diff --git a/lib/rubygems/commands/cert_command.rb b/lib/rubygems/commands/cert_command.rb
index fe03841ddb44..09ae43e35f68 100644
--- a/lib/rubygems/commands/cert_command.rb
+++ b/lib/rubygems/commands/cert_command.rb
@@ -96,8 +96,6 @@ def open_private_key(key_file)
     check_openssl
     passphrase = ENV["GEM_PRIVATE_KEY_PASSPHRASE"]
     key = OpenSSL::PKey.read File.read(key_file), passphrase
-    raise Gem::OptionParser::InvalidArgument,
-      "#{key_file}: private key not found" unless key.private?
     key
   rescue Errno::ENOENT
     raise Gem::OptionParser::InvalidArgument, "#{key_file}: does not exist"
@@ -161,7 +159,7 @@ def build_cert(email, key) # :nodoc:
       Gem::Security::ONE_DAY * expiration_length_days
     )
 
-    Gem::Security.write cert, "gem-public_cert.pem"
+    Gem::Security.write_certificate cert, "gem-public_cert.pem"
   end
 
   def build_key # :nodoc:
@@ -178,7 +176,7 @@ def build_key # :nodoc:
 
     algorithm = options[:key_algorithm] || Gem::Security::DEFAULT_KEY_ALGORITHM
     key = Gem::Security.create_key(algorithm)
-    key_path = Gem::Security.write key, "gem-private_key.pem", 0o600, passphrase
+    key_path = Gem::Security.write_private_key key, "gem-private_key.pem", 0o600, passphrase
 
     [key, key_path]
   end
@@ -298,7 +296,7 @@ def sign(cert_file)
 
     cert = Gem::Security.sign cert, issuer_key, issuer_cert
 
-    Gem::Security.write cert, cert_file, permissions
+    Gem::Security.write_certificate cert, cert_file, permissions
   end
 
   def sign_certificates # :nodoc:
diff --git a/lib/rubygems/security.rb b/lib/rubygems/security.rb
index 69ba87b07f8e..6b46a483fd1c 100644
--- a/lib/rubygems/security.rb
+++ b/lib/rubygems/security.rb
@@ -562,7 +562,12 @@ def self.sign(certificate, signing_key, signing_cert, age = ONE_YEAR, extensions
     signed = create_cert signee_subject, signee_key, age, extensions, serial
     signed.issuer = signing_cert.subject
 
-    signed.sign signing_key, Gem::Security::DIGEST_NAME
+    begin
+      signed.sign signing_key, Gem::Security::DIGEST_NAME
+    rescue OpenSSL::PKey::PKeyError, ArgumentError
+      raise Gem::Security::Exception,
+        "incorrect signing key for signing"
+    end
   end
 
   ##
@@ -585,24 +590,36 @@ def self.trusted_certificates(&block)
   end
 
   ##
-  # Writes +pemmable+, which must respond to +to_pem+ to +path+ with the given
-  # +permissions+. If passed +cipher+ and +passphrase+ those arguments will be
-  # passed to +to_pem+.
+  # Writes the private +key+ to +path+ with the given +permissions+.
+  # If passed +passphrase+ and +cipher+, the key is encrypted.
 
-  def self.write(pemmable, path, permissions = 0o600, passphrase = nil, cipher = KEY_CIPHER)
+  def self.write_private_key(key, path, permissions = 0o600, passphrase = nil, cipher = KEY_CIPHER)
     path = File.expand_path path
 
     File.open path, "wb", permissions do |io|
       if passphrase && cipher
-        io.write pemmable.to_pem cipher, passphrase
+        io.write key.private_to_pem cipher, passphrase
       else
-        io.write pemmable.to_pem
+        io.write key.private_to_pem
       end
     end
 
     path
   end
 
+  ##
+  # Writes the +certificate+ to +path+ with the given +permissions+.
+
+  def self.write_certificate(certificate, path, permissions = 0o600)
+    path = File.expand_path path
+
+    File.open path, "wb", permissions do |io|
+      io.write certificate.to_pem
+    end
+
+    path
+  end
+
   reset
 end
 
diff --git a/lib/rubygems/security/policy.rb b/lib/rubygems/security/policy.rb
index 128958ab802a..03ddbe530e48 100644
--- a/lib/rubygems/security/policy.rb
+++ b/lib/rubygems/security/policy.rb
@@ -165,9 +165,9 @@ def check_trust(chain, digester, trust_dir)
     end
 
     save_cert = OpenSSL::X509::Certificate.new File.read path
-    save_dgst = digester.digest save_cert.public_key.to_pem
+    save_dgst = digester.digest save_cert.public_key.public_to_pem
 
-    pkey_str = root.public_key.to_pem
+    pkey_str = root.public_key.public_to_pem
     cert_dgst = digester.digest pkey_str
 
     raise Gem::Security::Exception,
diff --git a/lib/rubygems/security/signer.rb b/lib/rubygems/security/signer.rb
index eeeeb52906cb..044562137cb8 100644
--- a/lib/rubygems/security/signer.rb
+++ b/lib/rubygems/security/signer.rb
@@ -47,7 +47,7 @@ def self.re_sign_cert(expired_cert, expired_cert_path, private_key)
     expired_cert_file = "#{File.basename(expired_cert_path)}.expired.#{expiry}"
     new_expired_cert_path = File.join(Gem.user_home, ".gem", expired_cert_file)
 
-    Gem::Security.write(expired_cert, new_expired_cert_path)
+    Gem::Security.write_certificate(expired_cert, new_expired_cert_path)
 
     re_signed_cert = Gem::Security.re_sign(
       expired_cert,
@@ -55,7 +55,7 @@ def self.re_sign_cert(expired_cert, expired_cert_path, private_key)
       Gem::Security::ONE_DAY * Gem.configuration.cert_expiration_length_days
     )
 
-    Gem::Security.write(re_signed_cert, expired_cert_path)
+    Gem::Security.write_certificate(re_signed_cert, expired_cert_path)
 
     yield(expired_cert_path, new_expired_cert_path) if block_given?
   end
@@ -190,17 +190,17 @@ def re_sign_key(expiration_length: Gem::Security::ONE_YEAR) # :nodoc:
 
     return unless disk_key
 
-    if disk_key.to_pem == @key.to_pem && disk_cert == old_cert.to_pem
+    if disk_key.private_to_pem == @key.private_to_pem && disk_cert == old_cert.to_pem
       expiry = old_cert.not_after.strftime("%Y%m%d%H%M%S")
       old_cert_file = "gem-public_cert.pem.expired.#{expiry}"
       old_cert_path = File.join(Gem.user_home, ".gem", old_cert_file)
 
       unless File.exist?(old_cert_path)
-        Gem::Security.write(old_cert, old_cert_path)
+        Gem::Security.write_certificate(old_cert, old_cert_path)
 
         cert = Gem::Security.re_sign(old_cert, @key, expiration_length)
 
-        Gem::Security.write(cert, disk_cert_path)
+        Gem::Security.write_certificate(cert, disk_cert_path)
 
