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

2021-04-27 06:53:36 +00:00 · 2021-04-27 06:53:36 +00:00 · 3b7909ed5c
parent f46b8712a1
commit 3b7909ed5c
58 changed files with 1558 additions and 1314 deletions
--- a/app/models/smime_certificate.rb
+++ b/app/models/smime_certificate.rb
@ -4,7 +4,7 @@ class SMIMECertificate < ApplicationModel
  validates :fingerprint, uniqueness: true

  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

  # Search for the certificate of the given sender email address
--- a/lib/secure_mailing/smime/incoming.rb
+++ b/lib/secure_mailing/smime/incoming.rb
@ -103,37 +103,12 @@ class SecureMailing::SMIME::Incoming < SecureMailing::Backend::Handler

    success = false
    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
-        verify_ca.add_cert(cert.parsed)
+    result = verify_certificate_chain(p7enc.certificates)
+    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|
        signed?(attachment.dig(:preferences, 'Content-Type'))
      end
@ -145,6 +120,46 @@ class SecureMailing::SMIME::Incoming < SecureMailing::Backend::Handler
    }
  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
    OpenSSL::PKCS7.read_smime(@mail[:raw])
  end
--- a/lib/secure_mailing/smime/outgoing.rb
+++ b/lib/secure_mailing/smime/outgoing.rb
@ -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?

    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
    log('sign', 'failed', e.message)
    raise
  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)
    certificates = SMIMECertificate.for_recipipent_email_addresses!(@mail.to)
    expired_cert = certificates.detect(&:expired?)
--- a/spec/fixtures/smime/CaseInsenstive@eXample.COM.crt
+++ b/spec/fixtures/smime/CaseInsenstive@eXample.COM.crt
@ -1,37 +1,41 @@
 -----BEGIN TRUSTED CERTIFICATE-----
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 -----END TRUSTED CERTIFICATE-----
--- a/spec/fixtures/smime/CaseInsenstive@eXample.COM.csr
+++ b/spec/fixtures/smime/CaseInsenstive@eXample.COM.csr
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 -----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/CaseInsenstive@eXample.COM.key
+++ b/spec/fixtures/smime/CaseInsenstive@eXample.COM.key
@ -1,54 +1,54 @@
 -----BEGIN RSA PRIVATE KEY-----
 Proc-Type: 4,ENCRYPTED
-DEK-Info: AES-256-CBC,897152EBDB085F8EFC4E413FBF5A35FD
+DEK-Info: AES-256-CBC,5D7F2D252AEDDB36881E1B7FD72C1159

