diff --git a/django/db/backends/mysql/compiler.py b/django/db/backends/mysql/compiler.py
index bd2715fb43..33ef2a12dc 100644
--- a/django/db/backends/mysql/compiler.py
+++ b/django/db/backends/mysql/compiler.py
@@ -78,3 +78,7 @@ class SQLUpdateCompiler(compiler.SQLUpdateCompiler, SQLCompiler):
 
 class SQLAggregateCompiler(compiler.SQLAggregateCompiler, SQLCompiler):
     pass
+
+
+class SQLCheckCompiler(compiler.SQLCheckCompiler, SQLCompiler):
+    pass
diff --git a/django/db/backends/oracle/compiler.py b/django/db/backends/oracle/compiler.py
new file mode 100644
index 0000000000..6fdf6d3163
--- /dev/null
+++ b/django/db/backends/oracle/compiler.py
@@ -0,0 +1,55 @@
+from django.db.models.sql import compiler
+
+
+class SQLCompiler(compiler.SQLCompiler):
+    pass
+
+
+class SQLInsertCompiler(compiler.SQLInsertCompiler, SQLCompiler):
+    pass
+
+
+class SQLDeleteCompiler(compiler.SQLDeleteCompiler, SQLCompiler):
+    pass
+
+
+class SQLUpdateCompiler(compiler.SQLUpdateCompiler, SQLCompiler):
+    pass
+
+
+class SQLAggregateCompiler(compiler.SQLAggregateCompiler, SQLCompiler):
+    pass
+
+
+class SQLCheckCompiler(compiler.SQLCheckCompiler, SQLCompiler):
+    # Oracle doesn't support boolean types yet PL/SQL does, meaning that although we
+    # can't compare boolean expressions to NULL in SELECT or WHERE clauses we can in
+    # a function which we can then call from a WHERE clause.
+    check_sql = """\
+WITH
+  FUNCTION f RETURN NUMBER IS
+    b BOOLEAN;
+  BEGIN
+    b := COALESCE(%s, TRUE);
+    IF b THEN
+        RETURN 1;
+    ELSE
+        RETURN 0;
+    END IF;
+  END f;
+SELECT 1 FROM dual WHERE f = 1
+"""
+
+    def as_sql(self):
+        # Avoid case wrapping.
+        self.connection.vendor = "sqlite"
+        condition, params = self.compile(self.query.where)
+        self.connection.vendor = "oracle"
+
+        # Oracle doesn't allow binding params within functions so bind manually
+        # with quote_value().
+        condition %= tuple(
+            self.connection.schema_editor().quote_value(param) for param in params
+        )
+        check_sql = self.check_sql % condition
+        return check_sql, []
diff --git a/django/db/backends/oracle/operations.py b/django/db/backends/oracle/operations.py
index 78f998183e..fad29a51aa 100644
--- a/django/db/backends/oracle/operations.py
+++ b/django/db/backends/oracle/operations.py
@@ -19,6 +19,8 @@ from .utils import BulkInsertMapper, InsertVar, Oracle_datetime
 
 
 class DatabaseOperations(BaseDatabaseOperations):
+    compiler_module = "django.db.backends.oracle.compiler"
+
     # Oracle uses NUMBER(5), NUMBER(11), and NUMBER(19) for integer fields.
     # SmallIntegerField uses NUMBER(11) instead of NUMBER(5), which is used by
     # SmallAutoField, to preserve backward compatibility.
diff --git a/django/db/models/query_utils.py b/django/db/models/query_utils.py
index 4a83fc380d..0cbc0be823 100644
--- a/django/db/models/query_utils.py
+++ b/django/db/models/query_utils.py
@@ -7,16 +7,13 @@ circular import difficulties.
 """
 import functools
 import inspect
-import logging
 from collections import namedtuple
 
 from django.core.exceptions import FieldError
-from django.db import DEFAULT_DB_ALIAS, DatabaseError, connections
+from django.db import DEFAULT_DB_ALIAS
 from django.db.models.constants import LOOKUP_SEP
 from django.utils import tree
 
-logger = logging.getLogger("django.db.models")
-
 # PathInfo is used when converting lookups (fk__somecol). The contents
 # describe the relation in Model terms (model Options and Fields for both
 # sides of the relation. The join_field is the field backing the relation.
@@ -114,29 +111,10 @@ class Q(tree.Node):
         Do a database query to check if the expressions of the Q instance
         matches against the expressions.
         """
-        # Avoid circular imports.
-        from django.db.models import BooleanField, Value
-        from django.db.models.functions import Coalesce
-        from django.db.models.sql import Query
-        from django.db.models.sql.constants import SINGLE
+        from django.db.models.sql import CheckQuery
 
