diff --git a/doc/api/tls.md b/doc/api/tls.md
index 86644cea76b6a3..f0a5a6ba34127a 100644
--- a/doc/api/tls.md
+++ b/doc/api/tls.md
@@ -547,6 +547,12 @@ description are taken from deps/openssl/openssl/crypto/x509/x509_txt.c
 * `'CERT_REJECTED'`: Certificate rejected.
 * `'HOSTNAME_MISMATCH'`: Hostname mismatch.
 
+Note: When certificate errors like `UNABLE_TO_VERIFY_LEAF_SIGNATURE`,
+`DEPTH_ZERO_SELF_SIGNED_CERT`, or `UNABLE_TO_GET_ISSUER_CERT` occur, Node.js
+appends a hint suggesting that if the root CA is installed locally,
+try running with the `--use-system-ca` flag to direct developers towards a
+secure solution, to prevent unsafe workarounds.
+
 ## Class: `tls.CryptoStream`
 
 <!-- YAML
diff --git a/src/crypto/crypto_common.cc b/src/crypto/crypto_common.cc
index e81bda7ad36f2b..62ee6852213357 100644
--- a/src/crypto/crypto_common.cc
+++ b/src/crypto/crypto_common.cc
@@ -53,8 +53,20 @@ SSLSessionPointer GetTLSSession(const unsigned char* buf, size_t length) {
 }
 
 MaybeLocal<Value> GetValidationErrorReason(Environment* env, int err) {
-  auto reason = X509Pointer::ErrorReason(err).value_or("");
+  auto reason = std::string(X509Pointer::ErrorReason(err).value_or(""));
   if (reason == "") return Undefined(env->isolate());
+
+  // Suggest --use-system-ca if the error indicates a certificate issue
+  bool suggestSystemCA =
+    (err == X509_V_ERR_UNABLE_TO_VERIFY_LEAF_SIGNATURE) ||
+    (err == X509_V_ERR_DEPTH_ZERO_SELF_SIGNED_CERT) ||
+    ((err == X509_V_ERR_UNABLE_TO_GET_ISSUER_CERT) &&
+    !per_process::cli_options->use_system_ca);
+
+  if (suggestSystemCA)
+    reason.append("; if the root CA is installed locally, "
+                  "try running Node.js with --use-system-ca");
+
   return OneByteString(env->isolate(), reason);
 }
 
diff --git a/test/parallel/test-https-agent-create-connection.js b/test/parallel/test-https-agent-create-connection.js
index c053b7f24b809e..705a5f8bf709bc 100644
--- a/test/parallel/test-https-agent-create-connection.js
+++ b/test/parallel/test-https-agent-create-connection.js
@@ -17,7 +17,7 @@ const options = {
 
 const expectedHeader = /^HTTP\/1\.1 200 OK/;
 const expectedBody = /hello world\n/;
-const expectCertError = /^Error: unable to verify the first certificate$/;
+const expectCertError = /^UNABLE_TO_VERIFY_LEAF_SIGNATURE$/;
 
 const checkRequest = (socket, server) => {
   let result = '';
@@ -112,7 +112,7 @@ function createServer() {
     const options = null;
     const socket = agent.createConnection(port, host, options);
     socket.on('error', common.mustCall((e) => {
-      assert.match(e.toString(), expectCertError);
+      assert.match(e.code, expectCertError);
       server.close();
     }));
   }));
@@ -127,7 +127,7 @@ function createServer() {
     const options = undefined;
     const socket = agent.createConnection(port, host, options);
     socket.on('error', common.mustCall((e) => {
-      assert.match(e.toString(), expectCertError);
+      assert.match(e.code, expectCertError);
       server.close();
     }));
   }));
diff --git a/test/parallel/test-tls-addca.js b/test/parallel/test-tls-addca.js
index 5ca44f7a26e7db..a99d53f55d3fe4 100644
--- a/test/parallel/test-tls-addca.js
+++ b/test/parallel/test-tls-addca.js
@@ -34,7 +34,7 @@ connect({
   server: serverOptions,
 }, common.mustCall((err, pair, cleanup) => {
   assert(err);
-  assert.strictEqual(err.message, 'unable to verify the first certificate');
+  assert.strictEqual(err.code, 'UNABLE_TO_VERIFY_LEAF_SIGNATURE');
   cleanup();
 
