diff --git a/lldb/packages/Python/lldbsuite/test/tools/lldb-server/gdbremote_testcase.py b/lldb/packages/Python/lldbsuite/test/tools/lldb-server/gdbremote_testcase.py
--- a/lldb/packages/Python/lldbsuite/test/tools/lldb-server/gdbremote_testcase.py
+++ b/lldb/packages/Python/lldbsuite/test/tools/lldb-server/gdbremote_testcase.py
@@ -703,7 +703,7 @@
             self.sock,
             self.test_sequence,
             self._pump_queues,
-            self.DEFAULT_TIMEOUT,
+            self.DEFAULT_TIMEOUT * len(self.test_sequence),
             self.logger)
 
     _KNOWN_REGINFO_KEYS = [
diff --git a/lldb/packages/Python/lldbsuite/test/tools/lldb-server/lldbgdbserverutils.py b/lldb/packages/Python/lldbsuite/test/tools/lldb-server/lldbgdbserverutils.py
--- a/lldb/packages/Python/lldbsuite/test/tools/lldb-server/lldbgdbserverutils.py
+++ b/lldb/packages/Python/lldbsuite/test/tools/lldb-server/lldbgdbserverutils.py
@@ -809,6 +809,9 @@
         self.entries = []
         self.logger = logger
 
+    def __len__(self):
+        return len(self.entries)
+
     def add_log_lines(self, log_lines, remote_input_is_read):
         for line in log_lines:
             if isinstance(line, str):