diff --git a/app/models/smime_certificate.rb b/app/models/smime_certificate.rb
index 60e99e697..46958db8c 100644
--- 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
diff --git a/lib/secure_mailing/smime/incoming.rb b/lib/secure_mailing/smime/incoming.rb
index 1af48377b..8a6c560a1 100644
--- 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
diff --git a/lib/secure_mailing/smime/outgoing.rb b/lib/secure_mailing/smime/outgoing.rb
index af231a2b7..c0295ad72 100644
--- 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?)
diff --git a/spec/fixtures/smime/CaseInsenstive@eXample.COM.crt b/spec/fixtures/smime/CaseInsenstive@eXample.COM.crt
index 58fae7ec7..26890c41f 100644
--- a/spec/fixtures/smime/CaseInsenstive@eXample.COM.crt
+++ b/spec/fixtures/smime/CaseInsenstive@eXample.COM.crt
@@ -1,37 +1,41 @@
 -----BEGIN TRUSTED CERTIFICATE-----
-MIIGZDCCBEygAwIBAgIUAfZ9Sb8pCb7RN34x7oUVKZ/ftY8wDQYJKoZIhvcNAQEL
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 -----END TRUSTED CERTIFICATE-----
diff --git a/spec/fixtures/smime/CaseInsenstive@eXample.COM.csr b/spec/fixtures/smime/CaseInsenstive@eXample.COM.csr
index 40011bda2..03ae02520 100644
--- a/spec/fixtures/smime/CaseInsenstive@eXample.COM.csr
+++ b/spec/fixtures/smime/CaseInsenstive@eXample.COM.csr
@@ -3,27 +3,27 @@ MIIE6TCCAtECAQAwgaMxKTAnBgkqhkiG9w0BCQEWGkNhc2VJbnNlbnN0aXZlQGVY
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 -----END CERTIFICATE REQUEST-----
diff --git a/spec/fixtures/smime/CaseInsenstive@eXample.COM.key b/spec/fixtures/smime/CaseInsenstive@eXample.COM.key
index dab0bc3e2..e246552ff 100644
--- 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-----
diff --git a/spec/fixtures/smime/ChainCA.crt b/spec/fixtures/smime/ChainCA.crt
new file mode 100644
index 000000000..8b325dfe3
--- /dev/null
+++ b/spec/fixtures/smime/ChainCA.crt
@@ -0,0 +1,33 @@
+-----BEGIN CERTIFICATE-----
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+-----END CERTIFICATE-----
diff --git a/spec/fixtures/smime/ChainCA.csr b/spec/fixtures/smime/ChainCA.csr
new file mode 100644
index 000000000..b32d20409
--- /dev/null
+++ b/spec/fixtures/smime/ChainCA.csr
@@ -0,0 +1,29 @@
+-----BEGIN CERTIFICATE REQUEST-----
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+-----END CERTIFICATE REQUEST-----
diff --git a/spec/fixtures/smime/ChainCA.key b/spec/fixtures/smime/ChainCA.key
new file mode 100644
index 000000000..3a94558ae
--- /dev/null
+++ b/spec/fixtures/smime/ChainCA.key
@@ -0,0 +1,52 @@
+-----BEGIN PRIVATE KEY-----
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+-----END PRIVATE KEY-----
diff --git a/spec/fixtures/smime/ca.secret b/spec/fixtures/smime/ChainCA.secret
similarity index 100%
rename from spec/fixtures/smime/ca.secret
rename to spec/fixtures/smime/ChainCA.secret
diff --git a/spec/fixtures/smime/ExpiredCA.crt b/spec/fixtures/smime/ExpiredCA.crt
