx, &doc, strategy)
+		if err != nil {
+			fmt.Printf("Failed to reindex document %s: %v\n", doc.ID, err)
+			failed++
+			continue
+		}
+
+		processed++
+		if processed%10 == 0 {
+			fmt.Printf("Progress: %d/%d documents processed\n", processed, len(documents))
+		}
+	}
+
+	fmt.Printf("Reindex completed: %d processed, %d failed\n", processed, failed)
+	if failed > 0 {
+		return fmt.Errorf("reindex completed with %d failures", failed)
+	}
+
+	return nil
+}
+
 // reindexDocument reprocesses a single document with current chunking settings
 func (m *LilRag) reindexDocument(ctx context.Context, doc *DocumentInfo) error {
 	// If document has a source path, try to reprocess from the original file
@@ -826,6 +872,63 @@ func (m *LilRag) reindexWithChunks(ctx context.Context, doc *DocumentInfo, chunk
 	return m.storage.IndexChunks(ctx, doc.ID, combinedText.String(), chunks, embeddings)
 }
 
+// reindexDocumentWithStrategy reprocesses a single document with the specified chunking strategy
+func (m *LilRag) reindexDocumentWithStrategy(ctx context.Context, doc *DocumentInfo, strategy string) error {
+	// If document has a source path, try to reprocess from the original file
+	if doc.SourcePath != "" {
+		// Check if the source file still exists
+		if _, err := os.Stat(doc.SourcePath); err == nil {
+			// File exists, reprocess from original with strategy
+			return m.reindexFromFileWithStrategy(ctx, doc, strategy)
+		}
+		// File doesn't exist, fall back to reprocessing stored text
+		fmt.Printf("Source file %s not found, reprocessing from stored text\n", doc.SourcePath)
+	}
+
+	// Reprocess from stored text content with strategy
+	return m.reindexFromTextWithStrategy(ctx, doc, strategy)
+}
+
+// reindexFromFileWithStrategy reprocesses a document from its original file with the specified strategy
+func (m *LilRag) reindexFromFileWithStrategy(ctx context.Context, doc *DocumentInfo, strategy string) error {
+	if !m.documentHandler.IsSupported(doc.SourcePath) {
+		return fmt.Errorf("unsupported file format: %s", doc.SourcePath)
+	}
+
+	// Parse the file to get text content
+	text, err := m.documentHandler.ParseFile(doc.SourcePath)
+	if err != nil {
+		return fmt.Errorf("failed to parse file %s: %w", doc.SourcePath, err)
+	}
+
+	if text == "" {
+		return fmt.Errorf("no content found in file %s", doc.SourcePath)
+	}
+
+	// Apply the specified chunking strategy
+	chunks := m.chunker.ChunkTextWithStrategy(text, strategy)
+	if len(chunks) == 0 {
+		return fmt.Errorf("failed to create chunks from file %s", doc.SourcePath)
+	}
+
+	return m.reindexWithChunks(ctx, doc, chunks)
+}
+
+// reindexFromTextWithStrategy reprocesses a document from its stored text with the specified strategy
+func (m *LilRag) reindexFromTextWithStrategy(ctx context.Context, doc *DocumentInfo, strategy string) error {
+	if doc.Text == "" {
+		return fmt.Errorf("no text content available for document %s", doc.ID)
+	}
+
+	// Apply the specified chunking strategy
+	chunks := m.chunker.ChunkTextWithStrategy(doc.Text, strategy)
+	if len(chunks) == 0 {
+		return fmt.Errorf("failed to create chunks from text for document %s", doc.ID)
+	}
+
+	return m.reindexWithChunks(ctx, doc, chunks)
+}
+
 // Services returns the modern service interfaces
 func (m *LilRag) Services() *Services {
 	return m.services