4 files changed, 56 insertions, 6 deletions
diff --git a/test/dialect/postgresql/test_types.py b/test/dialect/postgresql/test_types.py
index 83cea8f15..39e7d7317 100644
--- a/test/dialect/postgresql/test_types.py
+++ b/test/dialect/postgresql/test_types.py
@@ -1528,8 +1528,9 @@ class ArrayTest(AssertsCompiledSQL, fixtures.TestBase):
                 return "MYTYPE"
 
         with expect_raises_message(
-            NotImplementedError,
-            r"Don't know how to literal-quote value \[1, 2, 3\]",
+            exc.CompileError,
+            r"No literal value renderer is available for literal "
+            r"value \"\[1, 2, 3\]\" with datatype ARRAY",
         ):
             self.assert_compile(
                 select(literal([1, 2, 3], ARRAY(MyType()))),
diff --git a/test/sql/test_compiler.py b/test/sql/test_compiler.py
index 97b1b9124..4eea11795 100644
--- a/test/sql/test_compiler.py
+++ b/test/sql/test_compiler.py
@@ -98,6 +98,7 @@ from sqlalchemy.testing import is_true
 from sqlalchemy.testing import mock
 from sqlalchemy.testing import ne_
 from sqlalchemy.testing.schema import pep435_enum
+from sqlalchemy.types import UserDefinedType
 
 table1 = table(
     "mytable",
@@ -4609,6 +4610,51 @@ class BindParameterTest(AssertsCompiledSQL, fixtures.TestBase):
             "OR mytable.myid = :myid_2 OR mytable.myid = :myid_3",
         )
 
+    @testing.combinations("plain", "expanding", argnames="exprtype")
+    def test_literal_bind_typeerror(self, exprtype):
+        """test #8800"""
+
+        if exprtype == "expanding":
+            stmt = select(table1).where(
+                table1.c.myid.in_([("tuple",), ("tuple",)])
+            )
+        elif exprtype == "plain":
+            stmt = select(table1).where(table1.c.myid == ("tuple",))
+        else:
+            assert False
+
+        with expect_raises_message(
+            exc.CompileError,
+            r"Could not render literal value \"\(\'tuple\',\)\" "
+            r"with datatype INTEGER; see parent "
+            r"stack trace for more detail.",
+        ):
+            stmt.compile(compile_kwargs={"literal_binds": True})
+
+    @testing.combinations("plain", "expanding", argnames="exprtype")
+    def test_literal_bind_dont_know_how_to_quote(self, exprtype):
+        """test #8800"""
+
+        class MyType(UserDefinedType):
+            def get_col_spec(self, **kw):
+                return "MYTYPE"
+
+        col = column("x", MyType())
+
+        if exprtype == "expanding":
+            stmt = select(table1).where(col.in_([("tuple",), ("tuple",)]))
+        elif exprtype == "plain":
+            stmt = select(table1).where(col == ("tuple",))
+        else:
+            assert False
+
+        with expect_raises_message(
+            exc.CompileError,
+            r"No literal value renderer is available for literal "
+            r"value \"\('tuple',\)\" with datatype MYTYPE",
+        ):
+            stmt.compile(compile_kwargs={"literal_binds": True})
+
     @testing.fixture
     def ansi_compiler_fixture(self):
         dialect = default.DefaultDialect()
diff --git a/test/sql/test_types.py b/test/sql/test_types.py
index a608d0040..3b1df3498 100644
--- a/test/sql/test_types.py
+++ b/test/sql/test_types.py
@@ -3125,8 +3125,9 @@ class ArrayTest(AssertsCompiledSQL, fixtures.TestBase):
                 return "MYTYPE"
 
         with expect_raises_message(
-            NotImplementedError,
-            r"Don't know how to literal-quote value \[1, 2, 3\]",
+            exc.CompileError,
+            r"No literal value renderer is available for literal value "
+            r"\"\[1, 2, 3\]\" with datatype ARRAY",
         ):
             self.assert_compile(
                 select(literal([1, 2, 3], ARRAY(MyType()))),
@@ -3629,7 +3630,8 @@ class CompileTest(fixtures.TestBase, AssertsCompiledSQL):
     def test_compile_err_formatting(self):
         with expect_raises_message(
             exc.CompileError,
-            r"Don't know how to render literal SQL value: \(1, 2, 3\)",
+            r"No literal value renderer is available for literal "
+            r"value \"\(1, 2, 3\)\" with datatype NULL",
         ):
             func.foo((1, 2, 3)).compile(compile_kwargs={"literal_binds": True})
 
diff --git a/test/sql/test_values.py b/test/sql/test_values.py
index d14de9aee..b943c4701 100644
--- a/test/sql/test_values.py
+++ b/test/sql/test_values.py
@@ -277,7 +277,8 @@ class ValuesTest(fixtures.TablesTest, AssertsCompiledSQL):
 
         with expect_raises_message(
             exc.CompileError,
-            "Don't know how to render literal SQL value: 'textA'",
+            r"No literal value renderer is available for literal "
+            r"value \"'textA'\" with datatype NULL",
         ):
             str(stmt)