new file mode 100644
index 000000000..653354027
--- /dev/null
+++ b/spec/fixtures/smime/ExpiredCA.crt
@@ -0,0 +1,35 @@
+-----BEGIN CERTIFICATE-----
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+-----END CERTIFICATE-----
diff --git a/spec/fixtures/smime/ExpiredCA.key b/spec/fixtures/smime/ExpiredCA.key
new file mode 100644
index 000000000..b8ce9e54d
--- /dev/null
+++ 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-----
diff --git a/spec/fixtures/smime/expiredca.secret b/spec/fixtures/smime/ExpiredCA.secret
similarity index 100%
rename from spec/fixtures/smime/expiredca.secret
rename to spec/fixtures/smime/ExpiredCA.secret
diff --git a/spec/fixtures/smime/IntermediateCA.crt b/spec/fixtures/smime/IntermediateCA.crt
new file mode 100644
index 000000000..77d6a6227
--- /dev/null
+++ b/spec/fixtures/smime/IntermediateCA.crt
@@ -0,0 +1,33 @@
+-----BEGIN CERTIFICATE-----
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+-----END CERTIFICATE-----
diff --git a/spec/fixtures/smime/IntermediateCA.csr b/spec/fixtures/smime/IntermediateCA.csr
new file mode 100644
index 000000000..99757e7e0
--- /dev/null
+++ b/spec/fixtures/smime/IntermediateCA.csr
@@ -0,0 +1,29 @@
+-----BEGIN CERTIFICATE REQUEST-----
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+-----END CERTIFICATE REQUEST-----
diff --git a/spec/fixtures/smime/IntermediateCA.key b/spec/fixtures/smime/IntermediateCA.key
new file mode 100644
index 000000000..cbb2ba0dc
--- /dev/null
+++ b/spec/fixtures/smime/IntermediateCA.key
@@ -0,0 +1,52 @@
+-----BEGIN PRIVATE KEY-----
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diff --git a/spec/fixtures/smime/oldca.secret b/spec/fixtures/smime/IntermediateCA.secret
similarity index 100%
rename from spec/fixtures/smime/oldca.secret
rename to spec/fixtures/smime/IntermediateCA.secret
diff --git a/spec/fixtures/smime/RootCA.crt b/spec/fixtures/smime/RootCA.crt
new file mode 100644
index 000000000..7a2d897d7
--- /dev/null
+++ b/spec/fixtures/smime/RootCA.crt
@@ -0,0 +1,33 @@
+-----BEGIN CERTIFICATE-----
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+-----END CERTIFICATE-----
diff --git a/spec/fixtures/smime/RootCA.csr b/spec/fixtures/smime/RootCA.csr
new file mode 100644
index 000000000..9dfd87d53
--- /dev/null
+++ b/spec/fixtures/smime/RootCA.csr
@@ -0,0 +1,29 @@
+-----BEGIN CERTIFICATE REQUEST-----
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+UT9Sjf4=
+-----END CERTIFICATE REQUEST-----
diff --git a/spec/fixtures/smime/RootCA.key b/spec/fixtures/smime/RootCA.key
new file mode 100644
index 000000000..9b9819daa
--- /dev/null
+++ b/spec/fixtures/smime/RootCA.key
@@ -0,0 +1,52 @@
+-----BEGIN PRIVATE KEY-----
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+-----END PRIVATE KEY-----
diff --git a/spec/fixtures/smime/oldsmime1@example.com.secret b/spec/fixtures/smime/RootCA.secret
