Index: lldb/source/Plugins/Process/FreeBSDRemote/NativeProcessFreeBSD.cpp
===================================================================
--- lldb/source/Plugins/Process/FreeBSDRemote/NativeProcessFreeBSD.cpp
+++ lldb/source/Plugins/Process/FreeBSDRemote/NativeProcessFreeBSD.cpp
@@ -192,7 +192,8 @@
   }
   assert(info.pl_event == PL_EVENT_SIGNAL);
 
-  LLDB_LOG(log, "got SIGTRAP, pid = {0}, lwpid = {1}", pid, info.pl_lwpid);
+  LLDB_LOG(log, "got SIGTRAP, pid = {0}, lwpid = {1}, flags = {2:x}",
+           pid, info.pl_lwpid, info.pl_flags);
   NativeThreadFreeBSD *thread = nullptr;
 
   if (info.pl_flags & (PL_FLAG_BORN | PL_FLAG_EXITED)) {
@@ -240,6 +241,8 @@
 
   if (info.pl_flags & PL_FLAG_SI) {
     assert(info.pl_siginfo.si_signo == SIGTRAP);
+    LLDB_LOG(log, "SIGTRAP siginfo: si_code = {0}, pid = {1}",
+             info.pl_siginfo.si_code, info.pl_siginfo.si_pid);
 
     switch (info.pl_siginfo.si_code) {
     case TRAP_BRKPT:
@@ -273,6 +276,11 @@
 
       SetState(StateType::eStateStopped, true);
       break;
+    case SI_USER:
+    case SI_LWP:
+      // User-generated SIGTRAP
+      MonitorSignal(pid, SIGTRAP);
+      break;
     }
   }
 }
Index: lldb/test/API/functionalities/signal/raise/TestRaise.py
===================================================================
--- lldb/test/API/functionalities/signal/raise/TestRaise.py
+++ lldb/test/API/functionalities/signal/raise/TestRaise.py
@@ -30,7 +30,6 @@
         self.signal_test('SIGRTMIN', True)
 
     @skipIfNetBSD  # Hangs on NetBSD
-    @skipIfFreeBSD  # hangs
     def test_sigtrap(self):
         self.build()
         self.signal_test('SIGTRAP', True)