diff --git a/CHANGELOG.md b/CHANGELOG.md
index 1dbd93d..4ef7c48 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,9 +1,22 @@
+## 2.14.4 - 2021-10-14
+
+This is a patch release that fixes:
+
+- a memory leak of analyzer plugins (issue [flutter/flutter#90868][]).
+- the Dart VM sometimes loading expired certificates on Windows (issues
+  [#46370][] and [#47420][]).
+
+[flutter/flutter#90868]: https://github.com/flutter/flutter/issues/90868
+[#46370]: https://github.com/dart-lang/sdk/issues/46370
+[#47420]: https://github.com/dart-lang/sdk/issues/47420
+
 ## 2.14.3 - 2021-09-30
 
 This is a patch release that fixes:
 
-- a code completion performance regression [flutter/flutter-intellij#5761][].
-- debug information emitted by the Dart VM [#47289][].
+- a code completion performance regression (issue
+  [flutter/flutter-intellij#5761][]).
+- debug information emitted by the Dart VM (issue [#47289][]).
 
 [flutter/flutter-intellij#5761]:
   https://github.com/flutter/flutter-intellij/issues/5761
@@ -203,7 +216,7 @@
 - fix `curly_braces_in_flow_control_structures` to properly flag terminating `else-if`
   blocks.
 - improve `always_specify_types` to support type aliases.
-- fix a false positive in `unnecessary_string_interpolations` w/ nullable interpolated 
+- fix a false positive in `unnecessary_string_interpolations` w/ nullable interpolated
   strings
 - fix a false positive in `avoid_function_literals_in_foreach_calls` for nullable
   iterables.
@@ -291,7 +304,7 @@
     `--legacy-javascript` flag will let you opt out of this update, but this
     flag will be removed in a future release. Modern browsers will not be
     affected, as Dart2JS continues to support [last two major releases][1] of
-    Edge, Safari, Firefox, and Chrome. 
+    Edge, Safari, Firefox, and Chrome.
 
 [#46545]: https://github.com/dart-lang/sdk/issues/46545
 [1]: https://dart.dev/faq#q-what-browsers-do-you-support-as-javascript-compilation-targets
diff --git a/pkg/analysis_server/lib/src/plugin/plugin_manager.dart b/pkg/analysis_server/lib/src/plugin/plugin_manager.dart
index 07c4956..5972a14 100644
--- a/pkg/analysis_server/lib/src/plugin/plugin_manager.dart
+++ b/pkg/analysis_server/lib/src/plugin/plugin_manager.dart
@@ -330,8 +330,10 @@
       try {
         var session = await plugin.start(byteStorePath, sdkPath);
         session?.onDone.then((_) {
-          _pluginMap.remove(path);
-          _notifyPluginsChanged();
+          if (_pluginMap[path] == plugin) {
+            _pluginMap.remove(path);
+            _notifyPluginsChanged();
+          }
         });
       } catch (exception, stackTrace) {
         // Record the exception (for debugging purposes) and record the fact
diff --git a/runtime/bin/BUILD.gn b/runtime/bin/BUILD.gn
index 438cec8..3296a97 100644
--- a/runtime/bin/BUILD.gn
+++ b/runtime/bin/BUILD.gn
@@ -905,6 +905,7 @@
     ":dart_snapshot_cc",
     ":standalone_dart_io",
     "..:libdart_precompiler",
+    "//third_party/boringssl",  # for secure_socket_utils_test
     "//third_party/zlib",
   ]
   include_dirs = [
diff --git a/runtime/bin/builtin_impl_sources.gni b/runtime/bin/builtin_impl_sources.gni
index d1f7d95..9c14afb 100644
--- a/runtime/bin/builtin_impl_sources.gni
+++ b/runtime/bin/builtin_impl_sources.gni
@@ -4,7 +4,7 @@
 
 # This file contains all C++ sources for the dart:_builtin library and
 # some of the C++ sources for the dart:io library.  The rest are in
-# io_impl_sources.gypi.
+# io_impl_sources.gni.
 
 builtin_impl_sources = [
   "crypto.cc",
diff --git a/runtime/bin/io_impl_sources.gni b/runtime/bin/io_impl_sources.gni
index 846c775..8c368bb 100644
--- a/runtime/bin/io_impl_sources.gni
+++ b/runtime/bin/io_impl_sources.gni
@@ -3,7 +3,7 @@
 # BSD-style license that can be found in the LICENSE file.
 
