diff --git a/lldb/source/Plugins/Process/gdb-remote/GDBRemoteCommunicationClient.cpp b/lldb/source/Plugins/Process/gdb-remote/GDBRemoteCommunicationClient.cpp
--- a/lldb/source/Plugins/Process/gdb-remote/GDBRemoteCommunicationClient.cpp
+++ b/lldb/source/Plugins/Process/gdb-remote/GDBRemoteCommunicationClient.cpp
@@ -82,6 +82,8 @@
 
   // Start the read thread after we send the handshake ack since if we fail to
   // send the handshake ack, there is no reason to continue...
+  std::chrono::steady_clock::time_point start_of_handshake =
+      std::chrono::steady_clock::now();
   if (SendAck()) {
     // Wait for any responses that might have been queued up in the remote
     // GDB server and flush them all
@@ -97,8 +99,24 @@
     if (QueryNoAckModeSupported()) {
       return true;
     } else {
-      if (error_ptr)
-        error_ptr->SetErrorString("failed to get reply to handshake packet");
+      std::chrono::steady_clock::time_point end_of_handshake =
+          std::chrono::steady_clock::now();
+      auto handshake_timeout =
+          std::chrono::duration<double>(end_of_handshake - start_of_handshake)
+              .count();
+      if (error_ptr) {
+        if (packet_result == PacketResult::ErrorDisconnected)
+          error_ptr->SetErrorString("Connection shut down by remote side "
+                                    "while waiting for reply to initial "
+                                    "handshake packet");
+        else if (packet_result == PacketResult::ErrorReplyTimeout)
+          error_ptr->SetErrorStringWithFormat(
+              "failed to get reply to handshake packet within timeout of "
+              "%.1f seconds",
+              handshake_timeout);
+        else
+          error_ptr->SetErrorString("failed to get reply to handshake packet");
+      }
     }
   } else {
     if (error_ptr)