diff --git a/llvm/lib/Transforms/InstCombine/InstCombineCompares.cpp b/llvm/lib/Transforms/InstCombine/InstCombineCompares.cpp
--- a/llvm/lib/Transforms/InstCombine/InstCombineCompares.cpp
+++ b/llvm/lib/Transforms/InstCombine/InstCombineCompares.cpp
@@ -2255,8 +2255,11 @@
     }
     if (Pred == CmpInst::ICMP_UGT) {
       // icmp ugt (ashr X, ShAmtC), C --> icmp ugt X, ((C + 1) << ShAmtC) - 1
+      // 'C + 1 << ShAmtC' can overflow as a signed number, so the 2nd
+      // clause accounts for that pattern.
       APInt ShiftedC = (C + 1).shl(ShAmtVal) - 1;
-      if ((ShiftedC + 1).ashr(ShAmtVal) == (C + 1))
+      if ((ShiftedC + 1).ashr(ShAmtVal) == (C + 1) ||
+          (C + 1).shl(ShAmtVal).isMinSignedValue())
         return new ICmpInst(Pred, X, ConstantInt::get(ShrTy, ShiftedC));
     }
 
diff --git a/llvm/test/Transforms/InstCombine/icmp-shr.ll b/llvm/test/Transforms/InstCombine/icmp-shr.ll
--- a/llvm/test/Transforms/InstCombine/icmp-shr.ll
+++ b/llvm/test/Transforms/InstCombine/icmp-shr.ll
@@ -594,13 +594,9 @@
   ret i1 %r
 }
 
-; negative test
-; TODO: This is a sign-bit test, but we don't recognize the pattern.
-
 define i1 @ashr_ugt_3(i4 %x) {
 ; CHECK-LABEL: @ashr_ugt_3(
-; CHECK-NEXT:    [[S:%.*]] = ashr i4 [[X:%.*]], 1
-; CHECK-NEXT:    [[R:%.*]] = icmp ugt i4 [[S]], 3
+; CHECK-NEXT:    [[R:%.*]] = icmp slt i4 [[X:%.*]], 0
 ; CHECK-NEXT:    ret i1 [[R]]
 ;
   %s = ashr i4 %x, 1
@@ -859,7 +855,6 @@
 }
 
 ; negative test
-; TODO: This is a sign-bit test, but we don't recognize the pattern.
 
 define i1 @ashr_ult_12(i4 %x) {
 ; CHECK-LABEL: @ashr_ult_12(