         alert("Your cert: #{disk_cert_path} has been auto re-signed with the key: #{disk_key_path}")
         alert("Your expired cert will be located at: #{old_cert_path}")
diff --git a/test/rubygems/alternate_cert.pem b/test/rubygems/alternate_cert.pem
index 55303190f5d8..80b9a2a932ba 100644
--- a/test/rubygems/alternate_cert.pem
+++ b/test/rubygems/alternate_cert.pem
@@ -3,17 +3,17 @@ MIIDFjCCAf6gAwIBAgIBBDANBgkqhkiG9w0BAQsFADAtMRIwEAYDVQQDDAlhbHRl
 cm5hdGUxFzAVBgoJkiaJk/IsZAEZFgdleGFtcGxlMCAXDTEyMDEwMTAwMDAwMFoY
 Dzk5OTkxMjMxMjM1OTU5WjAtMRIwEAYDVQQDDAlhbHRlcm5hdGUxFzAVBgoJkiaJ
 k/IsZAEZFgdleGFtcGxlMIIBIjANBgkqhkiG9w0BAQEFAAOCAQ8AMIIBCgKCAQEA
-pebGm7NOnx+DtWG1xQsJBfTfwNlZvfzY61nlZccrhU6vx0AnYNiDZAG3J/gFQmYZ
-9gJ98rzEwfLMCGq9R/TZM+lAEaLhzYZCu3X4QdhKxr1xZ/SFC+1f8KVuH4tLXORW
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-NT/EqoE72tffaDnLq6rQrVtw4Kr9fy775DjNAWXyiCBjnJgOQSXCGPsM/AEdFrh/
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-ZXhhbXBsZTAdBgNVHQ4EFgQUYPwS8g98+4Tq/8gcEK1iilkGXH4wDQYJKoZIhvcN
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-fISkJd1Sn5j+Vx/NJ7EfZcOGGQMdxHC+c90=
+w1JNbNmBLCW7Cw6lZePL9d3gOi7ZoNSXEu4v3d1b0oMLuG1k1KPbB3GcXn/4T2wZ
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+AQELBQADggEBAEVErszzPGB6raXPlBRNhZJKzXZSRNBG0lR3th+we1W1loW1udaU
+pT65RDyRB0CoQ1e3JneYp5/qfXpY2lXk4RryMF0j4Ze9aqg0gqO97deA9Lu7xlr6
+Th1KXR1f8UXgKbgGS/hhw0AhF/4MM6HXu4dJORdRoQtM+GvSNPeDfLA3keKrXL1W
+WUgv5zC3xjm7xfWTv/zLUJhNNemQDPVfQzZoNxygp1tZVL8za+4ZmN8dGfc/GJur
+wM4mCj1Z/7NDYRoscAXsKgIsHUGa4dJPfdC8x8pbrOrnfbvtmRDcwFiyNGaTtu5p
+NUZUbCC0MqWI1pcW2VytWBuxcRD3J3IPv3s=
 -----END CERTIFICATE-----
diff --git a/test/rubygems/alternate_cert_32.pem b/test/rubygems/alternate_cert_32.pem
index e727189470e0..c3a8cc9e9a2e 100644
--- a/test/rubygems/alternate_cert_32.pem
+++ b/test/rubygems/alternate_cert_32.pem
@@ -2,18 +2,18 @@
 MIIDFDCCAfygAwIBAgIBBTANBgkqhkiG9w0BAQsFADAtMRIwEAYDVQQDDAlhbHRl
 cm5hdGUxFzAVBgoJkiaJk/IsZAEZFgdleGFtcGxlMB4XDTEyMDEwMTAwMDAwMFoX
 DTM4MDExOTAzMTQwN1owLTESMBAGA1UEAwwJYWx0ZXJuYXRlMRcwFQYKCZImiZPy
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+H8bfzw21G1/51AWX0xKRij+YshWkKreL
 -----END CERTIFICATE-----
diff --git a/test/rubygems/alternate_key.pem b/test/rubygems/alternate_key.pem
index ae587b342580..7ad67fde5e52 100644
--- a/test/rubygems/alternate_key.pem
+++ b/test/rubygems/alternate_key.pem
@@ -1,27 +1,28 @@
------BEGIN RSA PRIVATE KEY-----
-MIIEpQIBAAKCAQEApebGm7NOnx+DtWG1xQsJBfTfwNlZvfzY61nlZccrhU6vx0An
-YNiDZAG3J/gFQmYZ9gJ98rzEwfLMCGq9R/TZM+lAEaLhzYZCu3X4QdhKxr1xZ/SF
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-2M3MZEjqOGQrqY50khXUDi77H1sAHMIBQ8yF6mdb+YU+OayRwBZmHiI=
------END RSA PRIVATE KEY-----
+-----BEGIN PRIVATE KEY-----
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+mTt2nuHoeBWdnBcp7ufoeg==
+-----END PRIVATE KEY-----
diff --git a/test/rubygems/child_cert.pem b/test/rubygems/child_cert.pem
index 26c916cf96ad..593d1bf9e03c 100644
--- a/test/rubygems/child_cert.pem
+++ b/test/rubygems/child_cert.pem
@@ -2,18 +2,18 @@
 MIIDLDCCAhSgAwIBAgIBAjANBgkqhkiG9w0BAQsFADAqMQ8wDQYDVQQDDAZub2Jv
 ZHkxFzAVBgoJkiaJk/IsZAEZFgdleGFtcGxlMCAXDTEyMDEwMTAwMDAwMFoYDzk5
 OTkxMjMxMjM1OTU5WjApMQ4wDAYDVQQDDAVjaGlsZDEXMBUGCgmSJomT8ixkARkW
-B2V4YW1wbGUwggEiMA0GCSqGSIb3DQEBAQUAA4IBDwAwggEKAoIBAQCHyxiIjR9Z
-m3tznMc8OqAvm5h14DAUin+2eq1HzjQZ1fxkTtP4i05ieppHLTxfJrM9mH5H6sb3
-NSNtX/L7p229tM3on8UPUZRp7qDmFNTpgdRbf03ZJFDp3MTprA85wq++gc7GMI6q
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-fK8yCoTA6qYnYQrMPy3jcr0g3aak5+z5Gn55qIJklaAXV7vAyoNgYIq6MjXs9J0f
-kedZWwJTEfAarZDo2s9wEQi7McPzv4HmNB3H6JfJsAVgaD0WtQcAVr7Ngr24lIx4
-AMY7koGayD+VAgMBAAGjXDBaMBgGA1UdEQQRMA+BDWNoaWxkQGV4YW1wbGUwHQYD
-VR0OBBYEFEVZPH+Sg200JF29GN4RJ13XfpIWMA8GA1UdEwEB/wQFMAMBAf8wDgYD
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+q2GrNH+9DLZlzSpZu+z7VwejbGOCSgUsDNKLTOQItRxex5U3CBSI05xm6iystDOk
+AYCYKUqXgbBr1Spoc/L1dpHjrt7ZI9lDvW4GrP1mGwKCWDik4yF3TleiyO5Q6WI+
+cehXghrNYCk/5LWU0AOlv0qRiS/EriRvUNr56rZSRJs48bKIYX6GmgGLrGtZz5qg
+1NV5kT/l04cI6ZVGzAXy+8QP3/yYzK9tT7bly7Rc7qgtraqCh21bJT8dS/hjVKxM
 -----END CERTIFICATE-----
diff --git a/test/rubygems/child_cert_32.pem b/test/rubygems/child_cert_32.pem
index 4e2fcf10df3f..3082b0e1e716 100644
--- a/test/rubygems/child_cert_32.pem
+++ b/test/rubygems/child_cert_32.pem
@@ -2,18 +2,18 @@
 MIIDKjCCAhKgAwIBAgIBAzANBgkqhkiG9w0BAQsFADAqMQ8wDQYDVQQDDAZub2Jv
 ZHkxFzAVBgoJkiaJk/IsZAEZFgdleGFtcGxlMB4XDTEyMDEwMTAwMDAwMFoXDTM4
 MDExOTAzMTQwN1owKTEOMAwGA1UEAwwFY2hpbGQxFzAVBgoJkiaJk/IsZAEZFgdl
-eGFtcGxlMIIBIjANBgkqhkiG9w0BAQEFAAOCAQ8AMIIBCgKCAQEAh8sYiI0fWZt7
-c5zHPDqgL5uYdeAwFIp/tnqtR840GdX8ZE7T+ItOYnqaRy08XyazPZh+R+rG9zUj
-bV/y+6dtvbTN6J/FD1GUae6g5hTU6YHUW39N2SRQ6dzE6awPOcKvvoHOxjCOqkB4
-S7nN4LIbsuIhc1X61hNDERf2lZBIh/dYjVAmd72U2oQxv402n8jGJwAxPtupo3yv
-MgqEwOqmJ2EKzD8t43K9IN2mpOfs+Rp+eaiCZJWgF1e7wMqDYGCKujI17PSdH5Hn
-WVsCUxHwGq2Q6NrPcBEIuzHD87+B5jQdx+iXybAFYGg9FrUHAFa+zYK9uJSMeADG
-O5KBmsg/lQIDAQABo1wwWjAYBgNVHREEETAPgQ1jaGlsZEBleGFtcGxlMB0GA1Ud
-DgQWBBRFWTx/koNtNCRdvRjeESdd136SFjAPBgNVHRMBAf8EBTADAQH/MA4GA1Ud
-DwEB/wQEAwICBDANBgkqhkiG9w0BAQsFAAOCAQEAR53288aEhg6x3zMHv0Y8ZSqB
-+xPTrKzouqmHdaFBvEowIkfK6V29A2LAoIBi5DfsnkbKMGCD4mOlX3ipGoi7x2CZ
-UspOfXQ93CdiG9laS4sr4f5ZUJR1sc083UT1PBwqtnajjVUPxYz9I8g2ZxxawmA/
-bybbft/l4xHDv7RUP56uzm/BoCyiUdEC9gvq+5NYS95+M7v2J/CsvV34d5xnb8cl
-49zOoboN1JoZErPZ2dGnxpHvExOcQhz6CVUIEPri5eqRae+zln3RRd8RJ4gPe1FG
-H2aDHUwX7NKxY5Xq2NT2vUmnhTmNzFT5HC9gjG8Zu+2dPw0tTZNxyuctSAhAgw==
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+5cFW6+8ISXgqLmkK4iwEI5dVqwbuhyqImdq3DDa9PqARdfwD0Ma6+ZQDIkF0jxKq
+51q72r48l0+DpPmhOcJ2k55PQ4d5WJsHFE/GDnT60B5dM0DLqFSU46Fdl2/tn7dn
+plwsBeGjNiGLK8u4zokwnCs6h3ZmU8p2cKWh0HebZAVTh65MpB2FwMPyObGmCQ==
 -----END CERTIFICATE-----
diff --git a/test/rubygems/child_key.pem b/test/rubygems/child_key.pem
index 61fdfb628e3c..66bf52dafaa6 100644
--- a/test/rubygems/child_key.pem
+++ b/test/rubygems/child_key.pem
@@ -1,27 +1,28 @@
------BEGIN RSA PRIVATE KEY-----
-MIIEowIBAAKCAQEAh8sYiI0fWZt7c5zHPDqgL5uYdeAwFIp/tnqtR840GdX8ZE7T
-+ItOYnqaRy08XyazPZh+R+rG9zUjbV/y+6dtvbTN6J/FD1GUae6g5hTU6YHUW39N
-2SRQ6dzE6awPOcKvvoHOxjCOqkB4S7nN4LIbsuIhc1X61hNDERf2lZBIh/dYjVAm
-d72U2oQxv402n8jGJwAxPtupo3yvMgqEwOqmJ2EKzD8t43K9IN2mpOfs+Rp+eaiC
-ZJWgF1e7wMqDYGCKujI17PSdH5HnWVsCUxHwGq2Q6NrPcBEIuzHD87+B5jQdx+iX
-ybAFYGg9FrUHAFa+zYK9uJSMeADGO5KBmsg/lQIDAQABAoIBAA9dClPKuakK9xLr
-wjvdeymfvkZZ3L66M7xa0VeOLCVfKTzVEVTtt+ra6bETXGD8kStvIRx0YtntvGof
-wK85sGgV+HTw/Jvg1DyO98vIQBWCL5tBgjaGzhPDe1Dfu2JC1VzltVYFgOKgxCt3
-JGSfahRZUsUIjYZibARXVHnz9szRJFYg3lzBcVeCMWDGlPVydGaV3ttrhs4cFgPk
-1TinEH80K9GfpZvkH5/4O1E2uVFetSLONRQiTs+WXpx9flEXP+mNwdrjECI6xvIP
-x7pMfIo9kI9XniXXTvbGdEIeVrOL5OpW/nBCA3+EsL9S72TBVaMuiPTqUPlxA8up
-v/oS2qkCgYEAu7Kj1t2M+NJtR50wQ2g3efY1qO3dQ41SCnoGEWJd/17riNV3u7Xw
-FwPpnpcQAceoctK095JTtRTFGRN6FPl0VWuEsCS9lnwLzS7mQXiBg5EO7474v2Ki
-JPgncJefmCbtjJwaB78l+ybk9iUkdRv80QCHqdeHA5CegbsnDGkcJSkCgYEAuTUx
-Tfd3zpIEz0qhUf1D4PpgtoTj1zbXIUEFWl1SkLqklTF7k4LXZoWj7i3LraFk+jC2
-769qkLzF0CTHRFr5d00v9tCDOT5Sv2lqJw5UAmouKSuLF7XBp5tAkICkFX7Lo61v
-4iS2HtpK9wzri+L2XnDD3bxcHFHsEaxuD0V6iI0CgYEAp6Nsa4pizxT53z1IDtw0
-uCwrTt5rgVrlzE+hvcMSWvPG/+ZQUwmzDotDC462EDDnhO4mDPvW4WNUign4PmVx
-/pzR3JRj89SEodRieFUNr5lOMq2KAz0vvj8Y0pnJQ5Z5Ed2V7hdN79uUITeZMTM3
-AOAtSochohB3UTz7Kj1ykskCgYBPXZAHTSi2CLSu79g5fkJ8Qk73Z/MK4qFFyss0
-chFTm+ezV0URbVxIvrQE+PLzMNpIrF94Tr9nzr0l+Ny7WhDVIuqO5cOV4DMte0rV
-+bneXwnw8ovkWSrnXAxK4BVwcKlrNoNfcUPp7Ll7LLozc8sHpWMJvhHqwOBcont3
-Z9qecQKBgAiiWHPgMKChKDg/JVQGEqILF67c7ZuzBMtUHmGNVn8NNr++NXZ4YIRB
-/TgYNXySTgEuD7tUE6B/iO9Mp1CpJbzRtdk8oqJlgJ4rza50N07k/SGIIWl7hAr8
-No1ibENOfw7aeMKRz3udLT50TFoluykWc/m1nJEaqtSEJLkBRM5c
------END RSA PRIVATE KEY-----
+-----BEGIN PRIVATE KEY-----
+MIIEvgIBADANBgkqhkiG9w0BAQEFAASCBKgwggSkAgEAAoIBAQC68VMf9g/hrskz
+ypXMML1PFYaEAIdSj7tExYFcAi2OFnnk7km/tZAcr9WPna/aWjD1v6mI35JPOshq
+8b6dXq74izXodm/bfTPYAMXWgeL4c5J+Gw+GgIbNU71ayyd0LIiwpdQZNHhlX1xu
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+2VaJMhBWhSCOspd40ntROD6mFRx3XK+aZB2AOqMLwrzcUE3rQi5C1Hf90hVEohCm
++hkyHZiVQXP/C3iwvbtOfmKIl2/7tpKJpLK+h6CZWrbx6BGw5FnEGLeU11A2VGIU
