diff --git a/src/main/java/org/owasp/wrongsecrets/challenges/docker/Challenge49.java b/src/main/java/org/owasp/wrongsecrets/challenges/docker/Challenge49.java
new file mode 100644
index 000000000..54184106b
--- /dev/null
+++ b/src/main/java/org/owasp/wrongsecrets/challenges/docker/Challenge49.java
@@ -0,0 +1,101 @@
+package org.owasp.wrongsecrets.challenges.docker;
+
+import static org.owasp.wrongsecrets.Challenges.ErrorResponses.DECRYPTION_ERROR;
+
+import edu.umd.cs.findbugs.annotations.SuppressFBWarnings;
+import java.nio.charset.StandardCharsets;
+import java.security.MessageDigest;
+import java.security.NoSuchAlgorithmException;
+import java.util.Base64;
+import javax.crypto.Cipher;
+import javax.crypto.SecretKey;
+import javax.crypto.spec.SecretKeySpec;
+import lombok.extern.slf4j.Slf4j;
+import org.owasp.wrongsecrets.challenges.Challenge;
+import org.owasp.wrongsecrets.challenges.Spoiler;
+import org.springframework.beans.factory.annotation.Value;
+import org.springframework.stereotype.Component;
+
+/** This is a challenge based on using weak KDF to protect secrets. */
+@Slf4j
+@Component
+public class Challenge49 implements Challenge {
+
+  private final String cipherText;
+  private final String pin;
+
+  public Challenge49(
+      @Value("${challenge49ciphertext}") String cipherText,
+      @Value("${challenge49pin}") String pin) {
+    this.cipherText = cipherText;
+    this.pin = pin;
+  }
+
+  @Override
+  public Spoiler spoiler() {
+    return new Spoiler(base64Decode(pin));
+  }
+
+  @Override
+  public boolean answerCorrect(String answer) {
+    String plainText = "the answer";
+
+    try {
+      int enteredPin = Integer.parseInt(answer);
+      if (enteredPin < 0 || enteredPin > 99999) {
+        return false;
+      }
+    } catch (Exception e) {
+      log.warn("given answer is not an integer", e);
+      return false;
+    }
+
+    try {
+      String md5Hash = hashWithMd5(answer);
+      return decrypt(cipherText, md5Hash).equals(plainText);
+    } catch (Exception e) {
+      log.warn("there was an exception with hashing content in challenge49", e);
+      return false;
+    }
+  }
+
+  @SuppressFBWarnings(
+      value = "WEAK_MESSAGE_DIGEST_MD5",
+      justification = "This is to allow md5 hashing")
+  private String hashWithMd5(String plainText) throws NoSuchAlgorithmException {
+    MessageDigest md = MessageDigest.getInstance("MD5");
+
+    byte[] result = md.digest(plainText.getBytes(StandardCharsets.UTF_8));
+    StringBuilder hexString = new StringBuilder();
+    for (byte b : result) {
+      hexString.append(String.format("%02x", b));
+    }
+    return hexString.toString();
+  }
+
+  @SuppressFBWarnings(
+      value = {"CIPHER_INTEGRITY", "ECB_MODE"},
+      justification = "This is to allow ecb encryption")
+  private String decrypt(String cipherText, String key) {
+    try {
+      byte[] decodedEncryptedText = Base64.getDecoder().decode(cipherText);
+
+      SecretKey secretKey = new SecretKeySpec(key.getBytes(StandardCharsets.UTF_8), "AES");
+
+      Cipher cipher = Cipher.getInstance("AES");
+      cipher.init(Cipher.DECRYPT_MODE, secretKey);
+
+      byte[] decryptedData = cipher.doFinal(decodedEncryptedText);
+
+      return new String(decryptedData, StandardCharsets.UTF_8);
+    } catch (Exception e) {
+      log.warn("there was an exception with decrypting content in challenge49", e);
+      return DECRYPTION_ERROR;
+    }
+  }
+
+  private String base64Decode(String base64) {
+    byte[] decodedBytes = Base64.getDecoder().decode(base64);
+    return new String(decodedBytes, StandardCharsets.UTF_8);
+  }
+}
diff --git a/src/main/resources/application.properties b/src/main/resources/application.properties
index 4043278b1..12905a57c 100644
--- a/src/main/resources/application.properties
+++ b/src/main/resources/application.properties
@@ -72,6 +72,8 @@ challenge26ciphertext=gbU5thfgy8nwzF/qc1Pq59PrJzLB+bfAdTOrx969JZx1CKeG4Sq7v1uUpz
 DEFAULT37=DEFAULT37
 challenge27ciphertext=gYPQPfb0TUgWK630tHCWGwwME6IWtPWA51eU0Qpb9H7/lMlZPdLGZWmYE83YmEDmaEvFr2hX
 challenge41password=UEBzc3dvcmQxMjM=
+challenge49pin=NDQ0NDQ=
+challenge49ciphertext=k800mdwu8vlQoqeAgRMHDQ==
 management.endpoint.health.probes.enabled=true
 management.health.livenessState.enabled=true
 management.health.readinessState.enabled=true
diff --git a/src/main/resources/explanations/challenge49.adoc b/src/main/resources/explanations/challenge49.adoc
new file mode 100644
index 000000000..be7dba7ae
--- /dev/null
+++ b/src/main/resources/explanations/challenge49.adoc
@@ -0,0 +1,9 @@
+=== Cracking AES Encryption with a Weak MD5 Key
+
+Imagine you're a security analyst investigating a mobile app that handles sensitive information. You discover that the developer is using AES encryption to protect a secret, but instead of using a strong Key Derivation Function (KDF), they rely on the insecure MD5 algorithm to derive encryption keys from a simple numeric PIN.
