diff --git a/lib/Sema/CMakeLists.txt b/lib/Sema/CMakeLists.txt
index 5bc72b050d4..14513cc2d54 100644
--- a/lib/Sema/CMakeLists.txt
+++ b/lib/Sema/CMakeLists.txt
@@ -11,6 +11,7 @@ add_swift_library(swiftSema STATIC
   CSRanking.cpp
   CSSimplify.cpp
   CSSolver.cpp
+  CSStep.cpp
   CSFix.cpp
   CSDiagnostics.cpp
   CalleeCandidateInfo.cpp
diff --git a/lib/Sema/CSSolver.cpp b/lib/Sema/CSSolver.cpp
index 06bbcc16eb6..530175d2c9e 100644
--- a/lib/Sema/CSSolver.cpp
+++ b/lib/Sema/CSSolver.cpp
@@ -13,6 +13,7 @@
 // This file implements the constraint solver used in the type checker.
 //
 //===----------------------------------------------------------------------===//
+#include "CSStep.h"
 #include "ConstraintGraph.h"
 #include "ConstraintSystem.h"
 #include "TypeCheckType.h"
@@ -24,6 +25,7 @@
 #include "llvm/Support/SaveAndRestore.h"
 #include "llvm/Support/raw_ostream.h"
 #include <algorithm>
+#include <list>
 #include <memory>
 #include <tuple>
 
@@ -1556,6 +1558,68 @@ bool ConstraintSystem::solveRec(SmallVectorImpl<Solution> &solutions) {
   return !anySolutions;
 }
 