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+htjwDQC9tZCT11Ya/Ch4/MroNTfWpwl+C7/0Amdj7eu3AnY2+fxWoK1KqvtH5dA+
+R3pkDUnWK3ruxnFlSUxjF/xD66oG75mpsl4vwtPBcQKBgQD1JtOZIA2752BO1T6w
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+vgOmDkcHSv1VniphHQBRQ2yf/XtUBCwZ0RKtSXqUF4nupBkq5ftSRktdJQ4tDg5z
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+UIPRis/+/kYKfb7nBoo0hOfUhE2WyfTv8HhH86pAGFPTbqMMea2PsBw4Hm6KL+iH
+wSrcJGy25OOt+IzCkA3pvG1K5i9T4UbDEOwkm9aPTMkux6HtivZC9Ng3d72fVfuL
+e5thLgj0nQKBgQCrthZgGuODyfzbOuI+QKkmaEOdN1Dh2zFSP026T5LqZLXsFPbL
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+Q0Sq/P+KmSysjfjf+yzA2WTGKmFcK3UDBfWKRsQvqPuMenvCln30mlCH85YqT1A3
+kQ1NYOxwn5jWMrxMSTFXa++EHC30aDQvTB+jPZAZAoGBAIIFBhAgm8yh6VM2JSZn
+819+OGuT6lvW7PWhoVaOH0cfrWm07ljBF5vCRfAlwY6R4k2ie6Poj1eQTguctaX9
+MwUTbMqK3ItsQ0/ZLN/fG+lLEbfJoqtHKHPaIoYLC9e5q3TbPyjy/9hI0i0uec5j
+4H4xUnsJ7hwz+1YUR6RPHWOu
+-----END PRIVATE KEY-----
diff --git a/test/rubygems/encrypted_private_key.pem b/test/rubygems/encrypted_private_key.pem
index 2d0022a6c005..ac65aff03075 100644
--- a/test/rubygems/encrypted_private_key.pem
+++ b/test/rubygems/encrypted_private_key.pem
@@ -1,30 +1,30 @@
------BEGIN RSA PRIVATE KEY-----
-Proc-Type: 4,ENCRYPTED
-DEK-Info: AES-256-CBC,4851D8D265711252BA5EAD983C957412
-
-0CH43Il/Lamd5AIkeYFRdCLJUUiUAEuAlE+DDYJ+Schulv9Lp+Au00VvAH/VVdqP
-jFzEJ7FIwcPac2y4SVSa8uMGdzezVhduMz3yrwWNSUPFAJCLazh4FhGMmK2kYRfx
-IReEBebwr1x+e3VqoREfTuwxQqpA5Ho7dgnrzSf2UeIQrnXfDh1rIn3SCqb/xYDI
-qqQ9bPlDs9iY/W24KM/ZfWOB/Dr6SQXXVDu1JS8EAxB9TK4PRMHZIBlIN+OVzju5
-v7FDysTu7g2BTH9BeHs4lWFpsUdJmrj0GjGoM9DCH/6xdPHQSWKpDptFu+06htBB
-zyr2chX5RMjlPxApqtz59YJaHLNhI/nABIAJdEvAgG3CAiYHB4G+X5kQwIYryJIt
-IeD8oerxNtNOVzunGL/QvYyiLB9EcDEBfPUIlriPCpTFz7r/GCLO2wX3y0u6m631
-rh/tVRPMzWTSd4HjJiBQZU/d2bVvdOKKY12b1ieai/QiaO7HjgrcVAgWLwJB8XKr
-QkXIo6W4uZv+W0YVTVQ5lPfwdNY6eQ1ZWPnqIOoczAZtFbs3zdBobgoIjyQ6cEgq
-fgRsIjJmLVYq39F2oDX7bLdUK5UaPgHWGbNi07cOIn0hqo6YNCw1YaQikUw4qfBb
-golYKoSV73/M6IVWlTjuzP6CRDRHY80epQjA3FR9P7ToT2VgcsG+pKxoYjZxotGm
-/E4PEEl+9lxNN9IXR4XuEzWSGTOiNUZ+iVOJIyNQN5tC8k6yYr08s12b9LVzvG+q
-Ro/bD/3UNaDwfujoSNgwKelZPBZmSkJIUECNDXE2i4hr6WqoJu7ZhpO5f/iU5d+i
-Ea0bbSne50zlYoIMIa7YG01zgI5Y+sV8BWSwwK+FaH5dORjpRUVat/yIw/Qx8VZ+
-f9RIfMnOShf5zvXIX8pF+Cayf8nPk4X8rhwrd+gL2cthHlYa58DkfKpJ4FxxRItJ
-mQ01K29PuQPYBdTXN0A8jurxQgETdM2R0JrLCnDOEleshUJqdsqC69Le5Sn5ucui
-ZWqxHjm+ycF4OAO99oq1T9QDyUCtIkMXPpf982KYVyzEbNw9hEr5/0CZdCaMEL4M
-gecBM9rpYeWy0ndmZ/Y9rBdTT6+en2WnONKQj3nCgL8e59y9S1VG+sgQ2LwQ2nxJ
-Mj2CeFi4B4D+2JdqyDKRFXfGKmzLIWW5Xw7/rrnMc7NtWZjRmUkvAOk3ILC81AmY
-QPCEuqju5q9hasKfIDBnB7/eNscAvf23Aa/P3A0NBTPcTko+M+Pkpc82m4eXx1Aw
-MfpfaIcfgPI4LEo+d8IfT0zcPNDuH9ACCcYa8/4q+PnKCmOsxgZ9wGpRHOQ2QfLR
-qTus6c0l9zab8EWJZBnQvuacUecU64OAryP3QAWZl/NerHsKZ/i9ZIDXtDIscCHl
-Yylu68l+vBZmfD455QN3iPVqSm4valJTGZnk40STtf8qLAuXdVhbyI921yGIz63n
-dcRx9+wd9M3VQqmvbrri8FuavTn9/uMMpKeOeR3AIhci8EJdLxhvz2A3+w9cxIO+
-Imj0syk5TWH0c3menzkYe2cO4P8jqBsb+QRdNcA2+YSTpEsvS7Tqvogl/RWnv7r4
------END RSA PRIVATE KEY-----
+-----BEGIN ENCRYPTED PRIVATE KEY-----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+-----END ENCRYPTED PRIVATE KEY-----
diff --git a/test/rubygems/expired_cert.pem b/test/rubygems/expired_cert.pem
index 12b883660786..7fd7034dc098 100644
--- a/test/rubygems/expired_cert.pem
+++ b/test/rubygems/expired_cert.pem
@@ -2,18 +2,18 @@
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 -----END CERTIFICATE-----
diff --git a/test/rubygems/future_cert.pem b/test/rubygems/future_cert.pem
index 06e08bb4c628..1f4ff9b81595 100644
--- a/test/rubygems/future_cert.pem
+++ b/test/rubygems/future_cert.pem
@@ -2,18 +2,18 @@
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 -----END CERTIFICATE-----
diff --git a/test/rubygems/future_cert_32.pem b/test/rubygems/future_cert_32.pem
index c0231101414f..7713645ad7ab 100644
--- a/test/rubygems/future_cert_32.pem
+++ b/test/rubygems/future_cert_32.pem
@@ -2,18 +2,18 @@
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 -----END CERTIFICATE-----
diff --git a/test/rubygems/grandchild_cert.pem b/test/rubygems/grandchild_cert.pem
index c1d9887b60ab..276f81368b66 100644
--- a/test/rubygems/grandchild_cert.pem
+++ b/test/rubygems/grandchild_cert.pem
@@ -2,18 +2,18 @@
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 -----END CERTIFICATE-----
diff --git a/test/rubygems/grandchild_cert_32.pem b/test/rubygems/grandchild_cert_32.pem
index 5d1ad45cb7b1..fc2f7ce75781 100644
--- a/test/rubygems/grandchild_cert_32.pem
+++ b/test/rubygems/grandchild_cert_32.pem
@@ -2,18 +2,18 @@
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-DkMr4MWfkMOyVlrSkvjPtW1oHVnxfZgqaE91J0Ht9qiHvekti3JDqxqcKaYuIgAL
-w9HK9z5uQA2KrMvqn/jiuD8lBFsnuA==
+GRYHZXhhbXBsZTCCASIwDQYJKoZIhvcNAQEBBQADggEPADCCAQoCggEBAI4LI2kY
+pjZvPG3C1+mBlx+X1qge8c1PNguotslWKUnOS2d6T5LyrGJQXNIeWgs2Ial2v/eh
++wzBEt6AZT84e/W/6i/dZ6UgiB3dyHhr8PoOBjZ3RP1QqTmYxFDOYV4qKNy3qVFI
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+sl0ILk6zrRTT/6N1G1RFIg7a6ft3dFCNBh5VA1a/bpbwfps1UlJq3N8G6wh4SRhh
+m6cLLeu1io30sTcCAwEAAaNAMD4wHQYDVR0RBBYwFIESZ3JhbmRjaGlsZEBleGFt
+cGxlMB0GA1UdDgQWBBTLh7cgH1IzYIZHfxQs9DU+5wdbgzANBgkqhkiG9w0BAQsF
+AAOCAQEArYO1ZeI10KQSc0mUiq++RRWj9w2wVE11ocld71DP6UyRLinOgSTM5jfJ
+LoNnMfswfEoRaUyUAGvr2EdBrQbPQafYf5ao5lrXF9vONT0OTyR7MfkJWxL7rci0
+fNKIHKJVxPtCkhyKPV2OKvNMkvuoNMTqsB2WSZY3fGr6TqJW23RSC2Dg1zvdbl0F
+L9icHjHF9cwZ4c5vAsi2iatvILHvmbT7s64fAIgwHlQHGE6/kCKyqJq3F4/htNJw
+EXFJIHwgkgZpoktQC6cY4CRaONkOCqwYLQsZ846M0ha3Ouq06YOKSRo+uGTm7yyU
+ccdnYZ0InEXVbbAA2r/4315/IVtviA==
 -----END CERTIFICATE-----
diff --git a/test/rubygems/grandchild_key.pem b/test/rubygems/grandchild_key.pem
index 63635844b0d3..c60cfdd133e5 100644
--- a/test/rubygems/grandchild_key.pem
+++ b/test/rubygems/grandchild_key.pem
@@ -1,27 +1,28 @@
------BEGIN RSA PRIVATE KEY-----
-MIIEpAIBAAKCAQEAyh7ulK+O7leQKBQzSSvhEur49Xu4sQJllkVbrVvkv2jSo68w
-oESgljSS8jCSX0I9IJ5T0kHzNRpiuOpfWKZx7E4cKeqW6nmV7D/B+Iy1QnJbMzUd
-nxp1Y+CMCK0JrLIsFBnxndVmiS/S817W3coqkmZqce4e33/O0qmCChGxGJZuAVQF
-GYI25SiYWPbysVEjwXoW6zO0D1m8QZLYYCeDSRpxKgItBoJK+Up+bm/nsrkFvUf4
-kAZNLgik5zvflM3/MjyxzxgY2MO07YaULOlr0vZN6Wxnq2F3jkuZY8JbEOpQSDGS
-gU2wJ1iFH+GLvj7LsBuRScjL0FJ4s1EjqjjP8QIDAQABAoIBACI/cwQxKiojHqtX
-3ufNXlYfB//Kjr05j36SsonRqhUv3Q88umPRtRc2gda1Wbv35JUwFrpoD96F4cf8
-+Jp0G5YjlxyYIinJX9i35fVoXDdN2ru2ypXgvRbnH7tBnMPNLfBbBAiPNhBVUOyJ
-e6V5odSMM4mqBEOxK5mg/MaZgFVOrNf/DEI5oFSny7duEEQAuGJadJHUJOh7al0b
-lByNVNAYNkdZMgvOdoAoyEzg5tvY9ykIwXUKdMwBgSlldolLYXyAjluXOVEj32m4
-p3rEV/vs+RQFTLLWXfyVyWoMIPYaK6nNaYpB8fMHnIjga8MzBgC6Hso3HqymRdg2
-Gttp4PUCgYEA2LQL72tzhUb+a0wo7dWJ4MY0ekyA7JxrqZRTWSNuqKMoAb6IxaXe
-quZcpht/430szpOOz52pEwEEKUsCMuqwHiqmO2ZiZqYJpDQet466GFnhYhmAqV/x
-bOaZLVbhGjiMQCD5YbpAmXjxF8SFbkqSKlSnpjxJKD2tGNX5FFWpN4UCgYEA7sXt
-Xsf0XaPbISe2gYdXMO3exHplayt7C/wqjcxMePwtSwAJD+/JrFvFSiPBKT6Ajl+M
-dcJIb9+WHhjk5GJI7KU4AVpf4feu5o1QnpnSAzCUlXpldYwSUS/7LZALvABm68Iy
-2gHU1Aj5DYB/4nesWVhExKrMZDAICVojS5jCJH0CgYEA10SsIo9cN4ZZ0J7cfb7F
-88sRcHg1DlcowFG/JmqDT/ScFnd/CNCITL8ARGZG+eZsL1333RiiT2WQC7EeoxPu
-FlmJvrIriAriwwKfjPq0tOH8eeYZoKfVfbfpbFfEz7Zi5IWdFk7eQ1cYMOMhJXng
-jzp/PCzhA5+ZJ3XPtDqQGb0CgYEA1AuwPuECUfqHSw1yldt0gj5s/D3aPW+SydT6
-kYziSPti2d1BLwb7Kfch4TKZgyA/mLCgE6AjJj8AmN/wviXOr2IWt5Tj29BTYeoT
-s5XVHQISoiDdY6OuTK14ukDXOvF8dVi0QkkoEdmaG/SHHb67r2ilQaaQ91R0fqGv
-AJ67ox0CgYBxkRfXPCnljxrJN7Fb1fS/DE1yVNWNkLiANOlUnPwzaD+jV0miCwEG
-mR1PoRBG0j4sYTp9RyVCwR1RASNPStDTF/VcSllDqI45IHToKqgfeIlApmnCu291
-km1gAveM0Ayg5mLsIfIHyOlPZRL0iuewDDkwFNtwOiR87o9BurhRow==
------END RSA PRIVATE KEY-----
+-----BEGIN PRIVATE KEY-----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+-----END PRIVATE KEY-----
diff --git a/test/rubygems/invalid_issuer_cert.pem b/test/rubygems/invalid_issuer_cert.pem
index 5cb9d22a87b9..9ec91669933b 100644
--- a/test/rubygems/invalid_issuer_cert.pem
+++ b/test/rubygems/invalid_issuer_cert.pem
@@ -2,19 +2,19 @@
 MIIDMDCCAhigAwIBAgIBCjANBgkqhkiG9w0BAQsFADAqMQ8wDQYDVQQDDAZub2Jv
 ZHkxFzAVBgoJkiaJk/IsZAEZFgdleGFtcGxlMCAXDTEyMDEwMTAwMDAwMFoYDzk5
 OTkxMjMxMjM1OTU5WjArMRAwDgYDVQQDDAdpbnZhbGlkMRcwFQYKCZImiZPyLGQB
-GRYHZXhhbXBsZTCCASIwDQYJKoZIhvcNAQEBBQADggEPADCCAQoCggEBAPEZZzId
