diff --git a/lldb/source/Plugins/Process/FreeBSDRemote/NativeProcessFreeBSD.cpp b/lldb/source/Plugins/Process/FreeBSDRemote/NativeProcessFreeBSD.cpp
--- a/lldb/source/Plugins/Process/FreeBSDRemote/NativeProcessFreeBSD.cpp
+++ b/lldb/source/Plugins/Process/FreeBSDRemote/NativeProcessFreeBSD.cpp
@@ -199,7 +199,25 @@
   if (info.pl_flags & (PL_FLAG_BORN | PL_FLAG_EXITED)) {
     if (info.pl_flags & PL_FLAG_BORN) {
       LLDB_LOG(log, "monitoring new thread, tid = {0}", info.pl_lwpid);
-      AddThread(info.pl_lwpid);
+      NativeThreadFreeBSD &t = AddThread(info.pl_lwpid);
+
+      // Technically, the FreeBSD kernel copies the debug registers to new
+      // threads.  However, there is a non-negligible delay between acquiring
+      // the DR values and reporting the new thread during which the user may
+      // establish a new watchpoint.  In order to ensure that watchpoints
+      // established during this period are propagated to new threads,
+      // explicitly copy the DR value at the time the new thread is reported.
+      //
+      // See also: https://bugs.freebsd.org/bugzilla/show_bug.cgi?id=250954
+
+      llvm::Error error = t.CopyWatchpointsFrom(
+          static_cast<NativeThreadFreeBSD &>(*GetCurrentThread()));
+      if (error) {
+        LLDB_LOG(log, "failed to copy watchpoints to new thread {0}: {1}",
+                 info.pl_lwpid, llvm::toString(std::move(error)));
+        SetState(StateType::eStateInvalid);
+        return;
+      }
     } else /*if (info.pl_flags & PL_FLAG_EXITED)*/ {
       LLDB_LOG(log, "thread exited, tid = {0}", info.pl_lwpid);
       RemoveThread(info.pl_lwpid);
diff --git a/lldb/source/Plugins/Process/FreeBSDRemote/NativeRegisterContextFreeBSD.h b/lldb/source/Plugins/Process/FreeBSDRemote/NativeRegisterContextFreeBSD.h
--- a/lldb/source/Plugins/Process/FreeBSDRemote/NativeRegisterContextFreeBSD.h
+++ b/lldb/source/Plugins/Process/FreeBSDRemote/NativeRegisterContextFreeBSD.h
@@ -29,6 +29,8 @@
   static NativeRegisterContextFreeBSD *
   CreateHostNativeRegisterContextFreeBSD(const ArchSpec &target_arch,
                                          NativeThreadProtocol &native_thread);
+  virtual llvm::Error
+  CopyHardwareWatchpointsFrom(NativeRegisterContextFreeBSD &source) = 0;
 
 protected:
   virtual NativeProcessFreeBSD &GetProcess();
diff --git a/lldb/source/Plugins/Process/FreeBSDRemote/NativeRegisterContextFreeBSD_x86_64.h b/lldb/source/Plugins/Process/FreeBSDRemote/NativeRegisterContextFreeBSD_x86_64.h
--- a/lldb/source/Plugins/Process/FreeBSDRemote/NativeRegisterContextFreeBSD_x86_64.h
+++ b/lldb/source/Plugins/Process/FreeBSDRemote/NativeRegisterContextFreeBSD_x86_64.h
@@ -50,6 +50,9 @@
 
   Status WriteAllRegisterValues(const lldb::DataBufferSP &data_sp) override;
 
+  llvm::Error
+  CopyHardwareWatchpointsFrom(NativeRegisterContextFreeBSD &source) override;
+
 private:
   // Private member types.
   enum { GPRegSet, FPRegSet, XSaveRegSet, DBRegSet };
diff --git a/lldb/source/Plugins/Process/FreeBSDRemote/NativeRegisterContextFreeBSD_x86_64.cpp b/lldb/source/Plugins/Process/FreeBSDRemote/NativeRegisterContextFreeBSD_x86_64.cpp
--- a/lldb/source/Plugins/Process/FreeBSDRemote/NativeRegisterContextFreeBSD_x86_64.cpp
+++ b/lldb/source/Plugins/Process/FreeBSDRemote/NativeRegisterContextFreeBSD_x86_64.cpp
@@ -1169,4 +1169,19 @@
   }
 }
 
