diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index 985a626b3..6d19e992d 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -11,7 +11,7 @@ jobs:
       fail-fast: false
       matrix:
         os: [ ubuntu-latest, macos-latest ]
-        ruby: [ head, 2.7, 2.6, 2.5, 2.4, 2.3 ]
+        ruby: [ head, "3.0", "2.7", "2.6", "2.5", "2.4", "2.3" ]
     steps:
       - name: repo checkout
         uses: actions/checkout@v2
@@ -38,7 +38,7 @@ jobs:
       fail-fast: false
       matrix:
         os: [ windows-latest ]
-        ruby: [ mswin, mingw, 2.7, 2.6, 2.5, 2.4, 2.3 ]
+        ruby: [ mswin, mingw, "3.0", "2.7", "2.6", "2.5", "2.4", "2.3" ]
     steps:
       - name: repo checkout
         uses: actions/checkout@v2
@@ -52,10 +52,11 @@ jobs:
       - name: depends
         run:  rake install_dependencies
 
+      # pkg-config is disabled because it can pick up the different OpenSSL installation
       # SSL_DIR is set as needed by MSP-Greg/setup-ruby-pkgs
       # only used with mswin
       - name: compile
-        run:  rake compile -- --enable-debug $env:SSL_DIR
+        run:  rake compile -- --enable-debug --without-pkg-config $env:SSL_DIR
 
       - name: test
         run:  rake test TESTOPTS="-v --no-show-detail-immediately" OSSL_MDEBUG=1
@@ -68,21 +69,15 @@ jobs:
       fail-fast: false
       matrix:
         os: [ ubuntu-latest ]
-        ruby: [ 2.7 ]
+        ruby: [ "3.0" ]
         openssl:
           - openssl-1.0.1u # EOL
           - openssl-1.0.2u # EOL
           - openssl-1.1.0l # EOL
-          - openssl-1.1.1g
-          # - libressl-2.3.7 # EOL
-          # - libressl-2.4.5 # EOL
-          # - libressl-2.5.5 # EOL
-          # - libressl-2.6.5 # EOL
-          # - libressl-2.7.5 # EOL
-          # - libressl-2.8.3 # EOL
+          - openssl-1.1.1j
           - libressl-2.9.2 # EOL
-          - libressl-3.0.2
-          - libressl-3.1.1
+          - libressl-3.1.5
+          - libressl-3.2.0
     steps:
       - name: repo checkout
         uses: actions/checkout@v2
diff --git a/ext/openssl/ossl_bn.c b/ext/openssl/ossl_bn.c
index d94b8e375..bec37299f 100644
--- a/ext/openssl/ossl_bn.c
+++ b/ext/openssl/ossl_bn.c
@@ -453,7 +453,7 @@ ossl_bn_is_negative(VALUE self)
 	if (!(result = BN_new())) {			\
 	    ossl_raise(eBNError, NULL);			\
 	}						\
-	if (!BN_##func(result, bn, ossl_bn_ctx)) {	\
+	if (BN_##func(result, bn, ossl_bn_ctx) <= 0) {	\
 	    BN_free(result);				\
 	    ossl_raise(eBNError, NULL);			\
 	}						\
@@ -479,7 +479,7 @@ BIGNUM_1c(sqr)
 	if (!(result = BN_new())) {			\
 	    ossl_raise(eBNError, NULL);			\
 	}						\
-	if (!BN_##func(result, bn1, bn2)) {		\
+	if (BN_##func(result, bn1, bn2) <= 0) {		\
 	    BN_free(result);				\
 	    ossl_raise(eBNError, NULL);			\
 	}						\
@@ -512,7 +512,7 @@ BIGNUM_2(sub)
 	if (!(result = BN_new())) {				\
 	    ossl_raise(eBNError, NULL);				\
 	}							\
-	if (!BN_##func(result, bn1, bn2, ossl_bn_ctx)) {	\
+	if (BN_##func(result, bn1, bn2, ossl_bn_ctx) <= 0) {	\
 	    BN_free(result);					\
 	    ossl_raise(eBNError, NULL);				\
 	}							\
@@ -556,11 +556,21 @@ BIGNUM_2c(gcd)
 BIGNUM_2c(mod_sqr)
 
 /*
- * Document-method: OpenSSL::BN#mod_inverse
  * call-seq:
- *   bn.mod_inverse(bn2) => aBN
+ *    bn.mod_inverse(bn2) => aBN
  */
-BIGNUM_2c(mod_inverse)
+static VALUE
+ossl_bn_mod_inverse(VALUE self, VALUE other)
+{
+    BIGNUM *bn1, *bn2 = GetBNPtr(other), *result;
+    VALUE obj;
+    GetBN(self, bn1);
+    obj = NewBN(rb_obj_class(self));
+    if (!(result = BN_mod_inverse(NULL, bn1, bn2, ossl_bn_ctx)))
+        ossl_raise(eBNError, "BN_mod_inverse");
+    SetBN(obj, result);
+    return obj;
+}
 
