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Fixes #3517 - Unable to verify S/MIME mail signature signed with certificate chain.

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This commit is contained in:
Thorsten Eckel 2021-04-27 06:53:36 +00:00
parent f46b8712a1
commit 3b7909ed5c
58 changed files with 1558 additions and 1314 deletions
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2
app/models/smime_certificate.rb
View file

@ -4,7 +4,7 @@ class SMIMECertificate < ApplicationModel
validates :fingerprint, uniqueness: true validates :fingerprint, uniqueness: true
def self.parse(raw) def self.parse(raw)
OpenSSL::X509::Certificate.new(raw.gsub!(/(?:TRUSTED\s)?(CERTIFICATE---)/, '\1')) OpenSSL::X509::Certificate.new(raw.gsub(/(?:TRUSTED\s)?(CERTIFICATE---)/, '\1'))
end end
# Search for the certificate of the given sender email address # Search for the certificate of the given sender email address

73
lib/secure_mailing/smime/incoming.rb
View file

@ -103,37 +103,12 @@ class SecureMailing::SMIME::Incoming < SecureMailing::Backend::Handler
success = false success = false
comment = 'Unable to find certificate for verification' comment = 'Unable to find certificate for verification'
::SMIMECertificate.find_each do |cert|
verify_certs = []
verify_ca = OpenSSL::X509::Store.new
if cert.parsed.issuer.to_s == cert.parsed.subject.to_s result = verify_certificate_chain(p7enc.certificates)
verify_ca.add_cert(cert.parsed) if result.present?
success = true
comment = result
# CA
verify_certs = p7enc.certificates.select do |message_cert|
message_cert.issuer.to_s == cert.parsed.subject.to_s && verify_ca.verify(message_cert)
end
else
# normal
verify_certs.push(cert.parsed)
end
success = p7enc.verify(verify_certs, verify_ca, nil, OPENSSL_PKCS7_VERIFY_FLAGS)
next if !success
comment = cert.subject
if cert.expired?
comment += " (Certificate #{cert.fingerprint} with start date #{cert.not_before_at} and end date #{cert.not_after_at} expired!)"
end
break
rescue => e
success = false
comment = e.message
end
if success
@mail[:attachments].delete_if do |attachment| @mail[:attachments].delete_if do |attachment|
signed?(attachment.dig(:preferences, 'Content-Type')) signed?(attachment.dig(:preferences, 'Content-Type'))
end end
@ -145,6 +120,46 @@ class SecureMailing::SMIME::Incoming < SecureMailing::Backend::Handler
} }
end end
def verify_certificate_chain(certificates)
return if certificates.blank?
subjects = p7enc.certificates.map(&:subject).map(&:to_s)
return if subjects.blank?
existing_certs = ::SMIMECertificate.where(subject: subjects).sort_by do |certificate|
# ensure that we have the same order as the certificates in the mail
subjects.index(certificate.subject)
end
return if existing_certs.blank?
if subjects.size > existing_certs.size
Rails.logger.debug { "S/MIME mail signed with chain '#{subjects.join(', ')}' but only found '#{existing_certs.map(&:subject).join(', ')}' in database." }
end
begin
existing_certs_store = OpenSSL::X509::Store.new
existing_certs.each do |existing_cert|
existing_certs_store.add_cert(existing_cert.parsed)
end
success = p7enc.verify(p7enc.certificates, existing_certs_store, nil, OPENSSL_PKCS7_VERIFY_FLAGS)
return if !success
existing_certs.map do |existing_cert|
result = existing_cert.subject
if existing_cert.expired?
result += " (Certificate #{existing_cert.fingerprint} with start date #{existing_cert.not_before_at} and end date #{existing_cert.not_after_at} expired!)"
end
result
end.join(', ')
rescue => e
Rails.logger.error "Error while verifying mail with S/MIME certificate subjects: #{subjects}"
Rails.logger.error e
nil
end
end
def p7enc def p7enc
OpenSSL::PKCS7.read_smime(@mail[:raw]) OpenSSL::PKCS7.read_smime(@mail[:raw])
end end

22
lib/secure_mailing/smime/outgoing.rb
View file

@ -68,12 +68,32 @@ class SecureMailing::SMIME::Outgoing < SecureMailing::Backend::Handler
raise "Expired certificate for #{from} (fingerprint #{cert_model.fingerprint}) with #{cert_model.not_before_at} to #{cert_model.not_after_at}" if !@security[:sign][:allow_expired] && cert_model.expired? raise "Expired certificate for #{from} (fingerprint #{cert_model.fingerprint}) with #{cert_model.not_before_at} to #{cert_model.not_after_at}" if !@security[:sign][:allow_expired] && cert_model.expired?
private_key = OpenSSL::PKey::RSA.new(cert_model.private_key, cert_model.private_key_secret) private_key = OpenSSL::PKey::RSA.new(cert_model.private_key, cert_model.private_key_secret)
OpenSSL::PKCS7.write_smime(OpenSSL::PKCS7.sign(cert_model.parsed, private_key, @mail.encoded, [], OpenSSL::PKCS7::DETACHED))
OpenSSL::PKCS7.write_smime(OpenSSL::PKCS7.sign(cert_model.parsed, private_key, @mail.encoded, chain(cert_model), OpenSSL::PKCS7::DETACHED))
rescue => e rescue => e
log('sign', 'failed', e.message) log('sign', 'failed', e.message)
raise raise
end end
def chain(cert)
lookup_issuer = cert.parsed.issuer.to_s
result = []
loop do
found_cert = SMIMECertificate.find_by(subject: lookup_issuer)
break if found_cert.blank?
subject = found_cert.parsed.subject.to_s
lookup_issuer = found_cert.parsed.issuer.to_s
result.push(found_cert.parsed)
# we've reached the root CA
break if subject == lookup_issuer
end
result
end
def encrypt(data) def encrypt(data)
certificates = SMIMECertificate.for_recipipent_email_addresses!(@mail.to) certificates = SMIMECertificate.for_recipipent_email_addresses!(@mail.to)
expired_cert = certificates.detect(&:expired?) expired_cert = certificates.detect(&:expired?)

