diff --git a/llvm/lib/Transforms/Utils/LoopRotationUtils.cpp b/llvm/lib/Transforms/Utils/LoopRotationUtils.cpp
--- a/llvm/lib/Transforms/Utils/LoopRotationUtils.cpp
+++ b/llvm/lib/Transforms/Utils/LoopRotationUtils.cpp
@@ -46,6 +46,11 @@
 
 STATISTIC(NumRotated, "Number of loops rotated");
 
+static cl::opt<bool>
+    MultiRotate("loop-rotate-multi", cl::init(false), cl::Hidden,
+                cl::desc("Allow loop rotation multiple times in order to reach "
+                         "a better latch exit"));
+
 namespace {
 /// A simple loop rotation transformation.
 class LoopRotate {
@@ -177,14 +182,16 @@
   }
 }
 
-// Look for a phi which is only used outside the loop (via a LCSSA phi)
-// in the exit from the header. This means that rotating the loop can
-// remove the phi.
-static bool shouldRotateLoopExitingLatch(Loop *L) {
+// Assuming both header and latch are exiting, look for a phi which is only
+// used outside the loop (via a LCSSA phi) in the exit from the header.
+// This means that rotating the loop can remove the phi.
+static bool profitableToRotateLoopExitingLatch(Loop *L) {
   BasicBlock *Header = L->getHeader();
-  BasicBlock *HeaderExit = Header->getTerminator()->getSuccessor(0);
+  BranchInst *BI = dyn_cast<BranchInst>(Header->getTerminator());
+  assert(BI && BI->isConditional() && "need header with conditional exit");
+  BasicBlock *HeaderExit = BI->getSuccessor(0);
   if (L->contains(HeaderExit))
-    HeaderExit = Header->getTerminator()->getSuccessor(1);
+    HeaderExit = BI->getSuccessor(1);
 
   for (auto &Phi : Header->phis()) {
     // Look for uses of this phi in the loop/via exits other than the header.
@@ -194,7 +201,50 @@
       continue;
     return true;
   }
+  return false;
+}
+
+// Check that latch exit is deoptimizing (which means - very unlikely to happen)
+// and there is another exit from the loop which is non-deoptimizing.
+// If we rotate latch to that exit our loop has a better chance of being fully
+// canonical.
+//
+// It can give false positives in some rare cases.
+static bool canRotateDeoptimizingLatchExit(Loop *L) {
+  BasicBlock *Latch = L->getLoopLatch();
+  assert(Latch && "need latch");
+  BranchInst *BI = dyn_cast<BranchInst>(Latch->getTerminator());
+  // Need normal exiting latch.
+  if (!BI || !BI->isConditional())
+    return false;
 
+  BasicBlock *Exit = BI->getSuccessor(1);
+  if (L->contains(Exit))
+    Exit = BI->getSuccessor(0);
+
+  // Latch exit is non-deoptimizing, no need to rotate.
+  if (!Exit->getPostdominatingDeoptimizeCall())
+    return false;
+
+  SmallVector<BasicBlock *, 4> Exits;
+  L->getUniqueExitBlocks(Exits);
+  if (!Exits.empty()) {
+    // There is at least one non-deoptimizing exit.
+    //
+    // Note, that BasicBlock::getPostdominatingDeoptimizeCall is not exact,
+    // as it can conservatively return false for deoptimizing exits with
+    // complex enough control flow down to deoptimize call.
+    //
+    // That means here we can report success for a case where
+    // all exits are deoptimizing but one of them has complex enough
+    // control flow (e.g. with loops).
+    //
+    // That should be a very rare case and false positives for this function
+    // have compile-time effect only.
+    return any_of(Exits, [](const BasicBlock *BB) {
+      return !BB->getPostdominatingDeoptimizeCall();
+    });
+  }
   return false;
 }
 
