src/crypto/x509/internal/macos/corefoundation.go |  7 +++++++
 src/crypto/x509/internal/macos/corefoundation.s  |  2 ++
 src/crypto/x509/internal/macos/security.go       | 19 ++++++++++++++-----
 src/crypto/x509/root_darwin.go                   | 14 ++++++++++++--
 src/crypto/x509/root_darwin_test.go              | 10 +++++-----

diff --git a/src/crypto/x509/internal/macos/corefoundation.go b/src/crypto/x509/internal/macos/corefoundation.go
index 75c212910b67cfa6e31c36a74c861b03ac8ca4c9..2b20b52dc6cb724d149c3c9757be544a8701baf6 100644
--- a/src/crypto/x509/internal/macos/corefoundation.go
+++ b/src/crypto/x509/internal/macos/corefoundation.go
@@ -184,6 +184,13 @@ 	return CFRef(ret)
 }
 func x509_CFErrorCopyDescription_trampoline()
 
+//go:cgo_import_dynamic x509_CFErrorGetCode CFErrorGetCode "/System/Library/Frameworks/CoreFoundation.framework/Versions/A/CoreFoundation"
+
+func CFErrorGetCode(errRef CFRef) int {
+	return int(syscall(abi.FuncPCABI0(x509_CFErrorGetCode_trampoline), uintptr(errRef), 0, 0, 0, 0, 0))
+}
+func x509_CFErrorGetCode_trampoline()
+
 //go:cgo_import_dynamic x509_CFStringCreateExternalRepresentation CFStringCreateExternalRepresentation "/System/Library/Frameworks/CoreFoundation.framework/Versions/A/CoreFoundation"
 
 func CFStringCreateExternalRepresentation(strRef CFRef) CFRef {
diff --git a/src/crypto/x509/internal/macos/corefoundation.s b/src/crypto/x509/internal/macos/corefoundation.s
index d69f72f795cd949504851c32a9b4be7599076f59..49cd084467b2c396e22cb2a06c983c6966dc8d7c 100644
--- a/src/crypto/x509/internal/macos/corefoundation.s
+++ b/src/crypto/x509/internal/macos/corefoundation.s
@@ -37,5 +37,7 @@ TEXT ·x509_CFDataCreate_trampoline(SB),NOSPLIT,$0-0
 	JMP x509_CFDataCreate(SB)
 TEXT ·x509_CFErrorCopyDescription_trampoline(SB),NOSPLIT,$0-0
 	JMP x509_CFErrorCopyDescription(SB)
+TEXT ·x509_CFErrorGetCode_trampoline(SB),NOSPLIT,$0-0
+	JMP x509_CFErrorGetCode(SB)
 TEXT ·x509_CFStringCreateExternalRepresentation_trampoline(SB),NOSPLIT,$0-0
 	JMP x509_CFStringCreateExternalRepresentation(SB)
diff --git a/src/crypto/x509/internal/macos/security.go b/src/crypto/x509/internal/macos/security.go
index ef64bda49fd258bf42807b3792d913076e6781a4..0b7958eaa2891b84039a80df1e12ef75fc304228 100644
--- a/src/crypto/x509/internal/macos/security.go
+++ b/src/crypto/x509/internal/macos/security.go
@@ -8,7 +8,6 @@ package macOS
 
 import (
 	"errors"
-	"fmt"
 	"internal/abi"
 	"strconv"
 	"unsafe"
@@ -49,6 +48,15 @@ const (
 	SecTrustSettingsDomainUser SecTrustSettingsDomain = iota
 	SecTrustSettingsDomainAdmin
 	SecTrustSettingsDomainSystem
+)
+
+const (
+	// various macOS error codes that can be returned from
+	// SecTrustEvaluateWithError that we can map to Go cert
+	// verification error types.
+	ErrSecCertificateExpired = -67818
+	ErrSecHostNameMismatch   = -67602
+	ErrSecNotTrusted         = -67843
 )
 
 type OSStatus struct {
@@ -190,17 +198,18 @@ func x509_SecTrustGetResult_trampoline()
 
 //go:cgo_import_dynamic x509_SecTrustEvaluateWithError SecTrustEvaluateWithError "/System/Library/Frameworks/Security.framework/Versions/A/Security"
 
