diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 396931de4..65213b3ee 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -6,7 +6,7 @@ on:
   pull_request:
     branches: [ main ]
   schedule:
-    - cron: '0 4 * * 0'
+    - cron: '0 4 * * *'
 
 jobs:
   test:
diff --git a/lib/arel/visitors/sqlserver.rb b/lib/arel/visitors/sqlserver.rb
index 539e34b9e..fac75c736 100644
--- a/lib/arel/visitors/sqlserver.rb
+++ b/lib/arel/visitors/sqlserver.rb
@@ -149,6 +149,12 @@ def visit_Arel_Nodes_HomogeneousIn(o, collector)
 
         if values.empty?
           collector << @connection.quote(nil)
+        elsif o.attribute.respond_to?(:comparison_expression)
+          # Comparison values need SQL around each bind, so they cannot use
+          # the collector's bulk bind path.
+          binds = values.map(&o.proc_for_binds)
+          expressions = binds.map { |bind| o.attribute.comparison_expression(bind) }
+          collector = inject_join(expressions, collector, ", ")
         elsif @connection.prepared_statements && !column_type.serialized?
           # Add query attribute bindings rather than just values.
           attrs = values.map { |value| ActiveRecord::Relation::QueryAttribute.new(column_name, value, column_type) }
diff --git a/test/cases/coerced_tests.rb b/test/cases/coerced_tests.rb
index fa18d3cd4..2bdf483e7 100644
--- a/test/cases/coerced_tests.rb
+++ b/test/cases/coerced_tests.rb
@@ -17,6 +17,7 @@
 require "models/tag"
 require "models/task"
 require "models/topic"
+require "models/book_encrypted"
 
 class UniquenessValidationTest < ActiveRecord::TestCase
   # So sp_executesql swallows this exception. Run without prepared to see it.
@@ -286,7 +287,7 @@ def test_belongs_to_with_primary_key_joins_on_correct_column_coerced
   def test_belongs_to_coerced
     client = Client.find(3)
     first_firm = companies(:first_firm)
-    assert_queries_and_values_match(/FETCH NEXT @. ROWS ONLY/, ["Firm", "Agency", 1, 1]) do
+    assert_queries_match(/FETCH NEXT @. ROWS ONLY/) do
       assert_equal first_firm, client.firm
       assert_equal first_firm.name, client.firm.name
     end
@@ -1399,17 +1400,166 @@ def test_registering_new_handlers_for_joins_coerced
     end
 
     # Same as original test except string has `N` prefix to indicate Unicode string.
-    coerce_tests! :test_attribute_type_can_transform_only_query_value
-    def test_attribute_type_can_transform_only_query_value_coerced
-      topic = topic_model_with_title_type(UuidToBinString.new)
-      uuid = "6ccd780c-baba-1026-9564-5b8c656024db"
-      sql = topic.where(title: uuid).to_sql
+    coerce_tests! :test_comparison_attribute_preserves_custom_type_casting
+    def test_comparison_attribute_preserves_custom_type_casting_coerced
+      type = LowerString.new
+      attribute = TypeCastingAttribute.new(Topic.arel_table, "title", type)
+      predicate = Topic.predicate_builder.build(attribute, "CAFE")
+
+      assert_same type, predicate.left.type_caster
+      assert_equal ["custom", "CAFE"], predicate.left.type_cast_for_database("CAFE")
+      assert_equal "SELECT #{quoted_topics}.* FROM #{quoted_topics} " \
+        "WHERE lower(#{quote_table_name("topics.title")}) = lower(N'CAFE')", Topic.where(predicate).to_sql
+    end
+
+    # Same as original test except string has `N` prefix to indicate Unicode string.
+    coerce_tests! :test_query_predicate_expression_decorators_stack
+    def test_query_predicate_expression_decorators_stack_coerced
+      type = OuterExpressionDecorator.new(InnerExpressionString.new)
+      topic = topic_model_with_title_type(type)
+      sql = topic.where(title: "VALUE").to_sql
       expected_sql = "SELECT #{quoted_topics}.* FROM #{quoted_topics} " \
-        "WHERE #{quote_table_name("topics.title")} = UUID_TO_BIN(N'#{uuid}')"
+        "WHERE outer_comparison(inner_comparison(#{quote_table_name("topics.title")})) = " \
+        "outer_comparison(inner_comparison(N'VALUE'))"
 