 /*
  * call-seq:
@@ -609,7 +619,7 @@ ossl_bn_div(VALUE self, VALUE other)
 	if (!(result = BN_new())) {				\
 	    ossl_raise(eBNError, NULL);				\
 	}							\
-	if (!BN_##func(result, bn1, bn2, bn3, ossl_bn_ctx)) {	\
+	if (BN_##func(result, bn1, bn2, bn3, ossl_bn_ctx) <= 0) { \
 	    BN_free(result);					\
 	    ossl_raise(eBNError, NULL);				\
 	}							\
@@ -651,7 +661,7 @@ BIGNUM_3c(mod_exp)
     {							\
 	BIGNUM *bn;					\
 	GetBN(self, bn);				\
-	if (!BN_##func(bn, NUM2INT(bit))) {		\
+	if (BN_##func(bn, NUM2INT(bit)) <= 0) {		\
 	    ossl_raise(eBNError, NULL);			\
 	}						\
 	return self;					\
@@ -711,7 +721,7 @@ ossl_bn_is_bit_set(VALUE self, VALUE bit)
 	if (!(result = BN_new())) {			\
 		ossl_raise(eBNError, NULL);		\
 	}						\
-	if (!BN_##func(result, bn, b)) {		\
+	if (BN_##func(result, bn, b) <= 0) {		\
 		BN_free(result);			\
 		ossl_raise(eBNError, NULL);		\
 	}						\
@@ -741,7 +751,7 @@ BIGNUM_SHIFT(rshift)
 	int b;						\
 	b = NUM2INT(bits);				\
 	GetBN(self, bn);				\
-	if (!BN_##func(bn, bn, b))			\
+	if (BN_##func(bn, bn, b) <= 0)			\
 		ossl_raise(eBNError, NULL);		\
 	return self;					\
     }
@@ -780,7 +790,7 @@ BIGNUM_SELF_SHIFT(rshift)
 	if (!(result = BN_new())) {				\
 	    ossl_raise(eBNError, NULL);				\
 	}							\
-	if (!BN_##func(result, b, top, bottom)) {		\
+	if (BN_##func(result, b, top, bottom) <= 0) {		\
 	    BN_free(result);					\
 	    ossl_raise(eBNError, NULL);				\
 	}							\
@@ -809,7 +819,7 @@ BIGNUM_RAND(pseudo_rand)
 	if (!(result = BN_new())) {				\
 	    ossl_raise(eBNError, NULL);				\
 	}							\
-	if (!BN_##func##_range(result, bn)) {			\
+	if (BN_##func##_range(result, bn) <= 0) {		\
 	    BN_free(result);					\
 	    ossl_raise(eBNError, NULL);				\
 	}							\
diff --git a/ext/openssl/ossl_ssl.c b/ext/openssl/ossl_ssl.c
index f4cc6dec7..c38142bfc 100644
--- a/ext/openssl/ossl_ssl.c
+++ b/ext/openssl/ossl_ssl.c
@@ -1647,6 +1647,11 @@ ossl_start_ssl(VALUE self, int (*func)(), const char *funcname, VALUE opts)
             rb_io_wait_readable(fptr->fd);
             continue;
 	case SSL_ERROR_SYSCALL:
+#ifdef __APPLE__
+            /* See ossl_ssl_write_internal() */
+            if (errno == EPROTOTYPE)
+                continue;
+#endif
 	    if (errno) rb_sys_fail(funcname);
 	    ossl_raise(eSSLError, "%s SYSCALL returned=%d errno=%d state=%s", funcname, ret2, errno, SSL_state_string_long(ssl));
 #if defined(SSL_R_CERTIFICATE_VERIFY_FAILED)
@@ -1938,6 +1943,16 @@ ossl_ssl_write_internal(VALUE self, VALUE str, VALUE opts)
                 rb_io_wait_readable(fptr->fd);
                 continue;
 	    case SSL_ERROR_SYSCALL:
+#ifdef __APPLE__
+                /*
+                 * It appears that send syscall can return EPROTOTYPE if the
+                 * socket is being torn down. Retry to get a proper errno to
+                 * make the error handling in line with the socket library.
+                 * [Bug #14713] https://bugs.ruby-lang.org/issues/14713
+                 */
+                if (errno == EPROTOTYPE)
+                    continue;
+#endif
 		if (errno) rb_sys_fail(0);
 	    default:
 		ossl_raise(eSSLError, "SSL_write");
diff --git a/ext/openssl/ossl_x509store.c b/ext/openssl/ossl_x509store.c
index 1eaaf4b3d..5e0ab8d85 100644
--- a/ext/openssl/ossl_x509store.c
+++ b/ext/openssl/ossl_x509store.c
@@ -546,7 +546,7 @@ static VALUE ossl_x509stctx_set_time(VALUE, VALUE);
 
 /*
  * call-seq:
- *   StoreContext.new(store, cert = nil, chain = nil)
+ *   StoreContext.new(store, cert = nil, untrusted = nil)
  *
  * Sets up a StoreContext for a verification of the X.509 certificate _cert_.
  */
@@ -558,15 +558,24 @@ ossl_x509stctx_initialize(int argc, VALUE *argv, VALUE self)
     X509_STORE *x509st;
     X509 *x509 = NULL;
     STACK_OF(X509) *x509s = NULL;
+    int state;
 
     rb_scan_args(argc, argv, "12", &store, &cert, &chain);
     GetX509StCtx(self, ctx);
     GetX509Store(store, x509st);
-    if(!NIL_P(cert)) x509 = DupX509CertPtr(cert); /* NEED TO DUP */
-    if(!NIL_P(chain)) x509s = ossl_x509_ary2sk(chain);
-    if(X509_STORE_CTX_init(ctx, x509st, x509, x509s) != 1){
+    if (!NIL_P(cert))
+        x509 = DupX509CertPtr(cert); /* NEED TO DUP */
+    if (!NIL_P(chain)) {
+        x509s = ossl_protect_x509_ary2sk(chain, &state);
+        if (state) {
+            X509_free(x509);
+            rb_jump_tag(state);
+        }
+    }
+    if (X509_STORE_CTX_init(ctx, x509st, x509, x509s) != 1){
+        X509_free(x509);
         sk_X509_pop_free(x509s, X509_free);
-        ossl_raise(eX509StoreError, NULL);
+        ossl_raise(eX509StoreError, "X509_STORE_CTX_init");
     }
     if (!NIL_P(t = rb_iv_get(store, "@time")))
 	ossl_x509stctx_set_time(self, t);