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feat: S/MIME certificate support in integration tests + test env docs
Add S/MIME (emailProtection EKU) end-to-end test coverage: - ValidateCommonName() now accepts email addresses for S/MIME certs - S/MIME test profile (prof-test-smime) in seed data - Phase 11 test: issuance, EKU, KeyUsage, email SAN verification - EST config enabled in test Docker Compose - Portable KeyUsage parsing (awk, works on BSD/GNU) - Full test environment documentation (docs/test-env.md) Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>
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Shankar
+179
-6
@@ -6,14 +6,16 @@
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# Automates the full lifecycle test from docs/test-env.md:
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# 1. Bring up all 7 containers (build from source)
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# 2. Wait for every service to be healthy
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# 3. Verify pre-seeded data (agents, issuers, targets)
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# 3. Verify pre-seeded data (agents, issuers, targets, profiles)
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# 4. Issue a certificate via Local CA → deploy to NGINX → verify TLS
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# 5. Issue a certificate via ACME/Pebble → verify
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# 6. Issue a certificate via step-ca → verify
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# 7. Test revocation + CRL
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# 8. Test discovery
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# 9. Test renewal (re-issue step-ca cert, check version history)
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# 10. Print summary
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# 10. EST enrollment (RFC 7030) — cacerts + simpleenroll
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# 11. S/MIME issuance — emailProtection EKU + adaptive KeyUsage
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# 12. API spot checks + print summary
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#
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# Usage:
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# cd certctl/deploy
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@@ -383,8 +385,8 @@ fi
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# Profile
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PROFILE_RESP=$(api_get "/api/v1/profiles" 2>/dev/null || echo '{"total":0}')
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PROFILE_COUNT=$(echo "$PROFILE_RESP" | python3 -c "import sys,json; print(json.load(sys.stdin).get('total',0))" 2>/dev/null || echo 0)
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if [ "$PROFILE_COUNT" -ge 1 ]; then
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pass "Profiles: $PROFILE_COUNT found (prof-test-tls)"
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if [ "$PROFILE_COUNT" -ge 2 ]; then
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pass "Profiles: $PROFILE_COUNT found (prof-test-tls, prof-test-smime)"
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else
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fail "Profiles: expected >= 1, got $PROFILE_COUNT"
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fi
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@@ -688,9 +690,180 @@ else
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fi
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# ---------------------------------------------------------------------------
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# PHASE 10: API Spot Checks
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# PHASE 10: EST Enrollment (RFC 7030)
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# ---------------------------------------------------------------------------
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header "Phase 10: API Spot Checks"
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header "Phase 10: EST Enrollment (RFC 7030)"
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# Test cacerts endpoint — should return PKCS#7 with CA cert chain
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info "Testing EST cacerts endpoint..."
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EST_CACERTS_RESP=$(curl -sf -H "${AUTH_HEADER}" "${API_URL}/.well-known/est/cacerts" 2>/dev/null || echo "ERROR")
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if [ "$EST_CACERTS_RESP" != "ERROR" ] && [ -n "$EST_CACERTS_RESP" ]; then
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# Response should be base64-encoded PKCS#7
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if echo "$EST_CACERTS_RESP" | base64 -d >/dev/null 2>&1; then
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pass "EST cacerts returns valid base64 PKCS#7 response"
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else
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fail "EST cacerts returned non-base64 data"
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fi
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else
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fail "EST cacerts endpoint failed" "$EST_CACERTS_RESP"
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fi
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# Test csrattrs endpoint
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info "Testing EST csrattrs endpoint..."
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EST_CSRATTRS_STATUS=$(curl -sf -o /dev/null -w "%{http_code}" -H "${AUTH_HEADER}" "${API_URL}/.well-known/est/csrattrs" 2>/dev/null || echo "000")
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if [ "$EST_CSRATTRS_STATUS" = "200" ] || [ "$EST_CSRATTRS_STATUS" = "204" ]; then
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pass "EST csrattrs returns $EST_CSRATTRS_STATUS"
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else
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fail "EST csrattrs returned $EST_CSRATTRS_STATUS (expected 200 or 204)"
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fi
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# Test simpleenroll — generate CSR, POST as base64-encoded DER
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info "Testing EST simpleenroll with generated CSR..."
