diff --git a/GleeBug/Debugger.Global.h b/GleeBug/Debugger.Global.h
index cd54981..b31c12c 100644
--- a/GleeBug/Debugger.Global.h
+++ b/GleeBug/Debugger.Global.h
@@ -12,6 +12,14 @@
 #define PAGE_SIZE 0x1000
 #endif // PAGE_SIZE
 
+#ifndef STATUS_WX86_SINGLE_STEP
+#define STATUS_WX86_SINGLE_STEP ((DWORD)0x4000001EL)
+#endif // STATUS_WX86_SINGLE_STEP
+
+#ifndef STATUS_WX86_BREAKPOINT
+#define STATUS_WX86_BREAKPOINT ((DWORD)0x4000001FL)
+#endif // STATUS_WX86_BREAKPOINT
+
 namespace GleeBug
 {
     //forward declarations
diff --git a/GleeBug/Debugger.Loop.Exception.cpp b/GleeBug/Debugger.Loop.Exception.cpp
index 1a430d5..fb28d39 100644
--- a/GleeBug/Debugger.Loop.Exception.cpp
+++ b/GleeBug/Debugger.Loop.Exception.cpp
@@ -560,9 +560,11 @@ namespace GleeBug
         switch(exceptionInfo.ExceptionRecord.ExceptionCode)
         {
         case STATUS_BREAKPOINT:
+        case STATUS_WX86_BREAKPOINT:
             exceptionBreakpoint(exceptionRecord, firstChance);
             break;
         case STATUS_SINGLE_STEP:
+        case STATUS_WX86_SINGLE_STEP:
             exceptionSingleStep(exceptionRecord, firstChance);
             break;
         case STATUS_GUARD_PAGE_VIOLATION:
diff --git a/GleeBug/Debugger.Loop.cpp b/GleeBug/Debugger.Loop.cpp
index 3b089e2..74a6be0 100644
--- a/GleeBug/Debugger.Loop.cpp
+++ b/GleeBug/Debugger.Loop.cpp
@@ -185,7 +185,9 @@ namespace GleeBug
                 unloadDllEvent(mDebugEvent.u.UnloadDll);
                 break;
             case EXCEPTION_DEBUG_EVENT:
-                if(IsDbgReplyLaterSupported && mDebugEvent.u.Exception.ExceptionRecord.ExceptionCode == STATUS_SINGLE_STEP)
+            {
+                auto exceptionCode = mDebugEvent.u.Exception.ExceptionRecord.ExceptionCode;
+                if(IsDbgReplyLaterSupported && (exceptionCode == STATUS_SINGLE_STEP || exceptionCode == STATUS_WX86_SINGLE_STEP))
                 {
                     // Resume the other threads since we are done processing the single step
                     for(auto & itr : SuspendedThreads)
@@ -196,6 +198,7 @@ namespace GleeBug
                 }
                 exceptionEvent(mDebugEvent.u.Exception);
                 break;
+            }
             case OUTPUT_DEBUG_STRING_EVENT:
                 debugStringEvent(mDebugEvent.u.DebugString);
                 break;
diff --git a/GleeBug/Debugger.Process.cpp b/GleeBug/Debugger.Process.cpp
index 19e8b45..19ae33e 100644
--- a/GleeBug/Debugger.Process.cpp
+++ b/GleeBug/Debugger.Process.cpp
@@ -62,15 +62,26 @@ namespace GleeBug
         }
     }
 
+    static ZydisMachineMode GetMachineMode(const Registers & registers)
+    {
+#ifdef _WIN64
+        return registers.Is32BitMode() ? ZYDIS_MACHINE_MODE_LONG_COMPAT_32 : ZYDIS_MACHINE_MODE_LONG_64;
+#else
+        return ZYDIS_MACHINE_MODE_LEGACY_32;
+#endif // _WIN64
+    }
+
     void Process::StepOver(const StepCallback & cbStep)
     {
-        auto gip = Registers(thread->hThread, CONTEXT_CONTROL).Gip();
+        Registers registers(thread->hThread, CONTEXT_CONTROL);
+        auto gip = registers.Gip();
+        auto machineMode = GetMachineMode(registers);
         unsigned char data[16];
         if(MemReadSafe(gip, data, sizeof(data)))
         {
             ZydisDisassembledInstruction instruction;
             if(ZYAN_SUCCESS(ZydisDisassembleIntel(
-                                GleeArchValue(ZYDIS_MACHINE_MODE_LONG_64, ZYDIS_MACHINE_MODE_LONG_COMPAT_32),
+                                machineMode,
                                 gip,
                                 data,
                                 sizeof(data),
@@ -111,6 +122,7 @@ namespace GleeBug
 
