3 files changed, 25 insertions, 10 deletions
diff --git a/lib/sqlalchemy/sql/compiler.py b/lib/sqlalchemy/sql/compiler.py
index 97397e9cf..9a00afc91 100644
--- a/lib/sqlalchemy/sql/compiler.py
+++ b/lib/sqlalchemy/sql/compiler.py
@@ -63,6 +63,7 @@ from . import roles
 from . import schema
 from . import selectable
 from . import sqltypes
+from . import util as sql_util
 from ._typing import is_column_element
 from ._typing import is_dml
 from .base import _from_objects
@@ -1530,7 +1531,8 @@ class SQLCompiler(Compiled):
                 replacement_expressions[
                     escaped_name
                 ] = self.render_literal_bindparam(
-                    parameter, render_literal_value=value
+                    parameter,
+                    render_literal_value=value,
                 )
                 continue
 
@@ -3154,10 +3156,22 @@ class SQLCompiler(Compiled):
 
         processor = type_._cached_literal_processor(self.dialect)
         if processor:
-            return processor(value)
+            try:
+                return processor(value)
+            except Exception as e:
+                raise exc.CompileError(
+                    f"Could not render literal value "
+                    f'"{sql_util._repr_single_value(value)}" '
+                    f"with datatype "
+                    f"{type_}; see parent stack trace for "
+                    "more detail."
+                ) from e
+
         else:
-            raise NotImplementedError(
-                "Don't know how to literal-quote value %r" % value
+            raise exc.CompileError(
+                f"No literal value renderer is available for literal value "
+                f'"{sql_util._repr_single_value(value)}" '
+                f"with datatype {type_}"
             )
 
     def _truncate_bindparam(self, bindparam):
diff --git a/lib/sqlalchemy/sql/sqltypes.py b/lib/sqlalchemy/sql/sqltypes.py
index 414ff03c3..b98a16b6f 100644
--- a/lib/sqlalchemy/sql/sqltypes.py
+++ b/lib/sqlalchemy/sql/sqltypes.py
@@ -3381,12 +3381,7 @@ class NullType(TypeEngine[None]):
     _isnull = True
 
     def literal_processor(self, dialect):
-        def process(value):
-            raise exc.CompileError(
-                "Don't know how to render literal SQL value: %r" % (value,)
-            )
-
-        return process
+        return None
 
     class Comparator(TypeEngine.Comparator[_T]):
         __slots__ = ()
diff --git a/lib/sqlalchemy/sql/util.py b/lib/sqlalchemy/sql/util.py
index 55c6a35f8..1f9944529 100644
--- a/lib/sqlalchemy/sql/util.py
+++ b/lib/sqlalchemy/sql/util.py
@@ -581,6 +581,12 @@ class _repr_base:
         return rep
 
 
+def _repr_single_value(value):
+    rp = _repr_base()
+    rp.max_chars = 300
+    return rp.trunc(value)
+
+
 class _repr_row(_repr_base):
     """Provide a string view of a row."""