diff --git a/src/AutoMapper/Mappers/CollectionMapper.cs b/src/AutoMapper/Mappers/CollectionMapper.cs
index 33b7bd4a65..b33434324b 100644
--- a/src/AutoMapper/Mappers/CollectionMapper.cs
+++ b/src/AutoMapper/Mappers/CollectionMapper.cs
@@ -141,7 +141,9 @@ void UseDestinationValue()
             Expression CheckContext()
             {
                 var elementTypeMap = configuration.ResolveTypeMap(sourceElementType, destinationElementType);
-                return elementTypeMap == null ? null : ExpressionBuilder.CheckContext(elementTypeMap);
+                var checkElement = elementTypeMap == null ? null : ExpressionBuilder.CheckContext(elementTypeMap);
+                // OverMaxDepth uses the containing type map, so honor its context requirements too
+                return checkElement ?? (memberMap?.TypeMap is { } containingTypeMap ? ExpressionBuilder.CheckContext(containingTypeMap) : null);
             }
         }
     }
diff --git a/src/UnitTests/Bug/CollectionMaxDepthContext.cs b/src/UnitTests/Bug/CollectionMaxDepthContext.cs
new file mode 100644
index 0000000000..de78da6eb2
--- /dev/null
+++ b/src/UnitTests/Bug/CollectionMaxDepthContext.cs
@@ -0,0 +1,44 @@
+namespace AutoMapper.UnitTests.Bug;
+
+public class CollectionMaxDepthContext
+{
+    public class Service { public string Description { get; set; } }
+    public class ServiceDto { public string Description { get; set; } }
+
+    // Self-referential, so CheckForCycles auto-enables PreserveReferences and MaxDepth
+    public class RecursiveLine { public RecursiveLine Parent { get; set; } public List<Service> Services { get; set; } }
+    public class RecursiveLineDto { public RecursiveLineDto Parent { get; set; } public IList<ServiceDto> Services { get; set; } }
+
+    // Plain type mapping the same List<Service> -> IList<ServiceDto> pair
+    public class PlainLine { public List<Service> Services { get; set; } }
+    public class PlainLineDto { public IList<ServiceDto> Services { get; set; } }
+
+    static IMapper CreateMapper() => new MapperConfiguration(cfg =>
+    {
+        cfg.CreateMap<Service, ServiceDto>();
+        cfg.CreateMap<RecursiveLine, RecursiveLineDto>().ForMember(d => d.Services, o => o.MapAtRuntime());
+        cfg.CreateMap<PlainLine, PlainLineDto>().ForMember(d => d.Services, o => o.MapAtRuntime());
+    }).CreateMapper();
+
+    static RecursiveLine NewRecursiveLine() => new() { Services = [new Service { Description = "recursive" }] };
+    static PlainLine NewPlainLine() => new() { Services = [new Service { Description = "plain" }] };
+
+    // The collection execution plan is cached per type pair, ignoring the member map it was built
+    // for. When the recursive line compiles it first, the plan carries a max depth check for the
+    // containing type map, which needs a non default context in every other caller too.
+    [Fact]
+    public void Should_map_the_plain_line_after_the_recursive_line()
+    {
+        var mapper = CreateMapper();
+        mapper.Map<RecursiveLineDto>(NewRecursiveLine()).Services.Count.ShouldBe(1);
+        mapper.Map<PlainLineDto>(NewPlainLine()).Services.Count.ShouldBe(1);
+    }
+
+    [Fact]
+    public void Should_map_the_recursive_line_after_the_plain_line()
+    {
+        var mapper = CreateMapper();
+        mapper.Map<PlainLineDto>(NewPlainLine()).Services.Count.ShouldBe(1);
+        mapper.Map<RecursiveLineDto>(NewRecursiveLine()).Services.Count.ShouldBe(1);
+    }
+}