Index: llvm/lib/Transforms/Scalar/IndVarSimplify.cpp
===================================================================
--- llvm/lib/Transforms/Scalar/IndVarSimplify.cpp
+++ llvm/lib/Transforms/Scalar/IndVarSimplify.cpp
@@ -1435,8 +1435,9 @@
 }
 
 static bool optimizeLoopExitWithUnknownExitCount(
-    const Loop *L, BranchInst *BI, BasicBlock *ExitingBB, const SCEV *MaxIter,
-    bool SkipLastIter, ScalarEvolution *SE, SCEVExpander &Rewriter,
+    const Loop *L, BranchInst *BI, BasicBlock *ExitingBB,
+    const SCEV *CurrMaxIter, const SCEV *MaxIter, bool SkipLastIter,
+    ScalarEvolution *SE, SCEVExpander &Rewriter,
     SmallVectorImpl<WeakTrackingVH> &DeadInsts) {
   assert(
       (L->contains(BI->getSuccessor(0)) != L->contains(BI->getSuccessor(1))) &&
@@ -1484,11 +1485,17 @@
   // conditions if there is another condition that gives the very same exit
   // count.
   bool TryMoreOptimisticLastIter = false;
-  if (!SkipLastIter && LeafConditions.size() <= MaxJoinedICmpsToAnalyze &&
-      SE->getExitCount(L, ExitingBB,
-                       ScalarEvolution::ExitCountKind::SymbolicMaximum) ==
-          MaxIter)
-    TryMoreOptimisticLastIter = true;
+  if (!SkipLastIter && LeafConditions.size() <= MaxJoinedICmpsToAnalyze) {
+    const SCEV *CurrBlockMaxExit = SE->getExitCount(
+        L, ExitingBB, ScalarEvolution::ExitCountKind::SymbolicMaximum);
+    if (!isa<SCEVCouldNotCompute>(CurrBlockMaxExit)) {
+      const SCEV *MaxUpToCurrentBlock =
+          isa<SCEVCouldNotCompute>(CurrMaxIter)
+              ? CurrBlockMaxExit
+              : SE->getUMinFromMismatchedTypes(CurrMaxIter, CurrBlockMaxExit);
+      TryMoreOptimisticLastIter |= MaxUpToCurrentBlock == MaxIter;
+    }
+  }
 
   bool Changed = false;
   for (size_t i = 0; i < LeafConditions.size(); ++i) {
@@ -1503,13 +1510,18 @@
           // conditions may skip it.
           auto *ExitMax = EL.SymbolicMaxNotTaken;
           if (!isa<SCEVCouldNotCompute>(ExitMax)) {
+            const SCEV *MaxUpToCurrentICmp =
+                isa<SCEVCouldNotCompute>(CurrMaxIter)
+                    ? ExitMax
+                    : SE->getUMinFromMismatchedTypes(CurrMaxIter, ExitMax);
             // They could be of different types (specifically this happens after
             // IV widening).
-            auto *WiderType =
-                SE->getWiderType(ExitMax->getType(), MaxIter->getType());
-            auto *WideExitMax = SE->getNoopOrZeroExtend(ExitMax, WiderType);
+            auto *WiderType = SE->getWiderType(MaxUpToCurrentICmp->getType(),
+                                               MaxIter->getType());
+            auto *WideMaxUpToCurrentICmp =
+                SE->getNoopOrZeroExtend(MaxUpToCurrentICmp, WiderType);
             auto *WideMaxIter = SE->getNoopOrZeroExtend(MaxIter, WiderType);
-            if (WideExitMax == WideMaxIter) {
+            if (WideMaxUpToCurrentICmp == WideMaxIter) {
               OptimisticSkipLastIter = true;
               break;
             }
@@ -1758,9 +1770,9 @@
       // will remain the same within iteration space?
       auto *BI = cast<BranchInst>(ExitingBB->getTerminator());
       auto OptimizeCond = [&](bool SkipLastIter) {
-        return optimizeLoopExitWithUnknownExitCount(L, BI, ExitingBB,
-                                                    MaxBECount, SkipLastIter,
-                                                    SE, Rewriter, DeadInsts);
+        return optimizeLoopExitWithUnknownExitCount(
+            L, BI, ExitingBB, CurrMaxExit, MaxBECount, SkipLastIter, SE,
+            Rewriter, DeadInsts);
       };
 