similarity index 100%
rename from spec/fixtures/smime/oldsmime1@example.com.secret
rename to spec/fixtures/smime/RootCA.secret
diff --git a/spec/fixtures/smime/ca.crt b/spec/fixtures/smime/ca.crt
deleted file mode 100644
index a21cece14..000000000
--- a/spec/fixtures/smime/ca.crt
+++ /dev/null
@@ -1,35 +0,0 @@
------BEGIN CERTIFICATE-----
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------END CERTIFICATE-----
diff --git a/spec/fixtures/smime/ca.key b/spec/fixtures/smime/ca.key
deleted file mode 100644
index ecf4b81bf..000000000
--- a/spec/fixtures/smime/ca.key
+++ /dev/null
@@ -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-----
diff --git a/spec/fixtures/smime/chain@example.com.crt b/spec/fixtures/smime/chain@example.com.crt
new file mode 100644
index 000000000..f67e74c2a
--- /dev/null
+++ b/spec/fixtures/smime/chain@example.com.crt
@@ -0,0 +1,40 @@
+-----BEGIN TRUSTED CERTIFICATE-----
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+-----END TRUSTED CERTIFICATE-----
diff --git a/spec/fixtures/smime/chain@example.com.csr b/spec/fixtures/smime/chain@example.com.csr
new file mode 100644
index 000000000..155e2ea99
--- /dev/null
+++ b/spec/fixtures/smime/chain@example.com.csr
@@ -0,0 +1,29 @@
+-----BEGIN CERTIFICATE REQUEST-----
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+IOo2jg==
+-----END CERTIFICATE REQUEST-----
diff --git a/spec/fixtures/smime/chain@example.com.key b/spec/fixtures/smime/chain@example.com.key
new file mode 100644
index 000000000..278f95141
--- /dev/null
+++ 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-----
diff --git a/spec/fixtures/smime/oldsmime2@example.com.secret b/spec/fixtures/smime/chain@example.com.secret
similarity index 100%
rename from spec/fixtures/smime/oldsmime2@example.com.secret
rename to spec/fixtures/smime/chain@example.com.secret
diff --git a/spec/fixtures/smime/expiredca.crt b/spec/fixtures/smime/expiredca.crt
deleted file mode 100644
index 0a290508a..000000000
--- a/spec/fixtures/smime/expiredca.crt
+++ /dev/null
@@ -1,35 +0,0 @@
------BEGIN CERTIFICATE-----
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------END CERTIFICATE-----
diff --git a/spec/fixtures/smime/expiredca.key b/spec/fixtures/smime/expiredca.key
deleted file mode 100644
index a379d1b8d..000000000
--- a/spec/fixtures/smime/expiredca.key
+++ /dev/null
@@ -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-----
diff --git a/spec/fixtures/smime/expiredsmime1@example.com.crt b/spec/fixtures/smime/expiredsmime1@example.com.crt
index fa1d90f69..65e894055 100644
--- 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-----
diff --git a/spec/fixtures/smime/expiredsmime1@example.com.csr b/spec/fixtures/smime/expiredsmime1@example.com.csr
index 5f2058ca6..b8b74d306 100644
--- a/spec/fixtures/smime/expiredsmime1@example.com.csr
+++ b/spec/fixtures/smime/expiredsmime1@example.com.csr
