diff --git a/src/MongoDB.Bson/Serialization/Serializers/DictionarySerializerBase.cs b/src/MongoDB.Bson/Serialization/Serializers/DictionarySerializerBase.cs
index 5910571aa82..614e2c20f78 100644
--- a/src/MongoDB.Bson/Serialization/Serializers/DictionarySerializerBase.cs
+++ b/src/MongoDB.Bson/Serialization/Serializers/DictionarySerializerBase.cs
@@ -499,6 +499,12 @@ obj is DictionarySerializerBase<TDictionary, TKey, TValue> other &&
         /// <inheritdoc/>
         public bool TryGetItemSerializationInfo(out BsonSerializationInfo serializationInfo)
         {
+            if (_dictionaryRepresentation == DictionaryRepresentation.Document && !IsNumericType(typeof(TKey)))
+            {
+                serializationInfo = null;
+                return false;
+            }
+
             var representation = _dictionaryRepresentation == DictionaryRepresentation.ArrayOfArrays
                 ? BsonType.Array
                 : BsonType.Document;
@@ -510,6 +516,14 @@ public bool TryGetItemSerializationInfo(out BsonSerializationInfo serializationI
             return true;
         }
 
+        private static bool IsNumericType(Type type)
+        {
+            return type == typeof(int) || type == typeof(long) ||
+                   type == typeof(short) || type == typeof(byte) ||
+                   type == typeof(uint) || type == typeof(ulong) ||
+                   type == typeof(ushort) || type == typeof(sbyte);
+        }
+
         /// <inheritdoc/>
         public bool TryGetMemberSerializationInfo(string memberName, out BsonSerializationInfo serializationInfo)
         {
diff --git a/src/MongoDB.Driver/Linq/Linq3Implementation/SerializerFinders/SerializerFinderHelperMethods.cs b/src/MongoDB.Driver/Linq/Linq3Implementation/SerializerFinders/SerializerFinderHelperMethods.cs
index 7ca8e8e5449..06f0374bf77 100644
--- a/src/MongoDB.Driver/Linq/Linq3Implementation/SerializerFinders/SerializerFinderHelperMethods.cs
+++ b/src/MongoDB.Driver/Linq/Linq3Implementation/SerializerFinders/SerializerFinderHelperMethods.cs
@@ -17,7 +17,9 @@
 using System.Collections.Generic;
 using System.Linq;
 using System.Linq.Expressions;
+using MongoDB.Bson;
 using MongoDB.Bson.Serialization;
+using MongoDB.Bson.Serialization.Options;
 using MongoDB.Bson.Serialization.Serializers;
 using MongoDB.Driver.Linq.Linq3Implementation.Misc;
 using MongoDB.Driver.Linq.Linq3Implementation.Serializers;
@@ -81,7 +83,21 @@ IBsonSerializer CreateCollectionSerializerFromCollectionSerializer(Type collecti
             return UnknowableSerializer.Create(collectionType);
         }
 
-        var itemSerializer = collectionSerializer.GetItemSerializer();
+        IBsonSerializer itemSerializer;
+        if (collectionSerializer is IBsonDictionarySerializer dictionarySerializer &&
+            collectionSerializer is IBsonArraySerializer arraySerializer &&
+            !arraySerializer.TryGetItemSerializationInfo(out _))
+        {
+            var representation = dictionarySerializer.DictionaryRepresentation == DictionaryRepresentation.ArrayOfArrays
+                ? BsonType.Array
+                : BsonType.Document;
+            itemSerializer = KeyValuePairSerializer.Create(representation, dictionarySerializer.KeySerializer, dictionarySerializer.ValueSerializer);
+        }
+        else
+        {
+            itemSerializer = collectionSerializer.GetItemSerializer();
+        }
+
         return CreateCollectionSerializerFromItemSerializer(collectionType, itemSerializer);
     }
 
