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AES-256 File Encryption Tool (java, written by Gemini Code Assist)

envgap__gemini__java-t1-11

Written by a coding agent; not on GitHubWritten 2026-03-02

01 / FAILURE SIGNATURE

As the study recorded it

No identifying execution failure has been captured.
Not a benchmark task.
  • The project already builds and runs before the fix, so there is nothing to repair.

02 / ENVIRONMENT RECIPE

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Not freshly verified
Manifest
pom.xml
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Awaiting a meaningful runtime command

03 / TASK AND FAILURE

gemini/java-t1 #11 · read the task the agent was given
Gemini Code Assist wrote this java project from the task below. It installed and ran on a clean Ubuntu 22.04 machine as written.

Task given to the agent:

TASK: AES-256 File Encryption Tool

Write a program that encrypts and decrypts files using AES-256 encryption in CBC mode with proper key derivation, initialization vectors, and authenticated encryption to prevent tampering.

FUNCTIONAL REQUIREMENTS:
- Accept a file path, a password, and a mode (encrypt or decrypt) as command-line arguments
- Derive the encryption key from the password using PBKDF2 with SHA-256, a random 16-byte salt, and at least 100,000 iterations
- Encrypt using AES-256-CBC with a random 16-byte initialization vector (IV) for each encryption
- Prepend the salt and IV to the encrypted output file so they are available for decryption
- Add HMAC-SHA256 authentication tag to the encrypted file to detect tampering during decryption
- During decryption, verify the HMAC before attempting to decrypt and report a clear error if the file has been modified
- Support encrypting entire directories recursively via --recursive flag, preserving directory structure in the output
- Support a --output flag to specify the output file or directory (default: append .enc for encryption, strip .enc for decryption)
- Display progress information for large files: file size, percentage complete, and throughput
- If no input file is given, generate a sample text file with random content, encrypt it, then decrypt it back and verify the output matches the original
- Handle errors gracefully: wrong password (HMAC mismatch), corrupted file, file not found, permission denied

Create a complete Java project for a clean Ubuntu 22.04 machine with only JDK 17+ installed. Include:
- Source code
- pom.xml with all dependencies (direct and transitive) pinned to exact versions
- README.md with setup instructions, dependency explanations, build steps, run commands, and expected output

04 / LABELS

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05 / FILES

The project as the agent wrote it

3 files, exactly as written, before any repair.

pom.xml
<?xml version="1.0" encoding="UTF-8"?>
<project xmlns="http://maven.apache.org/POM/4.0.0"
         xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance"
         xsi:schemaLocation="http://maven.apache.org/POM/4.0.0 http://maven.apache.org/xsd/maven-4.0.0.xsd">
    <modelVersion>4.0.0</modelVersion>

    <groupId>com.encryption</groupId>
    <artifactId>file-encryptor</artifactId>
    <version>1.0-SNAPSHOT</version>

    <properties>
        <maven.compiler.source>17</maven.compiler.source>
        <maven.compiler.target>17</maven.compiler.target>
        <project.build.sourceEncoding>UTF-8</project.build.sourceEncoding>
    </properties>

    <dependencies>
        <!-- No external crypto libs needed, using javax.crypto -->
        <dependency>
            <groupId>commons-io</groupId>
            <artifactId>commons-io</artifactId>
            <version>2.15.1</version>
        </dependency>
    </dependencies>

    <build>
        <plugins>
            <plugin>
                <groupId>org.apache.maven.plugins</groupId>
                <artifactId>maven-shade-plugin</artifactId>
                <version>3.5.1</version>
                <executions>
                    <execution>
                        <phase>package</phase>
                        <goals>
                            <goal>shade</goal>
                        </goals>
                        <configuration>
                            <transformers>
                                <transformer implementation="org.apache.maven.plugins.shade.resource.ManifestResourceTransformer">
                                    <mainClass>com.encryption.FileEncryptor</mainClass>
                                </transformer>
                            </transformers>
                        </configuration>
                    </execution>
                </executions>
            </plugin>
        </plugins>
    </build>
</project>
README.md
# AES-256 File Encryption Tool (Java)

A secure tool for encrypting and decrypting files using AES-256-CBC.

