diff --git a/lib/steep/type_construction.rb b/lib/steep/type_construction.rb
index 794bebaec..44a64bd13 100644
--- a/lib/steep/type_construction.rb
+++ b/lib/steep/type_construction.rb
@@ -1844,8 +1844,21 @@ def synthesize(node, hint: nil, condition: false)
             if cond
               branch_results = []
 
-              cond_type, constr = constr.synthesize(cond).to_ary
-              cond_value_node, cond_vars = interpreter.decompose_value(cond)
+              cond_type, constr = constr.synthesize(cond)
+              _, cond_vars = interpreter.decompose_value(cond)
+
+              var_name = :"_a#{SecureRandom.base64(4)}"
+              var_cond, value_node = extract_outermost_call(cond, var_name)
+              if value_node
+                unless constr.context.type_env[value_node]
+                  constr = constr.update_type_env do |env|
+                    env.assign_local_variable(var_name, cond_type, nil)
+                  end
+                  cond = var_cond
+                else
+                  value_node = nil
+                end
+              end
 
               when_constr = constr
               whens.each do |clause|
@@ -1893,7 +1906,11 @@ def synthesize(node, hint: nil, condition: false)
               types = branch_results.map(&:type)
               constrs = branch_results.map(&:constr)
 
-              cond_type = when_constr.context.type_env[cond_value_node]
+              cond_type = when_constr.context.type_env[var_name]
+              cond_type ||= when_constr.context.type_env[cond_vars.first || raise] unless cond_vars.empty?
+              cond_type ||= when_constr.context.type_env[value_node] if value_node
+              cond_type ||= typing.type_of(node: node.children[0])
+
               if cond_type.is_a?(AST::Types::Bot)
                 # Exhaustive
                 if els
@@ -4235,5 +4252,35 @@ def save_typing
       typing.save!
       with_new_typing(typing.parent)
     end
+
+    def extract_outermost_call(node, var_name)
+      case node.type
+      when :lvasgn
+        name, rhs = node.children
+        rhs, value_node = extract_outermost_call(rhs, var_name)
+        if value_node
+          [node.updated(nil, [name, rhs]), value_node]
+        else
+          [node, value_node]
+        end
+      when :begin
+        *children, last = node.children
+        last, value_node = extract_outermost_call(last, var_name)
+        if value_node
+          [node.updated(nil, children.push(last)), value_node]
+        else
+          [node, value_node]
+        end
+      when :lvar
+        [node, nil]
+      else
+        if value_node?(node)
+          [node, nil]
+        else
+          var_node = node.updated(:lvar, [var_name])
+          [var_node, node]
+        end
+      end
+    end
   end
 end
diff --git a/sig/steep/node_helper.rbs b/sig/steep/node_helper.rbs
index b5491946a..198f71676 100644
--- a/sig/steep/node_helper.rbs
+++ b/sig/steep/node_helper.rbs
@@ -6,6 +6,8 @@ module Steep
     def each_descendant_node: (Parser::AST::Node) -> Enumerator[Parser::AST::Node, void]
                             | (Parser::AST::Node) { (Parser::AST::Node) -> void } -> void
 
+    # Returns true if given node is a syntactic-value node
+    #
     def value_node?: (Parser::AST::Node) -> bool
   end
 end
diff --git a/sig/steep/type_construction.rbs b/sig/steep/type_construction.rbs
index aaa8dcecc..ca08c14db 100644
--- a/sig/steep/type_construction.rbs
+++ b/sig/steep/type_construction.rbs
@@ -283,5 +283,18 @@ module Steep
     # * All of the arguments are _pure_
     #
     def pure_send?: (TypeInference::MethodCall::Typed call, Parser::AST::Node receiver, Array[Parser::AST::Node] arguments) -> bool
+
+    # Transform given `node` to a node that has a local variable instead of the outer most call/non-value node
+    #
+    # Returns a pair of transformed node and the outer most call/non-value node if present.
+    #
+    # ```rb
+    # x = y = foo()   # Call `#transform_value_node` with the node and var_name `:__foo__`
+    #                 # => Returns [x = y = __foo__, foo()]
+    # ```
+    #
+    # This is typically used for transforming assginment node for case condition.
+    #
+    def extract_outermost_call: (Parser::AST::Node node, Symbol) -> [Parser::AST::Node, Parser::AST::Node?]
   end
 end
diff --git a/test/type_construction_test.rb b/test/type_construction_test.rb
index fbb56a230..64ddf4c8a 100644
--- a/test/type_construction_test.rb
+++ b/test/type_construction_test.rb
@@ -9758,12 +9758,36 @@ def test_lvar_special
 end
 
 -> (_) { 123 }
+RUBY
+      with_standard_construction(checker, source) do |construction, typing|
+        type, _, context = construction.synthesize(source.node)
+
+        assert_no_error typing
+      end
+    end
+  end
+
+  def test_type_narrowing_assignment
+    with_checker(<<-RBS) do |checker|
+class NarrowingAssignmentTest
+  def foo: () -> (Integer | String)
+end
+      RBS
+      source = parse_ruby(<<-RUBY)
+case value = NarrowingAssignmentTest.new.foo()
+when Integer
+  "hello"
+when String
+  value
+end
       RUBY
 
       with_standard_construction(checker, source) do |construction, typing|
         type, _, context = construction.synthesize(source.node)
 
         assert_no_error typing
+
+        assert_equal parse_type("::String"), type
       end
     end
   end