+bool ConstraintSystem::solveIteratively(
+    Expr *expr, SmallVectorImpl<Solution> &solutions,
+    FreeTypeVariableBinding allowFreeTypeVariables) {
+  SolverState state(expr, *this, allowFreeTypeVariables);
+
+  std::list<SolverStep> workList;
+  // First step is always wraps whole constraint system.
+  workList.push_back(
+      SolverStep::create(*this, TypeVariables, InactiveConstraints, solutions));
+
+  // Execute steps in LIFO order, which means that
+  // each individual step would either end up producing
+  // a solution, or producing another set of mergeable
+  // steps to take before arriving to solution.
+  while (!workList.empty()) {
+    auto &step = workList.back();
+
+    // Now let's try to advance to the next step,
+    // which should produce another steps to follow,
+    // or error, which means that we'll have to stop.
+    {
+      SolutionKind result;
+      std::list<SolverStep> followupSteps;
+
+      std::tie(result, followupSteps) = step.advance();
+      switch (result) {
+      // Step has been solved successfully by either
+      // producing a partial solution, or more steps
+      // toward that solution.
+      case SolutionKind::Solved: {
+        workList.pop_back();
+        break;
+      }
+
+      // Keep this step in the work list to return to it
+      // once all other steps are done, this could be a
+      // disjunction which has to peek a new choice until
+      // it completely runs out of choices, or type variable
+      // binding.
+      case SolutionKind::Unsolved:
+        break;
+
+      // It was impossible to produce a solution for this step,
+      // let's terminate the solver loop.
+      case SolutionKind::Error:
+        return true;
+      }
+
+      workList.splice(workList.end(), followupSteps);
+    }
+  }
+
+  // Filter deduced solutions, try to figure out if there is
+  // a single best solution to use, if not explicitly disabled
+  // by constraint system options.
+  if (!retainAllSolutions())
+    filterSolutions(solutions, state.ExprWeights);
+
+  // We fail if there is no solution or the expression was too complex.
+  return solutions.empty() || getExpressionTooComplex(solutions);
+}
+
 /// Whether we should short-circuit a disjunction that already has a
 /// solution when we encounter the given constraint.
 static bool shortCircuitDisjunctionAt(Constraint *constraint,
diff --git a/lib/Sema/CSStep.cpp b/lib/Sema/CSStep.cpp
new file mode 100644
index 00000000000..31a7beb8979
--- /dev/null
+++ b/lib/Sema/CSStep.cpp
@@ -0,0 +1,71 @@
+#include "CSStep.h"
+#include "ConstraintSystem.h"
+#include "swift/AST/Types.h"
+#include "llvm/ADT/ArrayRef.h"
+#include "llvm/ADT/SmallVector.h"
+#include <list>
+
+using namespace llvm;
+using namespace swift;
+using namespace constraints;
+
+SolverStep SolverStep::create(ConstraintSystem &cs,
+                              ArrayRef<TypeVariableType *> typeVars,
+                              ConstraintList &constraints,
+                              SmallVectorImpl<Solution> &solutions) {
+  SolverStep step(cs, solutions);
+
+  for (auto *typeVar : typeVars)
+    step.record(typeVar);
+
+  for (auto &constraint : constraints)
+    step.record(&constraint);
+
+  return step;
+}
+
+SolverStep::StepResult SolverStep::advance() {
+  if (!ActiveScope)
+    ActiveScope = new (CS.getAllocator()) Scope(*this);
+
+  auto *disjunction = CS.selectDisjunction();
+  auto bestBindings = CS.determineBestBindings();
+
+  // TODO: Add expression too complex into the mix
+  // TODO: This is where the generator comes in.
+
+  if (bestBindings && (!disjunction || (!bestBindings->InvolvesTypeVariables &&
+                                        !bestBindings->FullyBound))) {
+    // Attempt given "best" binding and record the current scope,
+    // we'll have to come back to this step later on when follow-up
+    // steps are solved.
+    return computeFollowupSteps();
+  }
+
+  // For disjunctions we need to figure out what all of the already
+  // attempted choices are, and try the next one.
+  auto choices = disjunction->getNestedConstraints();
+  for (unsigned i = ActiveScope->CurrChoice, n = choices.size(); i != n; ++i) {
+    auto *choice = choices[i];
+    if (choice->isDisabled())
+      continue;
+
+    // Attempt the choice and record it in the scope.
+    ActiveScope->CurrChoice = i;
+    return computeFollowupSteps();
+  }
+
+  // Since we are done with this step, it's a good time to
+  // roll-up all of the solutions produced by follow-up steps.
+  auto result = mergePartialSolutions() ? ConstraintSystem::SolutionKind::Solved
+                                        : ConstraintSystem::SolutionKind::Error;
+
+  return {result, {}};
+}
+
+SolverStep::StepResult SolverStep::computeFollowupSteps() const {
+  std::list<SolverStep> nextSteps;
+  // Compute next steps based on that connected components
+  // algorithm tells us is splittable.
+  return {ConstraintSystem::SolutionKind::Unsolved, std::move(nextSteps)};
+}
diff --git a/lib/Sema/CSStep.h b/lib/Sema/CSStep.h
new file mode 100644
index 00000000000..fb8be280e5f
--- /dev/null
+++ b/lib/Sema/CSStep.h
@@ -0,0 +1,137 @@
+//===--- CSFix.cpp - Constraint Fixes -------------------------------------===//
+//
+// This source file is part of the Swift.org open source project
+//
+// Copyright (c) 2014 - 2018 Apple Inc. and the Swift project authors