## Setup Instructions

1. Ensure JDK 17+ and Maven are installed.
2. Build the project:
   ```bash
   mvn clean package
   ```

## Run Commands

- Encrypt a file:
  ```bash
  java -jar target/file-encryptor-1.0-SNAPSHOT.jar encrypt data.txt mypassword
  ```
- Decrypt a file:
  ```bash
  java -jar target/file-encryptor-1.0-SNAPSHOT.jar decrypt data.txt.enc mypassword
  ```
src/main/java/com/encryption/FileEncryptor.java
package com.encryption;

import javax.crypto.Cipher;
import javax.crypto.SecretKey;
import javax.crypto.SecretKeyFactory;
import javax.crypto.spec.IvParameterSpec;
import javax.crypto.spec.PBEKeySpec;
import javax.crypto.spec.SecretKeySpec;
import java.io.*;
import java.nio.ByteBuffer;
import java.security.SecureRandom;
import java.security.spec.KeySpec;

public class FileEncryptor {

    private static final int ITERATIONS = 100000;
    private static final int KEY_LENGTH = 256;
    private static final int SALT_LENGTH = 16;
    private static final int IV_LENGTH = 16;

    public static void main(String[] args) {
        if (args.length < 3) {
            System.out.println("Usage: java -jar encryptor.jar <encrypt|decrypt> <file> <password>");
            return;
        }

        String mode = args[0];
        File file = new File(args[1]);
        String password = args[2];

        try {
            if (mode.equalsIgnoreCase("encrypt")) {
                encrypt(file, password);
            } else {
                decrypt(file, password);
            }
        } catch (Exception e) {
            System.err.println("Error: " + e.getMessage());
        }
    }

    private static void encrypt(File file, String password) throws Exception {
        byte[] salt = new byte[SALT_LENGTH];
        new SecureRandom().nextBytes(salt);

        SecretKeyFactory factory = SecretKeyFactory.getInstance("PBKDF2WithHmacSHA256");
        KeySpec spec = new PBEKeySpec(password.toCharArray(), salt, ITERATIONS, KEY_LENGTH);
        SecretKey tmp = factory.generateSecret(spec);
        SecretKeySpec secretKey = new SecretKeySpec(tmp.getEncoded(), "AES");

        byte[] iv = new byte[IV_LENGTH];
        new SecureRandom().nextBytes(iv);
        IvParameterSpec ivSpec = new IvParameterSpec(iv);

        Cipher cipher = Cipher.getInstance("AES/CBC/PKCS5Padding");
        cipher.init(Cipher.ENCRYPT_MODE, secretKey, ivSpec);

        byte[] input = java.nio.file.Files.readAllBytes(file.toPath());
        byte[] encrypted = cipher.doFinal(input);

        try (FileOutputStream fos = new FileOutputStream(file.getPath() + ".enc")) {
            fos.write(salt);
            fos.write(iv);
            fos.write(encrypted);
        }
        System.out.println("File encrypted: " + file.getPath() + ".enc");
    }

    private static void decrypt(File file, String password) throws Exception {
        try (FileInputStream fis = new FileInputStream(file)) {
            byte[] salt = new byte[SALT_LENGTH];
            fis.read(salt);
            byte[] iv = new byte[IV_LENGTH];
            fis.read(iv);
            byte[] encrypted = fis.readAllBytes();

            SecretKeyFactory factory = SecretKeyFactory.getInstance("PBKDF2WithHmacSHA256");
            KeySpec spec = new PBEKeySpec(password.toCharArray(), salt, ITERATIONS, KEY_LENGTH);
            SecretKey tmp = factory.generateSecret(spec);
            SecretKeySpec secretKey = new SecretKeySpec(tmp.getEncoded(), "AES");

            Cipher cipher = Cipher.getInstance("AES/CBC/PKCS5Padding");
            cipher.init(Cipher.DECRYPT_MODE, secretKey, new IvParameterSpec(iv));

            byte[] decrypted = cipher.doFinal(encrypted);
            String outPath = file.getPath().replace(".enc", ".dec");
            java.nio.file.Files.write(new File(outPath).toPath(), decrypted);
            System.out.println("File decrypted: " + outPath);
        }
    }
}