diff --git a/src/serde/mod.rs b/src/serde/mod.rs
index 09470389..c7b131b2 100644
--- a/src/serde/mod.rs
+++ b/src/serde/mod.rs
@@ -474,4 +474,119 @@ mod tests {
         assert_eq!(&from_ion::<IpAddr, _>(s).unwrap(), &ip);
         assert_eq!(&from_ion::<IpAddr, _>(binary).unwrap(), &ip);
     }
+
+    /// Regression tests for annotations being correctly written for all value types
+    /// when serialized through newtype variants (which produce annotations in Ion).
+    mod newtype_variant_annotations {
+        use super::*;
+        use std::collections::BTreeMap;
+
+        #[derive(Serialize, Deserialize, PartialEq, Debug)]
+        enum Wrapper {
+            Tag(bool),
+            Num(f32),
+            Big(f64),
+            Items(Vec<u32>),
+            Dict(BTreeMap<String, u32>),
+            Record { x: i32, y: i32 },
+            Price(Decimal),
+            When(Timestamp),
+        }
+
+        #[test]
+        fn newtype_variant_bool() {
+            let val = Wrapper::Tag(true);
+            let ion = to_string(&val).unwrap();
+            assert_eq!(Element::read_first("Tag::true"), Element::read_first(&ion));
+            let roundtrip: Wrapper = from_ion(&ion).unwrap();
+            assert_eq!(val, roundtrip);
+        }
+
+        #[test]
+        fn newtype_variant_f32() {
+            let val = Wrapper::Num(2.5f32);
+            let ion = to_string(&val).unwrap();
+            assert_eq!(Element::read_first("Num::2.5e0"), Element::read_first(&ion));
+            let roundtrip: Wrapper = from_ion(&ion).unwrap();
+            assert_eq!(val, roundtrip);
+        }
+
+        #[test]
+        fn newtype_variant_f64() {
+            let val = Wrapper::Big(1.234f64);
+            let ion = to_string(&val).unwrap();
+            assert_eq!(
+                Element::read_first("Big::1.234e0"),
+                Element::read_first(&ion)
+            );
+            let roundtrip: Wrapper = from_ion(&ion).unwrap();
+            assert_eq!(val, roundtrip);
+        }
+
+        #[test]
+        fn newtype_variant_seq() {
+            let val = Wrapper::Items(vec![1, 2, 3]);
+            let ion = to_string(&val).unwrap();
+            assert_eq!(
+                Element::read_first("Items::[1, 2, 3]"),
+                Element::read_first(&ion)
+            );
+            let roundtrip: Wrapper = from_ion(&ion).unwrap();
+            assert_eq!(val, roundtrip);
+        }
+
+        #[test]
+        fn newtype_variant_map() {
+            let mut map = BTreeMap::new();
+            map.insert("a".to_string(), 1u32);
+            let val = Wrapper::Dict(map);
+            let ion = to_string(&val).unwrap();
+            assert_eq!(
+                Element::read_first("Dict::{a: 1}"),
+                Element::read_first(&ion)
+            );
+            let roundtrip: Wrapper = from_ion(&ion).unwrap();
+            assert_eq!(val, roundtrip);
+        }
+
+        #[test]
+        fn newtype_variant_struct() {
+            let val = Wrapper::Record { x: 10, y: 20 };
+            let ion = to_string(&val).unwrap();
+            assert_eq!(
+                Element::read_first("Record::{x: 10, y: 20}"),
+                Element::read_first(&ion)
+            );
+            let roundtrip: Wrapper = from_ion(&ion).unwrap();
+            assert_eq!(val, roundtrip);
+        }
+
+        #[test]
+        fn newtype_variant_decimal() {
+            let val = Wrapper::Price(Decimal::new(199, -2));
+            let ion = to_string(&val).unwrap();
+            assert_eq!(
+                Element::read_first("Price::1.99"),
+                Element::read_first(&ion)
+            );
+            let roundtrip: Wrapper = from_ion(&ion).unwrap();
+            assert_eq!(val, roundtrip);
+        }
+
+        #[test]
+        fn newtype_variant_timestamp() {
+            let ts = Timestamp::with_ymd(2024, 6, 15)
+                .with_hms(12, 0, 0)
+                .build()
+                .unwrap();
+            let val = Wrapper::When(ts.clone());
+            let ion = to_string(&val).unwrap();
+            assert_eq!(
+                Element::read_first("When::2024-06-15T12:00:00-00:00"),
+                Element::read_first(&ion)
+            );
+            let roundtrip: Wrapper = from_ion(&ion).unwrap();
+            assert_eq!(val, roundtrip);
+        }
+    }
 }
diff --git a/src/serde/ser.rs b/src/serde/ser.rs
index eafe8375..dd43894f 100644
--- a/src/serde/ser.rs
+++ b/src/serde/ser.rs
@@ -87,12 +87,12 @@ impl<'a, V: ValueWriter + 'a> ser::Serializer for ValueSerializer<'a, V> {
     type Ok = ();
     type Error = IonError;
 