-        query = Query(None)
-        for name, value in against.items():
-            if not hasattr(value, "resolve_expression"):
-                value = Value(value)
-            query.add_annotation(value, name, select=False)
-        query.add_annotation(Value(1), "_check")
-        # This will raise a FieldError if a field is missing in "against".
-        if connections[using].features.supports_comparing_boolean_expr:
-            query.add_q(Q(Coalesce(self, True, output_field=BooleanField())))
-        else:
-            query.add_q(self)
-        compiler = query.get_compiler(using=using)
-        try:
-            return compiler.execute_sql(SINGLE) is not None
-        except DatabaseError as e:
-            logger.warning("Got a database error calling check() on %r: %s", self, e)
-            return True
+        query = CheckQuery()
+        return query.do_check(self, against, using)
 
     def deconstruct(self):
         path = "%s.%s" % (self.__class__.__module__, self.__class__.__name__)
diff --git a/django/db/models/sql/compiler.py b/django/db/models/sql/compiler.py
index c7efa469a8..ca06e14091 100644
--- a/django/db/models/sql/compiler.py
+++ b/django/db/models/sql/compiler.py
@@ -2028,6 +2028,17 @@ class SQLAggregateCompiler(SQLCompiler):
         return sql, params
 
 
+class SQLCheckCompiler(SQLCompiler):
+    col_count = 1
+    check_sql = """\
+SELECT 1 WHERE COALESCE(%s, TRUE)
+"""
+
+    def as_sql(self):
+        condition, params = self.compile(self.query.where)
+        return self.check_sql % condition, params
+
+
 def cursor_iter(cursor, sentinel, col_count, itersize):
     """
     Yield blocks of rows from a cursor and ensure the cursor is closed when
diff --git a/django/db/models/sql/subqueries.py b/django/db/models/sql/subqueries.py
index d8a246d369..fa35bf0d40 100644
--- a/django/db/models/sql/subqueries.py
+++ b/django/db/models/sql/subqueries.py
@@ -2,11 +2,21 @@
 Query subclasses which provide extra functionality beyond simple data retrieval.
 """
 
+import logging
+
 from django.core.exceptions import FieldError
-from django.db.models.sql.constants import CURSOR, GET_ITERATOR_CHUNK_SIZE, NO_RESULTS
+from django.db import DatabaseError
+from django.db.models.sql.constants import (
+    CURSOR,
+    GET_ITERATOR_CHUNK_SIZE,
+    NO_RESULTS,
+    SINGLE,
+)
 from django.db.models.sql.query import Query
 
-__all__ = ["DeleteQuery", "UpdateQuery", "InsertQuery", "AggregateQuery"]
+__all__ = ["DeleteQuery", "UpdateQuery", "InsertQuery", "AggregateQuery", "CheckQuery"]
+
+logger = logging.getLogger("django.db.models")
 
 
 class DeleteQuery(Query):
@@ -169,3 +179,26 @@ class AggregateQuery(Query):
     def __init__(self, model, inner_query):
         self.inner_query = inner_query
         super().__init__(model)
+
+
+class CheckQuery(Query):
+    compiler = "SQLCheckCompiler"
+
+    def __init__(self):
+        super().__init__(model=None)
+
+    def do_check(self, q, against, using):
+        from django.db.models import Value
+
+        for name, value in against.items():
+            if not hasattr(value, "resolve_expression"):
+                value = Value(value)
+            self.add_annotation(value, name, select=False)
+        # This will raise a FieldError if a field is missing in "against".
+        self.add_q(q)
+        compiler = self.get_compiler(using=using)
+        try:
+            return compiler.execute_sql(SINGLE) is not None
+        except DatabaseError as e:
+            logger.warning("Got a database error calling check() on %r: %s", self, e)
+            return True
diff --git a/tests/constraints/tests.py b/tests/constraints/tests.py
index 5a498f0d73..c105073177 100644
--- a/tests/constraints/tests.py
+++ b/tests/constraints/tests.py
@@ -6,7 +6,7 @@ from django.db.models import F
 from django.db.models.constraints import BaseConstraint
 from django.db.models.functions import Lower
 from django.db.transaction import atomic
-from django.test import SimpleTestCase, TestCase, skipIfDBFeature, skipUnlessDBFeature
+from django.test import SimpleTestCase, TestCase, skipUnlessDBFeature
 
 from .models import (
     ChildModel,
@@ -234,7 +234,6 @@ class CheckConstraintTests(TestCase):
         constraint.validate(Product, Product(price=501, discounted_price=5))
         constraint.validate(Product, Product(price=499, discounted_price=5))
 
-    @skipUnlessDBFeature("supports_comparing_boolean_expr")
     def test_validate_nullable_field_with_none(self):
         # Nullable fields should be considered valid on None values.
         constraint = models.CheckConstraint(
@@ -243,14 +242,6 @@ class CheckConstraintTests(TestCase):
         )
         constraint.validate(Product, Product())
 
-    @skipIfDBFeature("supports_comparing_boolean_expr")
-    def test_validate_nullable_field_with_isnull(self):
-        constraint = models.CheckConstraint(
-            check=models.Q(price__gte=0) | models.Q(price__isnull=True),
-            name="positive_price",
-        )
-        constraint.validate(Product, Product())
-
 
 class UniqueConstraintTests(TestCase):
     @classmethod