diff --git a/src/crypto/crypto_common.cc b/src/crypto/crypto_common.cc
index 1b863a1241edb3..f4b7bd3ad8548a 100644
--- a/src/crypto/crypto_common.cc
+++ b/src/crypto/crypto_common.cc
@@ -480,8 +480,16 @@ 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();
+
     // Delete previous cert and continue aggregating issuers.
     cert->reset(ca);
+
+    if (value_before_reset == ca)
+      break;
   }
   return MaybeLocal<Object>(issuer_chain);
 }
diff --git a/test/fixtures/keys/selfsigned-no-keycertsign/README.md b/test/fixtures/keys/selfsigned-no-keycertsign/README.md
new file mode 100644
index 00000000000000..0dcd69007a9142
--- /dev/null
+++ b/test/fixtures/keys/selfsigned-no-keycertsign/README.md
@@ -0,0 +1,2 @@
+# Self-signed certificate without keyCertSign bit
+The self-signed certificate ([cert.pem](./cert.pem)) and the key ([key.pem](./key.pem)) in this folder are used by the test [test-https-selfsigned-no-keycertsign-no-crash](../../../parallel/test-https-selfsigned-no-keycertsign-no-crash.js). The config ([cert.conf](./cert.conf)) and the file used to generate key and certificate in this folder ([https-renew-cert.sh](./https_renew_cert.sh)) are not used by the test but for reference.
diff --git a/test/fixtures/keys/selfsigned-no-keycertsign/cert.conf b/test/fixtures/keys/selfsigned-no-keycertsign/cert.conf
new file mode 100644
index 00000000000000..60901bb26d6937
--- /dev/null
+++ b/test/fixtures/keys/selfsigned-no-keycertsign/cert.conf
@@ -0,0 +1,17 @@
+[req]
+distinguished_name = req_distinguished_name
+req_extensions = v3_req
+prompt = no
+
+[req_distinguished_name]
+C = DE
+CN = localhost
+
+[v3_req]
+keyUsage = digitalSignature, keyEncipherment
+extendedKeyUsage = serverAuth
+subjectAltName = @alt_names
+[alt_names]
+DNS.1 = 127.0.0.1
+DNS.2 = localhost
+IP.1 = 127.0.0.1
diff --git a/test/fixtures/keys/selfsigned-no-keycertsign/cert.pem b/test/fixtures/keys/selfsigned-no-keycertsign/cert.pem
new file mode 100644
index 00000000000000..c0829b82caf8d3
--- /dev/null
+++ b/test/fixtures/keys/selfsigned-no-keycertsign/cert.pem
@@ -0,0 +1,18 @@
+-----BEGIN CERTIFICATE-----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+-----END CERTIFICATE-----
diff --git a/test/fixtures/keys/selfsigned-no-keycertsign/https_renew_cert.sh b/test/fixtures/keys/selfsigned-no-keycertsign/https_renew_cert.sh
new file mode 100644
index 00000000000000..092f27a8867cbb
--- /dev/null
+++ b/test/fixtures/keys/selfsigned-no-keycertsign/https_renew_cert.sh
@@ -0,0 +1,6 @@
+#!/bin/bash
+openssl genrsa -out rsa.pem 2048
+openssl rsa -in rsa.pem -out key.pem
+openssl req -sha256 -new -key key.pem -out csr.pem -subj "/CN=localhost"
+openssl x509 -req -extfile cert.conf -extensions v3_req -days 365 -in csr.pem -signkey key.pem -out cert.pem
+
diff --git a/test/fixtures/keys/selfsigned-no-keycertsign/key.pem b/test/fixtures/keys/selfsigned-no-keycertsign/key.pem
new file mode 100644
index 00000000000000..5f0549276a4cae
--- /dev/null
+++ b/test/fixtures/keys/selfsigned-no-keycertsign/key.pem
@@ -0,0 +1,27 @@
+-----BEGIN RSA PRIVATE KEY-----
+MIIEogIBAAKCAQEA0y3pMvD2AjG5xGBkGfyjBq8QgwB13ExOOQeJHuMZ9oGu+9VM
+HzKawiLPD9ApMA2a7avcQ6p5H0e3bkpkUrE4oIMx3dooeG3fwcidcgXoJB7xzk/T
+GxUpkBaR6WXyiEvTkSwWlysk4Mh0d9qi84Ou1fzDVZ7GoOxSg9B0STukhInYeGZf
+Ol/tCZXTRTHwn7ri/alODz8L1WClKDETiheV8kSp1IgDMYNP5Vf3oZZdOHtCouOJ
+D1P3pAdQkScHHRKvis72ZjaU5AbjTxC4ItH+eDYn6VjH7TdILwuruWu23gzToV+v
