diff --git a/Misc/NEWS.d/next/Library/2024-11-28-14-14-46.gh-issue-127257.n6-jU9.rst b/Misc/NEWS.d/next/Library/2024-11-28-14-14-46.gh-issue-127257.n6-jU9.rst
new file mode 100644
index 00000000000000..fb0380cba0b607
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2024-11-28-14-14-46.gh-issue-127257.n6-jU9.rst
@@ -0,0 +1,2 @@
+In :mod:`ssl`, system call failures that OpenSSL reports using
+``ERR_LIB_SYS`` are now raised as :exc:`OSError`.
diff --git a/Modules/_ssl.c b/Modules/_ssl.c
index 7a9f2c87239eca..f5113ddf7b29d0 100644
--- a/Modules/_ssl.c
+++ b/Modules/_ssl.c
@@ -651,6 +651,11 @@ PySSL_SetError(PySSLSocket *sslsock, int ret, const char *filename, int lineno)
                         ERR_GET_REASON(e) == SSL_R_CERTIFICATE_VERIFY_FAILED) {
                     type = state->PySSLCertVerificationErrorObject;
                 }
+                if (ERR_GET_LIB(e) == ERR_LIB_SYS) {
+                    // A system error is being reported; reason is set to errno
+                    errno = ERR_GET_REASON(e);
+                    return PyErr_SetFromErrno(PyExc_OSError);
+                }
                 p = PY_SSL_ERROR_SYSCALL;
             }
             break;
@@ -676,6 +681,11 @@ PySSL_SetError(PySSLSocket *sslsock, int ret, const char *filename, int lineno)
                 errstr = "EOF occurred in violation of protocol";
             }
 #endif
+            if (ERR_GET_LIB(e) == ERR_LIB_SYS) {
+                // A system error is being reported; reason is set to errno
+                errno = ERR_GET_REASON(e);
+                return PyErr_SetFromErrno(PyExc_OSError);
+            }
             break;
         }
         default: