diff --git a/Lib/test/capath/4e1295a3.0 b/Lib/test/capath/4e1295a3.0
new file mode 100644
index 0000000..9d7ac23
--- /dev/null
+++ b/Lib/test/capath/4e1295a3.0
@@ -0,0 +1,14 @@
+-----BEGIN CERTIFICATE-----
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+VQQIEwpRdWVlbnNsYW5kMQ8wDQYDVQQHEwZMaXNib2ExFzAVBgNVBAoTDk5ldXJv
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+9EBc0n6bVGhN7XaXd6sJ7dym9sbsWxb+pJdurnkxjx4=
+-----END CERTIFICATE-----
diff --git a/Lib/test/capath/5ed36f99.0 b/Lib/test/capath/5ed36f99.0
new file mode 100644
index 0000000..e7dfc82
--- /dev/null
+++ b/Lib/test/capath/5ed36f99.0
@@ -0,0 +1,41 @@
+-----BEGIN CERTIFICATE-----
+MIIHPTCCBSWgAwIBAgIBADANBgkqhkiG9w0BAQQFADB5MRAwDgYDVQQKEwdSb290
+IENBMR4wHAYDVQQLExVodHRwOi8vd3d3LmNhY2VydC5vcmcxIjAgBgNVBAMTGUNB
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+-----END CERTIFICATE-----
diff --git a/Lib/test/test_ssl.py b/Lib/test/test_ssl.py
index 80c586b..6cd3a5e 100644
--- a/Lib/test/test_ssl.py
+++ b/Lib/test/test_ssl.py
@@ -300,6 +300,10 @@
 
     def test_connect_capath(self):
         # Verify server certificates using the `capath` argument
+        # NOTE: the subject hashing algorithm has been changed between
+        # OpenSSL 0.9.8n and 1.0.0, as a result the capath directory must
+        # contain both versions of each certificate (same content, different
+        # filename) for this test to be portable accross OpenSSL releases.
         ctx = ssl.SSLContext(ssl.PROTOCOL_SSLv23)
         ctx.verify_mode = ssl.CERT_REQUIRED
         ctx.load_verify_locations(capath=CAPATH)