       assert_equal expected_sql, sql
     end
 
+    # Same as original test except string has `N` prefix to indicate Unicode string.
+    coerce_tests! :test_opaque_type_decorators_stop_query_predicate_composition
+    def test_opaque_type_decorators_stop_query_predicate_composition_coerced
+      type = OpaqueDecorator.new(LowerString.new)
+      topic = topic_model_with_title_type(type)
+      sql = topic.where(title: "value").to_sql
+      expected_sql = "SELECT #{quoted_topics}.* FROM #{quoted_topics} " \
+        "WHERE #{quote_table_name("topics.title")} = N'value'"
+
+      assert_equal expected_sql, sql
+    end
+
+    # Same as original test except string has `N` prefix to indicate Unicode string.
+    coerce_tests! :test_comparison_expression_composes_with_custom_predicate_handlers
+    def test_comparison_expression_composes_with_custom_predicate_handlers_coerced
+      topic = topic_model_with_title_type(UnaccentedString.new)
+      builder = RegexpPredicateBuilder.new(TableMetadata.new(topic, topic.arel_table))
+      topic.class_eval { @predicate_builder = builder }
+      sql = topic.where(title: /cafe/).to_sql
+      expected_sql = "SELECT #{quoted_topics}.* FROM #{quoted_topics} " \
+        "WHERE #{normalized_title} ~ N'cafe'"
+
+      assert_equal expected_sql, sql
+    end
+
+    # Same as original test except string has `N` prefix to indicate Unicode string.
+    coerce_tests! :test_custom_predicate_handlers_can_access_the_raw_attribute_and_type
+    def test_custom_predicate_handlers_can_access_the_raw_attribute_and_type_coerced
+      topic = topic_model_with_title_type(UnaccentedString.new)
+      builder = RawRegexpPredicateBuilder.new(TableMetadata.new(topic, topic.arel_table))
+      topic.class_eval { @predicate_builder = builder }
+      attribute = builder.predicate_attribute(topic.arel_table[:title])
+      sql = topic.where(title: /cafe/).to_sql
+      expected_sql = "SELECT #{quoted_topics}.* FROM #{quoted_topics} " \
+        "WHERE #{quote_table_name("topics.title")} ~ N'cafe'"
+
+      assert_equal expected_sql, sql
+      assert_instance_of UnaccentedString, attribute.type_caster
+    end
+
+    # SQL Server does not compose query predicate comparison expressions with array values.
+    coerce_tests! :test_attribute_type_comparison_expression_applies_to_array_values
+    def test_attribute_type_comparison_expression_applies_to_array_values_coerced
+      topic = topic_model_with_title_type(UnaccentedString.new)
+      relation = topic.where(title: ["CAFE", "BAR"])
+      values = relation.where_values_hash
+
+      assert_instance_of Arel::Nodes::HomogeneousIn, relation.where_clause.ast
+      sql = relation.to_sql
+      expected_sql = "SELECT #{quoted_topics}.* FROM #{quoted_topics} " \
+        "WHERE #{normalized_title} IN (#{normalized_value("CAFE")}, #{normalized_value("BAR")})"
+
+      assert_equal expected_sql, sql
+      assert_equal values, relation.where_values_hash
+    end
+
+    # Same as original test except string has `N` prefix to indicate Unicode string.
+    coerce_tests! :test_comparison_expression_preserves_serialized_values
+    def test_comparison_expression_preserves_serialized_values_coerced
+      type = MutableSerializedType.new
+      topic = topic_model_with_title_type(type)
+      value = {value: "original"}
+      relation = topic.where(title: value)
+      value[:value] = "changed"
+
+      assert_match(/= N'original'/, relation.to_sql)
+      assert_equal 1, type.serializations
+    end
+
+    # Same as original test except string has `N` prefix to indicate Unicode string.
+    coerce_tests! :test_query_predicates_compose_with_type_decorators
+    def test_query_predicates_compose_with_type_decorators_coerced
+      topic = Class.new(ActiveRecord::Base) do
+        self.table_name = "topics"
+        attribute :title, LowerString.new
+        normalizes :title, with: ->(title) { title.strip }
+      end
+      sql = topic.where(title: " PADDED ").to_sql
+      expected_sql = "SELECT #{quoted_topics}.* FROM #{quoted_topics} " \
+        "WHERE lower(#{quote_table_name("topics.title")}) = lower(N'PADDED')"
+
+      assert_equal expected_sql, sql
+    end
+
+    # Same as original test except string has `N` prefix to indicate Unicode string.
+    coerce_tests! :test_query_predicates_compose_with_enum_types
+    def test_query_predicates_compose_with_enum_types_coerced
+      topic = Class.new(ActiveRecord::Base) do
+        self.table_name = "topics"
+        attribute :title, LowerString.new
+        enum :title, {draft: "PUBLISHED"}
+      end
+      sql = topic.where(title: :draft).to_sql
+      expected_sql = "SELECT #{quoted_topics}.* FROM #{quoted_topics} " \
+        "WHERE lower(#{quote_table_name("topics.title")}) = lower(N'PUBLISHED')"
+
+      assert_equal expected_sql, sql
+    end
+
+    # Same as original test except string has `N` prefix to indicate Unicode string.
+    coerce_tests! :test_query_predicates_compose_with_serialized_types
+    def test_query_predicates_compose_with_serialized_types_coerced
+      type = ActiveRecord::Type::Serialized.new(LowerString.new, PrefixCoder)
+      topic = topic_model_with_title_type(type)
+      sql = topic.where(title: "VALUE").to_sql
+      expected_sql = "SELECT #{quoted_topics}.* FROM #{quoted_topics} " \
+        "WHERE lower(#{quote_table_name("topics.title")}) = lower(N'coded:VALUE')"
+
+      assert_equal expected_sql, sql
+    end
+
+    # SQL Server does not compose query predicate comparison expressions with array values.
+    coerce_tests! :test_query_predicates_compose_with_serialized_types_in_arrays
+    def test_query_predicates_compose_with_serialized_types_in_arrays_coerced
+      type = ActiveRecord::Type::Serialized.new(LowerString.new, PrefixCoder)
+      topic = topic_model_with_title_type(type)
+      sql = topic.where(title: ["ONE", "TWO"]).to_sql
+      expected_sql = "SELECT #{quoted_topics}.* FROM #{quoted_topics} " \
+        "WHERE lower(#{quote_table_name("topics.title")}) IN (lower(N'coded:ONE'), lower(N'coded:TWO'))"
+
+      assert_equal expected_sql, sql
+    end
+
+    # Same as original test except string has `N` prefix to indicate Unicode string.
+    coerce_tests! :test_through_association_scopes_use_query_predicate_expressions
+    def test_through_association_scopes_use_query_predicate_expressions_coerced
+      author = MatchableAuthor.create!(name: "Through Case")
+      sql = author.matches_of_matches.to_sql
+      middle_name = Regexp.escape(quote_table_name("matching_authors_matches_of_matches.name"))
+      owner_name = Regexp.escape(quote_table_name("authors.name"))
+
+      assert_match %r{ON lower\(#{owner_name}\) = lower\(#{middle_name}\)}, sql
+      assert_match %r{WHERE lower\(#{middle_name}\) = lower\(N'Through Case'\)}, sql
+    end
+
     private
 
