diff --git a/ChangeLog b/ChangeLog
index 1ee00ef947..d14b5f21e8 100644
--- a/ChangeLog
+++ b/ChangeLog
@@ -1,3 +1,8 @@
+Sat Jun 25 10:07:52 2016  Kazuki Yamaguchi  <k@rhe.jp>
+
+	* test/openssl/test_ocsp.rb: Ignore errors caused by bugs that exist in
+	  LibreSSL >= 2.3.1.
+
 Sat Jun 25 02:33:33 2016  Nobuyoshi Nakada  <nobu@ruby-lang.org>
 
 	* vm_method.c (vm_respond_to): try method_missing if respond_to?
diff --git a/test/openssl/test_ocsp.rb b/test/openssl/test_ocsp.rb
index f1e34982c5..f532a2536c 100644
--- a/test/openssl/test_ocsp.rb
+++ b/test/openssl/test_ocsp.rb
@@ -140,6 +140,12 @@ class OpenSSL::TestOCSP < OpenSSL::TestCase
     assert_equal cid.to_der, asn1.value[0].value.find { |a| a.class == OpenSSL::ASN1::Sequence }.value[0].value[0].to_der
     assert_equal OpenSSL::ASN1.Sequence([@cert2, @ca_cert]).to_der, asn1.value[3].value[0].to_der
     assert_equal der, OpenSSL::OCSP::BasicResponse.new(der).to_der
+  rescue TypeError
+    if /GENERALIZEDTIME/ =~ $!.message
+      skip "OCSP_basic_sign() is broken"
+    else
+      raise
+    end
   end
 
   def test_basic_response_sign_verify
@@ -177,7 +183,7 @@ class OpenSSL::TestOCSP < OpenSSL::TestCase
     assert_equal OpenSSL::OCSP::V_CERTSTATUS_REVOKED, single.cert_status
     assert_equal OpenSSL::OCSP::REVOKED_STATUS_UNSPECIFIED, single.revocation_reason
     assert_equal now - 400, single.revocation_time
-    assert_equal now - 300, single.this_update
+    assert (single.this_update - (now - 300)) < 2
     assert_equal nil, single.next_update
     assert_equal [], single.extensions
 
@@ -203,6 +209,12 @@ class OpenSSL::TestOCSP < OpenSSL::TestCase
     cid2 = OpenSSL::OCSP::CertificateId.new(@cert2, @ca_cert, OpenSSL::Digest::SHA1.new)
     bres.add_status(cid1, OpenSSL::OCSP::V_CERTSTATUS_REVOKED, OpenSSL::OCSP::REVOKED_STATUS_UNSPECIFIED, -400, -300, -50, [])
     bres.add_status(cid2, OpenSSL::OCSP::V_CERTSTATUS_REVOKED, OpenSSL::OCSP::REVOKED_STATUS_UNSPECIFIED, -400, -300, nil, [])
+    bres.add_status(cid2, OpenSSL::OCSP::V_CERTSTATUS_GOOD, nil, nil, Time.now + 100, nil, nil)
+
+    if bres.responses[2].check_validity # thisUpdate is in future; must fail
+      # LibreSSL bug; skip for now
+      skip "OCSP_check_validity() is broken"
+    end
 
     single1 = bres.responses[0]
     assert_equal false, single1.check_validity