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 -----END CERTIFICATE REQUEST-----
diff --git a/spec/fixtures/smime/expiredsmime1@example.com.key b/spec/fixtures/smime/expiredsmime1@example.com.key
index ada4921c2..d3bec634b 100644
--- 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-----
diff --git a/spec/fixtures/smime/expiredsmime2@example.com.crt b/spec/fixtures/smime/expiredsmime2@example.com.crt
index fd851f1f6..2e8c425bc 100644
--- 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-----
diff --git a/spec/fixtures/smime/expiredsmime2@example.com.csr b/spec/fixtures/smime/expiredsmime2@example.com.csr
index 622f6f785..f6bb20b02 100644
--- a/spec/fixtures/smime/expiredsmime2@example.com.csr
+++ b/spec/fixtures/smime/expiredsmime2@example.com.csr
@@ -3,27 +3,27 @@ MIIE6DCCAtACAQAwgaIxKDAmBgkqhkiG9w0BCQEWGWV4cGlyZWRzbWltZTJAZXhh
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+dZfu2l3Q0WgkTb1p
 -----END CERTIFICATE REQUEST-----
diff --git a/spec/fixtures/smime/expiredsmime2@example.com.key b/spec/fixtures/smime/expiredsmime2@example.com.key
index d7999ec23..c0bb41ced 100644
--- 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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+XZqK1Ue7mSvk7QVAh/7cTZ+gDQMzSC+PHZYNfBXlRjQtvIx8yd/pibT4qGVO5ukM
 -----END RSA PRIVATE KEY-----
diff --git a/spec/fixtures/smime/generate/docker-entrypoint.sh b/spec/fixtures/smime/generate/docker-entrypoint.sh
index 8e2b23015..212e9ffff 100755
--- 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
diff --git a/spec/fixtures/smime/oldca.crt b/spec/fixtures/smime/oldca.crt
deleted file mode 100644
index 4c6778f69..000000000
--- a/spec/fixtures/smime/oldca.crt
+++ /dev/null
@@ -1,35 +0,0 @@
------BEGIN CERTIFICATE-----
-MIIGFzCCA/+gAwIBAgIUMmCv8hoMpL1DxnfbdnB7B8toiJYwDQYJKoZIhvcNAQEL
-BQAwgZoxIDAeBgkqhkiG9w0BCQEWEW9sZGNhQGV4YW1wbGUuY29tMQswCQYDVQQG
-EwJERTEPMA0GA1UECAwGQmVybGluMQ8wDQYDVQQHDAZCZXJsaW4xGTAXBgNVBAoM
-EEV4YW1wbGUgU2VjdXJpdHkxFjAUBgNVBAsMDUlUIERlcGFydG1lbnQxFDASBgNV
-BAMMC2V4YW1wbGUuY29tMB4XDTEwMDUyMzA3MDUwOFoXDTEwMDUyNDA3MDUwOFow
-gZoxIDAeBgkqhkiG9w0BCQEWEW9sZGNhQGV4YW1wbGUuY29tMQswCQYDVQQGEwJE
-RTEPMA0GA1UECAwGQmVybGluMQ8wDQYDVQQHDAZCZXJsaW4xGTAXBgNVBAoMEEV4
-YW1wbGUgU2VjdXJpdHkxFjAUBgNVBAsMDUlUIERlcGFydG1lbnQxFDASBgNVBAMM
-C2V4YW1wbGUuY29tMIICIjANBgkqhkiG9w0BAQEFAAOCAg8AMIICCgKCAgEAtnoR
-t1oSnGD2p6EF/RwRH2qrj0crDtVMubda6sls6tO14a/4qQ/za6WcSKRaPdVtsZ1j
-r5yK8QaiaSZ4/jmfmuSpUvu0F7rQyhZ+bNI+ibF6YTHe2DGkdjH4rouoC7WEtfLz
-saSYvojXOCelelbiMf94w6uDvMCRu5A47AHgFRAYWh3PD/kPuxefd2OYpZBjUVF0
-fOs6tkPWpPzt03Xu8RiJP1/UkLk/ZISLvG5VriMOG+KeOMFAz7gDNaGxoKJ7wlUb
-A8Ht0FbQ5ZaYaDlmG0ENhnMoM74h6jxbPlRHvuDzAccZfb9m0e+HX9xP5Q8Cp+ib
-EMpSe0SBE3N56a7aCPHTiXoC2wYL32rMUhjC2dgLT/UwBDiMiIksDm7W4IQv10l0
-GYGvinDBFEE+fVmQF/g0XBJGmTFi4uN+ZcXaUpLQiBi075E89Rwm9+Xrqr9L/fcm
-y2GEnwN0KI2wyFnwMDDMRKfZXSMtU9sCEiqZTIXiAfy9t0wzjbG2P+cXh+p07TNv
