diff --git a/src/crypto/crypto_common.cc b/src/crypto/crypto_common.cc
index ec2379f15b55be..ed1aea868d8385 100644
--- a/src/crypto/crypto_common.cc
+++ b/src/crypto/crypto_common.cc
@@ -48,13 +48,18 @@ static constexpr int kX509NameFlagsMultiline =
     XN_FLAG_SEP_MULTILINE |
     XN_FLAG_FN_SN;
 
-bool SSL_CTX_get_issuer(SSL_CTX* ctx, X509* cert, X509** issuer) {
+X509Pointer SSL_CTX_get_issuer(SSL_CTX* ctx, X509* cert) {
   X509_STORE* store = SSL_CTX_get_cert_store(ctx);
   DeleteFnPtr<X509_STORE_CTX, X509_STORE_CTX_free> store_ctx(
       X509_STORE_CTX_new());
-  return store_ctx.get() != nullptr &&
-         X509_STORE_CTX_init(store_ctx.get(), store, nullptr, nullptr) == 1 &&
-         X509_STORE_CTX_get1_issuer(issuer, store_ctx.get(), cert) == 1;
+  X509Pointer result;
+  X509* issuer;
+  if (store_ctx.get() != nullptr &&
+      X509_STORE_CTX_init(store_ctx.get(), store, nullptr, nullptr) == 1 &&
+      X509_STORE_CTX_get1_issuer(&issuer, store_ctx.get(), cert) == 1) {
+    result.reset(issuer);
+  }
+  return result;
 }
 
 void LogSecret(
@@ -386,12 +391,12 @@ MaybeLocal<Object> GetLastIssuedCert(
     Environment* const env) {
   Local<Context> context = env->isolate()->GetCurrentContext();
   while (X509_check_issued(cert->get(), cert->get()) != X509_V_OK) {
-    X509* ca;
-    if (SSL_CTX_get_issuer(SSL_get_SSL_CTX(ssl.get()), cert->get(), &ca) <= 0)
+    X509Pointer ca;
+    if (!(ca = SSL_CTX_get_issuer(SSL_get_SSL_CTX(ssl.get()), cert->get())))
       break;
 
     Local<Object> ca_info;
-    MaybeLocal<Object> maybe_ca_info = X509ToObject(env, ca);
+    MaybeLocal<Object> maybe_ca_info = X509ToObject(env, ca.get());
     if (!maybe_ca_info.ToLocal(&ca_info))
       return MaybeLocal<Object>();
 
@@ -399,16 +404,14 @@ MaybeLocal<Object> GetLastIssuedCert(
       return MaybeLocal<Object>();
     issuer_chain = ca_info;
 
-    // Take the value of cert->get() before the call to cert->reset()
-    // in order to compare it to ca after and provide a way to exit this loop
-    // in case it gets stuck.
-    X509* value_before_reset = cert->get();
+    // For self-signed certificates whose keyUsage field does not include
+    // keyCertSign, X509_check_issued() will return false. Avoid going into an
+    // infinite loop by checking if SSL_CTX_get_issuer() returned the same
+    // certificate.
+    if (cert->get() == ca.get()) break;
 
     // Delete previous cert and continue aggregating issuers.
-    cert->reset(ca);
-
-    if (value_before_reset == ca)
-      break;
+    *cert = std::move(ca);
   }
   return MaybeLocal<Object>(issuer_chain);
 }
diff --git a/src/crypto/crypto_common.h b/src/crypto/crypto_common.h
index e0956395e91c18..96ca981aec9e44 100644
--- a/src/crypto/crypto_common.h
+++ b/src/crypto/crypto_common.h
@@ -25,7 +25,7 @@ struct StackOfXASN1Deleter {
 };
 using StackOfASN1 = std::unique_ptr<STACK_OF(ASN1_OBJECT), StackOfXASN1Deleter>;
 
-bool SSL_CTX_get_issuer(SSL_CTX* ctx, X509* cert, X509** issuer);
+X509Pointer SSL_CTX_get_issuer(SSL_CTX* ctx, X509* cert);
 
 void LogSecret(
     const SSLPointer& ssl,
diff --git a/src/crypto/crypto_context.cc b/src/crypto/crypto_context.cc
index f8125ab706b733..e2291f72b6622f 100644
--- a/src/crypto/crypto_context.cc
+++ b/src/crypto/crypto_context.cc
@@ -110,21 +110,21 @@ int SSL_CTX_use_certificate_chain(SSL_CTX* ctx,
   // Try getting issuer from a cert store
   if (ret) {
     if (issuer == nullptr) {
-      ret = SSL_CTX_get_issuer(ctx, x.get(), &issuer);
-      ret = ret < 0 ? 0 : 1;
+      // TODO(tniessen): SSL_CTX_get_issuer does not allow the caller to
+      // distinguish between a failed operation and an empty result. Fix that
+      // and then handle the potential error properly here (set ret to 0).
+      *issuer_ = SSL_CTX_get_issuer(ctx, x.get());
       // NOTE: get_cert_store doesn't increment reference count,
       // no need to free `store`
     } else {
       // Increment issuer reference count
-      issuer = X509_dup(issuer);
-      if (issuer == nullptr) {
+      issuer_->reset(X509_dup(issuer));
+      if (!*issuer_) {
         ret = 0;
       }
     }
   }
 
-  issuer_->reset(issuer);
-
   if (ret && x != nullptr) {
     cert->reset(X509_dup(x.get()));
     if (!*cert)