diff --git a/src/EFCore.SqlServer/Query/Internal/SqlServerSqlNullabilityProcessor.cs b/src/EFCore.SqlServer/Query/Internal/SqlServerSqlNullabilityProcessor.cs
index d58168196aa..255c3f460a7 100644
--- a/src/EFCore.SqlServer/Query/Internal/SqlServerSqlNullabilityProcessor.cs
+++ b/src/EFCore.SqlServer/Query/Internal/SqlServerSqlNullabilityProcessor.cs
@@ -118,6 +118,7 @@ protected override SqlExpression RewriteNullSemantics(
         var result = base.RewriteNullSemantics(sqlBinaryExpression, left, right, leftNullable, rightNullable, optimize, out nullable);
 
         if (_useIs
+            && IsSupportedSubExpression(left, leftNullable) && IsSupportedSubExpression(right, rightNullable)
             && sqlBinaryExpression.OperatorType is ExpressionType.Equal or ExpressionType.NotEqual
             && result is SqlBinaryExpression { OperatorType: ExpressionType.AndAlso or ExpressionType.OrElse })
         {
@@ -131,6 +132,14 @@ protected override SqlExpression RewriteNullSemantics(
         }
 
         return result;
+
+        // The provider for SqlServer is unable to translate `bool?` expressions
+        // when they are on Boolean values instead of `BIT`s. See #34001
+        static bool IsSupportedSubExpression(SqlExpression sqlExpression, bool nullable) =>
+            !nullable
+            || sqlExpression.Type != typeof(bool)
+            || (sqlExpression is not SqlUnaryExpression { OperatorType: ExpressionType.Not } or
+                SqlBinaryExpression { OperatorType: ExpressionType.AndAlso or ExpressionType.OrElse });
     }
 
     /// <summary>