74
spec/fixtures/smime/CaseInsenstive@eXample.COM.crt vendored
View file

@ -1,37 +1,41 @@
-----BEGIN TRUSTED CERTIFICATE----- -----BEGIN TRUSTED CERTIFICATE-----
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-----END TRUSTED CERTIFICATE----- -----END TRUSTED CERTIFICATE-----

46
spec/fixtures/smime/CaseInsenstive@eXample.COM.csr vendored
View file

@ -3,27 +3,27 @@ MIIE6TCCAtECAQAwgaMxKTAnBgkqhkiG9w0BCQEWGkNhc2VJbnNlbnN0aXZlQGVY
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-----END CERTIFICATE REQUEST----- -----END CERTIFICATE REQUEST-----

100
spec/fixtures/smime/CaseInsenstive@eXample.COM.key vendored
View file

@ -1,54 +1,54 @@
-----BEGIN RSA PRIVATE KEY----- -----BEGIN RSA PRIVATE KEY-----
Proc-Type: 4,ENCRYPTED Proc-Type: 4,ENCRYPTED
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-----END RSA PRIVATE KEY----- -----END RSA PRIVATE KEY-----

33
spec/fixtures/smime/ChainCA.crt vendored Normal file
View file

@ -0,0 +1,33 @@
-----BEGIN CERTIFICATE-----
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-----END CERTIFICATE-----

29
spec/fixtures/smime/ChainCA.csr vendored Normal file
View file

@ -0,0 +1,29 @@
-----BEGIN CERTIFICATE REQUEST-----
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-----END CERTIFICATE REQUEST-----

52
spec/fixtures/smime/ChainCA.key vendored Normal file
View file

@ -0,0 +1,52 @@
-----BEGIN PRIVATE KEY-----
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A8mKpH1ViikQLES3ejd1cSahAsM63vY=
-----END PRIVATE KEY-----

0
spec/fixtures/smime/ca.secret → spec/fixtures/smime/ChainCA.secret vendored
View file

35
spec/fixtures/smime/ExpiredCA.crt vendored Normal file
View file

@ -0,0 +1,35 @@
-----BEGIN CERTIFICATE-----
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-----END CERTIFICATE-----

54
spec/fixtures/smime/ExpiredCA.key vendored Normal file
View file

@ -0,0 +1,54 @@
-----BEGIN RSA PRIVATE KEY-----
Proc-Type: 4,ENCRYPTED
DEK-Info: AES-256-CBC,E208BBCB8457D2F4E25DFD3C951FC0B6
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-----END RSA PRIVATE KEY-----

0
spec/fixtures/smime/expiredca.secret → spec/fixtures/smime/ExpiredCA.secret vendored
View file

33
spec/fixtures/smime/IntermediateCA.crt vendored Normal file
View file

@ -0,0 +1,33 @@
-----BEGIN CERTIFICATE-----
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-----END CERTIFICATE-----

29
spec/fixtures/smime/IntermediateCA.csr vendored Normal file
View file

@ -0,0 +1,29 @@
-----BEGIN CERTIFICATE REQUEST-----
MIIE6TCCAtECAQAwgaMxKTAnBgkqhkiG9w0BCQEWGkludGVybWVkaWF0ZUNBQGV4
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0w5OwMlyv1ATW1qZwQ==
-----END CERTIFICATE REQUEST-----

52
spec/fixtures/smime/IntermediateCA.key vendored Normal file
View file

@ -0,0 +1,52 @@
-----BEGIN PRIVATE KEY-----
MIIJQwIBADANBgkqhkiG9w0BAQEFAASCCS0wggkpAgEAAoICAQDr+WGVKcNrmkFK
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-----END PRIVATE KEY-----

0
spec/fixtures/smime/oldca.secret → spec/fixtures/smime/IntermediateCA.secret vendored
View file

33
spec/fixtures/smime/RootCA.crt vendored Normal file
View file

@ -0,0 +1,33 @@
-----BEGIN CERTIFICATE-----
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-----END CERTIFICATE-----

29
spec/fixtures/smime/RootCA.csr vendored Normal file
View file

@ -0,0 +1,29 @@
-----BEGIN CERTIFICATE REQUEST-----
MIIE4TCCAskCAQAwgZsxITAfBgkqhkiG9w0BCQEWElJvb3RDQUBleGFtcGxlLmNv
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UT9Sjf4=
-----END CERTIFICATE REQUEST-----

