diff --git a/spec/compiler/macro/macro_methods_spec.cr b/spec/compiler/macro/macro_methods_spec.cr
index 38b08f44568a..385e165a3504 100644
--- a/spec/compiler/macro/macro_methods_spec.cr
+++ b/spec/compiler/macro/macro_methods_spec.cr
@@ -928,6 +928,16 @@ module Crystal
         assert_macro %({{["c".id, "b", "a".id].sort}}), %([a, "b", c])
       end
 
+      it "executes sort_by" do
+        assert_macro %({{["abc", "a", "ab"].sort_by { |x| x.size }}}), %(["a", "ab", "abc"])
+      end
+
+      it "calls block exactly once for each element in #sort_by" do
+        assert_macro <<-CRYSTAL, %(5)
+          {{ (i = 0; ["abc", "a", "ab", "abcde", "abcd"].sort_by { i += 1 }; i) }}
+          CRYSTAL
+      end
+
       it "executes uniq" do
         assert_macro %({{[1, 1, 1, 2, 3, 1, 2, 3, 4].uniq}}), %([1, 2, 3, 4])
       end
@@ -1020,10 +1030,6 @@ module Crystal
         assert_macro %({{{:a => 1, :b => 3}.size}}), "2"
       end
 
-      it "executes sort_by" do
-        assert_macro %({{["abc", "a", "ab"].sort_by { |x| x.size }}}), %(["a", "ab", "abc"])
-      end
-
       it "executes empty?" do
         assert_macro %({{{:a => 1}.empty?}}), "false"
       end
diff --git a/src/compiler/crystal/macros/methods.cr b/src/compiler/crystal/macros/methods.cr
index d3a1a1cc15a6..8a7aa569fa95 100644
--- a/src/compiler/crystal/macros/methods.cr
+++ b/src/compiler/crystal/macros/methods.cr
@@ -3232,12 +3232,17 @@ end
 private def sort_by(object, klass, block, interpreter)
   block_arg = block.args.first?
 
-  klass.new(object.elements.sort { |x, y|
-    block_arg.try { |arg| interpreter.define_var(arg.name, x) }
-    x_result = interpreter.accept(block.body)
-    block_arg.try { |arg| interpreter.define_var(arg.name, y) }
-    y_result = interpreter.accept(block.body)
-
-    x_result.interpret_compare(y_result)
-  })
+  klass.new(object.elements.sort_by do |elem|
+    block_arg.try { |arg| interpreter.define_var(arg.name, elem) }
+    result = interpreter.accept(block.body)
+    InterpretCompareWrapper.new(result)
+  end)
+end
+
+private record InterpretCompareWrapper, node : Crystal::ASTNode do
+  include Comparable(self)
+
+  def <=>(other : self)
+    node.interpret_compare(other.node)
+  end
 end