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 -----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/ChainCA.crt
+++ b/spec/fixtures/smime/ChainCA.crt
@ -0,0 +1,33 @@
+-----BEGIN CERTIFICATE-----
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+-----END CERTIFICATE-----
--- a/spec/fixtures/smime/ChainCA.csr
+++ b/spec/fixtures/smime/ChainCA.csr
@ -0,0 +1,29 @@
+-----BEGIN CERTIFICATE REQUEST-----
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+-----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/ChainCA.key
+++ b/spec/fixtures/smime/ChainCA.key
@ -0,0 +1,52 @@
+-----BEGIN PRIVATE KEY-----
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+-----END PRIVATE KEY-----
--- a/spec/fixtures/smime/ChainCA.secret
+++ b/spec/fixtures/smime/ChainCA.secret
--- a/spec/fixtures/smime/ExpiredCA.crt
+++ b/spec/fixtures/smime/ExpiredCA.crt
@ -0,0 +1,35 @@
+-----BEGIN CERTIFICATE-----
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+-----END CERTIFICATE-----
--- a/spec/fixtures/smime/ExpiredCA.key
+++ b/spec/fixtures/smime/ExpiredCA.key
@ -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-----
--- a/spec/fixtures/smime/ExpiredCA.secret
+++ b/spec/fixtures/smime/ExpiredCA.secret
--- a/spec/fixtures/smime/IntermediateCA.crt
+++ b/spec/fixtures/smime/IntermediateCA.crt
@ -0,0 +1,33 @@
+-----BEGIN CERTIFICATE-----
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+-----END CERTIFICATE-----
--- a/spec/fixtures/smime/IntermediateCA.csr
+++ b/spec/fixtures/smime/IntermediateCA.csr
@ -0,0 +1,29 @@
+-----BEGIN CERTIFICATE REQUEST-----
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+-----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/IntermediateCA.key
+++ b/spec/fixtures/smime/IntermediateCA.key
@ -0,0 +1,52 @@
+-----BEGIN PRIVATE KEY-----
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+-----END PRIVATE KEY-----
--- a/spec/fixtures/smime/IntermediateCA.secret
+++ b/spec/fixtures/smime/IntermediateCA.secret
--- a/spec/fixtures/smime/RootCA.crt
+++ b/spec/fixtures/smime/RootCA.crt
@ -0,0 +1,33 @@
+-----BEGIN CERTIFICATE-----
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+-----END CERTIFICATE-----
--- a/spec/fixtures/smime/RootCA.csr
+++ b/spec/fixtures/smime/RootCA.csr
@ -0,0 +1,29 @@
+-----BEGIN CERTIFICATE REQUEST-----
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+-----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/RootCA.key
+++ b/spec/fixtures/smime/RootCA.key
@ -0,0 +1,52 @@
+-----BEGIN PRIVATE KEY-----
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+-----END PRIVATE KEY-----
--- a/spec/fixtures/smime/oldsmime1@example.com.secret
+++ b/spec/fixtures/smime/oldsmime1@example.com.secret
--- a/spec/fixtures/smime/ca.crt
+++ b/spec/fixtures/smime/ca.crt
@ -1,35 +0,0 @@
-----BEGIN CERTIFICATE-----
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-----END CERTIFICATE-----
--- a/spec/fixtures/smime/ca.key
+++ b/spec/fixtures/smime/ca.key
@ -1,54 +0,0 @@
-----BEGIN RSA PRIVATE KEY-----
-Proc-Type: 4,ENCRYPTED
-DEK-Info: AES-256-CBC,C883629DF6D2EB2F339DA0E9DDE3A287
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-----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/chain@example.com.crt
+++ b/spec/fixtures/smime/chain@example.com.crt
@ -0,0 +1,40 @@
+-----BEGIN TRUSTED CERTIFICATE-----
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+-----END TRUSTED CERTIFICATE-----
--- a/spec/fixtures/smime/chain@example.com.csr
+++ b/spec/fixtures/smime/chain@example.com.csr
@ -0,0 +1,29 @@
+-----BEGIN CERTIFICATE REQUEST-----
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+-----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/chain@example.com.key
+++ b/spec/fixtures/smime/chain@example.com.key
@ -0,0 +1,54 @@
+-----BEGIN RSA PRIVATE KEY-----
+Proc-Type: 4,ENCRYPTED
+DEK-Info: AES-256-CBC,0B9AC9B9AFF482B0D6EE33EBB73F70E8
+
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+-----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/oldsmime2@example.com.secret
+++ b/spec/fixtures/smime/oldsmime2@example.com.secret
--- a/spec/fixtures/smime/expiredca.crt
+++ b/spec/fixtures/smime/expiredca.crt
@ -1,35 +0,0 @@
-----BEGIN CERTIFICATE-----
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-----END CERTIFICATE-----
--- a/spec/fixtures/smime/expiredca.key
+++ b/spec/fixtures/smime/expiredca.key
@ -1,54 +0,0 @@
-----BEGIN RSA PRIVATE KEY-----
-Proc-Type: 4,ENCRYPTED
-DEK-Info: AES-256-CBC,AFFF2A7AF6117991109A4B9D75D38008
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-----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/expiredsmime1@example.com.crt
+++ b/spec/fixtures/smime/expiredsmime1@example.com.crt
@ -1,37 +1,37 @@
 -----BEGIN TRUSTED CERTIFICATE-----
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 -----END TRUSTED CERTIFICATE-----
--- a/spec/fixtures/smime/expiredsmime1@example.com.csr
+++ b/spec/fixtures/smime/expiredsmime1@example.com.csr
@ -3,27 +3,27 @@ MIIE6DCCAtACAQAwgaIxKDAmBgkqhkiG9w0BCQEWGWV4cGlyZWRzbWltZTFAZXhh
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 -----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/expiredsmime1@example.com.key
+++ b/spec/fixtures/smime/expiredsmime1@example.com.key
@ -1,54 +1,54 @@
 -----BEGIN RSA PRIVATE KEY-----
 Proc-Type: 4,ENCRYPTED
-DEK-Info: AES-256-CBC,8CE77F705A91FC4378059C551C7C5A05
+DEK-Info: AES-256-CBC,78830C9BE3D572CF41DCC33126C1CF2F