52
spec/fixtures/smime/RootCA.key vendored Normal file
View file

@ -0,0 +1,52 @@
-----BEGIN PRIVATE KEY-----
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PQwd/hbN0F+pQpHsVggB2wouMKuy6/RbziBn0eTtVZQunAkSEmI9wbZcF6weLe6k
cL9jIlq+muOhs5draqSl1v4E4j8NPhyD+i5OnRvucrICkNdhWHOjHr9UPJlSIz2+
1i7GMV59kZhtSQKCAQEA1uvu6pjX3AjpRU7t4s3+bmb/8N7np8vhfBtoZrjcD/Gi
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pdmf01BoUcxrPNvg/DWga8Tb4TMUQnhIfM9C0sd9FfdBMg6xU5aX/coZPWwdY5ra
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1wRp+cCK4/ePWQtU1AZkNTabwAIv0wLO3apP2vzXlDSKYNSgS23h6ToPgagshaJ9
ponhAoIBAQDMiNJGau2Y/4I2Qghcv1ASjbEfDherJG6sL/z69i76zKNsI42wk+FB
NthpTvDL++zr8Xu1M908n6XLrjWfYht7YW1wpqdiMjw8sdl0rzBd3GB6KW6NpU8n
cDCWUbAV8CtAK+jna0HwleJEirLxor+gvLnnaDkPsF/V0ZqTOhyaZ2hOnmJDZ3hn
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xOEBTn5IZ8IXNJJQ7ruEQOFIimNKzM2Tb/8z9j5W50Smew3f0/fkq83Jmz+r86eB
PTKtWs0t9xNWUUy4YE4MDlsk7fHnWlMc
-----END PRIVATE KEY-----

0
spec/fixtures/smime/oldsmime1@example.com.secret → spec/fixtures/smime/RootCA.secret vendored
View file

35
spec/fixtures/smime/ca.crt vendored
View file

@ -1,35 +0,0 @@
-----BEGIN CERTIFICATE-----
MIIGEzCCA/ugAwIBAgIUdRCemO0RlIZ2tZTwO/1W2eeR/eEwDQYJKoZIhvcNAQEL
BQAwgZcxHTAbBgkqhkiG9w0BCQEWDmNhQGV4YW1wbGUuY29tMQswCQYDVQQGEwJE
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FglHwSJZSR2WTTsmd6f/9grOUVNt51I=
-----END CERTIFICATE-----

54
spec/fixtures/smime/ca.key vendored
View file

@ -1,54 +0,0 @@
-----BEGIN RSA PRIVATE KEY-----
Proc-Type: 4,ENCRYPTED
DEK-Info: AES-256-CBC,C883629DF6D2EB2F339DA0E9DDE3A287
k8zGHkcIbwXp/99xhnmtvtmZQW6Q9lxEB0cjAgUdC9llRRBFnEF+0WdRsY47iBs5
V8pcjT05/JN4v3rKoT5Lg2C1/HpNfseknVVw7i9tSV1Votc/GxwnRHR9j1g3aIVG
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v/4ema8SpALdMqyQG9pmMWajNpD3eRm6wIAhV1Qpcj+0a+QJTHGQPsDMaGfWVaW5
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-----END RSA PRIVATE KEY-----

40
spec/fixtures/smime/chain@example.com.crt vendored Normal file
View file

@ -0,0 +1,40 @@
-----BEGIN TRUSTED CERTIFICATE-----
MIIG9TCCBN2gAwIBAgIUDN6Q7JHXQC5XC42FyT6Pbps9744wDQYJKoZIhvcNAQEL
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-----END TRUSTED CERTIFICATE-----

29
spec/fixtures/smime/chain@example.com.csr vendored Normal file
View file

@ -0,0 +1,29 @@
-----BEGIN CERTIFICATE REQUEST-----
MIIE4DCCAsgCAQAwgZoxIDAeBgkqhkiG9w0BCQEWEWNoYWluQGV4YW1wbGUuY29t
MQswCQYDVQQGEwJERTEPMA0GA1UECAwGQmVybGluMQ8wDQYDVQQHDAZCZXJsaW4x
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IOo2jg==
-----END CERTIFICATE REQUEST-----

54
spec/fixtures/smime/chain@example.com.key vendored Normal file
View file

@ -0,0 +1,54 @@
-----BEGIN RSA PRIVATE KEY-----
Proc-Type: 4,ENCRYPTED
DEK-Info: AES-256-CBC,0B9AC9B9AFF482B0D6EE33EBB73F70E8
3NmSikaeg2LJxGSjQH9hFQ8+DsXPow3zi3HZdC/p/0u8KUDBvcQxEWE1r8MiKgEg
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c345tkaCn7m9AlYwGpm516jkuuzJvCe9tiBh3OVIKhGvrG7EfN43yjocYRVk65E7
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5lAEXR9hJmKpczs3XN+ZoWy2liUbnljVdSr/LhB6Pktpz7ryWbgMxE4iehicTym/
-----END RSA PRIVATE KEY-----

0
spec/fixtures/smime/oldsmime2@example.com.secret → spec/fixtures/smime/chain@example.com.secret vendored
View file

35
spec/fixtures/smime/expiredca.crt vendored
View file

@ -1,35 +0,0 @@
-----BEGIN CERTIFICATE-----
MIIGHzCCBAegAwIBAgIUYIratodSaS58JtEjE1cPRBaOADcwDQYJKoZIhvcNAQEL
BQAwgZ4xJDAiBgkqhkiG9w0BCQEWFWV4cGlyZWRjYUBleGFtcGxlLmNvbTELMAkG
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NkiZz+lwHxJ8b6Tm9xITXQdyMa/6jUOgYECu9RJO4qd38sg=
-----END CERTIFICATE-----

54
spec/fixtures/smime/expiredca.key vendored
View file

@ -1,54 +0,0 @@
-----BEGIN RSA PRIVATE KEY-----
Proc-Type: 4,ENCRYPTED
DEK-Info: AES-256-CBC,AFFF2A7AF6117991109A4B9D75D38008
tJc+dKbzF4ptKQWjrfnUsIa0Ihb44cVYtEQ63ouhN13xVNFSx0N0bBl4TehPo3c5
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-----END RSA PRIVATE KEY-----

