diff --git a/FEXCore/Source/Interface/Core/OpcodeDispatcher.cpp b/FEXCore/Source/Interface/Core/OpcodeDispatcher.cpp
index 51b305b65..20de85532 100644
--- a/FEXCore/Source/Interface/Core/OpcodeDispatcher.cpp
+++ b/FEXCore/Source/Interface/Core/OpcodeDispatcher.cpp
@@ -1526,7 +1526,7 @@ void OpDispatchBuilder::SHLDImmediateOp(OpcodeArgs) {
       Res = _Extr(OpSizeFromSrc(Op), Dest, Src, Size - Shift);
     }
 
-    CalculateFlags_ShiftLeftImmediate(OpSizeFromSrc(Op), Res, Dest, Shift);
+    CalculateFlags_ShiftLeftImmediate(OpSizeFromSrc(Op), Res, Dest, Shift, true);
     CalculateDeferredFlags();
     StoreResultGPR(Op, Res);
   } else if (Shift == 0 && Size == 32) {
diff --git a/FEXCore/Source/Interface/Core/OpcodeDispatcher.h b/FEXCore/Source/Interface/Core/OpcodeDispatcher.h
index 0b2b64083..416bec3b4 100644
--- a/FEXCore/Source/Interface/Core/OpcodeDispatcher.h
+++ b/FEXCore/Source/Interface/Core/OpcodeDispatcher.h
@@ -2375,7 +2375,7 @@ private:
   void CalculateFlags_MUL(IR::OpSize SrcSize, Ref Res, Ref High);
   void CalculateFlags_UMUL(Ref High);
   void CalculateFlags_Logical(IR::OpSize SrcSize, Ref Res);
-  void CalculateFlags_ShiftLeftImmediate(IR::OpSize SrcSize, Ref Res, Ref Src1, uint64_t Shift);
+  void CalculateFlags_ShiftLeftImmediate(IR::OpSize SrcSize, Ref Res, Ref Src1, uint64_t Shift, bool DoubleWide = false);
   void CalculateFlags_ShiftRightImmediate(IR::OpSize SrcSize, Ref Res, Ref Src1, uint64_t Shift);
   void CalculateFlags_ShiftRightDoubleImmediate(IR::OpSize SrcSize, Ref Res, Ref Src1, uint64_t Shift);
   void CalculateFlags_ShiftRightImmediateCommon(IR::OpSize SrcSize, Ref Res, Ref Src1, uint64_t Shift);
diff --git a/FEXCore/Source/Interface/Core/OpcodeDispatcher/Flags.cpp b/FEXCore/Source/Interface/Core/OpcodeDispatcher/Flags.cpp
index 82c1a1a6c..858e7a4ae 100644
--- a/FEXCore/Source/Interface/Core/OpcodeDispatcher/Flags.cpp
+++ b/FEXCore/Source/Interface/Core/OpcodeDispatcher/Flags.cpp
@@ -432,7 +432,7 @@ void OpDispatchBuilder::CalculateFlags_Logical(IR::OpSize SrcSize, Ref Res) {
   SetNZP_ZeroCV(SrcSize, Res);
 }
 
-void OpDispatchBuilder::CalculateFlags_ShiftLeftImmediate(IR::OpSize SrcSize, Ref UnmaskedRes, Ref Src1, uint64_t Shift) {
+void OpDispatchBuilder::CalculateFlags_ShiftLeftImmediate(IR::OpSize SrcSize, Ref UnmaskedRes, Ref Src1, uint64_t Shift, bool DoubleWide) {
   // No flags changed if shift is zero
   if (Shift == 0) {
     return;
@@ -447,8 +447,12 @@ void OpDispatchBuilder::CalculateFlags_ShiftLeftImmediate(IR::OpSize SrcSize, Re
     // Extract the last bit shifted in to CF. Shift is already masked, but for
     // 8/16-bit it might be >= SrcSizeBits, in which case CF is cleared. There's
     // nothing to do in that case since we already cleared CF above.
+    //
+    // - Double-wide shift has UB when shift is GREATER-THAN operand.
+    // - Single-wide shift has UB when shift is GREATER-THAN-EQUAL operand.
     const auto SrcSizeBits = IR::OpSizeAsBits(SrcSize);
-    if (Shift < SrcSizeBits) {
+    const bool ShouldSetCF = DoubleWide ? (Shift <= SrcSizeBits) : (Shift < SrcSizeBits);
+    if (ShouldSetCF) {
       SetCFDirect(Src1, SrcSizeBits - Shift, true);
     }
   }
diff --git a/unittests/ASM/FEX_bugs/SHLD_CF.asm b/unittests/ASM/FEX_bugs/SHLD_CF.asm
new file mode 100644
index 000000000..9575ccb8c
--- /dev/null
+++ b/unittests/ASM/FEX_bugs/SHLD_CF.asm
@@ -0,0 +1,52 @@
+%ifdef CONFIG
+{
+  "RegData": {
+      "RAX": "1",
+      "R15": "1",
+      "R14": "1",
+      "R13": "1",
+      "R12": "1"
+  }
+}
+%endif
+
+; FEX-Emu had a bug where operand-sized shifts with SHLD/SHRD wasn't matching behaviour.
+; We were expecting SAL/SAR/SHL/SHR undefined behaviour semantics but a `ge` comparison changes to `gt`.
+
+; Test with shld and immediate
+mov eax, 1
+mov edx, 0xbee8
+mov rcx, 0
+clc
+shld ax, dx, 16
+setc cl
+mov r15, rcx
+
+; Test with shld and CL
+mov eax, 1
+mov edx, 0xbee8
+mov rcx, 16
+clc
+shld ax, dx, cl
+setc cl
+mov r14, rcx
+
+; Test with shrd and immediate
+mov eax, 0x8eeb
+mov edx, 1
+mov rcx, 0
+clc
+shrd ax, dx, 16
+setc cl
+mov r13, rcx
+
+; Test with shrd and CL
+mov eax, 0x8eeb
+mov edx, 1
+mov rcx, 16
+clc
+shrd ax, dx, cl
+setc cl
+mov r12, rcx
+
+hlt