diff --git a/iocore/net/P_SSLNetVConnection.h b/iocore/net/P_SSLNetVConnection.h
index 7c8b94ae1b6..d38955251e2 100644
--- a/iocore/net/P_SSLNetVConnection.h
+++ b/iocore/net/P_SSLNetVConnection.h
@@ -331,6 +331,8 @@ class SSLNetVConnection : public UnixNetVConnection,
   ink_hrtime sslLastWriteTime = 0;
   int64_t sslTotalBytesSent   = 0;
 
+  SSL_SESSION *client_sess = nullptr;
+
   // The serverName is either a pointer to the (null-terminated) name fetched from the
   // SSL object or the empty string.
   const char *
diff --git a/iocore/net/SSLClientUtils.cc b/iocore/net/SSLClientUtils.cc
index 4d14569545a..231010bd079 100644
--- a/iocore/net/SSLClientUtils.cc
+++ b/iocore/net/SSLClientUtils.cc
@@ -165,13 +165,15 @@ ssl_new_session_callback(SSL *ssl, SSL_SESSION *sess)
     std::string lookup_key;
     ts::bwprint(lookup_key, "{}:{}:{}", sni_addr.c_str(), SSL_get_SSL_CTX(ssl), get_verify_str(ssl));
     origin_sess_cache->insert_session(lookup_key, sess, ssl);
-    return 1;
   } else {
     if (is_debug_tag_set("ssl.origin_session_cache")) {
       Debug("ssl.origin_session_cache", "Failed to fetch SNI/IP.");
     }
-    return 0;
   }
+
+  // return 0 here since we're converting the sessions using i2d_SSL_SESSION,
+  // meaning if we return 1, openssl will keep an extra refcount on the session.
+  return 0;
 }
 
 SSL_CTX *
diff --git a/iocore/net/SSLNetVConnection.cc b/iocore/net/SSLNetVConnection.cc
index da1b473f1b7..74e4e10f37b 100644
--- a/iocore/net/SSLNetVConnection.cc
+++ b/iocore/net/SSLNetVConnection.cc
@@ -946,10 +946,23 @@ SSLNetVConnection::clear()
   _ca_cert_file.reset();
   _ca_cert_dir.reset();
 
+  // SSL_SESSION_free() must only be called for SSL_SESSION objects,
+  // for which the reference count was explicitly incremented (e.g.
+  // by calling SSL_get1_session(), see SSL_get_session(3)) or when
+  // the SSL_SESSION object was generated outside a TLS handshake
+  // operation, e.g. by using d2i_SSL_SESSION(3). It must not be called
+  // on other SSL_SESSION objects, as this would cause incorrect
+  // reference counts and therefore program failures.
+  if (client_sess != nullptr) {
+    SSL_SESSION_free(client_sess);
+    client_sess = nullptr;
+  }
+
   if (ssl != nullptr) {
     SSL_free(ssl);
     ssl = nullptr;
   }
+
   ALPNSupport::clear();
   TLSBasicSupport::clear();
   TLSSessionResumptionSupport::clear();
@@ -2078,7 +2091,14 @@ SSLNetVConnection::_ssl_connect()
 
       sess = this->getOriginSession(ssl, lookup_key);
       if (sess) {
-        SSL_set_session(ssl, sess);
+        if (SSL_set_session(ssl, sess) == 0) {
+          SSL_SESSION_free(sess);
+        } else {
+          if (this->client_sess) {
+            SSL_SESSION_free(this->client_sess);
+          }
+          this->client_sess = sess;
+        }
       }
     }
   }
diff --git a/iocore/net/SSLSessionCache.cc b/iocore/net/SSLSessionCache.cc
index 93051a35c7f..1bcc52f41c7 100644
--- a/iocore/net/SSLSessionCache.cc
+++ b/iocore/net/SSLSessionCache.cc
@@ -326,8 +326,25 @@ SSLOriginSessionCache::insert_session(const std::string &lookup_key, SSL_SESSION
     Debug("ssl.origin_session_cache", "insert session: %s = %p", lookup_key.c_str(), sess);
   }
 
+  size_t len = i2d_SSL_SESSION(sess, nullptr); // make sure we're not going to need more than SSL_MAX_ORIG_SESSION_SIZE bytes
+
+  /* do not cache a session that's too big. */
+  if (len > static_cast<size_t>(SSL_MAX_ORIG_SESSION_SIZE)) {
+    Debug("ssl.origin_session_cache", "Unable to save SSL session because size of %zd exceeds the max of %d", len,
+          SSL_MAX_ORIG_SESSION_SIZE);
+    return;
+  } else if (len == 0) {
+    Debug("ssl.origin_session_cache", "Unable to save SSL session because size is 0");
+    return;
+  }
+
+  Ptr<IOBufferData> buf;
+  buf = new_IOBufferData(buffer_size_to_index(len, MAX_BUFFER_SIZE_INDEX), MEMALIGNED);
+  ink_release_assert(static_cast<size_t>(buf->block_size()) >= len);
+  unsigned char *loc = reinterpret_cast<unsigned char *>(buf->data());
+  i2d_SSL_SESSION(sess, &loc);
   ssl_curve_id curve = (ssl == nullptr) ? 0 : SSLGetCurveNID(ssl);
-  ats_scoped_obj<SSLOriginSession> ssl_orig_session(new SSLOriginSession(lookup_key, sess, curve));
+  ats_scoped_obj<SSLOriginSession> ssl_orig_session(new SSLOriginSession(lookup_key, buf, len, curve));
   auto new_node = ssl_orig_session.release();
 