@@ -235,11 +251,22 @@ private void DeduceUnknowableSerializer(Expression node)
     private bool IsItemSerializerKnown(Expression node, out IBsonSerializer itemSerializer)
     {
         if (IsKnown(node, out var nodeSerializer) &&
-            nodeSerializer is IBsonArraySerializer arraySerializer &&
-            arraySerializer.TryGetItemSerializationInfo(out var itemSerializationInfo))
+            nodeSerializer is IBsonArraySerializer arraySerializer)
         {
-            itemSerializer = itemSerializationInfo.Serializer;
-            return true;
+            if (arraySerializer.TryGetItemSerializationInfo(out var itemSerializationInfo))
+            {
+                itemSerializer = itemSerializationInfo.Serializer;
+                return true;
+            }
+
+            if (nodeSerializer is IBsonDictionarySerializer dictionarySerializer)
+            {
+                var representation = dictionarySerializer.DictionaryRepresentation == DictionaryRepresentation.ArrayOfArrays
+                    ? BsonType.Array
+                    : BsonType.Document;
+                itemSerializer = KeyValuePairSerializer.Create(representation, dictionarySerializer.KeySerializer, dictionarySerializer.ValueSerializer);
+                return true;
+            }
         }
 
         itemSerializer = null;
diff --git a/tests/MongoDB.Driver.Tests/UpdateDefinitionBuilderTests.cs b/tests/MongoDB.Driver.Tests/UpdateDefinitionBuilderTests.cs
index f19d684d00b..403e313b575 100644
--- a/tests/MongoDB.Driver.Tests/UpdateDefinitionBuilderTests.cs
+++ b/tests/MongoDB.Driver.Tests/UpdateDefinitionBuilderTests.cs
@@ -20,6 +20,7 @@
 using MongoDB.Bson;
 using MongoDB.Bson.Serialization;
 using MongoDB.Bson.Serialization.Attributes;
+using MongoDB.Bson.Serialization.Options;
 using MongoDB.Bson.TestHelpers;
 using MongoDB.Driver.Linq;
 using MongoDB.TestHelpers.XunitExtensions;
@@ -66,6 +67,102 @@ public void AddToSetEach_Typed()
             Assert(subject.AddToSetEach("FavoriteColors", new[] { "green", "violet" }), "{$addToSet: {colors: {$each: ['green', 'violet']}}}");
         }
 