-y0m1jSbcHBwUc0MLpq/+JJdwLpGrjD35CuI7DNP0MiH+mNHblyTqMadB3font26k
-QFIjDZtc1es1Zvt4mNo1lScQsvbVGRFDQK2/xdZ0O0GbK31C7IJ2Boa93F+74f7N
-eD6LKn++SWCxHNCKV83RumQ6diG/WdUZQu8k9xjpRywI2u2EwNDETkbhGamj5zNj
-7a8pcPyifBxzTiZ9FZvWVaCEODvdIrF4NdIteXyYEQwDRLWD/nQ9Z9wbw4KQCtA/
-UUd+rObocjveau1wLiZryumhZRwwIKZU4+aaANYTFb3tbmUKnoR9aLavKvxEnlF0
-5kHo9xcHoS5ftw8CAwEAAaNeMFwwGgYDVR0RBBMwEYEPaW52YWxpZEBleGFtcGxl
-MB0GA1UdDgQWBBR17dM2zZQQPor/k6N4/JXerWXhSDAPBgNVHRMBAf8EBTADAQH/
-MA4GA1UdDwEB/wQEAwICBDANBgkqhkiG9w0BAQsFAAOCAQEALrT6pmN79vdBA80a
-f8C1DnWAYNyXskmskWPVMnTtgrDGQkqz0Uqq7nBdWK75FiBjk3XAOiDonZegvho+
-NZUnotUFyTpkkn95q1qpkMwgTufamQlxsBxkDZLPiWqvZS4guSucVgZeEtEOy0R0
-AKXA1SZmhC7472z+pwXprGj86K4SX7w15LxsQ0wDP5qduKFItNo/CnBEP5w87/Eq
-nxSbUN3dt7Glqt0iIp/I4mZlA4OnvtKfqTitATKOnBvHxIzvm9/6BVItjET8DRXv
-2ZEVvEcnkNNRKwNbqtI3V7AzB3lf3E4nb86gFh/GLI2XRN4LlWZQ4PmyE22B8IaZ
-vpqxaQ==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 -----END CERTIFICATE-----
diff --git a/test/rubygems/invalid_issuer_cert_32.pem b/test/rubygems/invalid_issuer_cert_32.pem
index 2b7117927065..26f4d2010265 100644
--- a/test/rubygems/invalid_issuer_cert_32.pem
+++ b/test/rubygems/invalid_issuer_cert_32.pem
@@ -2,19 +2,19 @@
 MIIDLjCCAhagAwIBAgIBCzANBgkqhkiG9w0BAQsFADAqMQ8wDQYDVQQDDAZub2Jv
 ZHkxFzAVBgoJkiaJk/IsZAEZFgdleGFtcGxlMB4XDTEyMDEwMTAwMDAwMFoXDTM4
 MDExOTAzMTQwN1owKzEQMA4GA1UEAwwHaW52YWxpZDEXMBUGCgmSJomT8ixkARkW
-B2V4YW1wbGUwggEiMA0GCSqGSIb3DQEBAQUAA4IBDwAwggEKAoIBAQDxGWcyHctJ
-tY0m3BwcFHNDC6av/iSXcC6Rq4w9+QriOwzT9DIh/pjR25ck6jGnQd36J7dupEBS
-Iw2bXNXrNWb7eJjaNZUnELL21RkRQ0Ctv8XWdDtBmyt9QuyCdgaGvdxfu+H+zXg+
-iyp/vklgsRzQilfN0bpkOnYhv1nVGULvJPcY6UcsCNrthMDQxE5G4Rmpo+czY+2v
-KXD8onwcc04mfRWb1lWghDg73SKxeDXSLXl8mBEMA0S1g/50PWfcG8OCkArQP1FH
-fqzm6HI73mrtcC4ma8rpoWUcMCCmVOPmmgDWExW97W5lCp6EfWi2ryr8RJ5RdOZB
-6PcXB6EuX7cPAgMBAAGjXjBcMBoGA1UdEQQTMBGBD2ludmFsaWRAZXhhbXBsZTAd
-BgNVHQ4EFgQUde3TNs2UED6K/5OjePyV3q1l4UgwDwYDVR0TAQH/BAUwAwEB/zAO
-BgNVHQ8BAf8EBAMCAgQwDQYJKoZIhvcNAQELBQADggEBAGolEDY9meTGpP7j3Meb
-pxtLX/JYPiTMqQR+FOOdGJlXg4V9syMBYUMmUj3yEPnpBFmDgDtBaH+OQcFuvf43
-mQYOQoTJD6OpC08fkPdVw56Em+cuUCXtDDYY4gc+nVRKk4+tJqkizHNAazqKkZoQ
-PaHaCfXsrMGPLXxh/kbk14ESU9pL0LShh/bNn68hlAKwN2ctTSlfm81QgbNX83d1
-6kLSckj/9B1ksi6ks/eHkHWeMaiJe8H3vAU6PE6NeU3WRZY1ulSGOPleYfJA99fq
-z9yks8IxwMzubJStq2sQ0n6gu3XS4Qu0sn3ih0TwRyUOSQkWa2Bf5SwUZ3/YJ25S
-Wkw=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 -----END CERTIFICATE-----
diff --git a/test/rubygems/invalid_key.pem b/test/rubygems/invalid_key.pem
index bc02147403cd..b3abcda9122b 100644
--- a/test/rubygems/invalid_key.pem
+++ b/test/rubygems/invalid_key.pem
@@ -1,27 +1,28 @@
------BEGIN RSA PRIVATE KEY-----
-MIIEowIBAAKCAQEA8RlnMh3LSbWNJtwcHBRzQwumr/4kl3AukauMPfkK4jsM0/Qy
-If6Y0duXJOoxp0Hd+ie3bqRAUiMNm1zV6zVm+3iY2jWVJxCy9tUZEUNArb/F1nQ7
-QZsrfULsgnYGhr3cX7vh/s14Posqf75JYLEc0IpXzdG6ZDp2Ib9Z1RlC7yT3GOlH
-LAja7YTA0MRORuEZqaPnM2Ptrylw/KJ8HHNOJn0Vm9ZVoIQ4O90isXg10i15fJgR
-DANEtYP+dD1n3BvDgpAK0D9RR36s5uhyO95q7XAuJmvK6aFlHDAgplTj5poA1hMV
-ve1uZQqehH1otq8q/ESeUXTmQej3FwehLl+3DwIDAQABAoIBAAQ1PSEES8XZESzH
-nwakcBCQValGW8LNi+/cmSGEb7qxbNC5jIhzBkgfYjIcPkqc3TAeXQFlhNPfgGog
-7YDh7o60Ck2WAtOVjdy+AmZ+kH9Cf271719+mFHi3E2N8XY3k8Q9+2dJlHAvA0pg
-eq0L2k9kzWcuYmeZF50Q1xNfkf9U0qkb6tbx15NOGFhQMUZ/mMcbYifW/bQnU2YO
-2vgxWFDItk0c82gpi/uo22gu0TjhcBp/ByKMgXV8xrLCW7Lsh1DvJ3LtigD0Zp5s
-XtdXcF4KOo81VeUijDbByIQQJTxBlfmgdcyarAb7kV107wvDh55Xd8m68lZUrkj5
-tc3dRf0CgYEA+crRUXgtdeiHqN5gZRg6MF6S5yxFiAaKgeeKm/x/2xpMmoiyWhFv
-tK1DLxRHEGiFuWc9IGgrWu2udEg8VE4j2EExvtFi/w3lSHxBArjeq7oCabnDk261
-lRCNzYb0HU5UZL3vBsHW8pCdnDfaOxlrT2+cDVN7LHd20DsIZROG7T0CgYEA9xdH
-wSNsHqxcB44A7iNNvHxhU3Vi6QCIpzp8sfjc/fd7Ghe/MIn67gs5XPtT+DvQME0N
-4hNEy2GmbHjVJQXqlf4VSWdFJ1RnKwL+4rnOiWq5sNrxmlXuTvOTRLimpjOsLKCR
-G3dgKXiH7/qU9zjLljKOWgo7gqv3cPrPIL8H0jsCgYEAp99SRTpK8w7O/QJWLhrW
-IGOuvoXWRNCAjUUatjI/ivRlvwVXN4i4VeiLWjx6deCI3k0vm3PmjzllIOjbAp1x
-IYjO8bqumVKxYMGAv1+W5jogHQWnFpI0nnV9lz63GGrn9Lxgw13KI0JlafNvSoCO
-ydfsPFh6UywGQXMq9SLmbtECgYAHWC3N09u23bCumM32Rh5dZ+UMsgSKoHVvYxGp
-yJfpBJ4oHGSWcMOAp9zAosfQLRb3GJM9EQ2ObgygVMchHpfmdXL0h5lKnfujD6e7
-3YICG6YBV8CusbcvqZXLCSIK9qY7fVpS0q2NDgQcYfpjjtCeWkpY6szyCWKFfS8C
-7iqxWQKBgBIwdnksccXP01svXJ0tMhiAKx1jKY/aJBPIpcSqxTFNe2WpgzynRpUg
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-r4Dl5bcnDRL93Phbx7MAmjMO3TZWbQGfEgDuqk3sS1QzKMJnBLAO
------END RSA PRIVATE KEY-----
+-----BEGIN PRIVATE KEY-----
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+6f12dS6rEvyh/uef5Ve8AvsU
+-----END PRIVATE KEY-----
diff --git a/test/rubygems/invalid_signer_cert.pem b/test/rubygems/invalid_signer_cert.pem
index 59364ee51b59..43acb47d4d42 100644
--- a/test/rubygems/invalid_signer_cert.pem
+++ b/test/rubygems/invalid_signer_cert.pem
@@ -2,18 +2,18 @@
 MIIDEDCCAfigAwIBAgIBDjANBgkqhkiG9w0BAQsFADArMRAwDgYDVQQDDAdpbnZh
 bGlkMRcwFQYKCZImiZPyLGQBGRYHZXhhbXBsZTAgFw0xMjAxMDEwMDAwMDBaGA85
 OTk5MTIzMTIzNTk1OVowKzEQMA4GA1UEAwwHaW52YWxpZDEXMBUGCgmSJomT8ixk
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-6I58NEMCOuN4CxFK4oWD9xuD4j+wtHy/UYxqor4rn+UKYHfr5fWtAyRJ3gD8vMUu
-C+Nl2vB8t4OVwS5FCcn0ZK18bPU=
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+/14DAw/EE3cmyHJngmg+2q/rSw8=
 -----END CERTIFICATE-----
diff --git a/test/rubygems/invalid_signer_cert_32.pem b/test/rubygems/invalid_signer_cert_32.pem
index 97feb8fd0a9c..a2120c352da3 100644
--- a/test/rubygems/invalid_signer_cert_32.pem
+++ b/test/rubygems/invalid_signer_cert_32.pem
@@ -2,18 +2,18 @@
 MIIDDjCCAfagAwIBAgIBDzANBgkqhkiG9w0BAQsFADArMRAwDgYDVQQDDAdpbnZh
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-/xJ9J2AvFG6EXclDVmkDQpo1fUVhWM/SPKD6HJWuB/eyjA30xSj+UeLmBYjdKzHt
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+saBIHP3Rr1qr5FoYCNTBdXaC
 -----END CERTIFICATE-----
diff --git a/test/rubygems/invalidchild_cert.pem b/test/rubygems/invalidchild_cert.pem
index 281dcce655cf..b9de586e162b 100644
--- a/test/rubygems/invalidchild_cert.pem
+++ b/test/rubygems/invalidchild_cert.pem
@@ -2,18 +2,18 @@
 MIIDGDCCAgCgAwIBAgIBEDANBgkqhkiG9w0BAQsFADApMQ4wDAYDVQQDDAVjaGls
 ZDEXMBUGCgmSJomT8ixkARkWB2V4YW1wbGUwIBcNMTIwMTAxMDAwMDAwWhgPOTk5
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+/GLu9uVHlmKv8Mf+WtPWFfi719LEflj8TBWumkzIdQfkt0mGM7KOG5DeShQk8tE/
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+0qRM0RTPeb4V7biDzY8PzR1bWkMP9HSWxBB46g==
 -----END CERTIFICATE-----
diff --git a/test/rubygems/invalidchild_cert_32.pem b/test/rubygems/invalidchild_cert_32.pem
index 87885157f8da..19dbd252cdce 100644
--- a/test/rubygems/invalidchild_cert_32.pem
+++ b/test/rubygems/invalidchild_cert_32.pem
@@ -2,18 +2,18 @@
 MIIDFjCCAf6gAwIBAgIBETANBgkqhkiG9w0BAQsFADApMQ4wDAYDVQQDDAVjaGls
 ZDEXMBUGCgmSJomT8ixkARkWB2V4YW1wbGUwHhcNMTIwMTAxMDAwMDAwWhcNMzgw
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-xZoJvEHwpOMTxMaAFXSkyMjZAoOzAn9qP6eLbwwzeuckIrZXxYBfGcC29VOPPAN4
-IPX0IUZ7/LlzzOE5iuVS/RIBRcD+qpEzSXs=
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++j8g0VBBBJawarFvn3G390l/dEuFP8UC/LtaLbdT4b9t54iwAldTjo8HvjyeCqah
+QJd4TWo7FM9gVHwBwBKcHQHdJfbW8FpkNaQU1/1/QvqE3En7Q99xFBur/9bP6vFB
+UCc5lyBe7gTTWa9A6+GT4uZD5AkFfjyMqB0=
 -----END CERTIFICATE-----
diff --git a/test/rubygems/invalidchild_key.pem b/test/rubygems/invalidchild_key.pem
index 1c9997150d8b..83e2875dbe8e 100644
--- a/test/rubygems/invalidchild_key.pem
+++ b/test/rubygems/invalidchild_key.pem
@@ -1,27 +1,28 @@
------BEGIN RSA PRIVATE KEY-----
-MIIEowIBAAKCAQEA7Hai3rHJY9v+h5yS8OGpeLMIgxQQOFtCnjktw1zmtpOfqzXx
-mnCjkPwJHIlJ86i4gvQ+Pcf2C5Z5SWHkjBuewu4IsYSxxw74gp3kMMvE5QqboVF5
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-LAGbB3mm58bMPtKnUS5DlEqn6SPfXdQKhPj+SJh9dDMEkCHS7d+RPKoz96X3DkrU
-8nhZgr+k95kUd1CGxha1+5BDNqcbeU/pcBLXfO2RT0b0oauf2j8EtkE8Cx3PD+Se
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-PTqc9LLNaHpR/z/oFC/wUiMdJzHB1vBFUcwHvTmahVfqwaffqLj/zJa12ztMcZ/W
-efRFBb8CgYEA9c6JvqB0gR14Q6Shj7Yg6JM/dO3e8yllvGRsJm0S6IHHlblWeUEA
-OeY099wD0y0oK56XvgfZyd2k+hK/FKf5/otgCyzr1i64sx+hpHE6MZ/s08VLYZvt
-+N9fdk7Z5crZImo8vne+7AfBhY1UNk6QjwSUMe8U/zQ6BBGbNhKtgCcCgYEA9kTo
-6xyt836PGSXFSnup3wdjlbpMlXMnvZG2V0Aw3ILdTg2iGGf37UUBzDjnZFxVRPqm
