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TLS-Lab

readme.md

title author date
Transport Layer Security (TLS) Lab
Xinyi Li
\today{}

Instruction: https://seedsecuritylabs.org/Labs_20.04/Files/Crypto_TLS/Crypto_TLS.pdf

Lab Environment

Set up 3 containers:

client: 10.9.0.5
server: 10.9.0.43
proxy: 10.9.0.143

curl https://seedsecuritylabs.org/Labs_20.04/Files/Crypto_TLS/Labsetup.zip -o Labsetup.zip
unzip Labsetup.zip
cd Labsetup
dcbuild
dcup -d

Task 1

Task 1.a

We try to create a TCP connection between our VM (not container) with https://github.com/

cd volumes
./handshake.py github.com

It gives:

After making TCP connection. Press any key to continue ...
=== Cipher used: ('TLS_AES_128_GCM_SHA256', 'TLSv1.3', 128)
=== Server hostname: github.com
=== Server certificate:
{'OCSP': ('http://ocsp.digicert.com',),
 'caIssuers': ('http://cacerts.digicert.com/DigiCertSHA2HighAssuranceServerCA.crt',),
 'crlDistributionPoints': ('http://crl3.digicert.com/sha2-ha-server-g6.crl',
                           'http://crl4.digicert.com/sha2-ha-server-g6.crl'),
 'issuer': ((('countryName', 'US'),),
            (('organizationName', 'DigiCert Inc'),),
            (('organizationalUnitName', 'www.digicert.com'),),
            (('commonName', 'DigiCert SHA2 High Assurance Server CA'),)),
 'notAfter': 'May 10 12:00:00 2022 GMT',
 'notBefore': 'May  5 00:00:00 2020 GMT',
 'serialNumber': '0557C80B282683A17B0A114493296B79',
 'subject': ((('countryName', 'US'),),
             (('stateOrProvinceName', 'California'),),
             (('localityName', 'San Francisco'),),
             (('organizationName', 'GitHub, Inc.'),),
             (('commonName', 'github.com'),)),
 'subjectAltName': (('DNS', 'github.com'), ('DNS', 'www.github.com')),
 'version': 3}
[{'issuer': ((('countryName', 'US'),),
             (('organizationName', 'DigiCert Inc'),),
             (('organizationalUnitName', 'www.digicert.com'),),
             (('commonName', 'DigiCert High Assurance EV Root CA'),)),
  'notAfter': 'Nov 10 00:00:00 2031 GMT',
  'notBefore': 'Nov 10 00:00:00 2006 GMT',
  'serialNumber': '02AC5C266A0B409B8F0B79F2AE462577',
  'subject': ((('countryName', 'US'),),
              (('organizationName', 'DigiCert Inc'),),
              (('organizationalUnitName', 'www.digicert.com'),),
              (('commonName', 'DigiCert High Assurance EV Root CA'),)),
  'version': 3}]

Reference to the SSL module documentation, /etc/ssl/certs/ specifies the location of CA certificates that are used to validate the servers' certificates.

It may be hard to keep tracing of packets in TLS handshake when running VNC server. So we can run the script in one container via dockerps and focus on the corresponding network interface:

The captured packets depict a process as:

(the figure comes from https://www.cloudflare.com/learning/ssl/what-happens-in-a-tls-handshake/)

After a 3-way TCP handshake, a TCP connection is established (Line 23), the TLS handshake happens right after it (Line 29).

A clearer illustration of TLS handshake from the seed book:

Task 1.b

After creating the TCP connection, it fails to verify server's certificate:

Traceback (most recent call last):
  File "./handshake.py", line 29, in <module>
    ssock.do_handshake()   # Start the handshake
  File "/usr/lib/python3.8/ssl.py", line 1309, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: unable to get local issuer certificate (_ssl.c:1123)

As we see before, the CA used to verify GitHub server's certificate is "DigiCert High Assurance EV Root CA", which is displayed by subject -> commonName in previous output. But DigiCert_High_Assurance_EV_Root_CA.pem is just a symbolic link to /usr/share/ca-certificates/mozilla/ folder, the actual CA is stored as /usr/share/ca-certificates/mozilla/DigiCert_High_Assurance_EV_Root_CA.crt, copy it to your ./client-certs folder.

Tips: If you are still not sure which CA on earth is accessed by the program, you can use

inotifywait -me access /usr/share/ca-certificates/mozilla/

while running unchanged handshake.py to monitor which crt is being accessed.