 # This file contains some C++ sources for the dart:io library.  The other
-# implementation files are in builtin_impl_sources.gypi.
+# implementation files are in builtin_impl_sources.gni.
 io_impl_sources = [
   "console.h",
   "console_posix.cc",
@@ -109,4 +109,7 @@
   "typed_data_utils.h",
 ]
 
-io_impl_tests = [ "platform_macos_test.cc" ]
+io_impl_tests = [
+  "platform_macos_test.cc",
+  "secure_socket_utils_test.cc",
+]
diff --git a/runtime/bin/secure_socket_utils.cc b/runtime/bin/secure_socket_utils.cc
index ce38f8f..ad738e97 100644
--- a/runtime/bin/secure_socket_utils.cc
+++ b/runtime/bin/secure_socket_utils.cc
@@ -89,6 +89,22 @@
   SecureSocketUtils::CheckStatusSSL(status, type, message, NULL);
 }
 
+bool SecureSocketUtils::IsCurrentTimeInsideCertValidDateRange(X509* root_cert) {
+  ASN1_TIME* not_before = X509_get_notBefore(root_cert);
+  ASN1_TIME* not_after = X509_get_notAfter(root_cert);
+  int days_since_valid = 0;
+  int secs_since_valid = 0;
+  int days_before_invalid = 0;
+  int secs_before_invalid = 0;
+  // nullptr indicates current date/time
+  ASN1_TIME_diff(&days_since_valid, &secs_since_valid, not_before,
+                 /*to=*/nullptr);
+  ASN1_TIME_diff(&days_before_invalid, &secs_before_invalid,
+                 /*from=*/nullptr, not_after);
+  return days_since_valid >= 0 && secs_since_valid >= 0 &&
+         days_before_invalid >= 0 && secs_before_invalid >= 0;
+}
+
 }  // namespace bin
 }  // namespace dart
 
diff --git a/runtime/bin/secure_socket_utils.h b/runtime/bin/secure_socket_utils.h
index ddbd2b6..e8e306e 100644
--- a/runtime/bin/secure_socket_utils.h
+++ b/runtime/bin/secure_socket_utils.h
@@ -39,6 +39,8 @@
 
   static void CheckStatus(int status, const char* type, const char* message);
 