-PqHJwzjd8PZesDFvaZQ1Sn4nRLKZj0aLLOGuaUOoTAP04fQkYltWR+j8w+d4JxX6
-CDNbNtf4EYRVhfNO02WCNyE4xHya7s6u4tnySYsCgYBNlRPay/AZtIB58SNhJZ37
-akZUFKQS4ZUPwi50bmbSZevlsOq/OKnmnGdJd/LpG06bfeHtA7NUyJVCrNoMnfwE
-wF7fCB2jq3l2Z9xv96DjetOX/6SMOVgB/ha2U6rooX6pIxjrEQZ8nvIQwgu7XE66
-JTrVC933srdBA4GWrox+bwKBgQCRZLWuuUvpyfpp+ma0RrZPumkM6OR2B3qa7QAe
-GwO97HUDtADTL+6r4mXhUGcsVWbyRpkHuTUJUPWXYZ0doNIKHzonNLuyT09hy2A3
-qzXxZ8RgvKVDEYS5nPsfkWpJrsq9KLhpRwi/JFqM3PgxESiknfV23uJI/tfpzZRq
-0gm9aQKBgBuxr0xIXZpUuXwOnLIyp0qTPltXPentl71qV3tQvkqlBU+nCKnaa0ur
-7PuEGuFC0jiPiBuRbcO81kq9QTPX6poEYSEFhHphuj9o5/G8MqnC9GzHqVwjc+fI
-JPiixH1Dx9YWsCbnCw72lEdpnxMgk1efnzbV00tl63JgMjkyHBJz
------END RSA PRIVATE KEY-----
+-----BEGIN PRIVATE KEY-----
+MIIEvAIBADANBgkqhkiG9w0BAQEFAASCBKYwggSiAgEAAoIBAQCwK9EjfLPR6YGB
+R7bDDWh+83/VbRdXQB6n1q4Cu3RsXSF/wJ3ggCvyWgkv+ZtB+ZbJiosTbmDPe4k9
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+2JDyHi1UgJWYVKoRO8+MwOXX7LhWK7T4V80C4ZsvusdDQgYuqSi/GNcflYg3EWsy
+1WKCdly+Nv4hsHMEuptaMw==
+-----END PRIVATE KEY-----
diff --git a/test/rubygems/private_key.pem b/test/rubygems/private_key.pem
index 4e6ce13e65ba..97f34197e67e 100644
--- a/test/rubygems/private_key.pem
+++ b/test/rubygems/private_key.pem
@@ -1,27 +1,28 @@
------BEGIN RSA PRIVATE KEY-----
-MIIEpAIBAAKCAQEA0ULcfpDboY5uWVdOIkF4AtRui7PPFoaKfBl5hiGFcpYRx8DQ
-PyT7bbD8nKd14Rhzb0nHCMU3DEz8PLJCmWm3NszVDkEJws1BpCGak6vKiyNa5hZb
-UlQMZMbecSDSpEKu2PBWgBT74qg2RBugzTAVAnGQGezQnWyv47kyXvdjMoq11VZa
-+Dz2izHJvjBHGQShr1r9v39qIrtah5CEXTRxEqhr96gg3y6xOPMqxi50dS0RBaJs
-PsjFZ1jecye0Z/WPItiLjSVVRssUXK1a2VkYxUqkxUg4wwJD57H4TEZBomtAXlAS
-o+rUv8G9eBNmS/k/oJLdiMF1ULb+e1+izeAyGwIDAQABAoIBABS+vR8q+ysD9LqU
-piFNPjmBl8fvtmr0QYxV9i8u6YzXhcG4wqxP3UEdl51sGIqNIvx4YuviqTdl9meK
-AII28bvUCJcWKYKPWJ+N2UYkdLrgcWV39+use2IOOQUcDOXN2omVIe4mpmXs6RxN
-ZN6SkrKgUXnQeUnx+Wno9S5m9gWPfrAMTr8iwBquo5JMFqJmAlfq1cIActU7SE6M
-7LJZ8rbVGuGmZAyqJw/I5xvxts6NlTFBm2AyGq74wtbUD4OlFDtOTA57LmtRswmr
-MK+JG5LIJIyc6qKQwmHU8vLstJEcVUyCJDbpjDkApd6GQ2FwXXode+S9C40DZKvi
-hnaGfKECgYEA1ArI5tt3GdNR4CbY4e4yDHEuSdSkMVsRa9a7gdtrrjyNitBMbZNE
-HZNqswijBCPZnXPtBxeytMUmlU7uFc7xx3QQvuBSJ6HOb9j0qtWVL+jl8R9XLogH
-sE/m0yMPs2IowevJoQ95KRZIirLywZ8QgTsySEv9U4hx2CdKpn7IeRECgYEA/KR9
-WI1n6pxDbxcjWMaOdziIcgDBk7v05Qssb1OePiz+y+zfrBVqDjsvsokRLoElSAkR
-TAV+/9hRgAu4cZJpP0FMdFe+sVkr1UfcDqvJdgumBL+xUNxRV/QFvuprLa6XbiQO
-jUclJR6BPdXeVQPDUHuQBgnwXrJdRtMl9Fj8GGsCgYAhZKVo/e0OyyHczCFhy1Jk
-dTqV8//7qdzff8y90aFuqiicUNuIciXLBplKIrURhNfTnRsZ/9hr8ZR29Rw3oQSg
-pZ2xgcBOb4QER0WY1dQN3H7B726abF/Rm3O9kor5dB75EzoIvFgXaWP5O99RMMy3
-nWv4yMbXbeiH4wA1okfOEQKBgQDkaAnyrxUN5GyK2M5aCljurCufddOMrtb+5BUu
-KNjduWw6DVNCjrGtYBEFRipEcvmzoI8EvctNntJAA1ijRQzl5TEr1dBPIiEg17C5
-itG+aVWU4YF7a1QXQkSXj/OJ/1hkeTC2xWVto6CQuPQixB4mey+AZifsVTFDQM4F
-lRWFNQKBgQDQWRXaJgc4Jeur1/I1iMAcihN/o4Lra4baM07FdpFWrePJ4IimXHG+
-buws6BuytnQP56hqIQYLQSWCF192dcnHNbodXz48Ug6rKLSBalxH3pvThYLpkBSk
-7OrfHzO4TTVaCH1mcPjzj9vmRog2tvrF/m6/8UAZQIBGDv2+cHk4rA==
------END RSA PRIVATE KEY-----
+-----BEGIN PRIVATE KEY-----
+MIIEvAIBADANBgkqhkiG9w0BAQEFAASCBKYwggSiAgEAAoIBAQDAyPsAwtLYyqcu
+kL7YSn+8Pi2YbdSexPmCtpRZeMu/qQhSnxtTNVHshpEpLRBX2e7TI+9aIQXQph2D
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+PG7IQ9fNsygQJsYD7QPR/KbeJov8ToZ3uaEASoxYINpXp2zuVteq/bIRAoGADOwH
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+vdly8yYIhg039yKWpOOJrD3BuulZKGwoWKjkEHY+GZjT/L6/pH/OEiTPYaFUqDik
+mc5PGGx13AoyVw9N5G4VhA==
+-----END PRIVATE KEY-----
diff --git a/test/rubygems/public_cert.pem b/test/rubygems/public_cert.pem
index 7481c26b7946..e640a9132395 100644
--- a/test/rubygems/public_cert.pem
+++ b/test/rubygems/public_cert.pem
@@ -2,19 +2,19 @@
 MIIDLjCCAhagAwIBAgIBADANBgkqhkiG9w0BAQsFADAqMQ8wDQYDVQQDDAZub2Jv
 ZHkxFzAVBgoJkiaJk/IsZAEZFgdleGFtcGxlMCAXDTEyMDEwMTAwMDAwMFoYDzk5
 OTkxMjMxMjM1OTU5WjAqMQ8wDQYDVQQDDAZub2JvZHkxFzAVBgoJkiaJk/IsZAEZ
-FgdleGFtcGxlMIIBIjANBgkqhkiG9w0BAQEFAAOCAQ8AMIIBCgKCAQEA0ULcfpDb
-oY5uWVdOIkF4AtRui7PPFoaKfBl5hiGFcpYRx8DQPyT7bbD8nKd14Rhzb0nHCMU3
-DEz8PLJCmWm3NszVDkEJws1BpCGak6vKiyNa5hZbUlQMZMbecSDSpEKu2PBWgBT7
-4qg2RBugzTAVAnGQGezQnWyv47kyXvdjMoq11VZa+Dz2izHJvjBHGQShr1r9v39q
-Irtah5CEXTRxEqhr96gg3y6xOPMqxi50dS0RBaJsPsjFZ1jecye0Z/WPItiLjSVV
-RssUXK1a2VkYxUqkxUg4wwJD57H4TEZBomtAXlASo+rUv8G9eBNmS/k/oJLdiMF1
-ULb+e1+izeAyGwIDAQABo10wWzAZBgNVHREEEjAQgQ5ub2JvZHlAZXhhbXBsZTAd
-BgNVHQ4EFgQUsRpUCWdFYAIC1870HWBKid/nWNkwDwYDVR0TAQH/BAUwAwEB/zAO
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-QsiGLSVoF+ZcySQH+rpoqcvbd8zLKz/vH+SoMM6db4OUgD8BKaeBb8dGhzz/lE8m
-YUqW/La4xvf/ffW5yze51Rtr1bPw1Tjrk92nE630Unjf0ZZO0h8shTmq/WlXiEqg
-cXxfbZiPP0KZkhn4ulf+RBbKKQGrLYvaVrCZcowSjLWzcfredYxElOpcgHCrL2pl
-2ZAjCySqAUpYo8HTZwgY/DeeGS3V4fZ06ZDoG20cxi7t8R+AcNbEfaTMzG3oe5qN
-A8+a3Qcf5M4yiJtXRNusMKeoRwLDkYRX9u76iOI5LfKTSqnUyhrUQcSYCTFO4y/V
-P48=
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+KOSHHh8/ecp2NaX7E0u88kN6tMxkGYyJo+7otMkWvjOi5vAtuX/LXNFNev1ei8j1
+hjlBQu4skVlzYeZxTRDujnN+lqvdToxo587A0xKhw76joTlQy/2X2xxqNRcfKfY3
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+pwUyM/uNXiWrQHIhZK+S9wV5g1Jw4L/+c5SNKEYQfWsTuFYGiKxuvf+tQHt8ddWM
+ULQ=
 -----END CERTIFICATE-----
diff --git a/test/rubygems/public_cert_32.pem b/test/rubygems/public_cert_32.pem
index efcf7c0ed743..3b0b7efcdef2 100644
--- a/test/rubygems/public_cert_32.pem
+++ b/test/rubygems/public_cert_32.pem
@@ -2,18 +2,18 @@
 MIIDLDCCAhSgAwIBAgIBATANBgkqhkiG9w0BAQsFADAqMQ8wDQYDVQQDDAZub2Jv
 ZHkxFzAVBgoJkiaJk/IsZAEZFgdleGFtcGxlMB4XDTEyMDEwMTAwMDAwMFoXDTM4
 MDExOTAzMTQwN1owKjEPMA0GA1UEAwwGbm9ib2R5MRcwFQYKCZImiZPyLGQBGRYH
-ZXhhbXBsZTCCASIwDQYJKoZIhvcNAQEBBQADggEPADCCAQoCggEBANFC3H6Q26GO
-bllXTiJBeALUbouzzxaGinwZeYYhhXKWEcfA0D8k+22w/JyndeEYc29JxwjFNwxM
-/DyyQplptzbM1Q5BCcLNQaQhmpOryosjWuYWW1JUDGTG3nEg0qRCrtjwVoAU++Ko
-NkQboM0wFQJxkBns0J1sr+O5Ml73YzKKtdVWWvg89osxyb4wRxkEoa9a/b9/aiK7
-WoeQhF00cRKoa/eoIN8usTjzKsYudHUtEQWibD7IxWdY3nMntGf1jyLYi40lVUbL
-FFytWtlZGMVKpMVIOMMCQ+ex+ExGQaJrQF5QEqPq1L/BvXgTZkv5P6CS3YjBdVC2
-/ntfos3gMhsCAwEAAaNdMFswGQYDVR0RBBIwEIEObm9ib2R5QGV4YW1wbGUwHQYD
-VR0OBBYEFLEaVAlnRWACAtfO9B1gSonf51jZMA8GA1UdEwEB/wQFMAMBAf8wDgYD
-VR0PAQH/BAQDAgIEMA0GCSqGSIb3DQEBCwUAA4IBAQBqjR8ioUTAmRjZNvRPMGXc
-mx0nklEODMfG5k+X4QI2Hux/4CWuSZKh+LoIxOsqQJdm2rG1FkPr6JYQOj5HCFA7
-3gO/MoSOtqBBOY9uMnGJQUq0NrWvleO3giUhfHRzUh7utXy2u3umuwJLqF54vbuT
-a1yufGSzwBO2BP7iURt9SyVrDWFmHSX976ZFWIandPXgMCJTgO6tONOC6/sABctb
-YQKo2scrAiSsk+kgIMnebavL6gKgQud6xdjJzvUq3DV4s93ent9rpRzYRgnTM8Eo
-UcgFbpFsWR21+gEt6UKv1rO9ZaWBf6RUVdh/sJKa/7vK/shQmnWw0A/LewxKQWV3
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+/3blOIR1qIKVdH2hiu3ARhK38UVeVGszzENBDg4okM5DpQ6d+wOXZLcN9WyUdPI7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 -----END CERTIFICATE-----
diff --git a/test/rubygems/public_key.pem b/test/rubygems/public_key.pem
index c233b35e7c82..f7cfda4bb56b 100644
--- a/test/rubygems/public_key.pem
+++ b/test/rubygems/public_key.pem
@@ -1,9 +1,9 @@
 -----BEGIN PUBLIC KEY-----
-MIIBIjANBgkqhkiG9w0BAQEFAAOCAQ8AMIIBCgKCAQEA0ULcfpDboY5uWVdOIkF4
-AtRui7PPFoaKfBl5hiGFcpYRx8DQPyT7bbD8nKd14Rhzb0nHCMU3DEz8PLJCmWm3
-NszVDkEJws1BpCGak6vKiyNa5hZbUlQMZMbecSDSpEKu2PBWgBT74qg2RBugzTAV
-AnGQGezQnWyv47kyXvdjMoq11VZa+Dz2izHJvjBHGQShr1r9v39qIrtah5CEXTRx
-Eqhr96gg3y6xOPMqxi50dS0RBaJsPsjFZ1jecye0Z/WPItiLjSVVRssUXK1a2VkY
-xUqkxUg4wwJD57H4TEZBomtAXlASo+rUv8G9eBNmS/k/oJLdiMF1ULb+e1+izeAy
-GwIDAQAB
+MIIBIjANBgkqhkiG9w0BAQEFAAOCAQ8AMIIBCgKCAQEAwMj7AMLS2MqnLpC+2Ep/
+vD4tmG3UnsT5graUWXjLv6kIUp8bUzVR7IaRKS0QV9nu0yPvWiEF0KYdg9SnUhW3
+eNyYqqbqz2XZAWWQLUVz6C7XAFb2eP+ROdvkZoWH7LfdL57RjmXmJAnQWz7sLo4M
+IFD6/xrwYW6Rh60zApDt+WWG5qlwhAUFKa8bhRq5zmsuIvI1/YVLgWL/duU4hHWo
+gpV0faGK7cBGErfxRV5UazPMQ0EODiiQzkOlDp37A5dktw31bJR08junGmpMGcsF
+1JZIwBQwKWl7VkezIdLHdll7OKUWMCS4uTmaQEQ3Yoy6vBbIroJlO99eH3ZY8GyO
+UwIDAQAB
 -----END PUBLIC KEY-----
diff --git a/test/rubygems/test_gem_commands_cert_command.rb b/test/rubygems/test_gem_commands_cert_command.rb
index ed1a1c8627bf..b9207cdcbcd3 100644
--- a/test/rubygems/test_gem_commands_cert_command.rb
+++ b/test/rubygems/test_gem_commands_cert_command.rb
@@ -329,6 +329,21 @@ def test_execute_build_ec_key
     assert_path_not_exist File.join(@tempdir, "gem-private_key.pem")
   end
 
