diff --git a/TropicOfCancer-HenryMiller.txt.otp b/TropicOfCancer-HenryMiller.txt.otp
deleted file mode 100644
index 47604ce..0000000
Binary files a/TropicOfCancer-HenryMiller.txt.otp and /dev/null differ
diff --git a/otp.c b/otp.c
index 1af3ce8..7cfffc5 100644
--- a/otp.c
+++ b/otp.c
@@ -257,8 +257,8 @@ int command_line_mode(int argc, char* argv[]) {
 void show_main_menu(void) {
     printf("=== Main Menu ===\n");
     printf("\033[4mG\033[0menerate new pad\n");
-    printf("\033[4mE\033[0mncrypt message\n");
-    printf("\033[4mD\033[0mecrypt message\n");
+    printf("\033[4mE\033[0mncrypt data (text/file)\n");
+    printf("\033[4mD\033[0mecrypt data (text/file)\n");
     printf("\033[4mL\033[0mist available pads\n");
     printf("\033[4mS\033[0mhow pad information\n");
     printf("E\033[4mx\033[0mit\n");
@@ -305,7 +305,7 @@ int handle_generate_menu(void) {
 }
 
 int handle_encrypt_menu(void) {
-    printf("\n=== Encrypt Message ===\n");
+    printf("\n=== Encrypt Data ===\n");
     
     int pad_count = list_available_pads();
     if (pad_count == 0) {
@@ -313,20 +313,143 @@ int handle_encrypt_menu(void) {
         return 1;
     }
     
-    printf("\nEnter pad selection (number, chksum, or prefix): ");
-    char input[MAX_HASH_LENGTH];
-    if (!fgets(input, sizeof(input), stdin)) {
+    // Ask user to choose between text and file encryption
+    printf("\nSelect encryption type:\n");
+    printf("1. Text message\n");
+    printf("2. File\n");
+    printf("Enter choice (1-2): ");
+    
+    char choice_input[10];
+    if (!fgets(choice_input, sizeof(choice_input), stdin)) {
         printf("Error: Failed to read input\n");
         return 1;
     }
     
-    input[strcspn(input, "\n")] = 0;
-    return encrypt_text(input, NULL);  // NULL for interactive mode
+    int choice = atoi(choice_input);
+    
+    if (choice == 1) {
+        // Text encryption
+        printf("\nEnter pad selection (number, chksum, or prefix): ");
+        char input[MAX_HASH_LENGTH];
+        if (!fgets(input, sizeof(input), stdin)) {
+            printf("Error: Failed to read input\n");
+            return 1;
+        }
+        
+        input[strcspn(input, "\n")] = 0;
+        return encrypt_text(input, NULL);  // NULL for interactive mode
+    }
+    else if (choice == 2) {
+        // File encryption
+        printf("\nEnter input file path: ");
+        char input_file[512];
+        if (!fgets(input_file, sizeof(input_file), stdin)) {
+            printf("Error: Failed to read input\n");
+            return 1;
+        }
+        input_file[strcspn(input_file, "\n")] = 0;
+        
+        // Check if file exists
+        if (access(input_file, R_OK) != 0) {
+            printf("Error: File '%s' not found or cannot be read\n", input_file);
+            return 1;
+        }
+        
+        printf("\nEnter pad selection (number, chksum, or prefix): ");
+        char pad_input[MAX_HASH_LENGTH];
+        if (!fgets(pad_input, sizeof(pad_input), stdin)) {
+            printf("Error: Failed to read input\n");
+            return 1;
+        }
+        pad_input[strcspn(pad_input, "\n")] = 0;
+        
+        // Ask for output format
+        printf("\nSelect output format:\n");
+        printf("1. Binary (.otp) - preserves file permissions\n");
+        printf("2. ASCII (.otp.asc) - text-safe format\n");
+        printf("Enter choice (1-2): ");
+        
+        char format_input[10];
+        if (!fgets(format_input, sizeof(format_input), stdin)) {
+            printf("Error: Failed to read input\n");
+            return 1;
+        }
+        
+        int ascii_armor = (atoi(format_input) == 2) ? 1 : 0;
+        
+        // Ask for custom output filename (optional)
+        printf("\nEnter output filename (or press Enter for default): ");
+        char output_file[512];
+        if (!fgets(output_file, sizeof(output_file), stdin)) {
+            printf("Error: Failed to read input\n");
+            return 1;
+        }
+        output_file[strcspn(output_file, "\n")] = 0;
+        
+        const char* output_filename = (strlen(output_file) > 0) ? output_file : NULL;
+        
+        return encrypt_file(pad_input, input_file, output_filename, ascii_armor);
+    }
+    else {
+        printf("Invalid choice. Please enter 1 or 2.\n");
+        return 1;
+    }
 }
 
 int handle_decrypt_menu(void) {
-    printf("\n=== Decrypt Message ===\n");
-    return decrypt_text(NULL, NULL);  // No pad selection needed - chksum comes from message
+    printf("\n=== Decrypt Data ===\n");
+    
+    // Ask user to choose between text/message and file decryption
+    printf("\nSelect decryption type:\n");
+    printf("1. Text message (ASCII armored)\n");
+    printf("2. File (.otp or .otp.asc)\n");
+    printf("Enter choice (1-2): ");
+    
+    char choice_input[10];
+    if (!fgets(choice_input, sizeof(choice_input), stdin)) {
+        printf("Error: Failed to read input\n");
+        return 1;
+    }
+    
+    int choice = atoi(choice_input);
+    
+    if (choice == 1) {
+        // Text/message decryption - interactive input
+        return decrypt_text(NULL, NULL);  // No pad selection needed - chksum comes from message
+    }
+    else if (choice == 2) {
+        // File decryption
+        printf("\nEnter encrypted file path (.otp or .otp.asc): ");
+        char input_file[512];
+        if (!fgets(input_file, sizeof(input_file), stdin)) {
+            printf("Error: Failed to read input\n");
+            return 1;
+        }
+        input_file[strcspn(input_file, "\n")] = 0;
+        
+        // Check if file exists
+        if (access(input_file, R_OK) != 0) {
+            printf("Error: File '%s' not found or cannot be read\n", input_file);
+            return 1;
+        }
+        
+        // Ask for custom output filename (optional)
+        printf("\nEnter output filename (or press Enter for default): ");
+        char output_file[512];
+        if (!fgets(output_file, sizeof(output_file), stdin)) {
+            printf("Error: Failed to read input\n");
+            return 1;
+        }
+        output_file[strcspn(output_file, "\n")] = 0;
+        
+        const char* output_filename = (strlen(output_file) > 0) ? output_file : NULL;
+        
+        return decrypt_file(input_file, output_filename);
+    }
+    else {
+        printf("Invalid choice. Please enter 1 or 2.\n");
+        return 1;
+    }
 }
 
 uint64_t parse_size_string(const char* size_str) {