58
spec/fixtures/smime/expiredsmime1@example.com.crt vendored
View file

@ -1,37 +1,37 @@
-----BEGIN TRUSTED CERTIFICATE----- -----BEGIN TRUSTED CERTIFICATE-----
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-----END TRUSTED CERTIFICATE----- -----END TRUSTED CERTIFICATE-----

46
spec/fixtures/smime/expiredsmime1@example.com.csr vendored
View file

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-----END CERTIFICATE REQUEST----- -----END CERTIFICATE REQUEST-----

100
spec/fixtures/smime/expiredsmime1@example.com.key vendored
View file

@ -1,54 +1,54 @@
-----BEGIN RSA PRIVATE KEY----- -----BEGIN RSA PRIVATE KEY-----
Proc-Type: 4,ENCRYPTED Proc-Type: 4,ENCRYPTED
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-----END RSA PRIVATE KEY----- -----END RSA PRIVATE KEY-----

58
spec/fixtures/smime/expiredsmime2@example.com.crt vendored
View file

@ -1,37 +1,37 @@
-----BEGIN TRUSTED CERTIFICATE----- -----BEGIN TRUSTED CERTIFICATE-----
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-----END TRUSTED CERTIFICATE----- -----END TRUSTED CERTIFICATE-----

46
spec/fixtures/smime/expiredsmime2@example.com.csr vendored
View file

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-----END CERTIFICATE REQUEST----- -----END CERTIFICATE REQUEST-----

100
spec/fixtures/smime/expiredsmime2@example.com.key vendored
View file

@ -1,54 +1,54 @@
-----BEGIN RSA PRIVATE KEY----- -----BEGIN RSA PRIVATE KEY-----
Proc-Type: 4,ENCRYPTED Proc-Type: 4,ENCRYPTED
DEK-Info: AES-256-CBC,2D01520A669DCCAAC31310846FD3F95A DEK-Info: AES-256-CBC,B118997405683349F559112BE9480FA1
uVTH48B5k3TxkQgfo3lXllNxXLICC5UZXv6znRxk35fJD7PnDpeOMDijlW7S4+gi ibWsDvn+kHOwTjIL/A8dpQxOm1hzjMQ1C3x/TR9hWx5+iSgfNi0NUdUbaF5CnJcA
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CpGrAV1cdul64nR/+yUFdOuvz8jnHMD5sRCGagn2cAsOlOD6D54HSPzTnxLaFh7/ tUofNawWst00c8d2eKllm+kPcjGPstbTaMMag/3Sh4kzWRYaOVbTxLFyYm4VDXj1
5S8JYxfmkh/ddiIiC/RvaSgK8VCRhu4jwu3m9h1eJSZEepkMwZxPP7q6HN0pBt8V JvtmxzDvGagMkDes7337j/AdoOAL0T+HnJpsk9vZrCVh7yQQhDoqHvKjPk/qGKBU
6y5aidJ/b5Zcfu2fsxiDQKUR0w5wMm1Xx6/zOoJN4uzngYqkSjxaZtNDJHB3Tt1P XZqK1Ue7mSvk7QVAh/7cTZ+gDQMzSC+PHZYNfBXlRjQtvIx8yd/pibT4qGVO5ukM
-----END RSA PRIVATE KEY----- -----END RSA PRIVATE KEY-----