+  def test_execute_build_bad_key
+    @cmd.handle_options %W[
+      --build nobody@example.com
+      --private-key #{PUBLIC_KEY_FILE}
+    ]
+
+    e = assert_raise Gem::Security::Exception do
+      use_ui @ui do
+        @cmd.execute
+      end
+    end
+
+    assert_equal "incorrect signing key for signing", e.message
+  end
+
   def test_execute_certificate
     use_ui @ui do
       @cmd.handle_options %W[--certificate #{PUBLIC_CERT_FILE}]
@@ -377,7 +392,7 @@ def test_execute_private_key
     assert_equal "", @ui.output
     assert_equal "", @ui.error
 
-    assert_equal PRIVATE_KEY.to_pem, @cmd.options[:key].to_pem
+    assert_equal PRIVATE_KEY.private_to_pem, @cmd.options[:key].private_to_pem
   end
 
   def test_execute_encrypted_private_key
@@ -388,7 +403,7 @@ def test_execute_encrypted_private_key
     assert_equal "", @ui.output
     assert_equal "", @ui.error
 
-    assert_equal ENCRYPTED_PRIVATE_KEY.to_pem, @cmd.options[:key].to_pem
+    assert_equal ENCRYPTED_PRIVATE_KEY.private_to_pem, @cmd.options[:key].private_to_pem
   end
 
   def test_execute_remove
@@ -468,7 +483,7 @@ def test_execute_remove_twice
 
   def test_execute_sign
     path = File.join @tempdir, "cert.pem"
-    Gem::Security.write ALTERNATE_CERT, path, 0o600
+    Gem::Security.write_certificate ALTERNATE_CERT, path, 0o600
 
     assert_equal "/CN=alternate/DC=example", ALTERNATE_CERT.issuer.to_s
 
@@ -497,7 +512,7 @@ def test_execute_sign
 
   def test_execute_sign_encrypted_key
     path = File.join @tempdir, "cert.pem"
-    Gem::Security.write ALTERNATE_CERT, path, 0o600
+    Gem::Security.write_certificate ALTERNATE_CERT, path, 0o600
 
     assert_equal "/CN=alternate/DC=example", ALTERNATE_CERT.issuer.to_s
 
@@ -528,13 +543,13 @@ def test_execute_sign_default
     FileUtils.mkdir_p File.join Gem.user_home, ".gem"
 
     private_key_path = File.join Gem.user_home, ".gem", "gem-private_key.pem"
-    Gem::Security.write PRIVATE_KEY, private_key_path
+    Gem::Security.write_private_key PRIVATE_KEY, private_key_path
 
     public_cert_path = File.join Gem.user_home, ".gem", "gem-public_cert.pem"
-    Gem::Security.write PUBLIC_CERT, public_cert_path
+    Gem::Security.write_certificate PUBLIC_CERT, public_cert_path
 
     path = File.join @tempdir, "cert.pem"
-    Gem::Security.write ALTERNATE_CERT, path, 0o600
+    Gem::Security.write_certificate ALTERNATE_CERT, path, 0o600
 
     assert_equal "/CN=alternate/DC=example", ALTERNATE_CERT.issuer.to_s
 
@@ -560,13 +575,13 @@ def test_execute_sign_default_encrypted_key
     FileUtils.mkdir_p File.join(Gem.user_home, ".gem")
 
     private_key_path = File.join Gem.user_home, ".gem", "gem-private_key.pem"
-    Gem::Security.write ENCRYPTED_PRIVATE_KEY, private_key_path, 0o600, PRIVATE_KEY_PASSPHRASE
+    Gem::Security.write_private_key ENCRYPTED_PRIVATE_KEY, private_key_path, 0o600, PRIVATE_KEY_PASSPHRASE
 
     public_cert_path = File.join Gem.user_home, ".gem", "gem-public_cert.pem"
-    Gem::Security.write PUBLIC_CERT, public_cert_path
+    Gem::Security.write_certificate PUBLIC_CERT, public_cert_path
 
     path = File.join @tempdir, "cert.pem"
-    Gem::Security.write ALTERNATE_CERT, path, 0o600
+    Gem::Security.write_certificate ALTERNATE_CERT, path, 0o600
 
     assert_equal "/CN=alternate/DC=example", ALTERNATE_CERT.issuer.to_s
 
@@ -592,10 +607,10 @@ def test_execute_sign_no_cert
     FileUtils.mkdir_p File.join Gem.user_home, ".gem"
 
     private_key_path = File.join Gem.user_home, ".gem", "gem-private_key.pem"
-    Gem::Security.write PRIVATE_KEY, private_key_path
+    Gem::Security.write_private_key PRIVATE_KEY, private_key_path
 
     path = File.join @tempdir, "cert.pem"
-    Gem::Security.write ALTERNATE_CERT, path, 0o600
+    Gem::Security.write_certificate ALTERNATE_CERT, path, 0o600
 
     assert_equal "/CN=alternate/DC=example", ALTERNATE_CERT.issuer.to_s
 
@@ -620,10 +635,10 @@ def test_execute_sign_no_key
     FileUtils.mkdir_p File.join Gem.user_home, ".gem"
 
     public_cert_path = File.join Gem.user_home, ".gem", "gem-public_cert.pem"
-    Gem::Security.write PUBLIC_CERT, public_cert_path
+    Gem::Security.write_certificate PUBLIC_CERT, public_cert_path
 
     path = File.join @tempdir, "cert.pem"
-    Gem::Security.write ALTERNATE_CERT, path, 0o600
+    Gem::Security.write_certificate ALTERNATE_CERT, path, 0o600
 
     assert_equal "/CN=alternate/DC=example", ALTERNATE_CERT.issuer.to_s
 
@@ -644,12 +659,32 @@ def test_execute_sign_no_key
     assert_equal expected, @ui.error
   end
 