-POTCyaB98tfocIWIgB6GDFXfgZQJLtZN2Qwm1+MfG63OCFY9QCXoiTaja08+ukB8
-kZ8TNCzDs2E82D9fl5aldtaSwCuMJMc0cdIzi25SIJzc4UGtUrEFI8Olrk/QUQ+W
-/h0OYptIwJGvdwEquVAfQrPDoIPEN0iJeHfNqWUCAwEAAaNTMFEwHQYDVR0OBBYE
-FDw9N9kuUQx109fegyN/ZBWPLmYcMB8GA1UdIwQYMBaAFDw9N9kuUQx109fegyN/
-ZBWPLmYcMA8GA1UdEwEB/wQFMAMBAf8wDQYJKoZIhvcNAQELBQADggIBAC30oxIo
-LaQcXt/AS9FyOZ3dD/5ZzynqTyoSEcP1QzEIXdwIxY3nUaqFCiosBzsd7ZmrSA3S
-oaWyFYGutZppVtw39OsbJEKKOv5SX03HEJKoOHkbanPLVNBcdVytRGUI+b61VPEt
-SVtbLWD3tjF1Pl0HOtYyzy8gZZWUYRD4LBHtUeDIkY6f1XPTZJuFxpvhb+9l+nGq
-OYFhclxVtSNokP+/42vHiNgCuN+9XDhkI2nSC1hKHETEASEmXWCAJ1GI1RqDQ8yr
-wghe8LDxRI9R2jTwsd6KEIAufxbEksKw1pvvRS0c06i5cAMf9w/dPerOd1sEdE07
-iESaWTc73kjmgglakFRumuuOqsUVmoW9S/IMVt5gyX0wQVjNmV6Ic3LKF5tmEi3E
-7h0aFRtzQE+88QcldDLnU4hQA1IwGVpsKnohPq7YWi2HTSp6cJTsdB5c8Rl7zRCw
-cy3xWOyLDlUxmYJehfwlHQy+Nf2MZ/KPO8a6Sv9IPF9H6Stra3LD41Ac7+pHz2B/
-SrGKieCqoY1Moby/nipRbdwF3ExBjOyDUem+VyYZy7ldsCBW0OE8cwb0D87PN/lu
-PULhsWi4ZhPV72kQ5IOvQG/qj78tbVvsoxabY+cDvSrb1NA3aaoQC8T+1Q91YpQa
-8c1mJgWpM0EAmsUKjGvE3swfKDtSOPndr6vo
------END CERTIFICATE-----
diff --git a/spec/fixtures/smime/oldca.key b/spec/fixtures/smime/oldca.key
deleted file mode 100644
index 33b7882af..000000000
--- a/spec/fixtures/smime/oldca.key
+++ /dev/null
@@ -1,54 +0,0 @@
------BEGIN RSA PRIVATE KEY-----
-Proc-Type: 4,ENCRYPTED
-DEK-Info: AES-256-CBC,1B90035BC983D129D9910AA0D912DDE2
-
-WhX+qKY6nc6SGhUBYsxQtju7rzg/DdV1YCWoj0eydeIVYQyDPua8HzkSPCVBX++Y
-+voyWentJu9v8SnrQnOr0dI+rilpi8ibr6tkdrEiyLLWMHO11w5UEjb/R0VOJBG3
-2f0N0d/58xiur5Mi+x7v/YpEPU5CqNSro14SSIpSHv110mC8Se03tO3DzlnGAAPM
-JIcrkgEFmzzf7sOo0R3hEgNsM72ehFRomz/RsTfr2lRMNK5/s4Qd2+90cImG2QbN
-dGVhTMUUgkPFcIXQ3u2Vd3AowDCUi6KCCiMfs9laBSSf2TvH5d+V3wWVCNPHz63A
-NnmDQ4s7Cor3fVtrsus4KB2Aeg0+4gYA02MPymJ3Oqqjh0EsnF+DKPx9MRfdX0i6
-oZsRDxO+97zrBj8HSKxly1lDtrvTXLM4+25RL+PDUH7/inZOctm7m0F7zn+k9EeY
-p9DQDRTXFgVyMxqtFnFZtXf8YsOINDux/Ecidis+10QotJxswXWD/uEI8sKjnIXU
-BuWQZW/YqoT0Zlf7QdRYqx4cK6Ht2C6k8icwPzfubsG0b2zOz9sHMSOXS0vbWaEb
-T9szeFizubGW9jDWHpNmZqWhKyzH9EHfjZHVOa61Wot5P2ROfl3loTiOGd2TYRwD
-WqlBIthMUJVJ6hGqQY2wFfEdCGpL/h/gI+KA2m9GwbrrtxhulA/54OyfgyurOw/P
-M6or0rsYgy0n3lMElBCiMrlxfxg97O2x1Py1rIIlzO0N0VJVeKZHczsECNp9c6Hw
-P/CrSopCiILqlRIIo6CiyblhzUhPNi1u1YE3Rt1bDBKnRuo276h77+VkOG2l/JaQ
-YQfOzK0dQqeAHRsv8yS/o4IEO19JHjo9jtFbW4PgFanNOzWibYJBGzNk/RqDfcrF
-CUsqa+VQMtkZYSfp94MnZ+IgQhv3nikoLNlwpad5gVEqg8yuQ4q21ccmzDxWmKg2
-1uERa3pCyC+U/irOAtK90muL49oNseNpB5uEt0wkm35s4SupW6EEepJwKjexLFaC
-lLGNbX7xk22lD6MIrr7fhJPTNGlBK7NkHTENtb/23tKcL6D6PdRmaMB5n/HDI2CE
-Z/vUjg8SNr+yUiHnb4gXXiSoOdQWTMXLyPowaMqD6ef0xvgJkRFf9s314mKIabYH
-g/h6JBAO4PWohPR8t/VzDfmu0jxll8WQQlMg9sxlV3jXG/rMW1J4dYO/vlCKHMUD
-A1gMf/sk+GOUf9lV8TW14JrgkCrtZgkw/5mPhD35B4Gj2YfgWd+LA+BVS1t5UhvP
-Ns45nNvjiWoNqPa7d/b3/h+M2FcKPE+IJGrZvNv1yTgmkqGqmhLB2KhjgpDNVKy2
-dgqXglfu51YSXVr3D5tkUADD1+SWa+vtGg4Rw7IoswPjp3RSwGSoXsLvEZNVlyC6