And we need to make a symbolic with the hash value of its common name field:

openssl x509 -in client-certs/DigiCert_High_Assurance_EV_Root_CA.crt -noout -subject_hash
# 244b5494
ln -s client-certs/DigiCert_High_Assurance_EV_Root_CA.crt client-certs/244b5494.0

Comment out Line 10 and uncomment Line 11 in handshake.py, then re-run it, it can give the same output as before now.

Task 1.c

  • Step 1: get the IP address of github.com
dig github.com

# ;; ANSWER SECTION:
# github.com.             46      IN      A       140.82.112.3

# or it may be

# ;; ANSWER SECTION:
# github.com.             46      IN      A       140.82.114.4
  • Step 2: In the client container, edit /etc/hosts to add 2 lines (using nano):
140.82.112.3 www.github2021.com
140.82.114.4 www.github2021.com
  • Step 3: Change context.check_hostname as False in handshake.py

It works like what it did in Task 1.c, but if context.check_hostname is set back as True, an error appears when verifying certificate:

Traceback (most recent call last):
  File "./handshake.py", line 29, in <module>
    ssock.do_handshake()   # Start the handshake
  File "/usr/lib/python3.8/ssl.py", line 1309, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: Hostname mismatch, certificate is not valid for 'github2021.com'. (_ssl.c:1123)

Because the hostname we request to establish the connection is not the same one specified by the server's SSL certificate.

Task 1.d

Add HTTP request based on handshake.py and then get http-client.py, run:

./http-client.py github.com

It responds a bunch of bytecodes as if we browsing its website:

[b'HTTP/1.1 200 OK',
 b'Server: GitHub.com',
 b'Date: Tue, 12 Jan 2021 03:37:40 GMT',
 b'Content-Type: text/html; charset=utf-8',
 b'Status: 200 OK',
 b'Vary: X-PJAX, Accept-Encoding, Accept, X-Requested-With',
 b'ETag: W/"a4ef97fc825350d2e7db316e6bef68f5"',
 b'Cache-Control: max-age=0, private, must-revalidate',
 b'Strict-Transport-Security: max-age=31536000; includeSubdomains; preload',
 b'X-Frame-Options: deny',
 b'X-Content-Type-Options: nosniff',
 b'X-XSS-Protection: 1; mode=block',
 b'Referrer-Policy: origin-when-cross-origin, strict-origin-when-cross-origin',
 b'expect-ct: max-age=2592000, report-uri="https://api.github.com/_private/brow'
 b'ser/errors"',
 b"Content-Security-Policy: default-src 'none'; base-uri 'self'; block-all-mixe"
 b"d-content; connect-src 'self' uploads.github.com www.githubstatus.com collec"
 b'tor.githubapp.com api.github.com github-cloud.s3.amazonaws.com github-produc'
 b'tion-repository-file-5c1aeb.s3.amazonaws.com github-production-upload-manife'
 b'st-file-7fdce7.s3.amazonaws.com github-production-user-asset-6210df.s3.amazo'
 b'naws.com cdn.optimizely.com logx.optimizely.com/v1/events wss://alive.github'
 b'.com github.githubassets.com; font-src github.githubassets.com; form-action '
 b"'self' github.com gist.github.com; frame-ancestors 'none'; frame-src render."
 b"githubusercontent.com; img-src 'self' data: github.githubassets.com identico"
 b'ns.github.com collector.githubapp.com github-cloud.s3.amazonaws.com *.github']
[b'usercontent.com customer-stories-feed.github.com spotlights-feed.github.com;'
 b" manifest-src 'self'; media-src github.githubassets.com; script-src github.g"
 b"ithubassets.com; style-src 'unsafe-inline' github.githubassets.com; worker-s"
 b'rc github.com/socket-worker-5029ae85.js gist.github.com/socket-worker-5029ae'
 b'85.js',
...
[b'tails>\n</template>\n\n    <div class="Popover js-hovercard-content positio'
 b'n-absolute" style="display: none; outline: none;" tabindex="0">\n  <div c'
 b'lass="Popover-message Popover-message--bottom-left Popover-message--large Bo'
 b'x box-shadow-large" style="width:360px;">\n  </div>\n</div>\n\n\n  </body'
 b'>\n</html>\n\n']

To request for a certain image, specify its relative path as the second argument when running this script. For example:

./http-client.py seedsecuritylabs.org assets/images/seed_labs_b.png