+  def test_execute_sign_bad_key
+    path = File.join @tempdir, "cert.pem"
+    Gem::Security.write_certificate ALTERNATE_CERT, path, 0o600
+
+    @cmd.handle_options %W[
+      --private-key #{PUBLIC_KEY_FILE}
+      --certificate #{PUBLIC_CERT_FILE}
+
+      --sign #{path}
+    ]
+
+    e = assert_raise Gem::Security::Exception do
+      use_ui @ui do
+        @cmd.execute
+      end
+    end
+
+    assert_equal "incorrect signing key for signing", e.message
+  end
+
   def test_execute_re_sign
     gem_path = File.join Gem.user_home, ".gem"
     Dir.mkdir gem_path
 
     path = File.join @tempdir, "cert.pem"
-    Gem::Security.write EXPIRED_PUBLIC_CERT, path, 0o600
+    Gem::Security.write_certificate EXPIRED_PUBLIC_CERT, path, 0o600
 
     assert_equal "/CN=nobody/DC=example", EXPIRED_PUBLIC_CERT.issuer.to_s
 
@@ -681,7 +716,7 @@ def test_execute_re_sign_with_cert_expiration_length_days
     Dir.mkdir gem_path
 
     path = File.join @tempdir, "cert.pem"
-    Gem::Security.write EXPIRED_PUBLIC_CERT, path, 0o600
+    Gem::Security.write_certificate EXPIRED_PUBLIC_CERT, path, 0o600
 
     assert_equal "/CN=nobody/DC=example", EXPIRED_PUBLIC_CERT.issuer.to_s
 
@@ -793,14 +828,6 @@ def test_handle_options_key_bad
 
     assert_equal "invalid argument: --private-key #{bad}: invalid RSA, DSA, or EC key",
                  e.message
-
-    e = assert_raise Gem::OptionParser::InvalidArgument do
-      @cmd.handle_options %W[--private-key #{PUBLIC_KEY_FILE}]
-    end
-
-    assert_equal "invalid argument: " \
-                 "--private-key #{PUBLIC_KEY_FILE}: private key not found",
-                 e.message
   end
 
   def test_handle_options_sign
@@ -815,7 +842,7 @@ def test_handle_options_sign
       --sign #{CHILD_CERT_FILE}
     ]
 
-    assert_equal PRIVATE_KEY.to_pem, @cmd.options[:key].to_pem
+    assert_equal PRIVATE_KEY.private_to_pem, @cmd.options[:key].private_to_pem
     assert_equal PUBLIC_CERT.to_pem, @cmd.options[:issuer_cert].to_pem
 
     assert_equal [ALTERNATE_CERT_FILE, CHILD_CERT_FILE], @cmd.options[:sign]
@@ -833,7 +860,7 @@ def test_handle_options_sign_encrypted_key
       --sign #{CHILD_CERT_FILE}
     ]
 
-    assert_equal ENCRYPTED_PRIVATE_KEY.to_pem, @cmd.options[:key].to_pem
+    assert_equal ENCRYPTED_PRIVATE_KEY.private_to_pem, @cmd.options[:key].private_to_pem
     assert_equal PUBLIC_CERT.to_pem, @cmd.options[:issuer_cert].to_pem
 
     assert_equal [ALTERNATE_CERT_FILE, CHILD_CERT_FILE], @cmd.options[:sign]
diff --git a/test/rubygems/test_gem_package.rb b/test/rubygems/test_gem_package.rb
index be7cfd2843f5..99763f4df19e 100644
--- a/test/rubygems/test_gem_package.rb
+++ b/test/rubygems/test_gem_package.rb
@@ -272,7 +272,7 @@ def test_build_auto_signed
     FileUtils.mkdir_p File.join(Gem.user_home, ".gem")
 
     private_key_path = File.join Gem.user_home, ".gem", "gem-private_key.pem"
-    Gem::Security.write PRIVATE_KEY, private_key_path
+    Gem::Security.write_private_key PRIVATE_KEY, private_key_path
 
     public_cert_path = File.join Gem.user_home, ".gem", "gem-public_cert.pem"
     FileUtils.cp PUBLIC_CERT_PATH, public_cert_path
@@ -318,7 +318,7 @@ def test_build_auto_signed_encrypted_key
     FileUtils.cp ENCRYPTED_PRIVATE_KEY_PATH, private_key_path
 
     public_cert_path = File.join Gem.user_home, ".gem", "gem-public_cert.pem"
-    Gem::Security.write PUBLIC_CERT, public_cert_path
+    Gem::Security.write_certificate PUBLIC_CERT, public_cert_path
 
     spec = Gem::Specification.new "build", "1"
     spec.summary = "build"
diff --git a/test/rubygems/test_gem_security.rb b/test/rubygems/test_gem_security.rb
index 82449a862617..e97af3b959e9 100644
--- a/test/rubygems/test_gem_security.rb
+++ b/test/rubygems/test_gem_security.rb
@@ -29,7 +29,7 @@ def test_class_create_cert
 
     assert_equal    2,                     cert.version
     assert_equal    5,                     cert.serial
-    assert_equal    key.public_key.to_pem, cert.public_key.to_pem
+    assert_equal    key.public_key.public_to_pem, cert.public_key.public_to_pem
     assert_in_delta Time.now,              cert.not_before, 10
     assert_in_delta Time.now + 60,         cert.not_after, 10
     assert_equal    name.to_s,             cert.subject.to_s
@@ -46,8 +46,6 @@ def test_class_create_cert
 
     key_ident = cert.extensions.find {|ext| ext.oid == "subjectKeyIdentifier" }
     assert_equal 59, key_ident.value.length
-    assert_equal "B1:1A:54:09:67:45:60:02:02:D7:CE:F4:1D:60:4A:89:DF:E7:58:D9",
-                 key_ident.value
 
     assert_equal "", cert.issuer.to_s
     assert_equal name.to_s, cert.subject.to_s
@@ -73,7 +71,7 @@ def test_class_create_cert_email
 
     assert_equal    2,                     cert.version
     assert_equal    1,                     cert.serial
-    assert_equal    key.public_key.to_pem, cert.public_key.to_pem
+    assert_equal    key.public_key.public_to_pem, cert.public_key.public_to_pem
     assert_in_delta Time.now,              cert.not_before, 10
     assert_in_delta Time.now + 60,         cert.not_after, 10
     assert_equal    name.to_s,             cert.subject.to_s
@@ -94,8 +92,6 @@ def test_class_create_cert_email
 
     key_ident = cert.extensions.find {|ext| ext.oid == "subjectKeyIdentifier" }
     assert_equal 59, key_ident.value.length
-    assert_equal "B1:1A:54:09:67:45:60:02:02:D7:CE:F4:1D:60:4A:89:DF:E7:58:D9",
-                 key_ident.value
   end
 
   def test_class_create_key
@@ -120,15 +116,15 @@ def test_class_create_key_raises_unknown_algorithm
   end
 
   def test_class_get_public_key_rsa
-    pkey_pem = PRIVATE_KEY.public_key.to_pem
+    pkey_pem = PRIVATE_KEY.public_key.public_to_pem
 
-    assert_equal pkey_pem, Gem::Security.get_public_key(PRIVATE_KEY).to_pem
+    assert_equal pkey_pem, Gem::Security.get_public_key(PRIVATE_KEY).public_to_pem
   end
 
   def test_class_get_public_key_ec
     pkey = Gem::Security.get_public_key(EC_KEY)
 
-    assert_respond_to pkey, :to_pem
+    assert_respond_to pkey, :public_to_pem
   end
 
   def test_class_email_to_name
@@ -202,7 +198,7 @@ def test_class_sign
 
     signed = Gem::Security.sign cert, key, PUBLIC_CERT, 60
 
-    assert_equal    key.public_key.to_pem, signed.public_key.to_pem
+    assert_equal    key.public_key.public_to_pem, signed.public_key.public_to_pem
     assert_equal    signee.to_s,           signed.subject.to_s
     assert_equal    issuer.to_s,           signed.issuer.to_s
 
@@ -225,8 +221,6 @@ def test_class_sign
     key_ident =
       signed.extensions.find {|ext| ext.oid == "subjectKeyIdentifier" }
     assert_equal 59, key_ident.value.length
-    assert_equal "B1:1A:54:09:67:45:60:02:02:D7:CE:F4:1D:60:4A:89:DF:E7:58:D9",
-                 key_ident.value
 
     assert signed.verify key
   end
@@ -239,7 +233,7 @@ def test_class_sign_AltName
 
     signed = Gem::Security.sign cert, PRIVATE_KEY, PUBLIC_CERT, 60
 
-    assert_equal    PUBLIC_KEY.to_pem, signed.public_key.to_pem
+    assert_equal    PUBLIC_KEY.public_to_pem, signed.public_key.public_to_pem
     assert_equal    signee.to_s,       signed.subject.to_s
     assert_equal    issuer.to_s,       signed.issuer.to_s
 
@@ -267,8 +261,6 @@ def test_class_sign_AltName
     key_ident =
       signed.extensions.find {|ext| ext.oid == "subjectKeyIdentifier" }
     assert_equal 59, key_ident.value.length
-    assert_equal "B1:1A:54:09:67:45:60:02:02:D7:CE:F4:1D:60:4A:89:DF:E7:58:D9",
-                 key_ident.value
 
     assert signed.verify PUBLIC_KEY
   end
@@ -281,37 +273,37 @@ def test_class_trust_dir
     assert_equal expected, trust_dir.dir
   end
 
-  def test_class_write
+  def test_class_write_private_key
     key = Gem::Security.create_key "rsa"
 
     path = File.join @tempdir, "test-private_key.pem"
 
-    Gem::Security.write key, path
+    Gem::Security.write_private_key key, path
 
     assert_path_exist path
 
     key_from_file = File.read path
 
-    assert_equal key.to_pem, key_from_file
+    assert_equal key.private_to_pem, key_from_file
   end
 
-  def test_class_write_encrypted
+  def test_class_write_private_key_encrypted
     key = Gem::Security.create_key "rsa"
 
     path = File.join @tempdir, "test-private_encrypted_key.pem"
 
     passphrase = "It should be long."
 
