diff --git a/lib/liquid/context.rb b/lib/liquid/context.rb
index 3d6ffc96..270c902d 100644
--- a/lib/liquid/context.rb
+++ b/lib/liquid/context.rb
@@ -187,16 +187,11 @@ module Liquid
       # path and find_index() is optimized in MRI to reduce object allocation
       index = @scopes.find_index { |s| s.key?(key) }
 
-      variable = if index
+      if index
         lookup_and_evaluate(@scopes[index], key, raise_on_not_found: raise_on_not_found)
       else
         try_variable_find_in_environments(key, raise_on_not_found: raise_on_not_found)
       end
-
-      variable         = variable.to_liquid
-      variable.context = self if variable.respond_to?(:context=)
-
-      variable
     end
 
     def lookup_and_evaluate(obj, key, raise_on_not_found: true)
@@ -204,13 +199,17 @@ module Liquid
         raise Liquid::UndefinedVariable, "undefined variable #{key}"
       end
 
-      value = obj[key]
+      original = obj[key]
 
-      if value.is_a?(Proc) && obj.respond_to?(:[]=)
-        obj[key] = value.arity == 0 ? value.call : value.call(self)
-      else
-        value
+      value = contextualize(original)
+
+      # TODO: I'd like to fold this under the liquid sanitization
+      # Original text from VariableLookup: if its a proc we will replace the entry with the proc
+      if original.is_a?(Proc) && obj.respond_to?(:[]=)
+        obj[key] = value
       end
+
+      value
     end
 
     def with_disabled_tags(tag_names)
@@ -228,6 +227,25 @@ module Liquid
       @disabled_tags.fetch(tag_name, 0) > 0
     end
 
+    # TODO: Let's think as to how name this.
+    # The strait forward name is to use "to_liquid(object)" but I do not think this fully captures what it do.
+    # Also, "to_liquid" is already used anywhere and is more of a generic name at this point.
+    # When we call "to_liquid" we are "sanitizing" the input?
+    # We also want to "bind" the object to the current rendering "@context".
+    def contextualize(object)
+      if object.is_a?(Proc)
+        object = object.arity == 0 ? object.call : object.call(self)
+      end
+
+      object = object.to_liquid
+
+      # TODO: ideally all contextualized object would define "context=" even if they end up noop-ing it.
+      # For now this is not really a pressing issue to deal with.
+      object.context = self if object.respond_to?(:context=)
+
+      object
+    end
+
     protected
 
     attr_writer :base_scope_depth, :warnings, :errors, :strainer, :filters, :disabled_tags
diff --git a/lib/liquid/standardfilters.rb b/lib/liquid/standardfilters.rb
index f361c02b..6ff1fcd6 100644
--- a/lib/liquid/standardfilters.rb
+++ b/lib/liquid/standardfilters.rb
@@ -582,8 +582,11 @@ module Liquid
 
       def each
         @input.each do |e|
-          e.context = @context if e.respond_to?(:context=)
-          yield(e.respond_to?(:to_liquid) ? e.to_liquid : e)
+          # TODO: this conversion should occur outside the filter.
+          # This is a change I desire to make but might not make the cut for the current change at hand.
+          e = @context.contextualize(e)
+
+          yield(e)
         end
       end
     end
diff --git a/lib/liquid/variable_lookup.rb b/lib/liquid/variable_lookup.rb
index 9d5dba68..fa6b5199 100644
--- a/lib/liquid/variable_lookup.rb
+++ b/lib/liquid/variable_lookup.rb
@@ -49,15 +49,17 @@ module Liquid
             ((object.respond_to?(:key?) && object.key?(key)) ||
              (object.respond_to?(:fetch) && key.is_a?(Integer)))
 
-          # if its a proc we will replace the entry with the proc
-          res    = context.lookup_and_evaluate(object, key)
-          object = res.to_liquid
+          object = context.lookup_and_evaluate(object, key)
 
           # Some special cases. If the part wasn't in square brackets and
           # no key with the same name was found we interpret following calls
           # as commands and call them on the current object
         elsif @command_flags & (1 << i) != 0 && object.respond_to?(key)
-          object = object.send(key).to_liquid
+
+          # TODO: These do not go through lookup_and_evaluate.
+          # Let's see if we can move the conversion back to Context
+          object = object.send(key)
+          object = context.contextualize(object)
 
           # No key was present with the desired value and it wasn't one of the directly supported
           # keywords either. The only thing we got left is to return nil or
diff --git a/test/integration/standard_filter_test.rb b/test/integration/standard_filter_test.rb
index 90ba82bf..52dcb6a8 100644
--- a/test/integration/standard_filter_test.rb
+++ b/test/integration/standard_filter_test.rb
@@ -861,7 +861,7 @@ class StandardFiltersTest < Minitest::Test
       { foo: "bar" },
       [{ "foo" => "bar" }, { "foo" => 123 }, { "foo" => nil }, { "foo" => true }, { "foo" => ["foo", "bar"] }],
       { 1 => "bar" },
-      ["foo", 123, nil, true, false, Drop, ["foo"], { foo: "bar" }],
+      ["foo", 123, nil, true, false, test_drop, test_enum, ["foo"], { foo: "bar" }],
     ]
     StandardFilters.public_instance_methods(false).each do |method|
       arg_count = @filters.method(method).arity