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EST_KEY_FILE=$(mktemp /tmp/est-key-XXXXXX.pem)
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EST_CSR_PEM_FILE=$(mktemp /tmp/est-csr-XXXXXX.pem)
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EST_CSR_DER_FILE=$(mktemp /tmp/est-csr-XXXXXX.der)
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trap "rm -f $EST_KEY_FILE $EST_CSR_PEM_FILE $EST_CSR_DER_FILE" EXIT
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# Generate ECDSA key + CSR
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openssl ecparam -genkey -name prime256v1 -noout -out "$EST_KEY_FILE" 2>/dev/null
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openssl req -new -key "$EST_KEY_FILE" -out "$EST_CSR_PEM_FILE" -subj "/CN=est-device.certctl.test" 2>/dev/null
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openssl req -in "$EST_CSR_PEM_FILE" -out "$EST_CSR_DER_FILE" -outform DER 2>/dev/null
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# base64-encode the DER CSR (EST wire format)
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EST_CSR_B64=$(base64 < "$EST_CSR_DER_FILE" | tr -d '\n')
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EST_ENROLL_RESP=$(curl -sf \
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-X POST \
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-H "${AUTH_HEADER}" \
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-H "Content-Type: application/pkcs10" \
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-d "$EST_CSR_B64" \
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"${API_URL}/.well-known/est/simpleenroll" 2>/dev/null || echo "ERROR")
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if [ "$EST_ENROLL_RESP" != "ERROR" ] && [ -n "$EST_ENROLL_RESP" ]; then
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# Response should be base64-encoded PKCS#7 containing the issued cert
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if echo "$EST_ENROLL_RESP" | base64 -d >/dev/null 2>&1; then
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pass "EST simpleenroll issued certificate via PKCS#7 response"
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else
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fail "EST simpleenroll returned non-base64 data"
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fi
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else
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fail "EST simpleenroll failed" "$(curl -s -X POST -H "${AUTH_HEADER}" -H "Content-Type: application/pkcs10" -d "$EST_CSR_B64" "${API_URL}/.well-known/est/simpleenroll" 2>&1 | head -5)"
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fi
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# Test simplereenroll (should work identically)
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info "Testing EST simplereenroll..."
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EST_REENROLL_STATUS=$(curl -sf -o /dev/null -w "%{http_code}" \
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-X POST \
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-H "${AUTH_HEADER}" \
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-H "Content-Type: application/pkcs10" \
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-d "$EST_CSR_B64" \
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"${API_URL}/.well-known/est/simplereenroll" 2>/dev/null || echo "000")
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if [ "$EST_REENROLL_STATUS" = "200" ]; then
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pass "EST simplereenroll works (status 200)"
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else
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fail "EST simplereenroll returned $EST_REENROLL_STATUS (expected 200)"
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fi
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# ---------------------------------------------------------------------------
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# PHASE 11: S/MIME Certificate Issuance
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# ---------------------------------------------------------------------------
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header "Phase 11: S/MIME Certificate Issuance"
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info "Creating S/MIME certificate record..."
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SMIME_RESP=$(api_post "/api/v1/certificates" '{
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"id": "mc-smime-test",
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"name": "smime-test-cert",
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"common_name": "testuser@certctl.test",
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"sans": ["testuser@certctl.test"],
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"issuer_id": "iss-local",
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"owner_id": "owner-test-admin",
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"team_id": "team-test-ops",
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"renewal_policy_id": "rp-default",
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"certificate_profile_id": "prof-test-smime",
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"environment": "staging"
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}' 2>/dev/null || echo "ERROR")
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if echo "$SMIME_RESP" | python3 -c "import sys,json; d=json.load(sys.stdin); assert d.get('id')=='mc-smime-test'" 2>/dev/null; then
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pass "S/MIME certificate record created"
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else
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fail "S/MIME certificate creation failed" "$SMIME_RESP"
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fi
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info "Linking S/MIME cert to target (needed for agent work routing)..."
