diff --git a/src/xenia/cpu/processor.cc b/src/xenia/cpu/processor.cc
index 2982dfc4b..ee47e835b 100644
--- a/src/xenia/cpu/processor.cc
+++ b/src/xenia/cpu/processor.cc
@@ -644,7 +644,8 @@ bool Processor::OnThreadBreakpointHit(Exception* ex) {
       if ((scan_breakpoint->address_type() == Breakpoint::AddressType::kGuest &&
            scan_breakpoint->guest_address() == frame.guest_pc) ||
           (scan_breakpoint->address_type() == Breakpoint::AddressType::kHost &&
-           scan_breakpoint->host_address() == frame.host_pc)) {
+           scan_breakpoint->host_address() == frame.host_pc) ||
+          scan_breakpoint->ContainsHostAddress(frame.host_pc)) {
         breakpoint = scan_breakpoint;
         break;
       }
@@ -937,7 +938,10 @@ void Processor::StepHostInstruction(uint32_t thread_id) {
                        thread_info->step_breakpoint.reset();
                        OnStepCompleted(thread_info);
                      }));
-  AddBreakpoint(thread_info->step_breakpoint.get());
+
+  // Add to front of breakpoints map, so this should get evaluated first
+  breakpoints_.insert(breakpoints_.begin(), thread_info->step_breakpoint.get());
+
   thread_info->step_breakpoint->Resume();
 
   // ResumeAllBreakpoints();
@@ -970,7 +974,10 @@ void Processor::StepGuestInstruction(uint32_t thread_id) {
                        thread_info->step_breakpoint.reset();
                        OnStepCompleted(thread_info);
                      }));
-  AddBreakpoint(thread_info->step_breakpoint.get());
+
+  // Add to front of breakpoints map, so this should get evaluated first
+  breakpoints_.insert(breakpoints_.begin(), thread_info->step_breakpoint.get());
+
   thread_info->step_breakpoint->Resume();
 
   // ResumeAllBreakpoints();
diff --git a/src/xenia/debug/gdb/gdbstub.cc b/src/xenia/debug/gdb/gdbstub.cc
index 3dba51f5b..a0c8af71e 100644
--- a/src/xenia/debug/gdb/gdbstub.cc
+++ b/src/xenia/debug/gdb/gdbstub.cc
@@ -184,7 +184,8 @@ uint8_t from_hexchar(char c) {
   return 0;
 }
 
-std::string get_reg(xe::cpu::ThreadDebugInfo* thread, uint32_t rid) {
+std::string GDBStub::ReadRegister(xe::cpu::ThreadDebugInfo* thread,
+                                  uint32_t rid) {
   // Send registers as 32-bit, otherwise some debuggers will switch to 64-bit
   // mode (eg. IDA will switch to 64-bit and refuse to allow decompiler to work
   // with it)
@@ -195,6 +196,16 @@ std::string get_reg(xe::cpu::ThreadDebugInfo* thread, uint32_t rid) {
   switch (rid) {
     // pc
     case 64: {
+      // If we recently hit a BP then debugger is likely asking for registers
+      // for it
+      //
+      // Lie about the PC and say it's the BP address, since PC might not always
+      // match
+      if (cache_.notify_bp_guest_address != -1) {
+        auto ret = u32_to_padded_hex((uint32_t)cache_.notify_bp_guest_address);
+        cache_.notify_bp_guest_address = -1;
+        return ret;
+      }
       // Search for first frame that has guest_pc attached, GDB doesn't care
       // about host
       for (auto& frame : thread->frames) {
@@ -560,7 +571,7 @@ void GDBStub::UpdateCache() {
 
 std::string GDBStub::ReadRegister(const std::string& data) {
   uint32_t rid = hex_to_u32(data);
-  std::string result = get_reg(cache_.cur_thread_info(), rid);
+  std::string result = ReadRegister(cache_.cur_thread_info(), rid);
   if (result.empty()) {
     return kGdbReplyError;  // TODO: is this error correct?
   }
@@ -571,7 +582,7 @@ std::string GDBStub::ReadRegisters() {
   std::string result;
   result.reserve(68 * 16 + 3 * 8);
   for (int i = 0; i < 71; ++i) {
-    result += get_reg(cache_.cur_thread_info(), i);
+    result += ReadRegister(cache_.cur_thread_info(), i);
   }
   return result;
 }
@@ -594,7 +605,8 @@ std::string GDBStub::ExecutionContinue() {
 
 std::string GDBStub::ExecutionStep() {
 #ifdef DEBUG
-  debugging::DebugPrint("GDBStub: ExecutionStep (thread {})\n", cache_.last_bp_thread_id);
+  debugging::DebugPrint("GDBStub: ExecutionStep (thread {})\n",
+                        cache_.last_bp_thread_id);
 #endif
 
   if (cache_.last_bp_thread_id != -1)
@@ -666,6 +678,12 @@ std::string GDBStub::GetThreadStateReply(uint32_t thread_id, uint8_t signal) {
       }
     }
 
+    // If BP was hit use the address of it, so debugger can match it up to its
+    // BP list
+    if (cache_.notify_bp_guest_address != -1) {
+      pc_value = cache_.notify_bp_guest_address;
+    }
+
     return fmt::format(
         "T{:02x}{:02x}:{};{:02x}:{};thread:{:x};", signal, PC_REGISTER,
         u32_to_padded_hex((uint32_t)pc_value), LR_REGISTER,
@@ -786,6 +804,7 @@ void GDBStub::OnBreakpointHit(Breakpoint* breakpoint,
                         breakpoint->address(), thread_info->thread_id);
 #endif
 
+  cache_.notify_bp_guest_address = breakpoint->address();
   cache_.notify_bp_thread_id = thread_info->thread_id;
   cache_.last_bp_thread_id = thread_info->thread_id;
   UpdateCache();
diff --git a/src/xenia/debug/gdb/gdbstub.h b/src/xenia/debug/gdb/gdbstub.h
index 0763899f2..dc19e83b6 100644
--- a/src/xenia/debug/gdb/gdbstub.h
+++ b/src/xenia/debug/gdb/gdbstub.h
@@ -61,6 +61,7 @@ class GDBStub : public cpu::DebugListener {
 
   void UpdateCache();
 
+  std::string ReadRegister(xe::cpu::ThreadDebugInfo* thread, uint32_t rid);
   std::string ReadRegister(const std::string& data);
   std::string ReadRegisters();
   std::string ExecutionPause();
@@ -93,6 +94,7 @@ class GDBStub : public cpu::DebugListener {
     uint32_t cur_thread_id = -1;
     uint32_t last_bp_thread_id = -1;
 
+    uint64_t notify_bp_guest_address = -1;
     uint32_t notify_bp_thread_id = -1;
     bool notify_stopped = false;