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 -----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/expiredsmime2@example.com.crt
+++ b/spec/fixtures/smime/expiredsmime2@example.com.crt
@ -1,37 +1,37 @@
 -----BEGIN TRUSTED CERTIFICATE-----
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 -----END TRUSTED CERTIFICATE-----
--- a/spec/fixtures/smime/expiredsmime2@example.com.csr
+++ b/spec/fixtures/smime/expiredsmime2@example.com.csr
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+0S9W+U9UJTzY7CctfUbHnTLq2NwAR/l6ARsbRdLI/sm1B4VeEfDUTczJHUQVxL2N
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+cU9IJmaGSEynkq7wrkY3b657YVlJ52FW8O5ZbRm48hDpY1nHyPCo7fQX5Aayq2qS
+spUXggdelFw5Fwu+Yxp0whGwnn01dHGBDZhJXhkTHBBY+I9eH72p0ZfvUq5TqK5V
+03Q3s0AsvwwM3EsYCgXt/xaOeOabwvqaT1wjT2NZN16bMlJFqy6UHNZEoQeh410L
+dZfu2l3Q0WgkTb1p
 -----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/expiredsmime2@example.com.key
+++ b/spec/fixtures/smime/expiredsmime2@example.com.key
@ -1,54 +1,54 @@
 -----BEGIN RSA PRIVATE KEY-----
 Proc-Type: 4,ENCRYPTED
-DEK-Info: AES-256-CBC,2D01520A669DCCAAC31310846FD3F95A
+DEK-Info: AES-256-CBC,B118997405683349F559112BE9480FA1

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+DeJrhCPhQ2U+A4fVrQqJbD7qXzwjk6CfmNDOe8vxcCRcSNEsxGtNUiM5LHPdWvAE
+tUofNawWst00c8d2eKllm+kPcjGPstbTaMMag/3Sh4kzWRYaOVbTxLFyYm4VDXj1
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+XZqK1Ue7mSvk7QVAh/7cTZ+gDQMzSC+PHZYNfBXlRjQtvIx8yd/pibT4qGVO5ukM
 -----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/generate/docker-entrypoint.sh
+++ b/spec/fixtures/smime/generate/docker-entrypoint.sh
@ -2,16 +2,40 @@

 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
-  echo "Generating ca.key"
-  openssl genrsa -aes256 -passout file:pass.secret -out $CERT_DIR/ca.key 4096
+  echo "Generating RootCA.key and RootCA.csr"
+  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"
-  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"
+  echo "Generating RootCA.crt"
+  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"
-  cp pass.secret $CERT_DIR/ca.secret
+  echo "Generating RootCA.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

 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 \
        -days 73000 \
        -in $CERT_DIR/$EMAIL_ADDRESS.csr \
-        -CA $CERT_DIR/ca.crt \
-        -CAkey $CERT_DIR/ca.key \
+        -CA $CERT_DIR/RootCA.crt \
+        -CAkey $CERT_DIR/RootCA.key \
        -out $CERT_DIR/$EMAIL_ADDRESS.crt \
        -addtrust emailProtection \
        -addreject clientAuth \
        -addreject serverAuth \
        -trustout \
-        -CAcreateserial -CAserial /tmp/ca.seq \
+        -CAcreateserial -CAserial /tmp/RootCA.seq \
        -extensions smime \
        -extfile "$extfile" \
        -passin file:pass.secret
@ -54,19 +78,53 @@ do
  fi
 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"
 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
-  echo "Generating expiredca.key"
-  FAKETIME=-10y openssl genrsa -aes256 -passout file:pass.secret -out $CERT_DIR/expiredca.key 4096
+  echo "Generating ExpiredCA.key"
+  FAKETIME=-10y openssl genrsa -aes256 -passout file:pass.secret -out $CERT_DIR/ExpiredCA.key 4096

-  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"
+  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"

-  echo "Generating expiredca.secret"
-  cp pass.secret $CERT_DIR/expiredca.secret
+  echo "Generating ExpiredCA.secret"
+  cp pass.secret $CERT_DIR/ExpiredCA.secret
 fi