@@ -234,7 +284,8 @@
   // Rotate if either the loop latch does *not* exit the loop, or if the loop
   // latch was just simplified. Or if we think it will be profitable.
   if (L->isLoopExiting(OrigLatch) && !SimplifiedLatch && IsUtilMode == false &&
-      !shouldRotateLoopExitingLatch(L))
+      !profitableToRotateLoopExitingLatch(L) &&
+      !canRotateDeoptimizingLatchExit(L))
     return false;
 
   // Check size of original header and reject loop if it is very big or we can't
@@ -521,6 +572,17 @@
   LLVM_DEBUG(dbgs() << "LoopRotation: into "; L->dump());
 
   ++NumRotated;
+
+  // Check that new latch is a deoptimizing exit and then repeat rotation if
+  // possible.
+  if (MultiRotate && canRotateDeoptimizingLatchExit(L)) {
+    // Deoptimizing latch exit is not a generally typical case, so
+    // we just recursively loop over.
+    // TODO: if it becomes a performance bottleneck extend rotation algorithm
+    // to handle multiple rotations in one go.
+    rotateLoop(L, false);
+  }
+
   return true;
 }
 
diff --git a/llvm/test/Transforms/LoopRotate/multiple-deopt-exits.ll b/llvm/test/Transforms/LoopRotate/multiple-deopt-exits.ll
new file mode 100644
--- /dev/null
+++ b/llvm/test/Transforms/LoopRotate/multiple-deopt-exits.ll
@@ -0,0 +1,165 @@
+; NOTE: Assertions have been autogenerated by utils/update_test_checks.py
+; RUN: opt -S < %s -loop-rotate -loop-rotate-multi=true | FileCheck %s
+; RUN: opt -S < %s -passes='loop(rotate)' -loop-rotate-multi=true | FileCheck %s
+
+; Test loop rotation with multiple exits, some of them - deoptimizing.
+; We should end up with a latch which exit is non-deoptimizing, so we should rotate
+; more than once.
+
+declare i32 @llvm.experimental.deoptimize.i32(...)
+
+define i32 @test_cond_with_one_deopt_exit(i32 * nonnull %a, i64 %x) {
+; Rotation done twice.
+; Latch should be at the 2nd condition (for.cond2), exiting to %return.
+;
+; CHECK-LABEL: @test_cond_with_one_deopt_exit(
+; CHECK-NEXT:  entry:
+; CHECK-NEXT:    [[VAL_A_IDX3:%.*]] = load i32, i32* %a, align 4
+; CHECK-NEXT:    [[ZERO_CHECK4:%.*]] = icmp eq i32 [[VAL_A_IDX3]], 0
+; CHECK-NEXT:    br i1 [[ZERO_CHECK4]], label %deopt.exit, label %for.cond2.lr.ph
+; CHECK:       for.cond2.lr.ph:
+; CHECK-NEXT:    [[FOR_CHECK8:%.*]] = icmp ult i64 0, %x
+; CHECK-NEXT:    br i1 [[FOR_CHECK8]], label %for.body.lr.ph, label %return
+; CHECK:       for.body.lr.ph:
+; CHECK-NEXT:    br label %for.body
+; CHECK:       for.cond2:
+; CHECK:         [[FOR_CHECK:%.*]] = icmp ult i64 {{%.*}}, %x
+; CHECK-NEXT:    br i1 [[FOR_CHECK]], label %for.body, label %for.cond2.return_crit_edge
+; CHECK:       for.body:
+; CHECK:         br label %for.tail
+; CHECK:       for.tail:
+; CHECK:         [[VAL_A_IDX:%.*]] = load i32, i32*
+; CHECK-NEXT:    [[ZERO_CHECK:%.*]] = icmp eq i32 [[VAL_A_IDX]], 0
+; CHECK-NEXT:    br i1 [[ZERO_CHECK]], label %for.cond1.deopt.exit_crit_edge, label %for.cond2
+; CHECK:       for.cond2.return_crit_edge:
+; CHECK-NEXT:    {{%.*}} = phi i32
+; CHECK-NEXT:    br label %return
+; CHECK:       return:
+; CHECK-NEXT:    [[SUM_LCSSA2:%.*]] = phi i32
+; CHECK-NEXT:    ret i32 [[SUM_LCSSA2]]
+; CHECK:       for.cond1.deopt.exit_crit_edge:
+; CHECK-NEXT:    {{%.*}} = phi i32
+; CHECK-NEXT:    br label %deopt.exit
+; CHECK:       deopt.exit:
+; CHECK:         [[DEOPT_VAL:%.*]] = call i32 (...) @llvm.experimental.deoptimize.i32() [ "deopt"(i32 {{%.*}}) ]
+; CHECK-NEXT:    ret i32 [[DEOPT_VAL]]
+;
+entry:
+  br label %for.cond1
+
+for.cond1:
+  %idx = phi i64 [ 0, %entry ], [ %idx.next, %for.tail ]
+  %sum = phi i32 [ 0, %entry ], [ %sum.next, %for.tail ]
+  %a.idx = getelementptr inbounds i32, i32 *%a, i64 %idx
+  %val.a.idx = load i32, i32* %a.idx, align 4
+  %zero.check = icmp eq i32 %val.a.idx, 0
+  br i1 %zero.check, label %deopt.exit, label %for.cond2
+
+for.cond2:
+  %for.check = icmp ult i64 %idx, %x
+  br i1 %for.check, label %for.body, label %return
+
+for.body:
+  br label %for.tail
+
+for.tail:
+  %sum.next = add i32 %sum, %val.a.idx
+  %idx.next = add nuw nsw i64 %idx, 1
+  br label %for.cond1
+
+return:
+  ret i32 %sum
+
+deopt.exit:
+  %deopt.val = call i32(...) @llvm.experimental.deoptimize.i32() [ "deopt"(i32 %val.a.idx) ]
+  ret i32 %deopt.val
+}
+
+define i32 @test_cond_with_two_deopt_exits(i32 ** nonnull %a, i64 %x) {
+; Rotation done three times.
+; Latch should be at the 3rd condition (for.cond3), exiting to %return.
+;
+; CHECK-LABEL: @test_cond_with_two_deopt_exits(
+; CHECK-NEXT:  entry:
+; CHECK-NEXT:    [[A_IDX_DEREF4:%.*]] = load i32*, i32** %a
+; CHECK-NEXT:    [[NULL_CHECK5:%.*]] = icmp eq i32* [[A_IDX_DEREF4]], null
+; CHECK-NEXT:    br i1 [[NULL_CHECK5]], label %deopt.exit1, label %for.cond2.lr.ph
+; CHECK:       for.cond2.lr.ph:
+; CHECK-NEXT:    [[VAL_A_IDX9:%.*]] = load i32, i32* [[A_IDX_DEREF4]], align 4
+; CHECK-NEXT:    [[ZERO_CHECK10:%.*]] = icmp eq i32 [[VAL_A_IDX9]], 0
+; CHECK-NEXT:    br i1 [[ZERO_CHECK10]], label %deopt.exit2, label %for.cond3.lr.ph
+; CHECK:       for.cond3.lr.ph:
+; CHECK-NEXT:    [[FOR_CHECK14:%.*]] = icmp ult i64 0, %x
+; CHECK-NEXT:    br i1 [[FOR_CHECK14]], label %for.body.lr.ph, label %return
+; CHECK:       for.body.lr.ph:
+; CHECK-NEXT:    br label %for.body
+; CHECK:       for.cond2:
+; CHECK:         [[VAL_A_IDX:%.*]] = load i32, i32*
