diff --git a/docs/development/test-vectors.rst b/docs/development/test-vectors.rst
index 2cd9faa..a0849a4 100644
--- a/docs/development/test-vectors.rst
+++ b/docs/development/test-vectors.rst
@@ -104,6 +104,20 @@
   generated using OpenSSL that contains a UTF8String common name with the value
   "We heart UTF8!™".
 
+Custom X.509 Request Vectors
+~~~~~~~~~~~~~~~~~~~~~~~~~~~~
+
+* ``dsa_sha1.pem`` - Contains a certificate request using 1024-bit DSA
+  parameters and SHA1 generated using OpenSSL.
+* ``rsa_md4.pem`` - Contains a certificate request using 2048 bit RSA and MD4
+  generated using OpenSSL.
+* ``rsa_sha1.pem`` - Contains a certificate request using 2048 bit RSA and
+  SHA1 generated using OpenSSL.
+* ``rsa_sha256.pem`` - Contains a certificate request using 2048 bit RSA and
+  SHA256 generated using OpenSSL.
+* ``ec_sha256.pem`` - Contains a certificate request using EC (``secp384r1``)
+  and SHA256 generated using OpenSSL.
+
 Hashes
 ~~~~~~
 
diff --git a/vectors/cryptography_vectors/x509/requests/dsa_sha1.pem b/vectors/cryptography_vectors/x509/requests/dsa_sha1.pem
new file mode 100644
index 0000000..11688db
--- /dev/null
+++ b/vectors/cryptography_vectors/x509/requests/dsa_sha1.pem
@@ -0,0 +1,15 @@
+-----BEGIN CERTIFICATE REQUEST-----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+-----END CERTIFICATE REQUEST-----
diff --git a/vectors/cryptography_vectors/x509/requests/ec_sha256.pem b/vectors/cryptography_vectors/x509/requests/ec_sha256.pem
new file mode 100644
index 0000000..9497ae3
--- /dev/null
+++ b/vectors/cryptography_vectors/x509/requests/ec_sha256.pem
@@ -0,0 +1,10 @@
+-----BEGIN CERTIFICATE REQUEST-----
+MIIBTzCB1gIBADBXMRgwFgYDVQQDDA9jcnlwdG9ncmFwaHkuaW8xDTALBgNVBAoM
+BFB5Q0ExCzAJBgNVBAYTAlVTMQ4wDAYDVQQIDAVUZXhhczEPMA0GA1UEBwwGQXVz
+dGluMHYwEAYHKoZIzj0CAQYFK4EEACIDYgAE3hm1FMCzw66bOY6j4mtegWvc+RAs
+rY8S/gL55MkkhySzkpftdYLgTYsypVEDjQkIaAOm0/uRoaEWfsAhWLAO+tOck5ZG
+L6zP8P+vcVWBKQnTcmvVn94AHP9LubL1r4y6oAAwCgYIKoZIzj0EAwIDaAAwZQIw
+LBqffejBeHMy0jB6iGtHalnxcrmw4lAmLzI4sbRe4RK7brNbD7VqEjuSlushLf/D
+AjEAlM9EDJXFKCfVVq5tdlAOMAglXUfCn37ngu11WOUb/XaqRd9tmZ7VxGM0f+I4
+LRdR
+-----END CERTIFICATE REQUEST-----
diff --git a/vectors/cryptography_vectors/x509/requests/rsa_md4.pem b/vectors/cryptography_vectors/x509/requests/rsa_md4.pem
new file mode 100644
index 0000000..f62c8ef
--- /dev/null
+++ b/vectors/cryptography_vectors/x509/requests/rsa_md4.pem