         // Check if we're currently stepping on a pushf instruction
         auto isPushf = false;
+        auto pointerSize = registers.PointerSize();
         {
             auto gip = registers.Gip();
             unsigned char data[16];
@@ -118,7 +130,7 @@ namespace GleeBug
             {
                 ZydisDisassembledInstruction instruction;
                 if(ZYAN_SUCCESS(ZydisDisassembleIntel(
-                                    GleeArchValue(ZYDIS_MACHINE_MODE_LONG_64, ZYDIS_MACHINE_MODE_LONG_COMPAT_32),
+                                    GetMachineMode(registers),
                                     gip,
                                     data,
                                     sizeof(data),
@@ -141,15 +153,16 @@ namespace GleeBug
 
         if(isPushf)
         {
-            thread->cbInternalStep = [this, cbStep]()
+            thread->cbInternalStep = [this, cbStep, pointerSize]()
             {
-                // Remove the trap flag from the stack
+                // Remove the trap flag from the stack using the execution
+                // mode's pointer width (PUSHFD is four bytes under WoW64).
                 auto gsp = Registers(this->thread->hThread).Gsp();
-                GleeBug::ptr data;
-                if(MemReadUnsafe(gsp, &data, sizeof(data)))
+                uint64 data = 0;
+                if(MemReadUnsafe(gsp, &data, pointerSize))
                 {
-                    data &= ~(int)Registers::F::Trap;
-                    MemWriteUnsafe(gsp, &data, sizeof(data));
+                    data &= ~uint64(Registers::F::Trap);
+                    MemWriteUnsafe(gsp, &data, pointerSize);
                 }
 
                 cbStep();
diff --git a/GleeBug/Debugger.Thread.Registers.cpp b/GleeBug/Debugger.Thread.Registers.cpp
index b4d6bb4..e7f4811 100644
--- a/GleeBug/Debugger.Thread.Registers.cpp
+++ b/GleeBug/Debugger.Thread.Registers.cpp
@@ -106,6 +106,12 @@ namespace GleeBug
         TrapFlag(this),
         ResumeFlag(this)
     {
+#ifdef _WIN64
+        // Preserve hardware-breakpoint state across control-context updates,
+        // including transitions between WoW64 compatibility and native mode.
+        if((ContextFlags & CONTEXT_CONTROL) == CONTEXT_CONTROL)
+            ContextFlags |= CONTEXT_DEBUG_REGISTERS;
+#endif // _WIN64
         memset(&mContext, 0, sizeof(CONTEXT));
         mContext.ContextFlags = ContextFlags;
         if(!!GetThreadContext(hThread, &mContext))
@@ -129,4 +135,18 @@ namespace GleeBug
     {
         return &mContext;
     }
-};
\ No newline at end of file
+
+    bool Registers::Is32BitMode() const
+    {
+#ifdef _WIN64
+        return mContext.SegCs == 0x23;
+#else
+        return true;
+#endif // _WIN64
+    }
+
+    size_t Registers::PointerSize() const
+    {
+        return Is32BitMode() ? sizeof(uint32) : sizeof(ptr);
+    }
+};
diff --git a/GleeBug/Debugger.Thread.Registers.h b/GleeBug/Debugger.Thread.Registers.h
index 4fd81c5..78d8d72 100644
--- a/GleeBug/Debugger.Thread.Registers.h
+++ b/GleeBug/Debugger.Thread.Registers.h
@@ -159,6 +159,16 @@ namespace GleeBug
         */
         PCONTEXT GetContext();
 
+        /**
+        \brief Returns true when the thread is currently executing 32-bit code.
+        */
+        bool Is32BitMode() const;
+
+        /**
+        \brief Gets the pointer size for the thread's current execution mode.
+        */
+        size_t PointerSize() const;
+
     private:
         HANDLE hThread;
         CONTEXT mContext;