+  static bool IsCurrentTimeInsideCertValidDateRange(X509* root_cert);
+
   static bool NoPEMStartLine() {
     uint32_t last_error = ERR_peek_last_error();
     return (ERR_GET_LIB(last_error) == ERR_LIB_PEM) &&
diff --git a/runtime/bin/secure_socket_utils_test.cc b/runtime/bin/secure_socket_utils_test.cc
new file mode 100644
index 0000000..89bbb12
--- /dev/null
+++ b/runtime/bin/secure_socket_utils_test.cc
@@ -0,0 +1,152 @@
+// Copyright (c) 2021, the Dart project authors.  Please see the AUTHORS file
+// for details. All rights reserved. Use of this source code is governed by a
+// BSD-style license that can be found in the LICENSE file.
+
+#if !defined(DART_IO_SECURE_SOCKET_DISABLED)
+
+#include <openssl/bio.h>
+#include <openssl/ssl.h>
+#include <openssl/x509.h>
+
+#include "bin/secure_socket_utils.h"
+#include "platform/globals.h"
+#include "vm/unit_test.h"
+
+namespace dart {
+namespace bin {
+
+TEST_CASE(SecureSocketUtils_CertNotYetValid) {
+  const char* valid_after_2121 =
+      "-----BEGIN CERTIFICATE-----\n"
+      "MIIFbzCCA1egAwIBAgIUO6PLWc8zatZF5Cc07uYdjDy4UGowDQYJKoZIhvcNAQEL\n"
+      "BQAwRTELMAkGA1UEBhMCQVUxEzARBgNVBAgMClNvbWUtU3RhdGUxITAfBgNVBAoM\n"
+      "GEludGVybmV0IFdpZGdpdHMgUHR5IEx0ZDAiGA8yMTIxMDgwMTE3MDUwNFoYDzIx\n"
+      "MzEwNzMwMTcwNTA0WjBFMQswCQYDVQQGEwJBVTETMBEGA1UECAwKU29tZS1TdGF0\n"
+      "ZTEhMB8GA1UECgwYSW50ZXJuZXQgV2lkZ2l0cyBQdHkgTHRkMIICIjANBgkqhkiG\n"
+      "9w0BAQEFAAOCAg8AMIICCgKCAgEAvgmd8v2K4ngOI/dOa/sn63uetG9sUhzTdViO\n"
+      "87q7s4XeFmziS3BMQyMqTmrIHJAKuZp66ZH6ZOno54UX2KedI4hf0He3NbAitGgI\n"
+      "o6z/WBglH+ByORUEU1Yzh03akja5C8Hp9IUpC6PGJEolPsZeoBMZs1bCxwD9miHy\n"
+      "bs/NYsUGsDJwUZFEW2UTjYuyeTPSdkIgoZIPCp8tp9E6jy7fb2H2XE0Z+rJ4rU/e\n"
+      "0aQ1Q7gNBnBWrJAGgYfQj9XbFx6nNEW6XUBqIV/uUmz9y64pMQ21I9e64Qn5KHDo\n"
+      "08CzQ651dGY1GJkziUuQITkPN4EqS6D5R74ruTJW0lp/cg7RNPoTAXBXI+Nqz7WE\n"
+      "bscerDKFGgaAZ8WXqvwpHqwGeiilZT/OwSwjrN8zaW6eLljAStGhLgn6j/Te8rfW\n"
+      "9+AGSjesJ8dJ+dppFG8A+1Auvtii12Jk8hj/IM/udt5ZLs6meSOYPeNF3UqHrA7s\n"
+      "O39KsMy7ppFQPwBBXgKZMXQlt6uMmi/2s/OHXZRpf7c09n6+3NKYutMsYHO6SrlD\n"
+      "hYcWdpjlv632O5WAdjehohDLfYLugsPPt/hJC3UAA8QfNrEXVHx3D2qgowLB9Brx\n"
+      "zC7aT/0rmVQu2wXvekc8tIRUnDgr8tLjSuEyj9nBb7cWUOWi/1YiEb5T1x7/zyhP\n"
+      "5p8g8l8CAwEAAaNTMFEwHQYDVR0OBBYEFN1Mf9EDYiYYds9IB9qvOYEmDhs5MB8G\n"
+      "A1UdIwQYMBaAFN1Mf9EDYiYYds9IB9qvOYEmDhs5MA8GA1UdEwEB/wQFMAMBAf8w\n"
+      "DQYJKoZIhvcNAQELBQADggIBAA8DjwXFECGFKPNc//kTSUUcMxRLORBH/oSe2hml\n"
+      "dNRtjkVHWcPDsn5Md0cM6e0kOXw2AEqRK9keYN/27JGHBvzu1MbzSHd1czeGx46d\n"