     def topic_title
@@ -2534,7 +2684,7 @@ def serializer
 end
 
 class StoreTest < ActiveRecord::TestCase
-  # Set the attribute as JSON type for the `StoreTest#saved changes tracking for accessors with json column` test.
+  # Set the attribute as JSON type.
   Admin::User.attribute :json_options, ActiveRecord::Type::SQLServer::Json.new
 end
 
@@ -2881,3 +3031,13 @@ class HasManyThroughAssociationsTest < ActiveRecord::TestCase
   # SQL Server does not support delete based on composite key from another table.
   coerce_tests! :test_delete_all_nullify_on_through_with_composite_source_foreign_key
 end
+
+class ActiveRecord::Encryption::EncryptableFixtureTest < ActiveRecord::EncryptionTestCase
+  # Set the attribute as JSON type.
+  ::EncryptedBookWithJson.attribute :metadata, ActiveRecord::Type::SQLServer::Json.new
+
+  coerce_tests! %r{fixtures for json columns get encrypted automatically}
+  def fixtures_for_json_columns_get_encrypted_automatically
+    send(:"original_fixtures for json columns get encrypted automatically")
+  end
+end
diff --git a/test/cases/schema_dumper_test_sqlserver.rb b/test/cases/schema_dumper_test_sqlserver.rb
index 39f4e0dc1..89166394d 100644
--- a/test/cases/schema_dumper_test_sqlserver.rb
+++ b/test/cases/schema_dumper_test_sqlserver.rb
@@ -181,8 +181,8 @@ class SchemaDumperTestSQLServer < ActiveRecord::TestCase
   private
 
   def generate_schema_for_table(*table_names)
-    previous_ignore_tables = ActiveRecord::SchemaDumper.ignore_tables
-    ActiveRecord::SchemaDumper.ignore_tables = all_tables - table_names
+    previous_ignore_tables = ActiveRecord.schema_ignored_tables
+    ActiveRecord.schema_ignored_tables = all_tables - table_names
 
     stream = StringIO.new
     ActiveRecord::SchemaDumper.dump(ActiveRecord::Base.connection_pool, stream)
@@ -198,7 +198,7 @@ def generate_schema_for_table(*table_names)
     end
     @generated_schema
   ensure
-    ActiveRecord::SchemaDumper.ignore_tables = previous_ignore_tables
+    ActiveRecord.schema_ignored_tables = previous_ignore_tables
   end
 
   def line(column_name)