98
spec/fixtures/smime/generate/docker-entrypoint.sh vendored
View file

@ -2,16 +2,40 @@
echo "Zammad S/MIME test certificate generation" echo "Zammad S/MIME test certificate generation"
if [[ ! -e "$CERT_DIR/ca.key" ]] || [[ ! -e "$CERT_DIR/ca.crt" ]] if [[ ! -e "$CERT_DIR/RootCA.key" ]] || [[ ! -e "$CERT_DIR/RootCA.crt" ]]
then then
echo "Generating ca.key" echo "Generating RootCA.key and RootCA.csr"
openssl genrsa -aes256 -passout file:pass.secret -out $CERT_DIR/ca.key 4096 openssl req -new -newkey rsa:4096 -nodes -out $CERT_DIR/RootCA.csr -keyout $CERT_DIR/RootCA.key -extensions v3_ca -subj "/emailAddress=RootCA@example.com/C=DE/ST=Berlin/L=Berlin/O=Example Security/OU=IT Department/CN=example.com"
echo "Generating ca.crt" echo "Generating RootCA.crt"
openssl req -new -x509 -days 73000 -key $CERT_DIR/ca.key -passin file:pass.secret -out $CERT_DIR/ca.crt -subj "/emailAddress=ca@example.com/C=DE/ST=Berlin/L=Berlin/O=Example Security/OU=IT Department/CN=example.com" openssl x509 -signkey $CERT_DIR/RootCA.key -days 73000 -req -in $CERT_DIR/RootCA.csr -set_serial 01 -out $CERT_DIR/RootCA.crt
echo "Generating ca.secret" echo "Generating RootCA.secret"
cp pass.secret $CERT_DIR/ca.secret cp pass.secret $CERT_DIR/RootCA.secret
fi
if [[ ! -e "$CERT_DIR/IntermediateCA.key" ]] || [[ ! -e "$CERT_DIR/IntermediateCA.crt" ]]
then
echo "Generating IntermediateCA.key and IntermediateCA.csr"
openssl req -new -newkey rsa:4096 -nodes -out $CERT_DIR/IntermediateCA.csr -keyout $CERT_DIR/IntermediateCA.key -subj "/emailAddress=IntermediateCA@example.com/C=DE/ST=Berlin/L=Berlin/O=Example Security/OU=IT Department/CN=example.com"
echo "Generating IntermediateCA.crt"
openssl x509 -CA $CERT_DIR/RootCA.crt -CAkey $CERT_DIR/RootCA.key -passin file:pass.secret -days 73000 -req -in $CERT_DIR/IntermediateCA.csr -set_serial 02 -out $CERT_DIR/IntermediateCA.crt
echo "Generating IntermediateCA.secret"
cp pass.secret $CERT_DIR/IntermediateCA.secret
fi
if [[ ! -e "$CERT_DIR/ChainCA.key" ]] || [[ ! -e "$CERT_DIR/ChainCA.crt" ]]
then
echo "Generating ChainCA.key and ChainCA.csr"
openssl req -new -newkey rsa:4096 -nodes -out $CERT_DIR/ChainCA.csr -keyout $CERT_DIR/ChainCA.key -subj "/emailAddress=ChainCA@example.com/C=DE/ST=Berlin/L=Berlin/O=Example Security/OU=IT Department/CN=example.com"
echo "Generating ChainCA.crt"
openssl x509 -CA $CERT_DIR/IntermediateCA.crt -CAkey $CERT_DIR/IntermediateCA.key -passin file:pass.secret -days 73000 -req -in $CERT_DIR/ChainCA.csr -set_serial 03 -out $CERT_DIR/ChainCA.crt
echo "Generating ChainCA.secret"
cp pass.secret $CERT_DIR/ChainCA.secret
fi fi
for EMAIL_ADDRESS in smime1@example.com smime2@example.com smime3@example.com smimedouble@example.com CaseInsenstive@eXample.COM for EMAIL_ADDRESS in smime1@example.com smime2@example.com smime3@example.com smimedouble@example.com CaseInsenstive@eXample.COM
@ -37,14 +61,14 @@ do
openssl x509 -req \ openssl x509 -req \
-days 73000 \ -days 73000 \
-in $CERT_DIR/$EMAIL_ADDRESS.csr \ -in $CERT_DIR/$EMAIL_ADDRESS.csr \
-CA $CERT_DIR/ca.crt \ -CA $CERT_DIR/RootCA.crt \
-CAkey $CERT_DIR/ca.key \ -CAkey $CERT_DIR/RootCA.key \
-out $CERT_DIR/$EMAIL_ADDRESS.crt \ -out $CERT_DIR/$EMAIL_ADDRESS.crt \
-addtrust emailProtection \ -addtrust emailProtection \
-addreject clientAuth \ -addreject clientAuth \
-addreject serverAuth \ -addreject serverAuth \
-trustout \ -trustout \
-CAcreateserial -CAserial /tmp/ca.seq \ -CAcreateserial -CAserial /tmp/RootCA.seq \
-extensions smime \ -extensions smime \
-extfile "$extfile" \ -extfile "$extfile" \
-passin file:pass.secret -passin file:pass.secret
@ -54,19 +78,53 @@ do
fi fi
done done
echo "Generating from CA chain"
for EMAIL_ADDRESS in chain@example.com
do
if [[ ! -e "$CERT_DIR/$EMAIL_ADDRESS.crt" ]]
then
echo "Generating $EMAIL_ADDRESS.key"
openssl genrsa -aes256 -passout file:pass.secret -out $CERT_DIR/$EMAIL_ADDRESS.key 4096
echo "Generating $EMAIL_ADDRESS.csr (certificate signing request)"
openssl req -new -key $CERT_DIR/$EMAIL_ADDRESS.key -passin file:pass.secret -out $CERT_DIR/$EMAIL_ADDRESS.csr -subj "/emailAddress=$EMAIL_ADDRESS/C=DE/ST=Berlin/L=Berlin/O=Example Security/OU=IT Department/CN=example.com"
echo "Generating $EMAIL_ADDRESS.crt (certificate)"
openssl x509 -req \
-days 73000 \
-in $CERT_DIR/$EMAIL_ADDRESS.csr \
-CA $CERT_DIR/ChainCA.crt \
-CAkey $CERT_DIR/ChainCA.key \
-out $CERT_DIR/$EMAIL_ADDRESS.crt \
-addtrust emailProtection \
-addreject clientAuth \
-addreject serverAuth \
-trustout \
-CAcreateserial -CAserial /tmp/ChainCA.seq \
-extensions smime \
-extfile "config.cnf" \
-passin file:pass.secret
echo "Generating $EMAIL_ADDRESS.secret"
cp pass.secret $CERT_DIR/$EMAIL_ADDRESS.secret
fi
done
echo "Generating expired" echo "Generating expired"
FAKETIME=-10y date FAKETIME=-10y date
if [[ ! -e "$CERT_DIR/expiredca.key" ]] || [[ ! -e "$CERT_DIR/expiredca.crt" ]] if [[ ! -e "$CERT_DIR/ExpiredCA.key" ]] || [[ ! -e "$CERT_DIR/ExpiredCA.crt" ]]
then then
echo "Generating expiredca.key" echo "Generating ExpiredCA.key"
FAKETIME=-10y openssl genrsa -aes256 -passout file:pass.secret -out $CERT_DIR/expiredca.key 4096 FAKETIME=-10y openssl genrsa -aes256 -passout file:pass.secret -out $CERT_DIR/ExpiredCA.key 4096
echo "Generating expiredca.crt" echo "Generating ExpiredCA.crt"
FAKETIME=-10y openssl req -new -x509 -days 1 -key $CERT_DIR/expiredca.key -passin file:pass.secret -out $CERT_DIR/expiredca.crt -subj "/emailAddress=expiredca@example.com/C=DE/ST=Berlin/L=Berlin/O=Example Security/OU=IT Department/CN=example.com" FAKETIME=-10y openssl req -new -x509 -days 1 -key $CERT_DIR/ExpiredCA.key -passin file:pass.secret -out $CERT_DIR/ExpiredCA.crt -subj "/emailAddress=ExpiredCA@example.com/C=DE/ST=Berlin/L=Berlin/O=Example Security/OU=IT Department/CN=example.com"
echo "Generating expiredca.secret" echo "Generating ExpiredCA.secret"
cp pass.secret $CERT_DIR/expiredca.secret cp pass.secret $CERT_DIR/ExpiredCA.secret
fi fi
for EMAIL_ADDRESS in expiredsmime1@example.com expiredsmime2@example.com for EMAIL_ADDRESS in expiredsmime1@example.com expiredsmime2@example.com
@ -83,14 +141,14 @@ do
FAKETIME=-10y openssl x509 -req \ FAKETIME=-10y openssl x509 -req \
-days 1 \ -days 1 \
-in $CERT_DIR/$EMAIL_ADDRESS.csr \ -in $CERT_DIR/$EMAIL_ADDRESS.csr \
-CA $CERT_DIR/expiredca.crt \ -CA $CERT_DIR/ExpiredCA.crt \
-CAkey $CERT_DIR/expiredca.key \ -CAkey $CERT_DIR/ExpiredCA.key \
-out $CERT_DIR/$EMAIL_ADDRESS.crt \ -out $CERT_DIR/$EMAIL_ADDRESS.crt \
-addtrust emailProtection \ -addtrust emailProtection \
-addreject clientAuth \ -addreject clientAuth \
-addreject serverAuth \ -addreject serverAuth \
-trustout \ -trustout \
-CAcreateserial -CAserial /tmp/expiredca.seq \ -CAcreateserial -CAserial /tmp/ExpiredCA.seq \
-extensions smime \ -extensions smime \
-extfile config.cnf \ -extfile config.cnf \
-passin file:pass.secret -passin file:pass.secret