-QtuF5zmRxtjjtZsptNuUYbyDR8PLEHHSZkl9QckdrDCq50NbFwILsTV95uRvxqvB
-3Y1Ve8zzVcksaX0zRTaaDmkBRRUAhXsNd5TSdpbZnyul1/zTriy+axb8G1x/+eCS
-fJMhBSdCDJgB7H2zDY8im12qB5Zho3+KfeKBoV5XVYB8JaqXj1fYAuMl7yNbd3LZ
-wrKnW/8GWX9lgvSB/pvZtgLSSAEf1hjxbjr7q4VL4YVf2EODWpqFd+yjlyzsFelh
-jwxvrtsXK8AKbl20d+NXfmsxtdZ5004hYpjxoDDeBHh0CSaaM2Kqjt5ANZPV0fk9
-9N/bxCPouCa1MermAodoZLPKHeOJm3GxIUVarv8Iddrdn0Nlrkt2cOmpLS+L4KfW
-zcQ139lyBC6mHCEzQyku0MW31XYpKbXQvFef7xgDms1lNpESi9dHTRjJ5udtSDkX
-xG3aEFoB2dATzLNYN3xlRlP4ev+PD+HRQc/X+8p98EbYsfzqPOlQUn7LXLtJKGJp
-V/bp1i5avQE88DKTmDgcj4QYaJlBRZbVfCgxBytWQuLy/ZQV/XOszTgSzJwiWcZP
-UA5UkDgmCKUn7Pnup0nj/jd9zPMQ6a68WkeZAGwJXzX1fvv3S70kxdq+DRZNYbgV
-yYdv/Hy15V5PUV072H4mztPV024abidWqrI1vjGr7e1UZGt8c1FW+kQVExy16d6T
-tEdLElxSHhCP9N2hfAIRnD9Uh1L7GDeNVA3IBD13qNqx6A1lQBnYSrUElwkrKtfI
-CXF3p/8mCLVFr04B8f8WojKkZe9UkX8z9mHW9C7MtWQiBts4K/0vmrcoWtMtSBXZ
-lPX5Jbp6B+mgkdw+USHwGgaYBH4b8lTnEmUl9OZDl5PPQBnWsA6fj+XbngbB/n8+
-5lMkAKKi8mWDrpUwWmiq0VHUO419R9ckf8tAN22VamFfq2+mXmP8jUGvxR/qfN97
-1J/KKcdT/8yfFENgmGrOD56sfX2DOzjVZqro/+xJVJakzVsBy9Jfo+93l714qNhr
-I/3xURPdX2BS2cDNDhAYqEME/6VfPbDtaP/JpFqonIlAOkfcwW5HUpwwW+DMneAE
-LtRIfDf86dqppTC9lPPKTh/8/tBnTa1IZMO83jWrBu7vG+Ch910LhXbgfKqMpNES
-YWmdjx1oG9YMOV6ZTDcWfmaiL5zDOR+/07aXD8+qnG0SOb6UoIjmSwR8fmBSHJM+
-2YEJem4/7dgPCleTx+zX8HUCWVlvqk8R7ZcPAS2AU8O9mulU+X7COVgqMA/kZRzH
-L42VuRWhkomHnY7KMzFZNTv+pNVi1DRmu9YxNYOW5LcCbjF52+FI+GpeZO/Phseq
-XTSFwf8P9d/VXvkdeGcEKKRfJPwdA6z+3owx88LVd7VUzvyscEw0WyIZf+6w5bJi
-joZxPFrQdZyjVUKWGVdOa276f9tw3d/k3R+T/Pl4Rb8mOua8fdXMfIvFo8El2gev
-rid1CdNCxtedX/fwKX55x94oeF9+g0hkQlKK/E5+3CtDg7nKRyMFP4jG0IM5FaBU
-GkE7/5y14TXPtX+B48l4K31/eHdsOBcuGthrrF4MjgKLe3eELUHlHom6syMPxUwe
-SRz53DIzXNuux3M6POkPozJHO/MUVOfavUh/v9E05daqKg/9mjkmxMKtsr9ZTNew
-130LA0N/HHthJKCZeNLsUQY8J6M3kUXVuOw8cb6cCLuVkT8WIgropcJCXhy8chha
------END RSA PRIVATE KEY-----
diff --git a/spec/fixtures/smime/oldsmime1@example.com.crt b/spec/fixtures/smime/oldsmime1@example.com.crt
deleted file mode 100644
index 5934ad9bd..000000000
--- a/spec/fixtures/smime/oldsmime1@example.com.crt
+++ /dev/null
@@ -1,37 +0,0 @@
------BEGIN TRUSTED CERTIFICATE-----
-MIIGWzCCBEOgAwIBAgIUIUrCfVRV1i03o1zHmhtNv8XMpBQwDQYJKoZIhvcNAQEL
-BQAwgZoxIDAeBgkqhkiG9w0BCQEWEW9sZGNhQGV4YW1wbGUuY29tMQswCQYDVQQG
-EwJERTEPMA0GA1UECAwGQmVybGluMQ8wDQYDVQQHDAZCZXJsaW4xGTAXBgNVBAoM
-EEV4YW1wbGUgU2VjdXJpdHkxFjAUBgNVBAsMDUlUIERlcGFydG1lbnQxFDASBgNV
-BAMMC2V4YW1wbGUuY29tMB4XDTEwMDUyMzA3MDUwOVoXDTEwMDUyNDA3MDUwOVow
-gZ4xJDAiBgkqhkiG9w0BCQEWFW9sZHNtaW1lMUBleGFtcGxlLmNvbTELMAkGA1UE
-BhMCREUxDzANBgNVBAgMBkJlcmxpbjEPMA0GA1UEBwwGQmVybGluMRkwFwYDVQQK
-DBBFeGFtcGxlIFNlY3VyaXR5MRYwFAYDVQQLDA1JVCBEZXBhcnRtZW50MRQwEgYD
-VQQDDAtleGFtcGxlLmNvbTCCAiIwDQYJKoZIhvcNAQEBBQADggIPADCCAgoCggIB
-AOlZ96ydfW6IGP3roFTyqDTs37MAdHH2VyEYU0qxM98HhDcpXn3iNVeyyOTbeCwy
-7yw67EdMwukXZ7VQnxeaz37e7n6tYG/S2lIKYZJkNr2kZ66QACfhSN54wH8sz7H4
-giwBV1NShdCtdcjUqV1r8srCOIsUGsW4b8W6HqZ6XDHzmkV6N3pJueUrQdWfY1El