+; CHECK-NEXT:    [[ZERO_CHECK:%.*]] = icmp eq i32 [[VAL_A_IDX]], 0
+; CHECK-NEXT:    br i1 [[ZERO_CHECK]], label %for.cond2.deopt.exit2_crit_edge, label %for.cond3
+; CHECK:       for.cond3:
+; CHECK:         [[FOR_CHECK:%.*]] = icmp ult i64 {{%.*}}, %x
+; CHECK-NEXT:    br i1 [[FOR_CHECK]], label %for.body, label %for.cond3.return_crit_edge
+; CHECK:       for.body:
+; CHECK:         br label %for.tail
+; CHECK:       for.tail:
+; CHECK:         [[IDX_NEXT:%.*]] = add nuw nsw i64 {{%.*}}, 1
+; CHECK:         [[NULL_CHECK:%.*]] = icmp eq i32* {{%.*}}, null
+; CHECK-NEXT:    br i1 [[NULL_CHECK]], label %for.cond1.deopt.exit1_crit_edge, label %for.cond2
+; CHECK:       for.cond3.return_crit_edge:
+; CHECK-NEXT:    [[SPLIT18:%.*]] = phi i32
+; CHECK-NEXT:    br label %return
+; CHECK:       return:
+; CHECK-NEXT:    [[SUM_LCSSA2:%.*]] = phi i32
+; CHECK-NEXT:    ret i32 [[SUM_LCSSA2]]
+; CHECK:       for.cond1.deopt.exit1_crit_edge:
+; CHECK-NEXT:    br label %deopt.exit1
+; CHECK:       deopt.exit1:
+; CHECK-NEXT:    [[DEOPT_VAL1:%.*]] = call i32 (...) @llvm.experimental.deoptimize.i32() [ "deopt"(i32 0) ]
+; CHECK-NEXT:    ret i32 [[DEOPT_VAL1]]
+; CHECK:       for.cond2.deopt.exit2_crit_edge:
+; CHECK-NEXT:    [[SPLIT:%.*]] = phi i32
+; CHECK-NEXT:    br label %deopt.exit2
+; CHECK:       deopt.exit2:
+; CHECK-NEXT:    [[VAL_A_IDX_LCSSA:%.*]] = phi i32
+; CHECK-NEXT:    [[DEOPT_VAL2:%.*]] = call i32 (...) @llvm.experimental.deoptimize.i32() [ "deopt"(i32 [[VAL_A_IDX_LCSSA]]) ]
+; CHECK-NEXT:    ret i32 [[DEOPT_VAL2]]
+;
+entry:
+  br label %for.cond1
+
+for.cond1:
+  %idx = phi i64 [ 0, %entry ], [ %idx.next, %for.tail ]
+  %sum = phi i32 [ 0, %entry ], [ %sum.next, %for.tail ]
+  %a.idx = getelementptr inbounds i32*, i32 **%a, i64 %idx
+  %a.idx.deref = load i32*, i32** %a.idx
+  %null.check = icmp eq i32* %a.idx.deref, null
+  br i1 %null.check, label %deopt.exit1, label %for.cond2
+
+for.cond2:
+  %val.a.idx = load i32, i32* %a.idx.deref, align 4
+  %zero.check = icmp eq i32 %val.a.idx, 0
+  br i1 %zero.check, label %deopt.exit2, label %for.cond3
+
+for.cond3:
+  %for.check = icmp ult i64 %idx, %x
+  br i1 %for.check, label %for.body, label %return
+
+for.body:
+  br label %for.tail
+
+for.tail:
+  %sum.next = add i32 %sum, %val.a.idx
+  %idx.next = add nuw nsw i64 %idx, 1
+  br label %for.cond1
+
+return:
+  ret i32 %sum
+
+deopt.exit1:
+  %deopt.val1 = call i32(...) @llvm.experimental.deoptimize.i32() [ "deopt"(i32 0) ]
+  ret i32 %deopt.val1
+deopt.exit2:
+  %deopt.val2 = call i32(...) @llvm.experimental.deoptimize.i32() [ "deopt"(i32 %val.a.idx) ]
+  ret i32 %deopt.val2
+}