   // This time it should connect because contextWithCert includes the needed CA
diff --git a/test/parallel/test-tls-friendly-error-message.js b/test/parallel/test-tls-friendly-error-message.js
index 4ae9d3f3f956d4..84471da487b2e9 100644
--- a/test/parallel/test-tls-friendly-error-message.js
+++ b/test/parallel/test-tls-friendly-error-message.js
@@ -40,6 +40,5 @@ tls.createServer({ key, cert }).on('connection', common.mustCall(function() {
   const options = { port: this.address().port, rejectUnauthorized: true };
   tls.connect(options).on('error', common.mustCall(function(err) {
     assert.strictEqual(err.code, 'UNABLE_TO_VERIFY_LEAF_SIGNATURE');
-    assert.strictEqual(err.message, 'unable to verify the first certificate');
   }));
 }));
diff --git a/test/parallel/test-tls-set-secure-context.js b/test/parallel/test-tls-set-secure-context.js
index 3d2de6b3321414..ef7ccce0375815 100644
--- a/test/parallel/test-tls-set-secure-context.js
+++ b/test/parallel/test-tls-set-secure-context.js
@@ -13,7 +13,6 @@ const assert = require('assert');
 const events = require('events');
 const https = require('https');
 const timers = require('timers/promises');
-const { hasOpenSSL3 } = require('../common/crypto');
 const fixtures = require('../common/fixtures');
 const credentialOptions = [
   {
@@ -57,17 +56,20 @@ server.listen(0, common.mustCall(() => {
 
     server.setSecureContext(credentialOptions[1]);
     firstResponse.write('request-');
-    const errorMessageRegex = hasOpenSSL3 ?
-      /^Error: self-signed certificate$/ :
-      /^Error: self signed certificate$/;
-    await assert.rejects(makeRequest(port, 3), errorMessageRegex);
+    await assert.rejects(makeRequest(port, 3), (err) => {
+      assert.strictEqual(err.code, 'DEPTH_ZERO_SELF_SIGNED_CERT');
+      return true;
+    });
 
     server.setSecureContext(credentialOptions[0]);
     assert.strictEqual(await makeRequest(port, 4), 'success');
 
     server.setSecureContext(credentialOptions[1]);
     firstResponse.end('fun!');
-    await assert.rejects(makeRequest(port, 5), errorMessageRegex);
+    await assert.rejects(makeRequest(port, 3), (err) => {
+      assert.strictEqual(err.code, 'DEPTH_ZERO_SELF_SIGNED_CERT');
+      return true;
+    });
 
     assert.strictEqual(await firstRequest, 'multi-request-success-fun!');
     server.close();
diff --git a/test/parallel/test-tls-socket-default-options.js b/test/parallel/test-tls-socket-default-options.js
index 87f785dab5e1b3..bcd32c55dfe720 100644
--- a/test/parallel/test-tls-socket-default-options.js
+++ b/test/parallel/test-tls-socket-default-options.js
@@ -10,11 +10,11 @@ const {
 } = require(fixtures.path('tls-connect'));
 
 test(undefined, (err) => {
-  assert.strictEqual(err.message, 'unable to verify the first certificate');
+  assert.strictEqual(err.code, 'UNABLE_TO_VERIFY_LEAF_SIGNATURE');
 });
 
 test({}, (err) => {
-  assert.strictEqual(err.message, 'unable to verify the first certificate');
+  assert.strictEqual(err.code, 'UNABLE_TO_VERIFY_LEAF_SIGNATURE');
 });
 
 test(
@@ -30,8 +30,8 @@ test(
 test(
   { secureContext: tls.createSecureContext(), ca: keys.agent1.ca },
   (err) => {
-    assert.strictEqual(err.message,
-                       'unable to verify the first certificate');
+    assert.strictEqual(err.code,
+                       'UNABLE_TO_VERIFY_LEAF_SIGNATURE');
   });
 
 function test(client, callback) {
@@ -42,7 +42,7 @@ function test(client, callback) {
       cert: keys.agent1.cert,
     },
   }, function(err, pair, cleanup) {
-    assert.strictEqual(err.message, 'unable to verify the first certificate');
+    assert.strictEqual(err.code, 'UNABLE_TO_VERIFY_LEAF_SIGNATURE');
     let recv = '';
     pair.server.server.once('secureConnection', common.mustCall((conn) => {
       conn.on('data', (data) => recv += data);