 for EMAIL_ADDRESS in expiredsmime1@example.com expiredsmime2@example.com
@ -83,14 +141,14 @@ do
    FAKETIME=-10y openssl x509 -req \
        -days 1 \
        -in $CERT_DIR/$EMAIL_ADDRESS.csr \
-        -CA $CERT_DIR/expiredca.crt \
-        -CAkey $CERT_DIR/expiredca.key \
+        -CA $CERT_DIR/ExpiredCA.crt \
+        -CAkey $CERT_DIR/ExpiredCA.key \
        -out $CERT_DIR/$EMAIL_ADDRESS.crt \
        -addtrust emailProtection \
        -addreject clientAuth \
        -addreject serverAuth \
        -trustout \
-        -CAcreateserial -CAserial /tmp/expiredca.seq \
+        -CAcreateserial -CAserial /tmp/ExpiredCA.seq \
        -extensions smime \
        -extfile config.cnf \
        -passin file:pass.secret
--- a/spec/fixtures/smime/oldca.crt
+++ b/spec/fixtures/smime/oldca.crt
@ -1,35 +0,0 @@
-----BEGIN CERTIFICATE-----
-MIIGFzCCA/+gAwIBAgIUMmCv8hoMpL1DxnfbdnB7B8toiJYwDQYJKoZIhvcNAQEL
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-8c1mJgWpM0EAmsUKjGvE3swfKDtSOPndr6vo
-----END CERTIFICATE-----
--- a/spec/fixtures/smime/oldca.key
+++ b/spec/fixtures/smime/oldca.key
@ -1,54 +0,0 @@
-----BEGIN RSA PRIVATE KEY-----
-Proc-Type: 4,ENCRYPTED
-DEK-Info: AES-256-CBC,1B90035BC983D129D9910AA0D912DDE2
-
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-----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/oldsmime1@example.com.crt
+++ b/spec/fixtures/smime/oldsmime1@example.com.crt
@ -1,37 +0,0 @@
-----BEGIN TRUSTED CERTIFICATE-----
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-IjAKBggrBgEFBQcDBKAUBggrBgEFBQcDAgYIKwYBBQUHAwE=
-----END TRUSTED CERTIFICATE-----
--- a/spec/fixtures/smime/oldsmime1@example.com.csr
+++ b/spec/fixtures/smime/oldsmime1@example.com.csr
@ -1,29 +0,0 @@
-----BEGIN CERTIFICATE REQUEST-----
-MIIE5DCCAswCAQAwgZ4xJDAiBgkqhkiG9w0BCQEWFW9sZHNtaW1lMUBleGFtcGxl
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-L+2plCWZr5gtkypczMJFw5ZOlK+SwI0TydCoWkQQxLjaWnqoxigsx3jF9W2uCQDX
-iJZ6c2DEnLU=
-----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/oldsmime1@example.com.key
+++ b/spec/fixtures/smime/oldsmime1@example.com.key
@ -1,54 +0,0 @@
-----BEGIN RSA PRIVATE KEY-----
-Proc-Type: 4,ENCRYPTED
-DEK-Info: AES-256-CBC,075058C49FC97E93DC2A6598E450A08C
-
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-----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/oldsmime2@example.com.crt
+++ b/spec/fixtures/smime/oldsmime2@example.com.crt
@ -1,37 +0,0 @@
-----BEGIN TRUSTED CERTIFICATE-----
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-----END TRUSTED CERTIFICATE-----
--- a/spec/fixtures/smime/oldsmime2@example.com.csr
+++ b/spec/fixtures/smime/oldsmime2@example.com.csr
@ -1,29 +0,0 @@
-----BEGIN CERTIFICATE REQUEST-----
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-----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/oldsmime2@example.com.key
+++ b/spec/fixtures/smime/oldsmime2@example.com.key
@ -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-----
--- a/spec/fixtures/smime/smime1@example.com.crt
+++ b/spec/fixtures/smime/smime1@example.com.crt
@ -1,37 +1,40 @@
 -----BEGIN TRUSTED CERTIFICATE-----
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 -----END TRUSTED CERTIFICATE-----
--- a/spec/fixtures/smime/smime1@example.com.csr
+++ b/spec/fixtures/smime/smime1@example.com.csr
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 -----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/smime1@example.com.key
+++ b/spec/fixtures/smime/smime1@example.com.key
@ -1,54 +1,54 @@
 -----BEGIN RSA PRIVATE KEY-----
 Proc-Type: 4,ENCRYPTED
-DEK-Info: AES-256-CBC,C02E7FD1CD5C829F69D753D19B84384A
+DEK-Info: AES-256-CBC,19EB1017C1E4A6824D8287E4F87D570A

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 -----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/smime2@example.com.crt
+++ b/spec/fixtures/smime/smime2@example.com.crt
@ -1,37 +1,40 @@
 -----BEGIN TRUSTED CERTIFICATE-----
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 -----END TRUSTED CERTIFICATE-----
--- a/spec/fixtures/smime/smime2@example.com.csr
+++ b/spec/fixtures/smime/smime2@example.com.csr
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 -----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/smime2@example.com.key
+++ b/spec/fixtures/smime/smime2@example.com.key
@ -1,54 +1,54 @@
 -----BEGIN RSA PRIVATE KEY-----
 Proc-Type: 4,ENCRYPTED
-DEK-Info: AES-256-CBC,E635B30D63879480FEACF294E0B57BB7
+DEK-Info: AES-256-CBC,BBE7B609718A5F8B3F93A5B20FD2E75C