   std::unique_lock lock(mutex);
@@ -358,7 +375,8 @@ SSLOriginSessionCache::get_session(const std::string &lookup_key, SSL_SESSION **
     return false;
   }
 
-  *sess = entry->second->session;
+  const unsigned char *loc = reinterpret_cast<const unsigned char *>(entry->second->asn1_data->data());
+  *sess                    = d2i_SSL_SESSION(nullptr, &loc, entry->second->len_asn1_data);
   if (curve != nullptr) {
     *curve = entry->second->curve_id;
   }
@@ -380,3 +398,23 @@ SSLOriginSessionCache::remove_oldest_session(const std::unique_lock<std::shared_
     delete node;
   }
 }
+
+void
+SSLOriginSessionCache::remove_session(const std::string &lookup_key)
+{
+  // We can't bail on contention here because this session MUST be removed.
+  if (is_debug_tag_set("ssl.origin_session_cache")) {
+    Debug("ssl.origin_session_cache", "remove session: %s", lookup_key.c_str());
+  }
+
+  std::unique_lock lock(mutex);
+  auto entry = orig_sess_map.find(lookup_key);
+  if (entry != orig_sess_map.end()) {
+    auto node = entry->second;
+    orig_sess_que.remove(node);
+    orig_sess_map.erase(entry);
+    delete node;
+  }
+
+  return;
+}
diff --git a/iocore/net/SSLSessionCache.h b/iocore/net/SSLSessionCache.h
index fdf99660867..2a099d36c1e 100644
--- a/iocore/net/SSLSessionCache.h
+++ b/iocore/net/SSLSessionCache.h
@@ -33,6 +33,7 @@
 #include <shared_mutex>
 
 #define SSL_MAX_SESSION_SIZE 256
+#define SSL_MAX_ORIG_SESSION_SIZE 4096
 
 struct ssl_session_cache_exdata {
   ssl_curve_id curve = 0;
@@ -187,16 +188,15 @@ class SSLOriginSession
 {
 public:
   std::string key;
-  SSL_SESSION *session;
+  Ptr<IOBufferData> asn1_data; /* this is the ASN1 representation of the SSL_CTX */
+  size_t len_asn1_data;
   ssl_curve_id curve_id;
 
-  SSLOriginSession(const std::string &lookup_key, SSL_SESSION *sess, ssl_curve_id curve)
-    : key(lookup_key), session(sess), curve_id(curve)
+  SSLOriginSession(const std::string &lookup_key, const Ptr<IOBufferData> &asn1, size_t len_asn1, ssl_curve_id curve)
+    : key(lookup_key), asn1_data(asn1), len_asn1_data(len_asn1), curve_id(curve)
   {
   }
 
-  ~SSLOriginSession() { SSL_SESSION_free(session); }
-
   LINK(SSLOriginSession, link);
 };
 
@@ -208,6 +208,7 @@ class SSLOriginSessionCache
 
   void insert_session(const std::string &lookup_key, SSL_SESSION *sess, SSL *ssl);
   bool get_session(const std::string &lookup_key, SSL_SESSION **sess, ssl_curve_id *curve);
+  void remove_session(const std::string &lookup_key);
 
 private:
   void remove_oldest_session(const std::unique_lock<std::shared_mutex> &lock);
diff --git a/iocore/net/TLSSessionResumptionSupport.cc b/iocore/net/TLSSessionResumptionSupport.cc
index e8e981e7639..2ae41eb5a08 100644
--- a/iocore/net/TLSSessionResumptionSupport.cc
+++ b/iocore/net/TLSSessionResumptionSupport.cc
@@ -183,6 +183,8 @@ TLSSessionResumptionSupport::getOriginSession(SSL *ssl, const std::string &looku
     // Double check the timeout
     if (is_ssl_session_timed_out(session)) {
       SSL_INCREMENT_DYN_STAT(ssl_origin_session_cache_miss);
+      origin_sess_cache->remove_session(lookup_key);
+      SSL_SESSION_free(session);
       session = nullptr;
     } else {
       SSL_INCREMENT_DYN_STAT(ssl_origin_session_cache_hit);