-    Gem::Security.write key, path, 0o600, passphrase
+    Gem::Security.write_private_key key, path, 0o600, passphrase
 
     assert_path_exist path
 
     key_from_file = OpenSSL::PKey::RSA.new File.read(path), passphrase
 
-    assert_equal key.to_pem, key_from_file.to_pem
+    assert_equal key.private_to_pem, key_from_file.private_to_pem
   end
 
-  def test_class_write_encrypted_cipher
+  def test_class_write_private_key_encrypted_cipher
     key = Gem::Security.create_key "rsa"
 
     path = File.join @tempdir, "test-private_encrypted__with_non_default_cipher_key.pem"
@@ -320,16 +312,27 @@ def test_class_write_encrypted_cipher
 
     cipher = OpenSSL::Cipher.new "AES-192-CBC"
 
-    Gem::Security.write key, path, 0o600, passphrase, cipher
+    Gem::Security.write_private_key key, path, 0o600, passphrase, cipher
 
     assert_path_exist path
 
-    key_file_contents = File.read(path)
+    # Gem::Security.write_private_key outputs PKCS #8 format which doesn't have
+    # DEK-Info header to assert cipher name unlike PKCS #1 RSAPrivateKey.
+    # We cannot assert the cipher name in the PEM text.
+    key_from_file = OpenSSL::PKey.read File.read(path), passphrase
 
-    assert key_file_contents.split("\n")[2].match(cipher.name)
+    assert_equal key.private_to_pem, key_from_file.private_to_pem
+  end
+
+  def test_class_write_certificate
+    path = File.join @tempdir, "test-public_cert.pem"
+
+    Gem::Security.write_certificate PUBLIC_CERT, path
+
+    assert_path_exist path
 
-    key_from_file = OpenSSL::PKey::RSA.new key_file_contents, passphrase
+    cert_from_file = File.read path
 
-    assert_equal key.to_pem, key_from_file.to_pem
+    assert_equal PUBLIC_CERT.to_pem, cert_from_file
   end
 end if Gem::HAVE_OPENSSL && !Gem.java_platform?
diff --git a/test/rubygems/test_gem_security_signer.rb b/test/rubygems/test_gem_security_signer.rb
index f4799cbd4686..d0541b0a341f 100644
--- a/test/rubygems/test_gem_security_signer.rb
+++ b/test/rubygems/test_gem_security_signer.rb
@@ -58,14 +58,14 @@ def test_initialize_default
     FileUtils.mkdir_p File.join(Gem.user_home, ".gem")
 
     private_key_path = File.join Gem.user_home, ".gem", "gem-private_key.pem"
-    Gem::Security.write PRIVATE_KEY, private_key_path
+    Gem::Security.write_private_key PRIVATE_KEY, private_key_path
 
     public_cert_path = File.join Gem.user_home, ".gem", "gem-public_cert.pem"
-    Gem::Security.write PUBLIC_CERT, public_cert_path
+    Gem::Security.write_certificate PUBLIC_CERT, public_cert_path
 
     signer = Gem::Security::Signer.new nil, nil
 
-    assert_equal PRIVATE_KEY.to_pem, signer.key.to_pem
+    assert_equal PRIVATE_KEY.private_to_pem, signer.key.private_to_pem
     assert_equal [PUBLIC_CERT.to_pem], signer.cert_chain.map(&:to_pem)
   end
 
@@ -120,16 +120,8 @@ def test_sign
 
     signature = signer.sign "hello"
 
-    expected = <<-EXPECTED
-FmrCYxEXW3dgYYNMxPdS16VrdXT+d5nyXTVlRm64ZHSgMxMAaPtQJsVYv73m
-DWHTzNnLhhINSpgBMLh5a4atM52yxVdkPUTgqIH+LeIPBXn8xaP5JLmfDcmI
-tBpc/9DhS3v9iKCX40igAArFu7Gg3swbgQ61SP+U22LvG5nDQZQz3sudtsw3
-qKPykFVaYjrRwzvBdSdJ1PwlAsanSwcwS/GKPtmE/ykZ6X5XOx7wvCDL/zGy
-B8khkB8hDKC6moCzebmUxCBmTmXD0Wjzon+bf4MOriVE3a0ySGRvpr1mKR2+
-9EaVo7pDJLEM487+xg1CAZHRhwshd6II00XEzG/jBQ==
-    EXPECTED
-
-    assert_equal expected, [signature].pack("m")
+    digest = OpenSSL::Digest.new(Gem::Security::DIGEST_NAME)
+    assert PRIVATE_KEY.verify(digest, signature, "hello")
   end
 
   def test_sign_expired
@@ -147,10 +139,10 @@ def test_sign_expired_auto_update
     FileUtils.mkdir_p File.join(Gem.user_home, ".gem"), mode: 0o700
 
     private_key_path = File.join(Gem.user_home, ".gem", "gem-private_key.pem")
-    Gem::Security.write PRIVATE_KEY, private_key_path
+    Gem::Security.write_private_key PRIVATE_KEY, private_key_path
 
     cert_path = File.join Gem.user_home, ".gem", "gem-public_cert.pem"
-    Gem::Security.write EXPIRED_CERT, cert_path
+    Gem::Security.write_certificate EXPIRED_CERT, cert_path
 
     signer = Gem::Security::Signer.new PRIVATE_KEY, [EXPIRED_CERT]
 
@@ -177,13 +169,13 @@ def test_sign_expired_auto_update_exists
     expired_path =
       File.join Gem.user_home, "gem-public_cert.pem.expired.#{expiry}"
 
-    Gem::Security.write EXPIRED_CERT, expired_path
+    Gem::Security.write_certificate EXPIRED_CERT, expired_path
 
     private_key_path = File.join(Gem.user_home, "gem-private_key.pem")
-    Gem::Security.write PRIVATE_KEY, private_key_path
+    Gem::Security.write_private_key PRIVATE_KEY, private_key_path
 
     cert_path = File.join Gem.user_home, "gem-public_cert.pem"
-    Gem::Security.write EXPIRED_CERT, cert_path
+    Gem::Security.write_certificate EXPIRED_CERT, cert_path
 
     signer = Gem::Security::Signer.new PRIVATE_KEY, [EXPIRED_CERT]
 
diff --git a/test/rubygems/wrong_key_cert.pem b/test/rubygems/wrong_key_cert.pem
index 2f2cffbc61c8..47a9f5a5c1ac 100644
--- a/test/rubygems/wrong_key_cert.pem
+++ b/test/rubygems/wrong_key_cert.pem
@@ -2,18 +2,18 @@
 MIIDDTCCAfWgAwIBAgIBEjANBgkqhkiG9w0BAQsFADAqMQ8wDQYDVQQDDAZub2Jv
 ZHkxFzAVBgoJkiaJk/IsZAEZFgdleGFtcGxlMCAXDTEyMDEwMTAwMDAwMFoYDzk5
 OTkxMjMxMjM1OTU5WjAqMQ8wDQYDVQQDDAZub2JvZHkxFzAVBgoJkiaJk/IsZAEZ
-FgdleGFtcGxlMIIBIjANBgkqhkiG9w0BAQEFAAOCAQ8AMIIBCgKCAQEApebGm7NO
-nx+DtWG1xQsJBfTfwNlZvfzY61nlZccrhU6vx0AnYNiDZAG3J/gFQmYZ9gJ98rzE
-wfLMCGq9R/TZM+lAEaLhzYZCu3X4QdhKxr1xZ/SFC+1f8KVuH4tLXORW30DwayPh
-NxnrOvup4pWLiYuXUSZpV9CGMvPSUCW2odhMkBMKqaTTPjxoXJIcgacyprkNgIq4
-8cSvqWG/e/HrMRtkqvFbD5ta00uO1mlpajYYw1RRftEwktFo8vQgDBo9NT/EqoE7
-2tffaDnLq6rQrVtw4Kr9fy775DjNAWXyiCBjnJgOQSXCGPsM/AEdFrh/LKQQv2M/
-M7WNevnEUgsEIwIDAQABozwwOjAZBgNVHREEEjAQgQ5ub2JvZHlAZXhhbXBsZTAd
-BgNVHQ4EFgQUYPwS8g98+4Tq/8gcEK1iilkGXH4wDQYJKoZIhvcNAQELBQADggEB
-AJacpAT2GQQn5Rmb/LYaPhguWFHEdjHBO6rU0p7tE8QJW5pwMgim0mFtQlbuXE2L
-mbHrYCyRgVyaPV9gNiFg1sLzQMmmG4Afg1N4cpdg8zLZFZho+eyYGRkH+EtrAN0Q
-l8l603zovMXj8q8Q1eeurxkDHA6mDgwwMGiBQgAiPixQVOjvL+5M5PkwNw/kVzjA
-0EXumGQkeZ1jUAkVjp7uWbyoVatamUcpYvo51NQQQeuqwzdo2oDYLa27axWxaqj2
-m4TKsz2WnnrSnrpq3NnflXfWcOrnXI3odNlhQoPmtZQVt6P8pNbGrx4XD/WTGkGw
-i/6jlkwwjK7A7dSepfnTI4Y=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 -----END CERTIFICATE-----
diff --git a/test/rubygems/wrong_key_cert_32.pem b/test/rubygems/wrong_key_cert_32.pem
index aca829ab4487..a17ecd46f228 100644
--- a/test/rubygems/wrong_key_cert_32.pem
+++ b/test/rubygems/wrong_key_cert_32.pem
@@ -2,18 +2,18 @@
 MIIDCzCCAfOgAwIBAgIBEzANBgkqhkiG9w0BAQsFADAqMQ8wDQYDVQQDDAZub2Jv
 ZHkxFzAVBgoJkiaJk/IsZAEZFgdleGFtcGxlMB4XDTEyMDEwMTAwMDAwMFoXDTM4
 MDExOTAzMTQwN1owKjEPMA0GA1UEAwwGbm9ib2R5MRcwFQYKCZImiZPyLGQBGRYH
-ZXhhbXBsZTCCASIwDQYJKoZIhvcNAQEBBQADggEPADCCAQoCggEBAKXmxpuzTp8f
-g7VhtcULCQX038DZWb382OtZ5WXHK4VOr8dAJ2DYg2QBtyf4BUJmGfYCffK8xMHy
-zAhqvUf02TPpQBGi4c2GQrt1+EHYSsa9cWf0hQvtX/Clbh+LS1zkVt9A8Gsj4TcZ
-6zr7qeKVi4mLl1EmaVfQhjLz0lAltqHYTJATCqmk0z48aFySHIGnMqa5DYCKuPHE
-r6lhv3vx6zEbZKrxWw+bWtNLjtZpaWo2GMNUUX7RMJLRaPL0IAwaPTU/xKqBO9rX
-32g5y6uq0K1bcOCq/X8u++Q4zQFl8oggY5yYDkElwhj7DPwBHRa4fyykEL9jPzO1
-jXr5xFILBCMCAwEAAaM8MDowGQYDVR0RBBIwEIEObm9ib2R5QGV4YW1wbGUwHQYD
-VR0OBBYEFGD8EvIPfPuE6v/IHBCtYopZBlx+MA0GCSqGSIb3DQEBCwUAA4IBAQBE
-lq/rPaPT+5uui42u4BTFayrQU9EFik9xPG6WJw+IJ/5CprECj6h90FC+GaMNeu2Z
-R0l+iEfgx4xBM4DERiRVLZIlHbZzuPp0YRYH9gyJot/+0piaAcnUEvjz2Z8axoFq
-lE3/q4s6Yw8xdqwxvc5kiwymv2nEm4+v5w6Pb3K/fP/QQLvDUBWrBUMHPgdYXYk2
-zvc58BBwgGDSpFRO0tw+lnqMTM1y+fbpfuvP9TY1m4y13nuw/g7KxVxYolAWVQs3
-TptnJqqzEwdFa2S9BidUIlDRRY8cuhY6R3DM6THNLjR3c1oyf04nhT3sd/ilAJdD
-YjnEtcLlkjxZyLLoWjn2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 -----END CERTIFICATE-----
diff --git a/tool/create_certs.rb b/tool/create_certs.rb
index 8bfdbae9b6f9..1a13950a5f74 100644
--- a/tool/create_certs.rb
+++ b/tool/create_certs.rb
@@ -156,13 +156,14 @@ def validity_for(time)
 
 keys.each do |name, key|
   dest = File.join base_dir, "#{name}_key.pem"
-  File.write dest, key.to_pem
+  pem = name == :public ? key.public_to_pem : key.private_to_pem
+  File.write dest, pem
 end
 
 # Create an encrypted private key protected by a passphrase from the new keys[:private]
 # it has to be the same as is in # test/rubygems/helper.rb in PRIVATE_KEY_PASSPHRASE
 dest = File.join base_dir, "encrypted_private_key.pem"
-File.write dest, keys[:private].to_pem(OpenSSL::Cipher.new("aes-256-cbc"), "Foo bar")
+File.write dest, keys[:private].private_to_pem(OpenSSL::Cipher.new("aes-256-cbc"), "Foo bar")
 
 certs.each do |name, (cert, cert_32)|
   dest = File.join base_dir, "#{name}_cert.pem"
diff --git a/tool/create_encrypted_key.rb b/tool/create_encrypted_key.rb
index 829a750fbdff..3f7f7f500a22 100644
--- a/tool/create_encrypted_key.rb
+++ b/tool/create_encrypted_key.rb
@@ -13,5 +13,5 @@
 encrypted_key_path = "#{test_path}/encrypted_private_key.pem"
 
 File.open encrypted_key_path, "w" do |io|
-  io.write key.to_pem cipher, "Foo bar"
+  io.write key.private_to_pem cipher, "Foo bar"
 end