-    type SerializeSeq = SeqWriter<V>;
+    type SerializeSeq = SeqWriter<V::AnnotatedValueWriter<'a>>;
     type SerializeTuple = SeqWriter<V::AnnotatedValueWriter<'a>>;
     type SerializeTupleStruct = SeqWriter<V::AnnotatedValueWriter<'a>>;
     type SerializeTupleVariant = SeqWriter<V::AnnotatedValueWriter<'a>>;
-    type SerializeMap = MapWriter<V>;
-    type SerializeStruct = MapWriter<V>;
+    type SerializeMap = MapWriter<V::AnnotatedValueWriter<'a>>;
+    type SerializeStruct = MapWriter<V::AnnotatedValueWriter<'a>>;
     type SerializeStructVariant = MapWriter<V::AnnotatedValueWriter<'a>>;
 
     /// Determine whether Serialize implementations should serialize in human-readable form.
@@ -103,7 +103,9 @@ impl<'a, V: ValueWriter + 'a> ser::Serializer for ValueSerializer<'a, V> {
 
     /// Serialize a boolean to a bool value
     fn serialize_bool(self, v: bool) -> Result<Self::Ok, Self::Error> {
-        self.value_writer.write(v)
+        self.value_writer
+            .with_annotations(self.annotations)?
+            .write(v)
     }
 
     /// Serialize all integer types using the `Integer` intermediary type.
@@ -163,7 +165,9 @@ impl<'a, V: ValueWriter + 'a> ser::Serializer for ValueSerializer<'a, V> {
     }
 
     fn serialize_f32(self, v: f32) -> Result<Self::Ok, Self::Error> {
-        self.value_writer.write(v)
+        self.value_writer
+            .with_annotations(self.annotations)?
+            .write(v)
     }
 
     fn serialize_f64(self, v: f64) -> Result<Self::Ok, Self::Error> {
@@ -253,7 +257,9 @@ impl<'a, V: ValueWriter + 'a> ser::Serializer for ValueSerializer<'a, V> {
             // The assert statement above that compares the sizes of the Decimal and value types
             assert_eq!(std::mem::size_of_val(value), std::mem::size_of::<Decimal>());
             let decimal = unsafe { std::mem::transmute_copy::<&T, &Decimal>(&value) };
-            self.value_writer.write_decimal(decimal)
+            self.value_writer
+                .with_annotations(self.annotations)?
+                .write_decimal(decimal)
         } else {
             value.serialize(self)
         }
@@ -275,7 +281,10 @@ impl<'a, V: ValueWriter + 'a> ser::Serializer for ValueSerializer<'a, V> {
 
     fn serialize_seq(self, _len: Option<usize>) -> Result<Self::SerializeSeq, Self::Error> {
         Ok(SeqWriter {
-            seq_writer: self.value_writer.list_writer()?,
+            seq_writer: self
+                .value_writer
+                .with_annotations(self.annotations)?
+                .list_writer()?,
             is_human_readable: self.is_human_readable,
         })
     }
@@ -328,7 +337,10 @@ impl<'a, V: ValueWriter + 'a> ser::Serializer for ValueSerializer<'a, V> {
 
     fn serialize_map(self, _len: Option<usize>) -> Result<Self::SerializeMap, Self::Error> {
         Ok(MapWriter {
-            map_writer: self.value_writer.struct_writer()?,
+            map_writer: self
+                .value_writer
+                .with_annotations(self.annotations)?
+                .struct_writer()?,
             is_human_readable: self.is_human_readable,
         })
     }
@@ -339,7 +351,10 @@ impl<'a, V: ValueWriter + 'a> ser::Serializer for ValueSerializer<'a, V> {
         _len: usize,
     ) -> Result<Self::SerializeStruct, Self::Error> {
         Ok(MapWriter {
-            map_writer: self.value_writer.struct_writer()?,
+            map_writer: self
+                .value_writer
+                .with_annotations(self.annotations)?
+                .struct_writer()?,
             is_human_readable: self.is_human_readable,
         })
     }