+xNBGCkMCORTRiK1u7KwPleC0J4WrQWLe/XPvTQIDAQABAoIBAFIlWMIVE0z1NNLb
+v/SP3oaaEK00v6QLFp5+fOtD4fSOq5eQeATmtWZxDeSTz4G+uRZctNipdmYhiovf
+ajj0cReXEQ3Ab9+wtcp2lDAndg6e7uaXDIJLcBh5fxawLnCwNkMRSFRTVwwNTajV
+pm9dOORKZ11l3tP4OXzG2IUoKy3Wj/1SKLL4zrdHi7802+L/GstK6/BGma+NFrFz
+U6yNqpvuzv7BH7w9G3nSz7u+8SjcY22Vs6q69GAQG3yf356cYCJhV7QIJXU0/VAF
+GFx5UDwlsOT2NhoOd/b9Q9RexKDl+qDupXQo0YFOObHIjHs8UGLOZkBtv4apCarA
+6u+BOwECgYEA9GbrP/5SfmN8xvF2XVjqjk9IUcvWAuTM4Bxav72e6aR9IOdye9vi
++GhwM6qON+LOnMVNhUKJ0+R/jjLy6Jq+00uKU65Q79x7lCBVSDDXWacV0IFIoAOp
+P4LkykjRZyzpIvjK5HGL1JYqZi89im93uuOiyMjoFS2syU+19b83UUECgYEA3TNk
+JVGWYLMcD3uVTe2e/yZSsX+0+QL8hm3bUSOIJ/mIe2dqCXb6MK0ndMS0aCLGtDSt
+wGTWwuc4rFattHYEI8Iro+tshgQs9bLM037hmiCrZvmcQsgt+3FNuYv4oCGp5U85
+mWYF5SVUYRyv8M9aZoKTjc8meR0Wv3ZGGC9iDw0CgYA0XKyAPGO+MmB0Wx1J6Jfw
+P2o2JB7I5e5DAbArrluSoSwx1YSApt6c6/tGBn+L16r+iYMPTu8ql6UAeUfzr9u8
+d02+mfU7Ppi3Zqn+2n/49ERHNLuzlLU5JzkPYcSDf2q/lGAby3vy4u1YkTx1IWac
+gtLIg8q9ZtjDFLHeYcZfQQKBgCCOpdjQT1/gPOsSd4FGzjYjv9wcPdjA1cY7eSJS
+JoIruijfqb3G40Ay3DHVmfAR3kk7z68XqHx7Z94Fy/9Zt3ZD6ARybEC1cKChNoCS
+lkYHNPMtHhC+QfZWUOhUb72x9r2nkYTAfXGisu6wOD0rZ9TatzkSGkmNPIHluJ9q
+qfYpAoGAPJiBBdSt7DC9ZZraQGMEHfRkE5CxEIRbIHJ9+U3Z7LTQT6MJ1y3VfcGs
+PetHcWtbU0Cl8blShaSwpxyCI01x3tUPw/b7tXMan/ImzjUgRe7kQXh2sf39V3b/
+fvzKXWBvOvc1lgG0pFgI/2xtGQQGTe74MzX5xFgw6eadRUnJeKI=
+-----END RSA PRIVATE KEY-----
diff --git a/test/parallel/test-https-selfsigned-no-keycertsign-no-crash.js b/test/parallel/test-https-selfsigned-no-keycertsign-no-crash.js
new file mode 100644
index 00000000000000..2dd46ac878c5b0
--- /dev/null
+++ b/test/parallel/test-https-selfsigned-no-keycertsign-no-crash.js
@@ -0,0 +1,63 @@
+'use strict';
+const common = require('../common');
+const fixtures = require('../common/fixtures');
+
+// This test starts an https server and tries
+// to connect to it using a self-signed certificate.
+// This certificate´s keyUsage does not include the keyCertSign
+// bit, which used to crash node. The test ensures node
+// will not crash. Key and certificate are from #37889.
+// Note: This test assumes that the connection will succeed.
+
+if (!common.hasCrypto)
+  common.skip('missing crypto');
+
+const crypto = require('crypto');
+
+// See #37990 for details on why this is problematic with FIPS.
+if (process.config.variables.openssl_is_fips)
+  common.skip('Skipping as test uses non-fips compliant EC curve');
+
+// This test will fail for OpenSSL < 1.1.1h
+const minOpenSSL = 269488271;
+
+if (crypto.constants.OPENSSL_VERSION_NUMBER < minOpenSSL)
+  common.skip('OpenSSL < 1.1.1h');
+
+const https = require('https');
+const path = require('path');
+
+const key =
+  fixtures.readKey(path.join('selfsigned-no-keycertsign', 'key.pem'));
+
+const cert =
+  fixtures.readKey(path.join('selfsigned-no-keycertsign', 'cert.pem'));
+
+const serverOptions = {
+  key: key,
+  cert: cert
+};
+
+// Start the server
+const httpsServer = https.createServer(serverOptions, (req, res) => {
+  res.writeHead(200);
+  res.end('hello world\n');
+});
+httpsServer.listen(0);
+
+httpsServer.on('listening', () => {
+  // Once the server started listening, built the client config
+  // with the server´s used port
+  const clientOptions = {
+    hostname: '127.0.0.1',
+    port: httpsServer.address().port,
+    ca: cert
+  };
+  // Try to connect
+  const req = https.request(clientOptions, common.mustCall((res) => {
+    httpsServer.close();
+  }));
+
+  req.on('error', common.mustNotCall());
+  req.end();
+});