@@ -0,0 +1,16 @@
+-----BEGIN CERTIFICATE REQUEST-----
+MIICnDCCAYQCAQAwVzEYMBYGA1UEAwwPY3J5cHRvZ3JhcGh5LmlvMQ0wCwYDVQQK
+DARQeUNBMQswCQYDVQQGEwJVUzEOMAwGA1UECAwFVGV4YXMxDzANBgNVBAcMBkF1
+c3RpbjCCASIwDQYJKoZIhvcNAQEBBQADggEPADCCAQoCggEBAMpZCKiob1IpjL+4
+S/J9Jgcm0ewZ/TbgJw9MB2sTQu7Ljmad9MttNeMyd9wa9fQIhenlpKjJWPSBekSX
+P0uvbAKkY00eCM/mi5Deb2lZaXkfpFC2DlsOKm4uyzmyd/ob2/rSeml7+u+xnGSM
+1MeYjuS5R7KrQUX+HJyw53cxkEHykXcsAvu3WxpnpZzLSFBNiE6lJZUl4vH86aUl
+qrB4C87c150uT01ouEqpon8KfwCnuH1Zqw1e+XVoW6sMqvkoqx2uSJxlMzlWpXhI
+rd3bMXHJ+mJyuDP5UVhQU0WuWXPO1JzEfVwVKigbpy8heHare/6tFHXp3V98fhEO
+qJGaArUCAwEAAaAAMA0GCSqGSIb3DQEBAwUAA4IBAQCp9f8iBtvibyoBB5W+h9RS
+IsbL/bY46MzfjkWaCr1GACC3FefO88qsQYZJNsnqrHKwl8BJUNxf5bLMyFmyLW9D
+jBah8wfo3ftjos1u1F1Bt31FcL7UlDoDLZ1LA3cP/JodSbUVZ8ByVI1bj0MRdAx5
+16YNJvCtzXQtoRZxr940u+S10G6E8sSwfGjqJIgOTiF3oYmS1hSBsIGJzrJ4HOp/
+FAN5pxYW3C0sAM4Aq7qSRHQdFoIXovgRxB4XFedIveEidralOe1K0ShV675jmjwa
+zoO/bTZGCIISD3KoIaCdkJjKoN0r2ckwhBTxsQsC6iO/FU5rBS4DG7369Y7FNIJ6
+-----END CERTIFICATE REQUEST-----
diff --git a/vectors/cryptography_vectors/x509/requests/rsa_sha1.pem b/vectors/cryptography_vectors/x509/requests/rsa_sha1.pem
new file mode 100644
index 0000000..0656c31
--- /dev/null
+++ b/vectors/cryptography_vectors/x509/requests/rsa_sha1.pem
@@ -0,0 +1,16 @@
+-----BEGIN CERTIFICATE REQUEST-----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-----END CERTIFICATE REQUEST-----
diff --git a/vectors/cryptography_vectors/x509/requests/rsa_sha256.pem b/vectors/cryptography_vectors/x509/requests/rsa_sha256.pem
new file mode 100644
index 0000000..06393d2
--- /dev/null
+++ b/vectors/cryptography_vectors/x509/requests/rsa_sha256.pem
@@ -0,0 +1,16 @@
+-----BEGIN CERTIFICATE REQUEST-----
+MIICnDCCAYQCAQAwVzELMAkGA1UEBhMCVVMxDjAMBgNVBAgMBVRleGFzMQ8wDQYD
+VQQHDAZBdXN0aW4xDTALBgNVBAoMBFB5Q0ExGDAWBgNVBAMMD2NyeXB0b2dyYXBo
+eS5pbzCCASIwDQYJKoZIhvcNAQEBBQADggEPADCCAQoCggEBALWsaWBzupTPnC9A
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+QGSzX9XJjuyVUBRpou8muv0ZRcrJG08AP9pss4MMjkvTEfX6ldht9NWXlTz2AnOL
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+jzzQgRs8+29YFRyQHfHHT0K0YYEeiblvdNExXVD2s3ppP/C/X2lhs5Nif8YaHI1d
+wU0VDIeY55qMv1uhvnK34GkISl3U4v4VLm7bSoPHYmzNgtFQTKs3bZVSz2EtNGAJ
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+Qj3uFk6RyV3DyyM93L8bUSaX2gN/LC55sOnCaGR2t5MrvcrfRDe2EbrnqJsoOSu8
+-----END CERTIFICATE REQUEST-----