diff --git a/ssl/s3_lib.c b/ssl/s3_lib.c
index ffdf3a90fb..9060ee38f0 100644
--- a/ssl/s3_lib.c
+++ b/ssl/s3_lib.c
@@ -17,6 +17,7 @@
 #include <openssl/dh.h>
 #include <openssl/rand.h>
 #include <openssl/trace.h>
+#include <openssl/x509v3.h>
 #include "internal/cryptlib.h"
 
 #define TLS13_NUM_CIPHERS       OSSL_NELEM(tls13_ciphers)
@@ -3947,6 +3948,10 @@ long ssl3_ctx_ctrl(SSL_CTX *ctx, int cmd, long larg, void *parg)
                 return 0;
             }
         }
+        if (!X509v3_cache_extensions((X509 *)parg, ctx->libctx, ctx->propq)) {
+            SSLerr(0, ERR_LIB_X509);
+            return 0;
+        }
         if (!sk_X509_push(ctx->extra_certs, (X509 *)parg)) {
             SSLerr(SSL_F_SSL3_CTX_CTRL, ERR_R_MALLOC_FAILURE);
             return 0;
diff --git a/ssl/ssl_cert.c b/ssl/ssl_cert.c
index 56e3642fbd..f753bbee38 100644
--- a/ssl/ssl_cert.c
+++ b/ssl/ssl_cert.c
@@ -253,11 +253,20 @@ void ssl_cert_free(CERT *c)
 int ssl_cert_set0_chain(SSL *s, SSL_CTX *ctx, STACK_OF(X509) *chain)
 {
     int i, r;
-    CERT_PKEY *cpk = s ? s->cert->key : ctx->cert->key;
+    CERT_PKEY *cpk = s != NULL ? s->cert->key : ctx->cert->key;
+    SSL_CTX *realctx = s != NULL ? s->ctx : ctx;
+
     if (!cpk)
         return 0;
     for (i = 0; i < sk_X509_num(chain); i++) {
-        r = ssl_security_cert(s, ctx, sk_X509_value(chain, i), 0, 0);
+        X509 *x = sk_X509_value(chain, i);
+
+        if (!X509v3_cache_extensions(x, realctx->libctx, realctx->propq)) {
+            SSLerr(0, ERR_LIB_X509);
+            return 0;
+        }
+
+        r = ssl_security_cert(s, ctx, x, 0, 0);
         if (r != 1) {
             SSLerr(SSL_F_SSL_CERT_SET0_CHAIN, r);
             return 0;
diff --git a/ssl/ssl_rsa.c b/ssl/ssl_rsa.c
index b32a7b90bb..3a222e5571 100644
--- a/ssl/ssl_rsa.c
+++ b/ssl/ssl_rsa.c
@@ -14,6 +14,7 @@
 #include <openssl/objects.h>
 #include <openssl/evp.h>
 #include <openssl/x509.h>
+#include <openssl/x509v3.h>
 #include <openssl/pem.h>
 
 static int ssl_set_cert(CERT *c, X509 *x509);
@@ -31,6 +32,10 @@ int SSL_use_certificate(SSL *ssl, X509 *x)
         SSLerr(SSL_F_SSL_USE_CERTIFICATE, ERR_R_PASSED_NULL_PARAMETER);
         return 0;
     }
+    if (!X509v3_cache_extensions(x, ssl->ctx->libctx, ssl->ctx->propq)) {
+        SSLerr(0, ERR_LIB_X509);
+        return 0;
+    }
     rv = ssl_security_cert(ssl, NULL, x, 0, 1);
     if (rv != 1) {
         SSLerr(SSL_F_SSL_USE_CERTIFICATE, rv);
@@ -305,6 +310,10 @@ int SSL_CTX_use_certificate(SSL_CTX *ctx, X509 *x)
         SSLerr(SSL_F_SSL_CTX_USE_CERTIFICATE, ERR_R_PASSED_NULL_PARAMETER);
         return 0;
     }
+    if (!X509v3_cache_extensions(x, ctx->libctx, ctx->propq)) {
+        SSLerr(0, ERR_LIB_X509);
+        return 0;
+    }
     rv = ssl_security_cert(NULL, ctx, x, 0, 1);
     if (rv != 1) {
         SSLerr(SSL_F_SSL_CTX_USE_CERTIFICATE, rv);