diff --git a/src/MongoDB.Driver/Linq/Linq3Implementation/Translators/ExpressionToAggregationExpressionTranslators/ConvertExpressionToAggregationExpressionTranslator.cs b/src/MongoDB.Driver/Linq/Linq3Implementation/Translators/ExpressionToAggregationExpressionTranslators/ConvertExpressionToAggregationExpressionTranslator.cs
index 532e10c1609..3805b03aac4 100644
--- a/src/MongoDB.Driver/Linq/Linq3Implementation/Translators/ExpressionToAggregationExpressionTranslators/ConvertExpressionToAggregationExpressionTranslator.cs
+++ b/src/MongoDB.Driver/Linq/Linq3Implementation/Translators/ExpressionToAggregationExpressionTranslators/ConvertExpressionToAggregationExpressionTranslator.cs
@@ -28,7 +28,7 @@ internal static class ConvertExpressionToAggregationExpressionTranslator
     {
         public static TranslatedExpression Translate(TranslationContext context, UnaryExpression expression)
         {
-            if (expression.NodeType == ExpressionType.Convert || expression.NodeType == ExpressionType.TypeAs)
+            if (expression.NodeType == ExpressionType.Convert || expression.NodeType == ExpressionType.ConvertChecked || expression.NodeType == ExpressionType.TypeAs)
             {
                 var sourceExpression = expression.Operand;
                 var sourceType = sourceExpression.Type;
diff --git a/src/MongoDB.Driver/Linq/Linq3Implementation/Translators/ExpressionToAggregationExpressionTranslators/ExpressionToAggregationExpressionTranslator.cs b/src/MongoDB.Driver/Linq/Linq3Implementation/Translators/ExpressionToAggregationExpressionTranslators/ExpressionToAggregationExpressionTranslator.cs
index 9f019682a63..bec53b12e1f 100644
--- a/src/MongoDB.Driver/Linq/Linq3Implementation/Translators/ExpressionToAggregationExpressionTranslators/ExpressionToAggregationExpressionTranslator.cs
+++ b/src/MongoDB.Driver/Linq/Linq3Implementation/Translators/ExpressionToAggregationExpressionTranslators/ExpressionToAggregationExpressionTranslator.cs
@@ -40,6 +40,7 @@ public static TranslatedExpression TranslateWithoutUnwrapping(TranslationContext
             switch (expression.NodeType)
             {
                 case ExpressionType.Convert:
+                case ExpressionType.ConvertChecked:
                 case ExpressionType.TypeAs:
                     return ConvertExpressionToAggregationExpressionTranslator.Translate(context, (UnaryExpression)expression);
 
diff --git a/tests/MongoDB.Driver.Tests/Linq/Linq3Implementation/Jira/CSharp5606Tests.cs b/tests/MongoDB.Driver.Tests/Linq/Linq3Implementation/Jira/CSharp5606Tests.cs
new file mode 100644
index 00000000000..0d737ffc2df
--- /dev/null
+++ b/tests/MongoDB.Driver.Tests/Linq/Linq3Implementation/Jira/CSharp5606Tests.cs
@@ -0,0 +1,133 @@
+/* Copyright 2010-present MongoDB Inc.
+*
+* Licensed under the Apache License, Version 2.0 (the "License");
+* you may not use this file except in compliance with the License.
+* You may obtain a copy of the License at
+*
+* http://www.apache.org/licenses/LICENSE-2.0
+*
+* Unless required by applicable law or agreed to in writing, software
+* distributed under the License is distributed on an "AS IS" BASIS,
+* WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+* See the License for the specific language governing permissions and
+* limitations under the License.
+*/
+
+using System;
+using System.Collections.Generic;
+using System.Linq;
+using System.Linq.Expressions;
+using MongoDB.Driver.TestHelpers;
+using FluentAssertions;
+using MongoDB.TestHelpers.XunitExtensions;
+using Xunit;
+
+namespace MongoDB.Driver.Tests.Linq.Linq3Implementation.Jira;
+
+public class CSharp5606Tests : LinqIntegrationTest<CSharp5606Tests.ClassFixture>
+{
+    public CSharp5606Tests(ClassFixture fixture)
+        : base(fixture)
+    {
+    }
+
+    [Theory]
+    [ParameterAttributeData]
+    public void Aggregage_Group_with_checked_or_unchecked_int_to_long_conversion_should_work(
+            [Values(false, true)] bool @checked)
+    {
+        var collection = Fixture.Collection;
+
+        Expression<Func<IGrouping<string, C>, MyResult>> groupLambdaExpression;
+        if (@checked)
+        {
+            checked // default compiler setting is not checked
+            {
+                groupLambdaExpression = x => new MyResult { Name = x.Key, Count = x.Count() };
+            }
+        }
+        else
+        {
+            groupLambdaExpression = x => new MyResult { Name = x.Key, Count = x.Count() };
+        }
+
+        var aggregate = collection.Aggregate()
+            .Group(
+                x => x.MyField,
+                groupLambdaExpression);
+
+        var stages = Translate(collection, aggregate);
+        AssertStages(
+            stages,
+            "{ $group : { _id : '$MyField', __agg0 : { $sum : 1 } } }",
+            "{ $project : { Name : '$_id', Count : { $toLong : '$__agg0' }, _id : 0 } }");
+
+        var results = aggregate.ToList().OrderBy(x => x.Name).ToList();
+        results.Count.Should().Be(2);
+        results[0].Name.Should().Be("a");
+        results[0].Count.Should().Be(1L);
+        results[1].Name.Should().Be("b");
+        results[1].Count.Should().Be(2L);
+    }
+
+    [Theory]
+    [ParameterAttributeData]
+    public void Select_GroupBy_with_checked_or_unchecked_int_to_long_conversion_should_work(
+        [Values(false, true)] bool @checked)
+    {
+        var collection = Fixture.Collection;
+
+        Expression<Func<string, IEnumerable<C>, MyResult>> resultSelectorLambdaExpression;
+        if (@checked)
+        {
+            checked // default compiler setting is not checked
+            {
+                resultSelectorLambdaExpression = (key, grouping) => new MyResult { Name = key, Count = grouping.Count() };
+            }
+        }
+        else
+        {
+            resultSelectorLambdaExpression = (key, grouping) => new MyResult { Name = key, Count = grouping.Count() };
+        }
+
+        var queryable = collection.AsQueryable()
+            .GroupBy(
+                x => x.MyField,
+                resultSelectorLambdaExpression);
+
+        var stages = Translate(collection, queryable);
+        AssertStages(
+            stages,
+            "{ $group : { _id : '$MyField', __agg0 : { $sum : 1 } } }",
+            "{ $project : { Name : '$_id', Count : { $toLong : '$__agg0' }, _id : 0 } }");
+
+        var results = queryable.ToList().OrderBy(x => x.Name).ToList();
+        results.Count.Should().Be(2);
+        results[0].Name.Should().Be("a");
+        results[0].Count.Should().Be(1L);
+        results[1].Name.Should().Be("b");
+        results[1].Count.Should().Be(2L);
+    }
+
+    public class C
+    {
+        public int Id { get; set; }
+        public string MyField { get; set; }
+    }
+
+    public class MyResult
+    {
+        public string Name { get; set; }
+        public long Count { get; set; }
+    }
+
+    public sealed class ClassFixture : MongoCollectionFixture<C>
+    {
+        protected override IEnumerable<C> InitialData =>
+        [
+            new C { Id = 1, MyField = "a" },
+            new C { Id = 2, MyField = "b" },
+            new C { Id = 3, MyField = "b" },
+        ];
+    }
+}