-7BBgJY6nsTSQzoycEA5PiWxo9b3Br7z34dj7sHvnQmT8qdlkPq9xfT1tiOpWF5Pk
-3Xj6lwqSueYVWpCgohcrxuSi8DpZLwAXXjx410e1YuRMDcC6EbIQioePbFDfgcHv
-tgluMZkY5JR0q25na16ONuFYx8FOL+7JzIyxvnUZYUQEvuFXaZk5YhxeRjITvNHr
-iV4A7iINBkfwLXeo8GDywSK89VxC6g7p435CBBJfg2kE5jHIy2qVdw83zWfWRuhJ
-Xg0NEUV7K8ktDL07w5EJOhhaEqUkvSeNSxUbR/eXyRyrs7kl1VLCI+Ug1x/YBRFn
-br8NSKohqvv4s4aZ66bF7nkNlLVEZYmvZorL2VGjCGztbw7nEoft8FPDMfMseKiC
-i5lhc4B54d93H06HuDG7TenkXfyCB70kmBSZpImpCJVdP8E3scYbys4zSomu1BQy
-/CHn/GBVnS2spE27EWEm6vfF3sghJbFjXmW4O761XM0DAgMBAAGjgZIwgY8wCQYD
-VR0TBAIwADALBgNVHQ8EBAMCBeAwHQYDVR0OBBYEFGlwE9fYOr/AGCyldJcQvvTz
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------END TRUSTED CERTIFICATE-----
diff --git a/spec/fixtures/smime/oldsmime1@example.com.csr b/spec/fixtures/smime/oldsmime1@example.com.csr
deleted file mode 100644
index eed51f03d..000000000
--- a/spec/fixtures/smime/oldsmime1@example.com.csr
+++ /dev/null
@@ -1,29 +0,0 @@
------BEGIN CERTIFICATE REQUEST-----
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------END CERTIFICATE REQUEST-----
diff --git a/spec/fixtures/smime/oldsmime1@example.com.key b/spec/fixtures/smime/oldsmime1@example.com.key
deleted file mode 100644
index ba3952b75..000000000
--- a/spec/fixtures/smime/oldsmime1@example.com.key
+++ /dev/null
@@ -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-----
diff --git a/spec/fixtures/smime/oldsmime2@example.com.crt b/spec/fixtures/smime/oldsmime2@example.com.crt
deleted file mode 100644
index 8ef99aabd..000000000
--- a/spec/fixtures/smime/oldsmime2@example.com.crt
+++ /dev/null
@@ -1,37 +0,0 @@
------BEGIN TRUSTED CERTIFICATE-----
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------END TRUSTED CERTIFICATE-----
diff --git a/spec/fixtures/smime/oldsmime2@example.com.csr b/spec/fixtures/smime/oldsmime2@example.com.csr
deleted file mode 100644
index 191ed2c03..000000000
--- a/spec/fixtures/smime/oldsmime2@example.com.csr
+++ /dev/null
@@ -1,29 +0,0 @@
------BEGIN CERTIFICATE REQUEST-----
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------END CERTIFICATE REQUEST-----
diff --git a/spec/fixtures/smime/oldsmime2@example.com.key b/spec/fixtures/smime/oldsmime2@example.com.key
deleted file mode 100644
index 6486109f9..000000000
--- a/spec/fixtures/smime/oldsmime2@example.com.key
+++ /dev/null
@@ -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-----
diff --git a/spec/fixtures/smime/smime1@example.com.crt b/spec/fixtures/smime/smime1@example.com.crt
index 4781ff97e..cce4005fa 100644
--- 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-----
diff --git a/spec/fixtures/smime/smime1@example.com.csr b/spec/fixtures/smime/smime1@example.com.csr
index 13003027a..0d0a53aa5 100644
--- a/spec/fixtures/smime/smime1@example.com.csr
+++ b/spec/fixtures/smime/smime1@example.com.csr
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+kvr//LI=
