diff --git a/src/NHibernate.Test.VisualBasic/Issues/GH3716/Entity.vb b/src/NHibernate.Test.VisualBasic/Issues/GH3716/Entity.vb
new file mode 100644
index 00000000000..4fcdb0841e5
--- /dev/null
+++ b/src/NHibernate.Test.VisualBasic/Issues/GH3716/Entity.vb
@@ -0,0 +1,7 @@
+Namespace Issues.GH3716
+    Public Class Entity
+        Public Overridable Property Id As Guid
+
+        Public Overridable Property Date1 As Date?
+    End Class
+End Namespace
diff --git a/src/NHibernate.Test.VisualBasic/Issues/GH3716/Fixture.vb b/src/NHibernate.Test.VisualBasic/Issues/GH3716/Fixture.vb
new file mode 100644
index 00000000000..cff78cfc770
--- /dev/null
+++ b/src/NHibernate.Test.VisualBasic/Issues/GH3716/Fixture.vb
@@ -0,0 +1,58 @@
+Imports NHibernate.Linq
+Imports NUnit.Framework
+
+Namespace Issues.GH3716
+    <TestFixture>
+    Public Class Fixture
+        Inherits IssueTestCase
+
+        Protected Overrides Sub OnSetUp()
+
+            Using session As ISession = OpenSession()
+
+                Using transaction As ITransaction = session.BeginTransaction()
+
+                    Dim e1 = New Entity
+                    e1.Date1 = New Date(2017, 12, 3)
+                    session.Save(e1)
+
+                    Dim e2 = New Entity
+                    e2.Date1 = New Date(2017, 12, 1)
+                    session.Save(e2)
+
+                    Dim e3 = New Entity
+                    session.Save(e3)
+
+                    session.Flush()
+                    transaction.Commit()
+
+                End Using
+
+            End Using
+        End Sub
+
+        Protected Overrides Sub OnTearDown()
+
+            Using session As ISession = OpenSession()
+
+                Using transaction As ITransaction = session.BeginTransaction()
+
+                    session.Delete("from System.Object")
+
+                    session.Flush()
+                    transaction.Commit()
+
+                End Using
+
+            End Using
+        End Sub
+
+        <Test>
+        Public Sub ShouldBeAbleToUpdateWithAnonymousType()
+
+            Using session As ISession = OpenSession()
+                session.Query(Of Entity).Update(Function(x) New With {.Date1 = Date.Today})
+            End Using
+        End Sub
+    End Class
+End Namespace
diff --git a/src/NHibernate.Test.VisualBasic/Issues/GH3716/Issues.GH3716.Mappings.hbm.xml b/src/NHibernate.Test.VisualBasic/Issues/GH3716/Issues.GH3716.Mappings.hbm.xml
new file mode 100644
index 00000000000..5ce0f339870
--- /dev/null
+++ b/src/NHibernate.Test.VisualBasic/Issues/GH3716/Issues.GH3716.Mappings.hbm.xml
@@ -0,0 +1,11 @@
+<?xml version="1.0" encoding="utf-8" ?>
+<hibernate-mapping xmlns="urn:nhibernate-mapping-2.2" assembly="NHibernate.Test.VisualBasic" namespace="NHibernate.Test.VisualBasic.Issues.GH3716">
+
+	<class name="Entity">
+		<id name="Id">
+			<generator class="guid.comb"/>
+		</id>
+		<property name="Date1" />
+	</class>
+
+</hibernate-mapping>
diff --git a/src/NHibernate.Test.VisualBasic/NHibernate.Test.VisualBasic.vbproj b/src/NHibernate.Test.VisualBasic/NHibernate.Test.VisualBasic.vbproj
index 5ea684f06b2..ff258df5705 100644
--- a/src/NHibernate.Test.VisualBasic/NHibernate.Test.VisualBasic.vbproj
+++ b/src/NHibernate.Test.VisualBasic/NHibernate.Test.VisualBasic.vbproj
@@ -26,7 +26,6 @@
   </ItemGroup>
   <ItemGroup>
     <PackageReference Include="Microsoft.NET.Test.Sdk" Version="17.0.0" />
-    <PackageReference Include="Microsoft.VisualBasic" Version="10.3.0" />
     <PackageReference Include="NUnit" Version="3.14.0" />
     <PackageReference Include="NUnit3TestAdapter" Version="4.6.0" />
   </ItemGroup>
diff --git a/src/NHibernate/Linq/DmlExpressionRewriter.cs b/src/NHibernate/Linq/DmlExpressionRewriter.cs
index 782318a64a7..57415affbc4 100644
--- a/src/NHibernate/Linq/DmlExpressionRewriter.cs
+++ b/src/NHibernate/Linq/DmlExpressionRewriter.cs
@@ -25,10 +25,10 @@ void AddSettersFromBindings(IEnumerable<MemberBinding> bindings, string path)
 				switch (node.BindingType)
 				{
 					case MemberBindingType.Assignment:
-						AddSettersFromAssignment((MemberAssignment)node, subPath);
+						AddSettersFromAssignment((MemberAssignment) node, subPath);
 						break;
 					case MemberBindingType.MemberBinding:
-						AddSettersFromBindings(((MemberMemberBinding)node).Bindings, subPath);
+						AddSettersFromBindings(((MemberMemberBinding) node).Bindings, subPath);
 						break;
 					default:
 						throw new InvalidOperationException($"{node.BindingType} is not supported");
@@ -53,10 +53,10 @@ void AddSettersFromAnonymousConstructor(NewExpression newExpression, string path
 				switch (argument.NodeType)
 				{
 					case ExpressionType.New:
-						AddSettersFromAnonymousConstructor((NewExpression)argument, subPath);
+						AddSettersFromAnonymousConstructor((NewExpression) argument, subPath);
 						break;
 					case ExpressionType.MemberInit:
-						AddSettersFromBindings(((MemberInitExpression)argument).Bindings, subPath);
+						AddSettersFromBindings(((MemberInitExpression) argument).Bindings, subPath);
 						break;
 					default:
 						_assignments.Add(subPath.Substring(1), Expression.Lambda(argument, _parameters));
@@ -121,8 +121,8 @@ public static Expression PrepareExpressionFromAnonymous<TSource>(Expression sour
 			if (expression == null)
 				throw new ArgumentNullException(nameof(expression));
 
-			// Anonymous initializations are not implemented as member initialization but as plain constructor call.
-			var newExpression = expression.Body as NewExpression ??
+			// Anonymous initializations are not implemented as member initialization but as plain constructor call, potentially wrapped in a Convert expression
+			var newExpression = UnwrapConvertExpression(expression.Body) as NewExpression ??
 				throw new ArgumentException("The expression must be an anonymous initialization, e.g. x => new { Name = x.Name, Age = x.Age + 5 }");
 
 			var instance = new DmlExpressionRewriter(expression.Parameters);
@@ -130,6 +130,16 @@ public static Expression PrepareExpressionFromAnonymous<TSource>(Expression sour
 			return PrepareExpression<TSource>(sourceExpression, instance._assignments);
 		}
 
+		private static Expression UnwrapConvertExpression(Expression expression)
+		{
+			if (expression is UnaryExpression ue && ue.NodeType == ExpressionType.Convert)
+			{
+				return ue.Operand;
+			}
+
+			return expression;
+		}
+
 		public static Expression PrepareExpression<TSource>(Expression sourceExpression, IReadOnlyDictionary<string, Expression> assignments)
 		{
 			var lambda = ConvertAssignmentsToBlockExpression<TSource>(assignments);