diff --git a/llvm/lib/Target/RISCV/RISCVISelLowering.cpp b/llvm/lib/Target/RISCV/RISCVISelLowering.cpp
--- a/llvm/lib/Target/RISCV/RISCVISelLowering.cpp
+++ b/llvm/lib/Target/RISCV/RISCVISelLowering.cpp
@@ -9369,11 +9369,13 @@
     // shift amount.
     if (N->getOpcode() == ISD::SHL) {
       SDLoc DL(N);
+      SDNodeFlags Flags = N->getFlags();
       SDValue NewOp0 =
           DAG.getNode(ISD::ANY_EXTEND, DL, MVT::i64, N->getOperand(0));
       SDValue NewOp1 =
           DAG.getNode(ISD::ZERO_EXTEND, DL, MVT::i64, N->getOperand(1));
-      SDValue NewWOp = DAG.getNode(ISD::SHL, DL, MVT::i64, NewOp0, NewOp1);
+      SDValue NewWOp =
+          DAG.getNode(ISD::SHL, DL, MVT::i64, NewOp0, NewOp1, Flags);
       SDValue NewRes = DAG.getNode(ISD::SIGN_EXTEND_INREG, DL, MVT::i64, NewWOp,
                                    DAG.getValueType(MVT::i32));
       Results.push_back(DAG.getNode(ISD::TRUNCATE, DL, MVT::i32, NewRes));
@@ -13025,11 +13027,17 @@
 
   // What is the fewest number of bits we need to represent the negative number.
   unsigned MinSignedBits = ExpandedMask.getSignificantBits();
+  APInt NewMask = ShrunkMask;
+  NewMask.setBitsFrom(31);
+  if (Opcode == ISD::AND && MinSignedBits == 64 && NewMask.isSignedIntN(12) &&
+      ShrunkMask.isSignedIntN(32)) {
+    return UseMask(NewMask);
+  }
 
   // Try to make a 12 bit negative immediate. If that fails try to make a 32
   // bit negative immediate unless the shrunk immediate already fits in 32 bits.
   // If we can't create a simm12, we shouldn't change opaque constants.
-  APInt NewMask = ShrunkMask;
+  NewMask = ShrunkMask;
   if (MinSignedBits <= 12)
     NewMask.setBitsFrom(11);
   else if (!C->isOpaque() && MinSignedBits <= 32 && !ShrunkMask.isSignedIntN(32))
diff --git a/llvm/test/CodeGen/RISCV/branch-on-zero.ll b/llvm/test/CodeGen/RISCV/branch-on-zero.ll
--- a/llvm/test/CodeGen/RISCV/branch-on-zero.ll
+++ b/llvm/test/CodeGen/RISCV/branch-on-zero.ll
@@ -92,7 +92,7 @@
 ; RV64-NEXT:  .LBB2_2: # %for.body
 ; RV64-NEXT:    # =>This Inner Loop Header: Depth=1
 ; RV64-NEXT:    andi a2, a0, 1
-; RV64-NEXT:    srliw a0, a0, 1
+; RV64-NEXT:    srli a0, a0, 1
 ; RV64-NEXT:    addw a1, a1, a2
 ; RV64-NEXT:    bnez a0, .LBB2_2
 ; RV64-NEXT:  .LBB2_3: # %for.end
diff --git a/llvm/test/CodeGen/RISCV/rv64i-demanded-bits.ll b/llvm/test/CodeGen/RISCV/rv64i-demanded-bits.ll
--- a/llvm/test/CodeGen/RISCV/rv64i-demanded-bits.ll
+++ b/llvm/test/CodeGen/RISCV/rv64i-demanded-bits.ll
@@ -192,3 +192,15 @@
   %or = or i32 %and, 255
   ret i32 %or
 }
+
+; https://alive2.llvm.org/ce/z/RizyWW
+define i32 @shl_add_neg4(i32 noundef %x) {
+; CHECK-LABEL: shl_add_neg4:
+; CHECK:       # %bb.0:
+; CHECK-NEXT:    slli a0, a0, 1
+; CHECK-NEXT:    andi a0, a0, -4
+; CHECK-NEXT:    ret
+  %y = shl nuw nsw i32 %x, 1
+  %z = and i32 %y, 2147483644
+  ret i32 %z
+}