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psql_exec "INSERT INTO certificate_target_mappings (certificate_id, target_id) VALUES ('mc-smime-test', 'target-test-nginx') ON CONFLICT DO NOTHING;"
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info "Triggering S/MIME issuance..."
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SMIME_RENEW=$(api_post "/api/v1/certificates/mc-smime-test/renew" 2>/dev/null || echo "ERROR")
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if echo "$SMIME_RENEW" | grep -q "renewal_triggered\|status"; then
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pass "S/MIME issuance triggered"
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else
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fail "S/MIME trigger failed" "$SMIME_RENEW"
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fi
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info "Waiting for S/MIME issuance (up to 120s)..."
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if wait_for_jobs_done "mc-smime-test" 120; then
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pass "S/MIME jobs completed"
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# Fetch the issued cert and verify EKU
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info "Verifying S/MIME certificate EKU..."
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SMIME_VERSIONS=$(api_get "/api/v1/certificates/mc-smime-test/versions" 2>/dev/null || echo "[]")
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SMIME_PEM=$(echo "$SMIME_VERSIONS" | python3 -c "
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import sys, json
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data = json.load(sys.stdin)
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versions = data if isinstance(data, list) else data.get('data', [])
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if versions:
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print(versions[-1].get('pem_chain', versions[-1].get('pem', '')))
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" 2>/dev/null || echo "")
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if [ -n "$SMIME_PEM" ]; then
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# Parse the cert and check for emailProtection EKU
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SMIME_EKU=$(echo "$SMIME_PEM" | openssl x509 -noout -text 2>/dev/null | grep -A2 "Extended Key Usage" || echo "")
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if echo "$SMIME_EKU" | grep -qi "emailProtection\|E-mail Protection"; then
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pass "S/MIME cert has emailProtection EKU"
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else
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fail "S/MIME cert missing emailProtection EKU" "Got: $SMIME_EKU"
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fi
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# Check KeyUsage flags (S/MIME should have Digital Signature + Content Commitment)
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SMIME_KU=$(echo "$SMIME_PEM" | openssl x509 -noout -text 2>/dev/null | awk '/X509v3 Key Usage:/{getline; print; exit}')
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if echo "$SMIME_KU" | grep -qi "Digital Signature"; then
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pass "S/MIME cert has Digital Signature KeyUsage"
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else
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fail "S/MIME cert missing Digital Signature KeyUsage" "Got: $SMIME_KU"
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fi
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# Check that email SAN is present
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SMIME_SAN=$(echo "$SMIME_PEM" | openssl x509 -noout -ext subjectAltName 2>/dev/null || echo "")
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if echo "$SMIME_SAN" | grep -qi "email:testuser@certctl.test"; then
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pass "S/MIME cert has email SAN"
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else
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# Some implementations use rfc822Name instead of email:
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if echo "$SMIME_SAN" | grep -qi "testuser@certctl.test"; then
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pass "S/MIME cert has email SAN (rfc822Name)"
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else
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skip "S/MIME email SAN not found in cert (may be in CN only)"
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echo " SAN content: $SMIME_SAN"
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fi
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fi
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else
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skip "Could not extract S/MIME cert PEM for EKU verification"
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fi
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else
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fail "S/MIME issuance did not complete within 120s"
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info "Checking S/MIME job status..."
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api_get "/api/v1/jobs" 2>/dev/null | python3 -c "
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import sys, json
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data = json.load(sys.stdin)
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for j in data.get('data', []):
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if j.get('certificate_id') == 'mc-smime-test':
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print(f\" Job {j['id']}: type={j['type']} status={j['status']} error={j.get('last_error','')}\")" 2>/dev/null || true
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fi
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# ---------------------------------------------------------------------------
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# PHASE 12: API Spot Checks
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# ---------------------------------------------------------------------------
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header "Phase 12: API Spot Checks"
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# Health
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if api_get "/health" >/dev/null 2>&1; then
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