+llvm::Error NativeRegisterContextFreeBSD_x86_64::CopyHardwareWatchpointsFrom(
+    NativeRegisterContextFreeBSD &source) {
+  auto &r_source = static_cast<NativeRegisterContextFreeBSD_x86_64 &>(source);
+  Status res = r_source.ReadRegisterSet(DBRegSet);
+  if (!res.Fail()) {
+    // copy dbregs only if any watchpoints were set
+    if ((r_source.m_dbr.dr[7] & 0xFF) == 0)
+      return llvm::Error::success();
+
+    m_dbr = r_source.m_dbr;
+    res = WriteRegisterSet(DBRegSet);
+  }
+  return res.ToError();
+}
+
 #endif // defined(__x86_64__)
diff --git a/lldb/source/Plugins/Process/FreeBSDRemote/NativeThreadFreeBSD.h b/lldb/source/Plugins/Process/FreeBSDRemote/NativeThreadFreeBSD.h
--- a/lldb/source/Plugins/Process/FreeBSDRemote/NativeThreadFreeBSD.h
+++ b/lldb/source/Plugins/Process/FreeBSDRemote/NativeThreadFreeBSD.h
@@ -64,7 +64,7 @@
   void SetRunning();
   void SetStepping();
 
-  Status CopyWatchpointsFrom(NativeThreadFreeBSD &source);
+  llvm::Error CopyWatchpointsFrom(NativeThreadFreeBSD &source);
 
   // Member Variables
   lldb::StateType m_state;
diff --git a/lldb/source/Plugins/Process/FreeBSDRemote/NativeThreadFreeBSD.cpp b/lldb/source/Plugins/Process/FreeBSDRemote/NativeThreadFreeBSD.cpp
--- a/lldb/source/Plugins/Process/FreeBSDRemote/NativeThreadFreeBSD.cpp
+++ b/lldb/source/Plugins/Process/FreeBSDRemote/NativeThreadFreeBSD.cpp
@@ -165,14 +165,14 @@
     }
     if (error != 0) {
       len = 0;
-      LLDB_LOG(log, "tid = {0} in state {1} failed to get thread name: {2}", GetID(),
-               m_state, strerror(errno));
+      LLDB_LOG(log, "tid = {0} in state {1} failed to get thread name: {2}",
+               GetID(), m_state, strerror(errno));
     }
     kp.resize(len / sizeof(struct kinfo_proc));
     break;
   }
 
-  for (auto& procinfo : kp) {
+  for (auto &procinfo : kp) {
     if (procinfo.ki_tid == static_cast<lwpid_t>(GetID()))
       return procinfo.ki_tdname;
   }
@@ -273,3 +273,14 @@
 
   return Status("Clearing hardware breakpoint failed.");
 }
+
+llvm::Error
+NativeThreadFreeBSD::CopyWatchpointsFrom(NativeThreadFreeBSD &source) {
+  llvm::Error s = GetRegisterContext().CopyHardwareWatchpointsFrom(
+      source.GetRegisterContext());
+  if (!s) {
+    m_watchpoint_index_map = source.m_watchpoint_index_map;
+    m_hw_break_index_map = source.m_hw_break_index_map;
+  }
+  return s;
+}
diff --git a/lldb/test/API/commands/watchpoints/multiple_threads/TestWatchpointMultipleThreads.py b/lldb/test/API/commands/watchpoints/multiple_threads/TestWatchpointMultipleThreads.py
--- a/lldb/test/API/commands/watchpoints/multiple_threads/TestWatchpointMultipleThreads.py
+++ b/lldb/test/API/commands/watchpoints/multiple_threads/TestWatchpointMultipleThreads.py
@@ -22,7 +22,6 @@
         """Test that we can hit a watchpoint we set before starting another thread"""
         self.do_watchpoint_test("Before running the thread")
 
-    @expectedFailureAll(oslist=["freebsd"])
     def test_watchpoint_after_thread_launch(self):
         """Test that we can hit a watchpoint we set after launching another thread"""
         self.do_watchpoint_test("After launching the thread")