 -----END CERTIFICATE REQUEST-----
diff --git a/spec/fixtures/smime/smime1@example.com.key b/spec/fixtures/smime/smime1@example.com.key
index 6f569ab8a..4587acf17 100644
--- 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-----
diff --git a/spec/fixtures/smime/smime2@example.com.crt b/spec/fixtures/smime/smime2@example.com.crt
index 0fe5a6b63..31e09baf2 100644
--- 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-----
diff --git a/spec/fixtures/smime/smime2@example.com.csr b/spec/fixtures/smime/smime2@example.com.csr
index 863dacb4f..bb80dcf17 100644
--- a/spec/fixtures/smime/smime2@example.com.csr
+++ b/spec/fixtures/smime/smime2@example.com.csr
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 -----END CERTIFICATE REQUEST-----
diff --git a/spec/fixtures/smime/smime2@example.com.key b/spec/fixtures/smime/smime2@example.com.key
index e20b5e144..89aaf39a5 100644
--- 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-----
diff --git a/spec/fixtures/smime/smime3@example.com.crt b/spec/fixtures/smime/smime3@example.com.crt
index 76fa905a0..16956c861 100644
--- 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-----
diff --git a/spec/fixtures/smime/smime3@example.com.csr b/spec/fixtures/smime/smime3@example.com.csr
index ac58feb1a..224fd5028 100644
--- a/spec/fixtures/smime/smime3@example.com.csr
+++ b/spec/fixtures/smime/smime3@example.com.csr
@@ -3,27 +3,27 @@ MIIE4TCCAskCAQAwgZsxITAfBgkqhkiG9w0BCQEWEnNtaW1lM0BleGFtcGxlLmNv
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 -----END CERTIFICATE REQUEST-----
diff --git a/spec/fixtures/smime/smime3@example.com.key b/spec/fixtures/smime/smime3@example.com.key
index a2c968863..55a52179b 100644
--- 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-----
diff --git a/spec/fixtures/smime/smimedouble@example.com.crt b/spec/fixtures/smime/smimedouble@example.com.crt
index 098923d66..eff1376a8 100644
--- 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-----
diff --git a/spec/fixtures/smime/smimedouble@example.com.csr b/spec/fixtures/smime/smimedouble@example.com.csr
index 93c3c93a7..9715fc25a 100644
--- a/spec/fixtures/smime/smimedouble@example.com.csr
+++ b/spec/fixtures/smime/smimedouble@example.com.csr
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 -----END CERTIFICATE REQUEST-----
diff --git a/spec/fixtures/smime/smimedouble@example.com.key b/spec/fixtures/smime/smimedouble@example.com.key
index f27b0fa18..f1d9e619f 100644
--- 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-----
diff --git a/spec/lib/secure_mailing/smime_spec.rb b/spec/lib/secure_mailing/smime_spec.rb
index 7ade245b4..7af7f08cc 100644
--- 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
 
diff --git a/spec/models/smime_certificate_spec.rb b/spec/models/smime_certificate_spec.rb
index 6ac33e1bc..65e590356 100644
--- 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