35
spec/fixtures/smime/oldca.crt vendored
View file

@ -1,35 +0,0 @@
-----BEGIN CERTIFICATE-----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8c1mJgWpM0EAmsUKjGvE3swfKDtSOPndr6vo
-----END CERTIFICATE-----

54
spec/fixtures/smime/oldca.key vendored
View file

@ -1,54 +0,0 @@
-----BEGIN RSA PRIVATE KEY-----
Proc-Type: 4,ENCRYPTED
DEK-Info: AES-256-CBC,1B90035BC983D129D9910AA0D912DDE2
WhX+qKY6nc6SGhUBYsxQtju7rzg/DdV1YCWoj0eydeIVYQyDPua8HzkSPCVBX++Y
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130LA0N/HHthJKCZeNLsUQY8J6M3kUXVuOw8cb6cCLuVkT8WIgropcJCXhy8chha
-----END RSA PRIVATE KEY-----

37
spec/fixtures/smime/oldsmime1@example.com.crt vendored
View file

@ -1,37 +0,0 @@
-----BEGIN TRUSTED CERTIFICATE-----
MIIGWzCCBEOgAwIBAgIUIUrCfVRV1i03o1zHmhtNv8XMpBQwDQYJKoZIhvcNAQEL
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-----END TRUSTED CERTIFICATE-----

29
spec/fixtures/smime/oldsmime1@example.com.csr vendored
View file

@ -1,29 +0,0 @@
-----BEGIN CERTIFICATE REQUEST-----
MIIE5DCCAswCAQAwgZ4xJDAiBgkqhkiG9w0BCQEWFW9sZHNtaW1lMUBleGFtcGxl
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iJZ6c2DEnLU=
-----END CERTIFICATE REQUEST-----

54
spec/fixtures/smime/oldsmime1@example.com.key vendored
View file

@ -1,54 +0,0 @@
-----BEGIN RSA PRIVATE KEY-----
Proc-Type: 4,ENCRYPTED
DEK-Info: AES-256-CBC,075058C49FC97E93DC2A6598E450A08C
xskKR5EEormOQAsY17yBq+yojFhO8awIeNtLILVj5fElywccYSasmh3GzMCr+v8G
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-----END RSA PRIVATE KEY-----

37
spec/fixtures/smime/oldsmime2@example.com.crt vendored
View file

@ -1,37 +0,0 @@
-----BEGIN TRUSTED CERTIFICATE-----
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-----END TRUSTED CERTIFICATE-----

29
spec/fixtures/smime/oldsmime2@example.com.csr vendored
View file

@ -1,29 +0,0 @@
-----BEGIN CERTIFICATE REQUEST-----
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-----END CERTIFICATE REQUEST-----

54
spec/fixtures/smime/oldsmime2@example.com.key vendored
View file

@ -1,54 +0,0 @@
-----BEGIN RSA PRIVATE KEY-----
Proc-Type: 4,ENCRYPTED
DEK-Info: AES-256-CBC,422646293BBDFBBD651E2D08160A9FE1
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-----END RSA PRIVATE KEY-----

73
spec/fixtures/smime/smime1@example.com.crt vendored
View file

@ -1,37 +1,40 @@
-----BEGIN TRUSTED CERTIFICATE----- -----BEGIN TRUSTED CERTIFICATE-----
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-----END TRUSTED CERTIFICATE----- -----END TRUSTED CERTIFICATE-----

46
spec/fixtures/smime/smime1@example.com.csr vendored
View file

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-----END CERTIFICATE REQUEST----- -----END CERTIFICATE REQUEST-----

100
spec/fixtures/smime/smime1@example.com.key vendored
View file

@ -1,54 +1,54 @@
-----BEGIN RSA PRIVATE KEY----- -----BEGIN RSA PRIVATE KEY-----
Proc-Type: 4,ENCRYPTED Proc-Type: 4,ENCRYPTED
DEK-Info: AES-256-CBC,C02E7FD1CD5C829F69D753D19B84384A DEK-Info: AES-256-CBC,19EB1017C1E4A6824D8287E4F87D570A
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-----END RSA PRIVATE KEY----- -----END RSA PRIVATE KEY-----

73
spec/fixtures/smime/smime2@example.com.crt vendored
View file

@ -1,37 +1,40 @@
-----BEGIN TRUSTED CERTIFICATE----- -----BEGIN TRUSTED CERTIFICATE-----
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-----END TRUSTED CERTIFICATE----- -----END TRUSTED CERTIFICATE-----

46
spec/fixtures/smime/smime2@example.com.csr vendored
View file

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-----END CERTIFICATE REQUEST----- -----END CERTIFICATE REQUEST-----

100
spec/fixtures/smime/smime2@example.com.key vendored
View file

@ -1,54 +1,54 @@
-----BEGIN RSA PRIVATE KEY----- -----BEGIN RSA PRIVATE KEY-----
Proc-Type: 4,ENCRYPTED Proc-Type: 4,ENCRYPTED
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-----END RSA PRIVATE KEY----- -----END RSA PRIVATE KEY-----

73
spec/fixtures/smime/smime3@example.com.crt vendored
View file

@ -1,37 +1,40 @@
-----BEGIN TRUSTED CERTIFICATE----- -----BEGIN TRUSTED CERTIFICATE-----
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-----END TRUSTED CERTIFICATE----- -----END TRUSTED CERTIFICATE-----

46
spec/fixtures/smime/smime3@example.com.csr vendored
View file

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-----END CERTIFICATE REQUEST----- -----END CERTIFICATE REQUEST-----

100
spec/fixtures/smime/smime3@example.com.key vendored
View file

@ -1,54 +1,54 @@
-----BEGIN RSA PRIVATE KEY----- -----BEGIN RSA PRIVATE KEY-----
Proc-Type: 4,ENCRYPTED Proc-Type: 4,ENCRYPTED
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-----END RSA PRIVATE KEY----- -----END RSA PRIVATE KEY-----

77
spec/fixtures/smime/smimedouble@example.com.crt vendored
View file

@ -1,39 +1,42 @@
-----BEGIN TRUSTED CERTIFICATE----- -----BEGIN TRUSTED CERTIFICATE-----
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-----END TRUSTED CERTIFICATE----- -----END TRUSTED CERTIFICATE-----

46
spec/fixtures/smime/smimedouble@example.com.csr vendored
View file

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-----END CERTIFICATE REQUEST----- -----END CERTIFICATE REQUEST-----

100
spec/fixtures/smime/smimedouble@example.com.key vendored
View file

@ -1,54 +1,54 @@
-----BEGIN RSA PRIVATE KEY----- -----BEGIN RSA PRIVATE KEY-----
Proc-Type: 4,ENCRYPTED Proc-Type: 4,ENCRYPTED
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-----END RSA PRIVATE KEY----- -----END RSA PRIVATE KEY-----