+      "5QI5MyI0U8iiYoW8IJURrnAuD+9yS6O4b7c9qnTwwdsAy98gzfWZbrb++mgoWDrt\n"
+      "Ma4V1zKMUZYezV95zlBmB9sKxbJlLP6pMGPENsbNuqB1KK8uAYnd4YYdEx97lt7o\n"
+      "SeUySohZQasheI73jJuYdDwqDcGCtRvwaOyDuOsDZVNqjNiqiI3aaGVII2lNbjOO\n"
+      "g85pN4pWB+1b3wdEt+c5VETYX3SiJNOyhy3rp68liegeeNVTgNdp5vSxmogWxtCN\n"
+      "uv6uim0Lw//Ezz6acc15CLdaS1msS2V/5Ogk7/cYEajtWp8l7/dy9Gf8ekzRBaET\n"
+      "3vw7sla+YhsUI+NZQG79gfkDfYmRMpW6djaWgY9c5l/NJ8ev1ZQWj1i5t4w7lW5h\n"
+      "3wB8qVV7BQ3zY36iEes4hvmXmykCOgQ2yXTOVZVhKYAxoaRMgkJSWL9rsPvmHEM8\n"
+      "b3gjUC/5nwTzLZAw0iYLtPpSnFwhprZPPWF+k5FQAx/UQ+0qjqY8EbfWLzexm+7P\n"
+      "Sm35NlpFHH6vyyj48RVYQcw8KvDvbuUwjiauydhYCCLoQVdywec8d3fUu6NdBusm\n"
+      "q8uu\n"
+      "-----END CERTIFICATE-----\n";
+  size_t len = strlen(valid_after_2121);
+  BIO* cert_bio = BIO_new(BIO_s_mem());
+  BIO_write(cert_bio, valid_after_2121, len);
+  X509* cert_X509 = PEM_read_bio_X509(cert_bio, NULL, NULL, NULL);
+  EXPECT(cert_X509 != nullptr);
+  EXPECT(!SecureSocketUtils::IsCurrentTimeInsideCertValidDateRange(cert_X509));
+  BIO_free(cert_bio);
+  X509_free(cert_X509);
+}
+
+TEST_CASE(SecureSocketUtils_CertValid) {
+  const char* valid_in_2021 =
+      "-----BEGIN CERTIFICATE-----\n"
+      "MIIFbTCCA1WgAwIBAgIUFmzKjF/PfpFX+5+pF1LXzbFzL/4wDQYJKoZIhvcNAQEL\n"
+      "BQAwRTELMAkGA1UEBhMCQVUxEzARBgNVBAgMClNvbWUtU3RhdGUxITAfBgNVBAoM\n"
+      "GEludGVybmV0IFdpZGdpdHMgUHR5IEx0ZDAgFw0yMTA4MjUxNzA1NTNaGA8yMTIx\n"
+      "MDgwMTE3MDU1M1owRTELMAkGA1UEBhMCQVUxEzARBgNVBAgMClNvbWUtU3RhdGUx\n"
+      "ITAfBgNVBAoMGEludGVybmV0IFdpZGdpdHMgUHR5IEx0ZDCCAiIwDQYJKoZIhvcN\n"
+      "AQEBBQADggIPADCCAgoCggIBAMdupz2RQB1fHii6EACZq8MPbDk+xoxHb111Z85C\n"
+      "VK47tC+Sn16DmWKwmcMp7mbPIO8jUSJOk8FrZWsSFZ9xBzXb/H2W6kFNb8XqKyhH\n"
+      "vweeTekPuONrpJIqBJiIEXqyMoxiqwbtl38ZVo5DwFvc8mriFVYapMLb3DKQxOMR\n"
+      "uM32R40VVf1S/LcYab/UTdxdtoI6MINv5SFsmp7Cd+8nUMXdetCTdlu5aoHSTUE0\n"
+      "EzsYG4WTQqi3WpvnTuFlFq4LLd7NYmWUoiUJiB5u7vSEZM91u/eGtOm9Y7OzwJUp\n"
+      "Obv3hEIrNS0c/qXuG89+7vlcW5AqJkyWhNgoMRXFXYlqPFKWwYOU0t/vjSlFlB3u\n"
+      "8a0zNur6d95IC/9XSGFgW3FYnEzTPiorR8y/dbw8P5ioP2yMrm1b6v+TlyOyQ3Hu\n"
+      "gCKJy7Ah1IpUG7wefZIpTN8CaumusUwJdCcGBPfwyOD1yvF8UyETJ5ZB7JC7jXgj\n"
+      "KUpytSeN79m15s+ksn6tS9uLqTHr3Yr7J7ha3m2UO4gl2QOa20/fdmenVqEsq+Z7\n"
+      "1PuDaitEVaCQE3/286rwNQPgoDgDbIckZOzOzYq0b3lZZBlSZRpcsrBEf3KJIz9Y\n"
+      "X5R5bLvw/qtCVjHDankA2EqMYKf9LBCLkQ0GUMpu3aS7xZhn4A6tIcqtRpe1+ruZ\n"
+      "k5GdAgMBAAGjUzBRMB0GA1UdDgQWBBRzt8cxhCiZoLnnKWgLDt5nPctfYTAfBgNV\n"
