3 files changed, 24 insertions, 2 deletions
diff --git a/ext/openssl/extconf.rb b/ext/openssl/extconf.rb
index 56f4a1c3ab..4119c72c48 100644
--- a/ext/openssl/extconf.rb
+++ b/ext/openssl/extconf.rb
@@ -49,6 +49,7 @@ $defs.push("-D""OPENSSL_SUPPRESS_DEPRECATED")
 
 have_func("rb_io_descriptor")
 have_func("rb_io_maybe_wait(0, Qnil, Qnil, Qnil)", "ruby/io.h") # Ruby 3.1
+have_func("rb_io_timeout", "ruby/io.h")
 
 Logging::message "=== Checking for system dependent stuff... ===\n"
 have_library("nsl", "t_open")
diff --git a/ext/openssl/lib/openssl/ssl.rb b/ext/openssl/lib/openssl/ssl.rb
index 7e59400ccb..75a74a3f51 100644
--- a/ext/openssl/lib/openssl/ssl.rb
+++ b/ext/openssl/lib/openssl/ssl.rb
@@ -299,6 +299,16 @@ ssbzSibBsu/6iGtCOGEoXJf//////////wIBAg==
       def wait_writable(*args)
         to_io.wait_writable(*args)
       end
+
+      if IO.method_defined?(:timeout)
+        def timeout
+          to_io.timeout
+        end
+
+        def timeout=(value)
+          to_io.timeout=(value)
+        end
+      end
     end
 
     def verify_certificate_identity(cert, hostname)
diff --git a/ext/openssl/ossl_ssl.c b/ext/openssl/ossl_ssl.c
index 236d455ff2..9f374b65ff 100644
--- a/ext/openssl/ossl_ssl.c
+++ b/ext/openssl/ossl_ssl.c
@@ -1725,11 +1725,20 @@ no_exception_p(VALUE opts)
 #define RUBY_IO_TIMEOUT_DEFAULT Qnil
 #endif
 
+#ifdef HAVE_RB_IO_TIMEOUT
+#define IO_TIMEOUT_ERROR rb_eIOTimeoutError
+#else
+#define IO_TIMEOUT_ERROR rb_eIOError
+#endif
+
+
 static void
 io_wait_writable(VALUE io)
 {
 #ifdef HAVE_RB_IO_MAYBE_WAIT
-    rb_io_maybe_wait_writable(errno, io, RUBY_IO_TIMEOUT_DEFAULT);
+    if (!rb_io_maybe_wait_writable(errno, io, RUBY_IO_TIMEOUT_DEFAULT)) {
+        rb_raise(IO_TIMEOUT_ERROR, "Timed out while waiting to become writable!");
+    }
 #else
     rb_io_t *fptr;
     GetOpenFile(io, fptr);
@@ -1741,7 +1750,9 @@ static void
 io_wait_readable(VALUE io)
 {
 #ifdef HAVE_RB_IO_MAYBE_WAIT
-    rb_io_maybe_wait_readable(errno, io, RUBY_IO_TIMEOUT_DEFAULT);
+    if (!rb_io_maybe_wait_readable(errno, io, RUBY_IO_TIMEOUT_DEFAULT)) {
+        rb_raise(IO_TIMEOUT_ERROR, "Timed out while waiting to become readable!");
+    }
 #else
     rb_io_t *fptr;
     GetOpenFile(io, fptr);