104
spec/lib/secure_mailing/smime_spec.rb
View file

@ -15,7 +15,7 @@ RSpec.describe SecureMailing::SMIME do
let(:expired_email_address) { 'expiredsmime1@example.com' } let(:expired_email_address) { 'expiredsmime1@example.com' }
let(:ca_certificate_subject) { '/emailAddress=ca@example.com/C=DE/ST=Berlin/L=Berlin/O=Example Security/OU=IT Department/CN=example.com' } let(:ca_certificate_subject) { '/emailAddress=RootCA@example.com/C=DE/ST=Berlin/L=Berlin/O=Example Security/OU=IT Department/CN=example.com' }
let(:content_type) { 'text/plain' } let(:content_type) { 'text/plain' }
@ -74,7 +74,7 @@ RSpec.describe SecureMailing::SMIME do
context 'private key present' do context 'private key present' do
before do let!(:sender_certificate) do
create(:smime_certificate, :with_private, fixture: system_email_address) create(:smime_certificate, :with_private, fixture: system_email_address)
end end
@ -123,6 +123,29 @@ RSpec.describe SecureMailing::SMIME do
end end
end end
end end
context 'when certificate chain is present' do
let(:system_email_address) { 'chain@example.com' }
let!(:chain) do
[
sender_certificate,
create(:smime_certificate, fixture: 'ChainCA'),
create(:smime_certificate, fixture: 'IntermediateCA'),
create(:smime_certificate, fixture: 'RootCA'),
]
end
let(:p7enc) do
mail = Channel::EmailParser.new.parse(build_mail.to_s)
OpenSSL::PKCS7.read_smime(mail[:raw])
end
it 'is included in the generated mail' do
expect(p7enc.certificates).to eq(chain.map(&:parsed))
end
end
end end
context 'no private key present' do context 'no private key present' do
@ -308,7 +331,7 @@ RSpec.describe SecureMailing::SMIME do
context 'CA' do context 'CA' do
let(:not_related_fixture) { 'expiredca' } let(:not_related_fixture) { 'ExpiredCA' }
it 'fails' do it 'fails' do
expect(mail[:body]).to include(raw_body) expect(mail[:body]).to include(raw_body)
@ -323,17 +346,16 @@ RSpec.describe SecureMailing::SMIME do
end end
context 'usage not prevented' do context 'usage not prevented' do
let(:not_related_certificate_subject) { "/emailAddress=#{not_related_fixture}/C=DE/ST=Berlin/L=Berlin/O=Example Security/OU=IT Department/CN=example.com" }
before do before do
# remove OpenSSL::PKCS7::NOINTERN # remove OpenSSL::PKCS7::NOINTERN
stub_const('SecureMailing::SMIME::Incoming::OPENSSL_PKCS7_VERIFY_FLAGS', OpenSSL::PKCS7::NOVERIFY) stub_const('SecureMailing::SMIME::Incoming::OPENSSL_PKCS7_VERIFY_FLAGS', OpenSSL::PKCS7::NOVERIFY)
end end
it 'wrongly performs a verification' do it "won't perform verification" do
expect(mail[:body]).to include(raw_body) expect(mail[:body]).to include(raw_body)
expect(mail['x-zammad-article-preferences'][:security][:sign][:success]).to be true expect(mail['x-zammad-article-preferences'][:security][:sign][:success]).to be false
expect(mail['x-zammad-article-preferences'][:security][:sign][:comment]).to eq(not_related_certificate_subject) expect(mail['x-zammad-article-preferences'][:security][:sign][:comment]).to eq('Unable to find certificate for verification')
expect(mail['x-zammad-article-preferences'][:security][:encryption][:success]).to be false expect(mail['x-zammad-article-preferences'][:security][:encryption][:success]).to be false
expect(mail['x-zammad-article-preferences'][:security][:encryption][:comment]).to be nil expect(mail['x-zammad-article-preferences'][:security][:encryption][:comment]).to be nil
end end
@ -346,7 +368,7 @@ RSpec.describe SecureMailing::SMIME do
create(:smime_certificate, fixture: ca_fixture) create(:smime_certificate, fixture: ca_fixture)
end end
let(:ca_fixture) { 'ca' } let(:ca_fixture) { 'RootCA' }
it 'verifies' do it 'verifies' do
expect(mail[:body]).to include(raw_body) expect(mail[:body]).to include(raw_body)
@ -359,7 +381,7 @@ RSpec.describe SecureMailing::SMIME do
it_behaves_like 'HttpLog writer', 'success' it_behaves_like 'HttpLog writer', 'success'
context 'expired' do context 'expired' do
let(:ca_fixture) { 'expiredca' } let(:ca_fixture) { 'ExpiredCA' }
it 'fails' do it 'fails' do
expect(mail[:body]).to include(raw_body) expect(mail[:body]).to include(raw_body)
@ -388,6 +410,70 @@ RSpec.describe SecureMailing::SMIME do
end end
end end
end end
context 'certificate chain' do
let(:sender_email_address) { 'chain@example.com' }
let(:ca_subject_chain) { ca_chain.reverse.map(&:subject).join(', ') }
context 'incomplete certificate chain present' do
before do
create(:smime_certificate, fixture: 'RootCA')
create(:smime_certificate, fixture: 'IntermediateCA')
end
it 'fails' do
expect(mail[:body]).to include(raw_body)
expect(mail['x-zammad-article-preferences'][:security][:sign][:success]).to be false
expect(mail['x-zammad-article-preferences'][:security][:sign][:comment]).to eq('Unable to find certificate for verification')
expect(mail['x-zammad-article-preferences'][:security][:encryption][:success]).to be false
expect(mail['x-zammad-article-preferences'][:security][:encryption][:comment]).to be nil
end
end
context 'certificate chain only partly present' do
let(:ca_certificate_subject) { subject_chain }
let!(:ca_chain) do
[
create(:smime_certificate, fixture: 'IntermediateCA'),
create(:smime_certificate, fixture: 'ChainCA'),
]
end
it 'verifies' do
expect(mail[:body]).to include(raw_body)
expect(mail['x-zammad-article-preferences'][:security][:sign][:success]).to be true
expect(mail['x-zammad-article-preferences'][:security][:sign][:comment]).to eq(ca_subject_chain)
expect(mail['x-zammad-article-preferences'][:security][:encryption][:success]).to be false
expect(mail['x-zammad-article-preferences'][:security][:encryption][:comment]).to be nil
end
end
context 'complete certificate chain present' do
let!(:ca_chain) do
[
create(:smime_certificate, fixture: 'RootCA'),
create(:smime_certificate, fixture: 'IntermediateCA'),
create(:smime_certificate, fixture: 'ChainCA'),
]
end
it 'verifies' do
allow(Rails.logger).to receive(:warn)
expect(mail[:body]).to include(raw_body)
expect(mail['x-zammad-article-preferences'][:security][:sign][:success]).to be true
expect(mail['x-zammad-article-preferences'][:security][:sign][:comment]).to eq(ca_subject_chain)
expect(mail['x-zammad-article-preferences'][:security][:encryption][:success]).to be false
expect(mail['x-zammad-article-preferences'][:security][:encryption][:comment]).to be nil
expect(Rails.logger).not_to have_received(:warn).with(/#{Regexp.escape(ca_certificate_subject)}/)
end
end
end
end end
end end

4
spec/models/smime_certificate_spec.rb
View file

@ -185,7 +185,9 @@ RSpec.describe SMIMECertificate, type: :model do
it_behaves_like 'correctly parsed', 'smime2@example.com' it_behaves_like 'correctly parsed', 'smime2@example.com'
it_behaves_like 'correctly parsed', 'smime3@example.com' it_behaves_like 'correctly parsed', 'smime3@example.com'
it_behaves_like 'correctly parsed', 'CaseInsenstive@eXample.COM' it_behaves_like 'correctly parsed', 'CaseInsenstive@eXample.COM'
it_behaves_like 'correctly parsed', 'ca' it_behaves_like 'correctly parsed', 'RootCA'
it_behaves_like 'correctly parsed', 'IntermediateCA'
it_behaves_like 'correctly parsed', 'ChainCA'
end end
end end