+      "HSMEGDAWgBRzt8cxhCiZoLnnKWgLDt5nPctfYTAPBgNVHRMBAf8EBTADAQH/MA0G\n"
+      "CSqGSIb3DQEBCwUAA4ICAQCUzlwgMiwnNo4VM2FCroJpGP/8gEsMcUUpfeQnKALm\n"
+      "MudiNPWVQk7uHeAKXvzoSlq/7/ZYKqlXxqiNXhkawnBl0lyR4Bnj8GbQMkujZzUS\n"
+      "EUI5UlPqlvy4WJw9ybgPPyl5D/0D7dkK0xAVxMktjaCGKtPQ/UCY2APxyoISmhSl\n"
+      "0+ql1YpHM1XIty/mzlTAIZ7bnbKDPA3J3OjaCP0Skhf2g4Wkch3+6Wx5xfYnyRv1\n"
+      "UbihStrvN1dH9d+D642C45qpRa2l3GJvDxdyr6xSa3l9IajUYbpMFe0yymuxqWhX\n"
+      "bDLi0ouKmowKNiiqUmUEJhJBbt/XdTIeeyTcaz2ZHVmMU9E72OhsjzxAvajoDBv9\n"
+      "FJ3THlLlh7iHBv24Hghx5V6FCliO6uLUdLB1d8WNUtEWdzf17ZlPqRIkjSY+6kSJ\n"
+      "dNwQhl5kYL0caOKWvEEP9f2HondKxtVpYGHgtKvcvCj/hz8UCk9R3odcwweq48RK\n"
+      "fKNRHy3nQfWttSSbBH8SwSmtX2VesMu6jMcqwU/8YSrWTJa/5UexlNR9qRrDnhya\n"
+      "kqZCaETfx15LUkPPuyn+z76z2+hNW0VDpnUVRystHHkDz+q2cbH/bsfY47Et0Bsb\n"
+      "TozWCPRzEkmzTTaAZLtqXa5MzWsZweBzK5owXlOPTD2eo1UphgtOqsKPE/RB/Qgq\n"
+      "dw==\n"
+      "-----END CERTIFICATE-----\n";
+  size_t len = strlen(valid_in_2021);
+  BIO* cert_bio = BIO_new(BIO_s_mem());
+  BIO_write(cert_bio, valid_in_2021, len);
+  X509* cert_X509 = PEM_read_bio_X509(cert_bio, NULL, NULL, NULL);
+  EXPECT(cert_X509 != nullptr);
+  EXPECT(SecureSocketUtils::IsCurrentTimeInsideCertValidDateRange(cert_X509));
+  BIO_free(cert_bio);
+  X509_free(cert_X509);
+}
+
+TEST_CASE(SecureSocketUtils_CertAlreadyExpired) {
+  const char* valid_before_2021 =
+      "-----BEGIN CERTIFICATE-----\n"
+      "MIIFazCCA1OgAwIBAgIUY+S+GbniK1WC9821VgAJusuF33UwDQYJKoZIhvcNAQEL\n"
+      "BQAwRTELMAkGA1UEBhMCQVUxEzARBgNVBAgMClNvbWUtU3RhdGUxITAfBgNVBAoM\n"
+      "GEludGVybmV0IFdpZGdpdHMgUHR5IEx0ZDAeFw0yMDA4MjUxNzAyNDFaFw0yMDA5\n"
+      "MjQxNzAyNDFaMEUxCzAJBgNVBAYTAkFVMRMwEQYDVQQIDApTb21lLVN0YXRlMSEw\n"
+      "HwYDVQQKDBhJbnRlcm5ldCBXaWRnaXRzIFB0eSBMdGQwggIiMA0GCSqGSIb3DQEB\n"
+      "AQUAA4ICDwAwggIKAoICAQDNfCrlXNeGKpF0PHzjkG5UfsSYvwfNUTqnzC3AkTMY\n"
+      "AZyyqDCA780TPZH48aZ/QFegFdIBUkEijFLuRKUqAv5jHxaVhMQcr5ujdCAJWT+e\n"
+      "5jc0cvukdWnFFqZwJWur4/3RsUnaWXY+oDk0pGuZD7VeNm9PTi1pQogwAivhSynM\n"
+      "YxCq0cO0JPM0Dr7ks99V1gDWrEOqjJGeEzvRlwdx+GPkvMvmrSHxWOphN/ji2MRx\n"
+      "tZ0T5FrrrGEtfp8gtTe5q5V+di1GvbuE6Y+MVYGIJeu3yqHkoh/TTS9Ex+QRm9nh\n"
+      "QM1Pm4hi2PofSSEdj15cUw6vfPJWewZiytcVJFTt2in1YuYufZMwPLP/ylnAQLkM\n"
+      "dq3TIF1g4ym9xLgQ/ZgnMX6g6ReOqG/1Au5InPUXMo3n56N959gQD1K8J2C4xtQP\n"
+      "MxrDAbGuYOmCterPAmW4aIVgbxIXwEK7lzTZyHUOvwjNaEfu0fuVOd9NC2B+g8So\n"
+      "I188ty96/BVwQO5bAzGekJn9xHVcTUU067b5zNfCpo4XGKaKVNGGR+AXhtjRXbrX\n"