       // TODO: We might have proved that we can skip the last iteration for
Index: llvm/test/Transforms/IndVarSimplify/X86/widening-vs-and-elimination.ll
===================================================================
--- llvm/test/Transforms/IndVarSimplify/X86/widening-vs-and-elimination.ll
+++ llvm/test/Transforms/IndVarSimplify/X86/widening-vs-and-elimination.ll
@@ -66,6 +66,8 @@
 ; WIDENING_ON-LABEL: @test_02(
 ; WIDENING_ON-NEXT:  bb:
 ; WIDENING_ON-NEXT:    [[TMP0:%.*]] = zext i32 [[START:%.*]] to i64
+; WIDENING_ON-NEXT:    [[TMP1:%.*]] = add nsw i64 [[TMP0]], -1
+; WIDENING_ON-NEXT:    [[TMP2:%.*]] = zext i32 [[LIMIT:%.*]] to i64
 ; WIDENING_ON-NEXT:    br label [[LOOP:%.*]]
 ; WIDENING_ON:       loop:
 ; WIDENING_ON-NEXT:    [[INDVARS_IV:%.*]] = phi i64 [ [[INDVARS_IV_NEXT:%.*]], [[BACKEDGE:%.*]] ], [ [[TMP0]], [[BB:%.*]] ]
@@ -73,12 +75,10 @@
 ; WIDENING_ON-NEXT:    [[EXITCOND:%.*]] = icmp ne i32 [[CANONICAL_IV]], 65635
 ; WIDENING_ON-NEXT:    br i1 [[EXITCOND]], label [[CHECKED:%.*]], label [[FAILED:%.*]]
 ; WIDENING_ON:       checked:
-; WIDENING_ON-NEXT:    [[TMP1:%.*]] = add nsw i64 [[INDVARS_IV]], -1
 ; WIDENING_ON-NEXT:    [[INDVARS_IV_NEXT]] = add nsw i64 [[INDVARS_IV]], -1
 ; WIDENING_ON-NEXT:    [[NOT_ZERO:%.*]] = icmp ne i64 [[INDVARS_IV]], 0
-; WIDENING_ON-NEXT:    [[TMP2:%.*]] = zext i32 [[LIMIT:%.*]] to i64
-; WIDENING_ON-NEXT:    [[RANGE_CHECK_WIDE:%.*]] = icmp ult i64 [[TMP1]], [[TMP2]]
-; WIDENING_ON-NEXT:    [[AND:%.*]] = and i1 [[NOT_ZERO]], [[RANGE_CHECK_WIDE]]
+; WIDENING_ON-NEXT:    [[RANGE_CHECK_WIDE_FIRST_ITER:%.*]] = icmp ult i64 [[TMP1]], [[TMP2]]
+; WIDENING_ON-NEXT:    [[AND:%.*]] = and i1 [[NOT_ZERO]], [[RANGE_CHECK_WIDE_FIRST_ITER]]
 ; WIDENING_ON-NEXT:    br i1 [[AND]], label [[BACKEDGE]], label [[EXIT:%.*]]
 ; WIDENING_ON:       backedge:
 ; WIDENING_ON-NEXT:    [[CANONICAL_IV_NEXT]] = add nuw nsw i32 [[CANONICAL_IV]], 1
@@ -90,17 +90,18 @@
 ;
 ; WIDENING_OFF-LABEL: @test_02(
 ; WIDENING_OFF-NEXT:  bb:
+; WIDENING_OFF-NEXT:    [[TMP0:%.*]] = add i32 [[START:%.*]], -1
 ; WIDENING_OFF-NEXT:    br label [[LOOP:%.*]]
 ; WIDENING_OFF:       loop:
 ; WIDENING_OFF-NEXT:    [[CANONICAL_IV:%.*]] = phi i32 [ [[CANONICAL_IV_NEXT:%.*]], [[BACKEDGE:%.*]] ], [ 0, [[BB:%.*]] ]
-; WIDENING_OFF-NEXT:    [[IV:%.*]] = phi i32 [ [[IV_NEXT:%.*]], [[BACKEDGE]] ], [ [[START:%.*]], [[BB]] ]
+; WIDENING_OFF-NEXT:    [[IV:%.*]] = phi i32 [ [[IV_NEXT:%.*]], [[BACKEDGE]] ], [ [[START]], [[BB]] ]
 ; WIDENING_OFF-NEXT:    [[EXITCOND:%.*]] = icmp ne i32 [[CANONICAL_IV]], 65635
 ; WIDENING_OFF-NEXT:    br i1 [[EXITCOND]], label [[CHECKED:%.*]], label [[FAILED:%.*]]
 ; WIDENING_OFF:       checked:
 ; WIDENING_OFF-NEXT:    [[IV_NEXT]] = add i32 [[IV]], -1
 ; WIDENING_OFF-NEXT:    [[NOT_ZERO:%.*]] = icmp ne i32 [[IV]], 0
-; WIDENING_OFF-NEXT:    [[RANGE_CHECK:%.*]] = icmp ult i32 [[IV_NEXT]], [[LIMIT:%.*]]
-; WIDENING_OFF-NEXT:    [[AND:%.*]] = and i1 [[NOT_ZERO]], [[RANGE_CHECK]]
+; WIDENING_OFF-NEXT:    [[RANGE_CHECK_FIRST_ITER:%.*]] = icmp ult i32 [[TMP0]], [[LIMIT:%.*]]
+; WIDENING_OFF-NEXT:    [[AND:%.*]] = and i1 [[NOT_ZERO]], [[RANGE_CHECK_FIRST_ITER]]
 ; WIDENING_OFF-NEXT:    br i1 [[AND]], label [[BACKEDGE]], label [[EXIT:%.*]]
 ; WIDENING_OFF:       backedge:
 ; WIDENING_OFF-NEXT:    [[ZEXT:%.*]] = zext i32 [[IV_NEXT]] to i64