-func SecTrustEvaluateWithError(trustObj CFRef) error {
+func SecTrustEvaluateWithError(trustObj CFRef) (int, error) {
 	var errRef CFRef
 	ret := syscall(abi.FuncPCABI0(x509_SecTrustEvaluateWithError_trampoline), uintptr(trustObj), uintptr(unsafe.Pointer(&errRef)), 0, 0, 0, 0)
 	if int32(ret) != 1 {
 		errStr := CFErrorCopyDescription(errRef)
-		err := fmt.Errorf("x509: %s", CFStringToString(errStr))
+		err := errors.New(CFStringToString(errStr))
+		errCode := CFErrorGetCode(errRef)
 		CFRelease(errRef)
 		CFRelease(errStr)
-		return err
+		return errCode, err
 	}
-	return nil
+	return 0, nil
 }
 func x509_SecTrustEvaluateWithError_trampoline()
 
diff --git a/src/crypto/x509/root_darwin.go b/src/crypto/x509/root_darwin.go
index ad365f577e79634644672a03a47294931776e5d7..c35885ace8358985204235759f0b93b892dd14fa 100644
--- a/src/crypto/x509/root_darwin.go
+++ b/src/crypto/x509/root_darwin.go
@@ -7,6 +7,7 @@
 import (
 	macOS "crypto/x509/internal/macos"
 	"errors"
+	"fmt"
 )
 
 func (c *Certificate) systemVerify(opts *VerifyOptions) (chains [][]*Certificate, err error) {
@@ -54,8 +55,17 @@ 	// set them via SecTrustSetSignedCertificateTimestamps, since Apple will
 	// always enforce its SCT requirements, and there are still _some_ people
 	// using TLS or OCSP for that.
 
-	if err := macOS.SecTrustEvaluateWithError(trustObj); err != nil {
-		return nil, err
+	if ret, err := macOS.SecTrustEvaluateWithError(trustObj); err != nil {
+		switch ret {
+		case macOS.ErrSecCertificateExpired:
+			return nil, CertificateInvalidError{c, Expired, err.Error()}
+		case macOS.ErrSecHostNameMismatch:
+			return nil, HostnameError{c, opts.DNSName}
+		case macOS.ErrSecNotTrusted:
+			return nil, UnknownAuthorityError{Cert: c}
+		default:
+			return nil, fmt.Errorf("x509: %s", err)
+		}
 	}
 
 	chain := [][]*Certificate{{}}
diff --git a/src/crypto/x509/root_darwin_test.go b/src/crypto/x509/root_darwin_test.go
index 90a464f624960a75bd39d390d7e1d492a499a511..299cecf5563f682a2f18f1d51b440c0329d7b41c 100644
--- a/src/crypto/x509/root_darwin_test.go
+++ b/src/crypto/x509/root_darwin_test.go
@@ -42,23 +42,23 @@ 		},
 		{
 			name:        "expired leaf",
 			host:        "expired.badssl.com",
-			expectedErr: "x509: “*.badssl.com” certificate is expired",
+			expectedErr: "x509: certificate has expired or is not yet valid: “*.badssl.com” certificate is expired",
 		},
 		{
 			name:        "wrong host for leaf",
 			host:        "wrong.host.badssl.com",
 			verifyName:  "wrong.host.badssl.com",
-			expectedErr: "x509: “*.badssl.com” certificate name does not match input",
+			expectedErr: "x509: certificate is valid for *.badssl.com, badssl.com, not wrong.host.badssl.com",
 		},
 		{
 			name:        "self-signed leaf",
 			host:        "self-signed.badssl.com",
-			expectedErr: "x509: “*.badssl.com” certificate is not trusted",
+			expectedErr: "x509: certificate signed by unknown authority",
 		},
 		{
 			name:        "untrusted root",
 			host:        "untrusted-root.badssl.com",
-			expectedErr: "x509: “BadSSL Untrusted Root Certificate Authority” certificate is not trusted",
+			expectedErr: "x509: certificate signed by unknown authority",
 		},
 		{
 			name:        "revoked leaf",
@@ -74,7 +74,7 @@ 		{
 			name:        "expired leaf (custom time)",
 			host:        "google.com",
 			verifyTime:  time.Time{}.Add(time.Hour),
-			expectedErr: "x509: “*.google.com” certificate is expired",
+			expectedErr: "x509: certificate has expired or is not yet valid: “*.google.com” certificate is expired",
 		},
 		{
 			name:       "valid chain (custom time)",