diff --git a/llvm/lib/Transforms/InstCombine/InstCombineCompares.cpp b/llvm/lib/Transforms/InstCombine/InstCombineCompares.cpp
index 542a1c82b127a..49200d02ef339 100644
--- a/llvm/lib/Transforms/InstCombine/InstCombineCompares.cpp
+++ b/llvm/lib/Transforms/InstCombine/InstCombineCompares.cpp
@@ -2414,14 +2414,34 @@ Instruction *InstCombinerImpl::foldICmpShlConstant(ICmpInst &Cmp,
   // free on the target. It has the additional benefit of comparing to a
   // smaller constant that may be more target-friendly.
   unsigned Amt = ShiftAmt->getLimitedValue(TypeBits - 1);
-  if (Shl->hasOneUse() && Amt != 0 && C.countr_zero() >= Amt &&
-      DL.isLegalInteger(TypeBits - Amt)) {
-    Type *TruncTy = IntegerType::get(Cmp.getContext(), TypeBits - Amt);
-    if (auto *ShVTy = dyn_cast<VectorType>(ShType))
-      TruncTy = VectorType::get(TruncTy, ShVTy->getElementCount());
-    Constant *NewC =
-        ConstantInt::get(TruncTy, C.ashr(*ShiftAmt).trunc(TypeBits - Amt));
-    return new ICmpInst(Pred, Builder.CreateTrunc(X, TruncTy), NewC);
+  if (Shl->hasOneUse() && Amt != 0 &&
+      shouldChangeType(ShType->getScalarSizeInBits(), TypeBits - Amt)) {
+    ICmpInst::Predicate CmpPred = Pred;
+    APInt RHSC = C;
+
+    if (RHSC.countr_zero() < Amt && ICmpInst::isStrictPredicate(CmpPred)) {
+      // Try the flipped strictness predicate.
+      // e.g.:
+      // icmp ult i64 (shl X, 32), 8589934593 ->
+      // icmp ule i64 (shl X, 32), 8589934592 ->
+      // icmp ule i32 (trunc X, i32), 2 ->
+      // icmp ult i32 (trunc X, i32), 3
+      if (auto FlippedStrictness =
+              InstCombiner::getFlippedStrictnessPredicateAndConstant(
+                  Pred, ConstantInt::get(ShType->getContext(), C))) {
+        CmpPred = FlippedStrictness->first;
+        RHSC = cast<ConstantInt>(FlippedStrictness->second)->getValue();
+      }
+    }
+
+    if (RHSC.countr_zero() >= Amt) {
+      Type *TruncTy = ShType->getWithNewBitWidth(TypeBits - Amt);
+      Constant *NewC =
+          ConstantInt::get(TruncTy, RHSC.ashr(*ShiftAmt).trunc(TypeBits - Amt));
+      return new ICmpInst(
+          CmpPred, Builder.CreateTrunc(X, TruncTy, "", Shl->hasNoSignedWrap()),
+          NewC);
+    }
   }
 
   return nullptr;
diff --git a/llvm/test/Transforms/InstCombine/icmp.ll b/llvm/test/Transforms/InstCombine/icmp.ll
index 2d786c8f48833..4dbe2fc88ff71 100644
--- a/llvm/test/Transforms/InstCombine/icmp.ll
+++ b/llvm/test/Transforms/InstCombine/icmp.ll
@@ -5198,3 +5198,100 @@ define i1 @icmp_freeze_sext(i16 %x, i16 %y) {
   %cmp2 = icmp uge i16 %ext.fr, %y
   ret i1 %cmp2
 }
+
+define i1 @test_icmp_shl(i64 %x) {
+; CHECK-LABEL: @test_icmp_shl(
+; CHECK-NEXT:    [[TMP1:%.*]] = trunc i64 [[X:%.*]] to i32