+
+You’ve obtained an encrypted string: `k800mdwu8vlQoqeAgRMHDQ==`. You know that this string, when decrypted, reveals the text `the answer`.
+
+The key used for AES encryption is derived by taking the MD5 hash of a PIN, which is a number between 0 and 99999. Your task is to find the correct PIN that was used to derive the encryption key and decrypt the secret.
+
+Can you figure out the correct PIN and unlock the secret?
diff --git a/src/main/resources/explanations/challenge49_hint.adoc b/src/main/resources/explanations/challenge49_hint.adoc
new file mode 100644
index 000000000..0eee60e63
--- /dev/null
+++ b/src/main/resources/explanations/challenge49_hint.adoc
@@ -0,0 +1,5 @@
+The simplest way to crack the PIN in this scenario is to perform a brute-force attack due to the limited range of possible values (0 to 99,999).
+
+- Iterate over all possible PINs (from 0 to 99,999).
+- For each PIN, compute its MD5 hash to get the decryption key and try decrypting provided ciphertext.
+- If decrypted text is equal to `the answer`, you've found the correct PIN.
diff --git a/src/main/resources/explanations/challenge49_reason.adoc b/src/main/resources/explanations/challenge49_reason.adoc
new file mode 100644
index 000000000..037bf7435
--- /dev/null
+++ b/src/main/resources/explanations/challenge49_reason.adoc
@@ -0,0 +1,9 @@
+*Why Using MD5 as a KDF is Bad*
+
+Protecting keys effectively is crucial, and this means using the right Key Derivation Functions (KDFs) with additional entropy and contextual binding, as emphasized in the https://mas.owasp.org/MASTG/0x04g-Testing-Cryptography/#weak-key-generation-functions[Mobile Security Testing Guide (MSTG).]
+
+MD5 is too fast and easy to compute, enabling attackers to quickly try a vast number of inputs (like PINs) to derive the key. Additionally (although a bit harder to exploit), the collision space is relatively small, meaning multiple different inputs can lead to the same md5 hash.
+
+Stronger KDFs are crucial when dealing with sensitive data, as they provide much-needed resistance against brute-force attacks and protect secrets even if the attacker gains access to partial information.
+
+The MSTG recommends using robust KDFs like PBKDF2, bcrypt, or Argon2, which incorporate additional entropy and enforce computational hardness, making brute-force attacks more costly.
diff --git a/src/main/resources/wrong-secrets-configuration.yaml b/src/main/resources/wrong-secrets-configuration.yaml
index cf71de4c9..dc1004ead 100644
--- a/src/main/resources/wrong-secrets-configuration.yaml
+++ b/src/main/resources/wrong-secrets-configuration.yaml
@@ -775,3 +775,16 @@ configurations:
       category: *secrets
       ctf:
         enabled: false
+
+    - name: Challenge 49
+      short-name: "challenge-49"
+      sources:
+        - class-name: "org.owasp.wrongsecrets.challenges.docker.Challenge49"
+          explanation: "explanations/challenge49.adoc"
+          hint: "explanations/challenge49_hint.adoc"
+          reason: "explanations/challenge49_reason.adoc"
+          environments: *all_envs
+      difficulty: *hard
+      category: *crypto
+      ctf:
+        enabled: true
diff --git a/src/test/java/org/owasp/wrongsecrets/challenges/docker/Challenge49Test.java b/src/test/java/org/owasp/wrongsecrets/challenges/docker/Challenge49Test.java
new file mode 100644
index 000000000..c9fbd2048
--- /dev/null
+++ b/src/test/java/org/owasp/wrongsecrets/challenges/docker/Challenge49Test.java
@@ -0,0 +1,46 @@
+package org.owasp.wrongsecrets.challenges.docker;
+
+import org.assertj.core.api.Assertions;
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.extension.ExtendWith;
+import org.mockito.junit.jupiter.MockitoExtension;
+
+@ExtendWith(MockitoExtension.class)
+class Challenge49Test {
+
+  @Test
+  void spoilerShouldGiveAnswer() {
+    var challenge = new Challenge49("uz5cIFm0hW3LtWaqEX0S/Q==", "MTIzNDU=");
+    Assertions.assertThat(challenge.spoiler().solution()).isEqualTo("12345");
+  }
+
+  @Test
+  void correctPinShouldSolveChallenge() {
+    var challenge = new Challenge49("uz5cIFm0hW3LtWaqEX0S/Q==", "MTIzNDU=");
+    Assertions.assertThat(challenge.answerCorrect("12345")).isTrue();
+  }
+
+  @Test
+  void nonIntegerPinShouldNotSolveChallenge() {
+    var challenge = new Challenge49("uz5cIFm0hW3LtWaqEX0S/Q==", "MTIzNDU=");
+    Assertions.assertThat(challenge.answerCorrect("abcde")).isFalse();
+  }
+
+  @Test
+  void incorrectPinShouldNotSolveChallenge() {
+    var challenge = new Challenge49("uz5cIFm0hW3LtWaqEX0S/Q==", "MTIzNDU=");
+    Assertions.assertThat(challenge.answerCorrect("1234")).isFalse();
+  }
+
+  @Test
+  void pinGreaterThan99999ShouldNotSolveChallenge() {
+    var challenge = new Challenge49("uz5cIFm0hW3LtWaqEX0S/Q==", "MTIzNDU=");
+    Assertions.assertThat(challenge.answerCorrect("123456")).isFalse();
+  }
+
+  @Test
+  void pinLesserThan0ShouldNotSolveChallenge() {
+    var challenge = new Challenge49("uz5cIFm0hW3LtWaqEX0S/Q==", "MTIzNDU=");
+    Assertions.assertThat(challenge.answerCorrect("-123456")).isFalse();
+  }
+}