================================================================================ SIMULATED TLS/SSL AUDIT REPORT — FOR CTF / EDUCATIONAL USE ONLY All domains, IPs, and certificates are fictional. Report format modeled after SSLLabs / testssl.sh output. ================================================================================ ======================================================================== SERVER 1: legacy-api.acmecorp.example.com (192.0.2.10:443) Scan Date: 2026-04-07T14:32:00Z ======================================================================== Overall Grade: C Rating capped at C — TLS 1.0 and TLS 1.1 enabled Rating capped at C — weak cipher suites accepted Certificate Information: Subject: CN=legacy-api.acmecorp.example.com Issuer: CN=DigiCert SHA2 Extended Validation Server CA Serial: 0A:1B:2C:3D:4E:5F:6A:7B:8C:9D:0E:1F:2A:3B:4C:5D Valid From: 2025-06-15 00:00:00 UTC Valid Until: 2026-06-15 23:59:59 UTC Signature Alg: SHA256withRSA Key Type: RSA 2048 bit Key Usage: Digital Signature, Key Encipherment SAN: legacy-api.acmecorp.example.com OCSP Stapling: No Certificate Chain: [0] CN=legacy-api.acmecorp.example.com (2048 bit RSA) [1] CN=DigiCert SHA2 Extended Validation Server CA (2048 bit RSA) [2] CN=DigiCert Global Root CA (4096 bit RSA) Protocol Support: SSLv2 No SSLv3 No TLS 1.0 YES [VULNERABLE — POODLE, BEAST possible] TLS 1.1 YES [DEPRECATED since RFC 8996, March 2021] TLS 1.2 Yes TLS 1.3 No [NOT SUPPORTED] Cipher Suite Listing (in server preference order): TLS 1.2: TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384 256 bit (OK) TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 128 bit (OK) TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384 256 bit (WEAK — CBC mode) TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256 128 bit (WEAK — CBC mode) TLS_RSA_WITH_AES_256_GCM_SHA384 256 bit (NO PFS) TLS_RSA_WITH_AES_128_GCM_SHA256 128 bit (NO PFS) TLS_RSA_WITH_AES_256_CBC_SHA256 256 bit (WEAK — no PFS, CBC) TLS_RSA_WITH_AES_128_CBC_SHA 128 bit (WEAK — no PFS, CBC, SHA-1 MAC) TLS_RSA_WITH_3DES_EDE_CBC_SHA 112 bit (VULNERABLE — Sweet32, no PFS) TLS_RSA_WITH_RC4_128_SHA 128 bit (VULNERABLE — RC4, no PFS) TLS 1.1: TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA 256 bit (WEAK — CBC) TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA 128 bit (WEAK — CBC) TLS_RSA_WITH_AES_256_CBC_SHA 256 bit (WEAK — no PFS, CBC) TLS_RSA_WITH_3DES_EDE_CBC_SHA 112 bit (VULNERABLE — Sweet32) TLS_RSA_WITH_RC4_128_SHA 128 bit (VULNERABLE — RC4) TLS 1.0: TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA 256 bit (WEAK — CBC, BEAST) TLS_RSA_WITH_AES_256_CBC_SHA 256 bit (WEAK — no PFS, CBC, BEAST) TLS_RSA_WITH_3DES_EDE_CBC_SHA 112 bit (VULNERABLE — Sweet32, BEAST) TLS_RSA_WITH_RC4_128_SHA 128 bit (VULNERABLE — RC4) HTTP Security Headers: Strict-Transport-Security: NOT PRESENT [MISSING HSTS] X-Content-Type-Options: nosniff X-Frame-Options: DENY Vulnerabilities: BEAST (CVE-2011-3389): VULNERABLE (TLS 1.0 + CBC) Sweet32 (CVE-2016-2183): VULNERABLE (3DES cipher accepted) RC4 (CVE-2013-2566): VULNERABLE (RC4 cipher accepted) POODLE TLS: Not vulnerable Heartbleed (CVE-2014-0160): Not vulnerable ROBOT: Not vulnerable Downgrade Prevention: No (TLS_FALLBACK_SCSV not supported) ISSUES SUMMARY: [CRITICAL] RC4 cipher enabled — known broken, trivially exploitable [HIGH] 3DES cipher enabled — Sweet32 birthday attack [HIGH] TLS 1.0 enabled — deprecated, multiple known vulnerabilities [HIGH] TLS 1.1 enabled — deprecated per RFC 8996 [MEDIUM] CBC mode ciphers present — padding oracle risk [MEDIUM] Static RSA key exchange — no forward secrecy [MEDIUM] HSTS header missing — allows SSL stripping [LOW] TLS 1.3 not supported — missing modern performance/security [LOW] OCSP stapling not enabled ======================================================================== SERVER 2: portal.acmecorp.example.com (192.0.2.20:443) Scan Date: 2026-04-07T14:35:00Z ======================================================================== Overall Grade: B Rating capped at B — certificate expired Rating capped at B — HSTS header missing Certificate Information: Subject: CN=portal.acmecorp.example.com Issuer: CN=Let's Encrypt Authority X3 Serial: 03:A1:B2:C3:D4:E5:F6:07:18:29 Valid From: 2025-10-01 00:00:00 UTC Valid Until: 2025-12-30 23:59:59 UTC ** CERTIFICATE EXPIRED (99 days ago as of scan date) ** Signature Alg: SHA256withRSA Key Type: ECDSA P-256 Key Usage: Digital Signature SAN: portal.acmecorp.example.com, www.portal.acmecorp.example.com OCSP Stapling: Yes Certificate Chain: [0] CN=portal.acmecorp.example.com (256 bit ECDSA P-256) [1] CN=Let's Encrypt Authority X3 (2048 bit RSA) [2] CN=DST Root CA X3 (4096 bit RSA) ** WARNING: DST Root CA X3 expired Sept 30 2021 — some clients may reject ** Protocol Support: SSLv2 No SSLv3 No TLS 1.0 No TLS 1.1 No TLS 1.2 Yes TLS 1.3 Yes Cipher Suite Listing (in server preference order): TLS 1.3: TLS_AES_256_GCM_SHA384 256 bit (OK) TLS_CHACHA20_POLY1305_SHA256 256 bit (OK) TLS_AES_128_GCM_SHA256 128 bit (OK) TLS 1.2: TLS_ECDHE_ECDSA_WITH_AES_256_GCM_SHA384 256 bit (OK) TLS_ECDHE_ECDSA_WITH_CHACHA20_POLY1305_SHA256 256 bit (OK) TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256 128 bit (OK) TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA384 256 bit (WEAK — CBC mode) HTTP Security Headers: Strict-Transport-Security: NOT PRESENT [MISSING HSTS] X-Content-Type-Options: nosniff X-Frame-Options: SAMEORIGIN Content-Security-Policy: default-src 'self' Vulnerabilities: BEAST: Not vulnerable Sweet32: Not vulnerable RC4: Not vulnerable POODLE TLS: Not vulnerable Heartbleed: Not vulnerable ROBOT: Not vulnerable Downgrade: OK (TLS_FALLBACK_SCSV supported) ISSUES SUMMARY: [CRITICAL] Certificate expired — browsers will show security warnings [HIGH] Certificate chain includes expired root (DST Root CA X3) [MEDIUM] HSTS header missing — allows SSL stripping attacks [MEDIUM] One CBC mode cipher in TLS 1.2 list [LOW] Let's Encrypt auto-renewal appears to have failed [INFO] Consider certbot renew --force-renewal or check cron job ======================================================================== SERVER 3: api.acmecorp.example.com (192.0.2.30:443) Scan Date: 2026-04-07T14:38:00Z ======================================================================== Overall Grade: A+ No issues found — excellent configuration Certificate Information: Subject: CN=api.acmecorp.example.com Issuer: CN=Let's Encrypt Authority R3 Serial: 04:B2:C3:D4:E5:F6:07:18:29:3A Valid From: 2026-03-15 00:00:00 UTC Valid Until: 2026-06-13 23:59:59 UTC Signature Alg: SHA256withRSA (ECDSA leaf) Key Type: ECDSA P-384 Key Usage: Digital Signature SAN: api.acmecorp.example.com OCSP Stapling: Yes Certificate Transparency: Yes (2 SCTs) Certificate Chain: [0] CN=api.acmecorp.example.com (384 bit ECDSA P-384) [1] CN=R3 (2048 bit RSA, cross-signed) [2] CN=ISRG Root X1 (4096 bit RSA) Protocol Support: SSLv2 No SSLv3 No TLS 1.0 No TLS 1.1 No TLS 1.2 Yes TLS 1.3 Yes Cipher Suite Listing (in server preference order): TLS 1.3: TLS_AES_256_GCM_SHA384 256 bit (OK) TLS_CHACHA20_POLY1305_SHA256 256 bit (OK) TLS_AES_128_GCM_SHA256 128 bit (OK) TLS 1.2: TLS_ECDHE_ECDSA_WITH_AES_256_GCM_SHA384 256 bit (OK) TLS_ECDHE_ECDSA_WITH_CHACHA20_POLY1305_SHA256 256 bit (OK) TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256 128 bit (OK) HTTP Security Headers: Strict-Transport-Security: max-age=63072000; includeSubDomains; preload [OK] X-Content-Type-Options: nosniff X-Frame-Options: DENY Content-Security-Policy: default-src 'none'; script-src 'self'; connect-src 'self' Referrer-Policy: strict-origin-when-cross-origin Permissions-Policy: geolocation=(), camera=(), microphone=() Vulnerabilities: BEAST: Not vulnerable Sweet32: Not vulnerable RC4: Not vulnerable POODLE TLS: Not vulnerable Heartbleed: Not vulnerable ROBOT: Not vulnerable Downgrade: OK (TLS_FALLBACK_SCSV supported) ISSUES SUMMARY: No issues found. NOTES: - TLS 1.3 supported and preferred - Only AEAD cipher suites (GCM, ChaCha20-Poly1305) - All cipher suites provide forward secrecy (ECDHE) - HSTS with preload directive enabled - OCSP stapling active - Certificate Transparency SCTs present - ECDSA P-384 key provides strong authentication - Short-lived certificate (90-day) with automated renewal ================================================================================ CHALLENGE: For each server, identify all TLS/SSL configuration weaknesses, explain the security impact, and provide specific remediation commands or configuration changes to achieve an A+ rating. ================================================================================