+      "N9/BOHdABlV5W32HkhT4fr/BSSp/UyCnBZRPvLcI3Nvraok8snn/eGt6IW3y171O\n"
+      "3tYx4Gz7+M2K/T1rMuujVXOx6srtZ8oQIqFgZTR0sKKsim1umHAmoTJrG3wEOlUs\n"
+      "awIDAQABo1MwUTAdBgNVHQ4EFgQUzTOEhm+P6rWyBkKAkctA9FvheC8wHwYDVR0j\n"
+      "BBgwFoAUzTOEhm+P6rWyBkKAkctA9FvheC8wDwYDVR0TAQH/BAUwAwEB/zANBgkq\n"
+      "hkiG9w0BAQsFAAOCAgEABYYIBheuGRbmRhsS39zy0jDhqmDbsyIFd3/NoMZ+WvW4\n"
+      "NFcVRATalIX6ScXl7RGs1p855OiqOHij1tCzBClZXZ1zWD2v0KfWMFjR/S79HJOI\n"
+      "w3RGaMvALUJtOCz5in5Odryuo3GBkxKNonS+HAjnrWosqBCorerjn/TdIscTbA6h\n"
+      "7Iwy5umyyY63E69ehD7aANc/mxk++BWdAs3kPSXMI7PDpWUW5WV0hPUpe3sf0eY8\n"
+      "skfXa+UJ2qDmVkMmHUIOhi92zTRv6ROQXGY52JhHZOFSFxvqjWkk1M8q6Vm2ln2s\n"
+      "2GUa2j4emp+zti2JuFAwDgEK8wyqlq14hA8hTHL27mxpht990QGAU+qmcfhUf/qd\n"
+      "cIPkbz53Dpezzd96SuHQyjALaTbEw2vis9WpsejOKiaAp8264t0DgtLUndj4wVfC\n"
+      "3xti1jubmouUEdbNh7bnDfXxdxuAECFzhEG9mrosnTemuUVQSXIyrNfHRKDEaGv1\n"
+      "zh2Jij4HI+OKnJuao/9vsbNPib7k8tR0JKbXZD3HvOfQi5wMtlCUedu9eZ3Cq9Mu\n"
+      "1NwIwFoSU5pwO4PopiYL2hAEJXd0SN6TnWZThU28qTulrCb8enNU6BfkokTlkmYs\n"
+      "HUzvFarVyhKbQkyD/P3ckC/p2mg9aE7iLO5wTY1gegcSDF4R4479t/aDWMmevis=\n"
+      "-----END CERTIFICATE-----\n";
+  size_t len = strlen(valid_before_2021);
+  BIO* cert_bio = BIO_new(BIO_s_mem());
+  BIO_write(cert_bio, valid_before_2021, len);
+  X509* cert_X509 = PEM_read_bio_X509(cert_bio, NULL, NULL, NULL);
+  EXPECT(cert_X509 != nullptr);
+  EXPECT(!SecureSocketUtils::IsCurrentTimeInsideCertValidDateRange(cert_X509));
+  BIO_free(cert_bio);
+  X509_free(cert_X509);
+}
+
+}  // namespace bin
+}  // namespace dart
+
+#endif  // !defined(DART_IO_SECURE_SOCKET_DISABLED)
diff --git a/runtime/bin/security_context_win.cc b/runtime/bin/security_context_win.cc
index f61ae55..2be09d4 100644
--- a/runtime/bin/security_context_win.cc
+++ b/runtime/bin/security_context_win.cc
@@ -111,6 +111,14 @@
       Syslog::Print("\n");
     }
 
+    if (!SecureSocketUtils::IsCurrentTimeInsideCertValidDateRange(root_cert)) {
+      if (SSL_LOG_STATUS) {
+        Syslog::Print("...certificate is outside of its valid date range\n");
+      }
+      X509_free(root_cert);
+      continue;
+    }
+
     int status = X509_STORE_add_cert(store, root_cert);
     if (status == 0) {
       int error = ERR_get_error();
diff --git a/tools/VERSION b/tools/VERSION
index d26e6ca..86618d0 100644
--- a/tools/VERSION
+++ b/tools/VERSION
@@ -26,6 +26,6 @@
 CHANNEL stable
 MAJOR 2
 MINOR 14
-PATCH 3
+PATCH 4
 PRERELEASE 0
 PRERELEASE_PATCH 0
\ No newline at end of file