diff --git a/build/ac-macros/serf.m4 b/build/ac-macros/serf.m4
index b3650f61861e3..7332d0e88ca0e 100644
--- a/build/ac-macros/serf.m4
+++ b/build/ac-macros/serf.m4
@@ -89,6 +89,13 @@ AC_DEFUN(SVN_LIB_SERF,
 
   svn_lib_serf=$serf_found
 
+  if test "$svn_lib_serf" = "yes"; then
+    save_ldflags="$LDFLAGS"
+    LDFLAGS="$LDFLAGS $SVN_SERF_LIBS"
+    AC_CHECK_FUNCS(serf_ssl_error_cb_set)
+    LDFLAGS="$save_ldflags"
+  fi
+
   SVN_DOT_CLANGD([$SVN_SERF_INCLUDES])
   AC_SUBST(SVN_SERF_INCLUDES)
   AC_SUBST(SVN_SERF_LIBS)
diff --git a/subversion/libsvn_ra_serf/ra_serf.h b/subversion/libsvn_ra_serf/ra_serf.h
index eace1af5319ac..28c37f306f88f 100644
--- a/subversion/libsvn_ra_serf/ra_serf.h
+++ b/subversion/libsvn_ra_serf/ra_serf.h
@@ -113,6 +113,9 @@ struct svn_ra_serf__session_t {
   /* Are we using ssl */
   svn_boolean_t using_ssl;
 
+  /* What was the underlying detail of the last SSL failure, if any */
+  svn_error_t *ssl_error;
+
   /* Tristate flag that indicates if we should use compression for
      network transmissions.  If svn_tristate_true or svn_tristate_false,
      the compression should be enabled and disabled, respectively.
diff --git a/subversion/libsvn_ra_serf/util.c b/subversion/libsvn_ra_serf/util.c
index e010f82d62110..9fd85defe19f5 100644
--- a/subversion/libsvn_ra_serf/util.c
+++ b/subversion/libsvn_ra_serf/util.c
@@ -451,6 +451,23 @@ ssl_server_cert_cb(void *baton, int failures,
   return save_error(session, err);
 }
 
+#if defined(HAVE_SERF_SSL_ERROR_CB_SET)
+static apr_status_t
+ssl_error_cb(void *baton, apr_status_t status,
+             const char *message)
+{
+  svn_ra_serf__connection_t *conn = baton;
+  svn_ra_serf__session_t *session = conn->session;
+
+  session->ssl_error = svn_error_createf(status,
+                                         session->ssl_error,
+                                         _("TLS: %s"),
+                                         message);
+
+  return APR_SUCCESS;
+}
+#endif
+
 static svn_error_t *
 load_authorities(svn_ra_serf__connection_t *conn, const char *authorities,
                  apr_pool_t *pool)
@@ -567,7 +584,14 @@ conn_setup(apr_socket_t *sock,
                             SERF_CONNECTION_FRAMING_TYPE_NONE);
             }
 #endif
-        }
+
+#if defined(HAVE_SERF_SSL_ERROR_CB_SET)
+          serf_ssl_error_cb_set(conn->ssl_context,
+                                ssl_error_cb,
+                                conn);
+#endif
+
+	}
 
       if (write_bkt)
         {
@@ -958,7 +982,14 @@ svn_ra_serf__context_run(svn_ra_serf__session_t *sess,
                     _("Error running context"));
         }
 
-      return svn_ra_serf__wrap_err(status, _("Error running context"));
+      if (sess->ssl_error)
+        {
+          return sess->ssl_error;
+        }
+      else
+        {
+          return svn_ra_serf__wrap_err(status, _("Error running context"));
+        }
     }
 
   return SVN_NO_ERROR;