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 -----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/smime3@example.com.crt
+++ b/spec/fixtures/smime/smime3@example.com.crt
@ -1,37 +1,40 @@
 -----BEGIN TRUSTED CERTIFICATE-----
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 -----END TRUSTED CERTIFICATE-----
--- a/spec/fixtures/smime/smime3@example.com.csr
+++ b/spec/fixtures/smime/smime3@example.com.csr
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 -----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/smime3@example.com.key
+++ b/spec/fixtures/smime/smime3@example.com.key
@ -1,54 +1,54 @@
 -----BEGIN RSA PRIVATE KEY-----
 Proc-Type: 4,ENCRYPTED
-DEK-Info: AES-256-CBC,B60A858865943D0BF01E8FB0E2DF8999
+DEK-Info: AES-256-CBC,DB2015D4059E8A334A794102C31673D8

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 -----END RSA PRIVATE KEY-----
--- a/spec/fixtures/smime/smimedouble@example.com.crt
+++ b/spec/fixtures/smime/smimedouble@example.com.crt
@ -1,39 +1,42 @@
 -----BEGIN TRUSTED CERTIFICATE-----
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 -----END TRUSTED CERTIFICATE-----
--- a/spec/fixtures/smime/smimedouble@example.com.csr
+++ b/spec/fixtures/smime/smimedouble@example.com.csr
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 -----END CERTIFICATE REQUEST-----
--- a/spec/fixtures/smime/smimedouble@example.com.key
+++ b/spec/fixtures/smime/smimedouble@example.com.key
@ -1,54 +1,54 @@
 -----BEGIN RSA PRIVATE KEY-----
 Proc-Type: 4,ENCRYPTED
-DEK-Info: AES-256-CBC,AEB75ED78474CDCBB6810500E499387A
+DEK-Info: AES-256-CBC,B9F5D0F4B28140E5EB887FA32E5F664D

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 -----END RSA PRIVATE KEY-----
--- a/spec/lib/secure_mailing/smime_spec.rb
+++ b/spec/lib/secure_mailing/smime_spec.rb
@ -15,7 +15,7 @@ RSpec.describe SecureMailing::SMIME do

  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' }

@ -74,7 +74,7 @@ RSpec.describe SecureMailing::SMIME do

      context 'private key present' do

-        before do
+        let!(:sender_certificate) do
          create(:smime_certificate, :with_private, fixture: system_email_address)
        end

@ -123,6 +123,29 @@ RSpec.describe SecureMailing::SMIME do
            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

      context 'no private key present' do
@ -308,7 +331,7 @@ RSpec.describe SecureMailing::SMIME do

            context 'CA' do

-              let(:not_related_fixture) { 'expiredca' }
+              let(:not_related_fixture) { 'ExpiredCA' }

              it 'fails' do
                expect(mail[:body]).to include(raw_body)
@ -323,17 +346,16 @@ RSpec.describe SecureMailing::SMIME do
          end

          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
              # remove OpenSSL::PKCS7::NOINTERN
              stub_const('SecureMailing::SMIME::Incoming::OPENSSL_PKCS7_VERIFY_FLAGS', OpenSSL::PKCS7::NOVERIFY)
            end

-            it 'wrongly performs a verification' do
+            it "won't perform verification" 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(not_related_certificate_subject)
+              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
@ -346,7 +368,7 @@ RSpec.describe SecureMailing::SMIME do
            create(:smime_certificate, fixture: ca_fixture)
          end

-          let(:ca_fixture) { 'ca' }
+          let(:ca_fixture) { 'RootCA' }

          it 'verifies' do
            expect(mail[:body]).to include(raw_body)
@ -359,7 +381,7 @@ RSpec.describe SecureMailing::SMIME do
          it_behaves_like 'HttpLog writer', 'success'

          context 'expired' do
-            let(:ca_fixture) { 'expiredca' }
+            let(:ca_fixture) { 'ExpiredCA' }

            it 'fails' do
              expect(mail[:body]).to include(raw_body)
@ -388,6 +410,70 @@ RSpec.describe SecureMailing::SMIME do
            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

--- a/spec/models/smime_certificate_spec.rb
+++ b/spec/models/smime_certificate_spec.rb
@ -185,7 +185,9 @@ RSpec.describe SMIMECertificate, type: :model do
      it_behaves_like 'correctly parsed', 'smime2@example.com'
      it_behaves_like 'correctly parsed', 'smime3@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