+        [Fact]
+        public void AddToSet_with_string_path_through_dictionary_to_list_value()
+        {
+            var subject = CreateSubject<DocumentWithDictionaryOfLists>();
+
+            Assert(subject.AddToSet("Buckets.myKey", "newValue"), "{$addToSet: {'buckets.myKey': 'newValue'}}");
+        }
+
+        [Fact]
+        public void AddToSet_with_expression_path_through_dictionary_to_list_value()
+        {
+            var subject = CreateSubject<DocumentWithDictionaryOfLists>();
+
+            Assert(subject.AddToSet(x => x.Buckets["myKey"], "newValue"), "{$addToSet: {'buckets.myKey': 'newValue'}}");
+        }
+
+        [Fact]
+        public void AddToSetEach_with_string_path_through_dictionary_to_list_value()
+        {
+            var subject = CreateSubject<DocumentWithDictionaryOfLists>();
+
+            Assert(subject.AddToSetEach("Buckets.myKey", new[] { "a", "b" }), "{$addToSet: {'buckets.myKey': {$each: ['a', 'b']}}}");
+        }
+
+        [Fact]
+        public void AddToSetEach_with_expression_path_through_dictionary_to_list_value()
+        {
+            var subject = CreateSubject<DocumentWithDictionaryOfLists>();
+
+            Assert(subject.AddToSetEach(x => x.Buckets["myKey"], new[] { "a", "b" }), "{$addToSet: {'buckets.myKey': {$each: ['a', 'b']}}}");
+        }
+
+        [Fact]
+        public void AddToSet_with_string_path_through_dictionary_to_nested_list()
+        {
+            var subject = CreateSubject<DocumentWithDictionaryOfObjects>();
+
+            Assert(subject.AddToSet("Buckets.myKey.Items", "newValue"), "{$addToSet: {'buckets.myKey.items': 'newValue'}}");
+        }
+
+        [Fact]
+        public void AddToSet_with_expression_path_through_dictionary_to_nested_list()
+        {
+            var subject = CreateSubject<DocumentWithDictionaryOfObjects>();
+
+            Assert(subject.AddToSet(x => x.Buckets["myKey"].Items, "newValue"), "{$addToSet: {'buckets.myKey.items': 'newValue'}}");
+        }
+
+        [Fact]
+        public void AddToSet_with_string_path_through_dictionary_to_hashset_value()
+        {
+            var subject = CreateSubject<DocumentWithDictionaryOfHashSets>();
+
+            Assert(subject.AddToSet("Buckets.myKey", "newValue"), "{$addToSet: {'buckets.myKey': 'newValue'}}");
+        }
+
+        [Fact]
+        public void AddToSet_with_expression_path_through_dictionary_to_hashset_value()
+        {
+            var subject = CreateSubject<DocumentWithDictionaryOfHashSets>();
+
+            Assert(subject.AddToSet(x => x.Buckets["myKey"], "newValue"), "{$addToSet: {'buckets.myKey': 'newValue'}}");
+        }
+
+        [Fact]
+        public void AddToSet_with_string_path_through_array_rep_dictionary()
+        {
+            var subject = CreateSubject<DocumentWithArrayRepDictionary>();
+
+            Assert(subject.AddToSet("Buckets.myKey", "newValue"), "{$addToSet: {'buckets.myKey': 'newValue'}}");
+        }
+
+        [Fact]
+        public void AddToSet_with_string_path_through_dictionary_where_value_is_IEnumerable_interface()
+        {
+            var subject = CreateSubject<DocumentWithDictionaryOfIEnumerable>();
+
+            Assert(subject.AddToSet("Buckets.myKey", "newValue"), "{$addToSet: {'buckets.myKey': 'newValue'}}");
+        }
+
+        [Fact]
+        public void AddToSet_with_numeric_string_key_through_dictionary()
+        {
+            var subject = CreateSubject<DataContainer>();
+
+            Assert(subject.AddToSet("Buckets.10", new DataRecord { Label = "test" }), "{$addToSet: {'buckets.10': { CreatedAt: ISODate('0001-01-01T00:00:00Z'), Label: 'test' }}}");
+        }
+
+        [Fact]
+        public void AddToSet_with_numeric_string_key_through_dictionary_of_List()
+        {
+            var subject = CreateSubject<DocumentWithDictionaryOfLists>();
+
+            Assert(subject.AddToSet("Buckets.10", "newValue"), "{$addToSet: {'buckets.10': 'newValue'}}");
+        }
+
         [Fact]
         public void BitwiseAnd()
         {
@@ -742,5 +839,70 @@ public class F
         {
             public string Z { get; set; }
         }
+
+        private class DocumentWithDictionaryOfLists
+        {
+            public ObjectId Id { get; set; }
+
+            [BsonElement("buckets")]
+            public Dictionary<string, List<string>> Buckets { get; set; }
+        }
+
+        private class DocumentWithDictionaryOfObjects
+        {
+            public ObjectId Id { get; set; }
+
+            [BsonElement("buckets")]
+            public Dictionary<string, Bucket> Buckets { get; set; }
+        }
+
+        private class DocumentWithDictionaryOfHashSets
+        {
+            public ObjectId Id { get; set; }
+
+            [BsonElement("buckets")]
+            public Dictionary<string, HashSet<string>> Buckets { get; set; }
+        }
+
+        private class DocumentWithArrayRepDictionary
+        {
+            public ObjectId Id { get; set; }
+
+            [BsonElement("buckets")]
+            [BsonDictionaryOptions(DictionaryRepresentation.ArrayOfDocuments)]
+            public Dictionary<string, List<string>> Buckets { get; set; }
+        }
+
+        private class DocumentWithDictionaryOfIEnumerable
+        {
+            public ObjectId Id { get; set; }
+
+            [BsonElement("buckets")]
+            public Dictionary<string, IEnumerable<string>> Buckets { get; set; }
+        }
+
+        [BsonIgnoreExtraElements]
+        private class DataContainer
+        {
+            public string Id { get; set; }
+
+            [BsonElement("buckets")]
+            [BsonDictionaryOptions(DictionaryRepresentation.Document)]
+            public IDictionary<string, IEnumerable<DataRecord>> Buckets { get; set; }
+                = new Dictionary<string, IEnumerable<DataRecord>>();
+        }
+
+        [BsonIgnoreExtraElements]
+        private class DataRecord
+        {
+            public DateTime CreatedAt { get; set; }
+            public string Label { get; set; }
+        }
+
+        private class Bucket
+        {
+            [BsonElement("items")]
+            public List<string> Items { get; set; }
+        }
     }
 }