+// Licensed under Apache License v2.0 with Runtime Library Exception
+//
+// See https://swift.org/LICENSE.txt for license information
+// See https://swift.org/CONTRIBUTORS.txt for the list of Swift project authors
+//
+//===----------------------------------------------------------------------===//
+//
+// This file implements the \c SolverStep class and its related types,
+// which is used by constraint solver to do iterative constraint solving.
+//
+//===----------------------------------------------------------------------===//
+
+#ifndef SWIFT_SEMA_CSSTEP_H
+#define SWIFT_SEMA_CSSTEP_H
+
+#include "ConstraintSystem.h"
+#include "swift/AST/Types.h"
+#include "llvm/ADT/ArrayRef.h"
+#include "llvm/ADT/SmallVector.h"
+#include <list>
+#include <memory>
+
+using namespace llvm;
+
+namespace swift {
+namespace constraints {
+
+class SolverStep {
+  struct Scope;
+
+  ConstraintSystem &CS;
+
+  // Type variables and constraints "in scope" of this step.
+  SmallVector<TypeVariableType *, 16> TypeVars;
+  SmallVector<Constraint *, 16> Constraints;
+
+  // If this step depends on other smaller steps to be solved first
+  // we need to keep active scope until all of the work is done.
+  Scope *ActiveScope = nullptr;
+
+  /// Once step is complete this is a container to hold finalized solutions.
+  SmallVectorImpl<Solution> &Solutions;
+
+public:
+  using StepResult =
+      std::pair<ConstraintSystem::SolutionKind, std::list<SolverStep>>;
+
+  explicit SolverStep(ConstraintSystem &cs,
+                      SmallVectorImpl<Solution> &solutions)
+      : CS(cs), Solutions(solutions) {}
+
+  ~SolverStep() {
+    if (!ActiveScope)
+      return;
+
+    // Since the step is no longer needed, it's same to rewind active scope.
+    delete ActiveScope;
+    ActiveScope = nullptr;
+  }
+
+  /// Record a type variable as associated with this step.
+  void record(TypeVariableType *typeVar) { TypeVars.push_back(typeVar); }
+
+  /// Record a constraint as associated with this step.
+  void record(Constraint *constraint) { Constraints.push_back(constraint); }
+
+  /// Try to move solver forward by simplifying constraints if possible.
+  /// Such simplication might lead to either producing a solution, or
+  /// creating a set of "follow-up" more granular steps to execute.
+  StepResult advance();
+
+  /// If current step needs follow-up steps to get completely solved,
+  /// let's compute them using connected components algorithm.
+  StepResult computeFollowupSteps() const;
+
+  static SolverStep create(ConstraintSystem &cs,
+                           ArrayRef<TypeVariableType *> typeVars,
+                           ConstraintList &constraints,
+                           SmallVectorImpl<Solution> &solutions);
+
+  /// Once all of the follow-up steps are complete, let's try
+  /// to merge resulting solutions together, to form final solution(s)
+  /// for this step.
+  ///
+  /// \returns true if there are any solutions, false otherwise.
+  bool mergePartialSolutions() const { return false; }
+
+private:
+  struct Scope {
+    ConstraintSystem &CS;
+    ConstraintSystem::SolverScope *SolverScope;
+
+    SmallVector<TypeVariableType *, 16> TypeVars;
+    ConstraintList Constraints;
+
+    // Current disjunction choice index.
+    unsigned CurrChoice = 0;
+
+    // Partial solutions associated with given step, each element
+    // of the array presents a disjoint component (or follow-up step)
+    // that current step has been split into.
+    std::unique_ptr<SmallVector<Solution, 4>[]> PartialSolutions = nullptr;
+
+    Scope(SolverStep &step) : CS(step.CS) {
+      TypeVars = std::move(CS.TypeVariables);
+
+      for (auto *typeVar : step.TypeVars)
+        CS.TypeVariables.push_back(typeVar);
+
+      Constraints.splice(Constraints.end(), CS.InactiveConstraints);
+
+      for (auto *constraint : step.Constraints)
+        CS.InactiveConstraints.push_back(constraint);
+
+      SolverScope = new ConstraintSystem::SolverScope(CS);
+    }
+
+    ~Scope() {
+      delete SolverScope; // rewind back all of the changes.
+
+      // return all of the saved type variables back to the system.
+      CS.TypeVariables = std::move(TypeVars);
+      // return all of the saved constraints back to the system.
+      CS.InactiveConstraints.splice(CS.InactiveConstraints.end(), Constraints);
+    }
+  };
+};
+
+} // end namespace constraints
+} // end namespace swift
+
+#endif // SWIFT_SEMA_CSSTEP_H
diff --git a/lib/Sema/ConstraintSystem.h b/lib/Sema/ConstraintSystem.h
index d1a5206bdb6..89c430784fa 100644
--- a/lib/Sema/ConstraintSystem.h
+++ b/lib/Sema/ConstraintSystem.h
@@ -57,6 +57,7 @@ class DisjunctionChoiceProducer;
 class TypeBinding;
 class TypeVariableBinding;
 class TypeVarBindingProducer;
+class SolverStep;
 
 } // end namespace constraints
 
@@ -930,6 +931,7 @@ public:
   friend class FailureDiagnostic;
   friend class TypeVarBindingProducer;
   friend class TypeVariableBinding;
+  friend class SolverStep;
 
   class SolverScope;
 
@@ -3088,6 +3090,9 @@ public:
   /// \returns true if there are no solutions
   bool solveRec(SmallVectorImpl<Solution> &solutions);
 
+  bool solveIteratively(Expr *expr, SmallVectorImpl<Solution> &solutions,
+                        FreeTypeVariableBinding allowFreeTypeVariables);
+
   /// \brief Solve the system of constraints.
   ///
   /// \param allowFreeTypeVariables How to bind free type variables in