+; CHECK-NEXT:    [[CMP:%.*]] = icmp ult i32 [[TMP1]], 3
+; CHECK-NEXT:    ret i1 [[CMP]]
+;
+  %shl = shl i64 %x, 32
+  %cmp = icmp ult i64 %shl, 8589934593
+  ret i1 %cmp
+}
+
+define i1 @test_icmp_shl_multiuse(i64 %x) {
+; CHECK-LABEL: @test_icmp_shl_multiuse(
+; CHECK-NEXT:    [[SHL:%.*]] = shl i64 [[X:%.*]], 32
+; CHECK-NEXT:    call void @use_i64(i64 [[SHL]])
+; CHECK-NEXT:    [[CMP:%.*]] = icmp ult i64 [[SHL]], 8589934593
+; CHECK-NEXT:    ret i1 [[CMP]]
+;
+  %shl = shl i64 %x, 32
+  call void @use_i64(i64 %shl)
+  %cmp = icmp ult i64 %shl, 8589934593
+  ret i1 %cmp
+}
+
+define i1 @test_icmp_shl_illegal_length(i64 %x) {
+; CHECK-LABEL: @test_icmp_shl_illegal_length(
+; CHECK-NEXT:    [[SHL:%.*]] = shl i64 [[X:%.*]], 31
+; CHECK-NEXT:    [[CMP:%.*]] = icmp ult i64 [[SHL]], 8589934593
+; CHECK-NEXT:    ret i1 [[CMP]]
+;
+  %shl = shl i64 %x, 31
+  %cmp = icmp ult i64 %shl, 8589934593
+  ret i1 %cmp
+}
+
+define i1 @test_icmp_shl_invalid_rhsc(i64 %x) {
+; CHECK-LABEL: @test_icmp_shl_invalid_rhsc(
+; CHECK-NEXT:    [[SHL:%.*]] = shl i64 [[X:%.*]], 32
+; CHECK-NEXT:    [[CMP:%.*]] = icmp ult i64 [[SHL]], 8589934595
+; CHECK-NEXT:    ret i1 [[CMP]]
+;
+  %shl = shl i64 %x, 32
+  %cmp = icmp ult i64 %shl, 8589934595
+  ret i1 %cmp
+}
+
+define i1 @test_icmp_shl_nuw(i64 %x) {
+; CHECK-LABEL: @test_icmp_shl_nuw(
+; CHECK-NEXT:    [[CMP:%.*]] = icmp ult i64 [[X:%.*]], 3
+; CHECK-NEXT:    ret i1 [[CMP]]
+;
+  %shl = shl nuw i64 %x, 32
+  %cmp = icmp ult i64 %shl, 8589934593
+  ret i1 %cmp
+}
+
+define i1 @test_icmp_shl_nsw(i64 %x) {
+; CHECK-LABEL: @test_icmp_shl_nsw(
+; CHECK-NEXT:    [[CMP:%.*]] = icmp ult i64 [[X:%.*]], 3
+; CHECK-NEXT:    ret i1 [[CMP]]
+;
+  %shl = shl nsw i64 %x, 32
+  %cmp = icmp ult i64 %shl, 8589934593
+  ret i1 %cmp
+}
+
+define <2 x i1> @test_icmp_shl_vec(<2 x i64> %x) {
+; CHECK-LABEL: @test_icmp_shl_vec(
+; CHECK-NEXT:    [[TMP1:%.*]] = trunc <2 x i64> [[X:%.*]] to <2 x i32>
+; CHECK-NEXT:    [[CMP:%.*]] = icmp ult <2 x i32> [[TMP1]], <i32 3, i32 3>
+; CHECK-NEXT:    ret <2 x i1> [[CMP]]
+;
+  %shl = shl <2 x i64> %x, splat(i64 32)
+  %cmp = icmp ult <2 x i64> %shl, splat(i64 8589934593)
+  ret <2 x i1> %cmp
+}
+
+define i1 @test_icmp_shl_eq(i64 %x) {
+; CHECK-LABEL: @test_icmp_shl_eq(
+; CHECK-NEXT:    ret i1 false
+;
+  %shl = shl i64 %x, 32
+  %cmp = icmp eq i64 %shl, 8589934593
+  ret i1 %cmp
+}
+
+define i1 @test_icmp_shl_sgt(i64 %x) {
+; CHECK-LABEL: @test_icmp_shl_sgt(
+; CHECK-NEXT:    [[TMP1:%.*]] = trunc i64 [[X:%.*]] to i32
+; CHECK-NEXT:    [[CMP:%.*]] = icmp sgt i32 [[TMP1]], 1
+; CHECK-NEXT:    ret i1 [[CMP]]
+;
+  %shl = shl i64 %x, 32
+  %cmp = icmp sgt i64 %shl, 8589934591
+  ret i1 %cmp
+}