diff --git a/src/wasm/headline.rs b/src/wasm/headline.rs
index bd803f4..4e01435 100644
--- a/src/wasm/headline.rs
+++ b/src/wasm/headline.rs
@@ -5,14 +5,39 @@ use super::ast_node::WasmAstNode;
 use super::macros::to_wasm;
 use super::to_wasm::ToWasm;
 use super::AdditionalProperties;
+use super::AdditionalPropertyValue;
 use crate::compare::ElispFact;
 use crate::types::Heading;
+use crate::types::HeadlineLevel;
+use crate::types::PriorityCookie;
+use crate::types::TodoKeywordType;
 use crate::wasm::to_wasm::ToWasmStandardProperties;
 
 #[derive(Debug, Serialize, Deserialize)]
 pub struct WasmHeadline {
     #[serde(flatten)]
     pub(crate) additional_properties: AdditionalProperties,
+    pub(crate) level: HeadlineLevel,
+    pub(crate) tags: Vec<String>,
+    #[serde(rename = "todo-keyword")]
+    pub(crate) todo_keyword: Option<String>,
+    #[serde(rename = "todo-type")]
+    pub(crate) todo_type: Option<String>,
+    pub(crate) title: Vec<WasmAstNode>,
+    pub(crate) priority: Option<PriorityCookie>,
+    #[serde(rename = "archivedp")]
+    pub(crate) is_archived: bool,
+    #[serde(rename = "commentedp")]
+    pub(crate) is_comment: bool,
+    #[serde(rename = "raw-value")]
+    pub(crate) raw_value: String,
+    #[serde(rename = "footnote-section-p")]
+    pub(crate) is_footnote_section: bool,
+    pub(crate) scheduled: Option<Box<WasmAstNode>>,
+    pub(crate) deadline: Option<Box<WasmAstNode>>,
+    pub(crate) closed: Option<Box<WasmAstNode>>,
+    #[serde(rename = "pre-blank")]
+    pub(crate) pre_blank: usize,
 }
 
 to_wasm!(
@@ -21,8 +46,18 @@ to_wasm!(
     original,
     wasm_context,
     { WasmAstNode::Headline(original) },
-    { "TODO".into() },
+    { "headline".into() },
     {
+        let mut additional_properties = AdditionalProperties::default();
+        for (name, val) in original.get_additional_properties().map(|node_property| {
+            (
+                node_property.property_name.to_uppercase(),
+                AdditionalPropertyValue::SingleString(node_property.value.unwrap_or("").to_owned()),
+            )
+        }) {
+            additional_properties.properties.insert(name, val);
+        }
+
         let children = original
             .children
             .iter()
@@ -36,7 +71,65 @@ to_wasm!(
         Ok((
             children,
             WasmHeadline {
-                additional_properties: AdditionalProperties::default(),
+                additional_properties,
+                level: original.level,
+                tags: original.tags.iter().map(|tag| (*tag).to_owned()).collect(),
+                todo_keyword: original
+                    .todo_keyword
+                    .as_ref()
+                    .map(|(_, keyword)| (*keyword).to_owned()),
+                todo_type: original
+                    .todo_keyword
+                    .as_ref()
+                    .map(|(keyword, _)| match keyword {
+                        TodoKeywordType::Done => "done".to_owned(),
+                        TodoKeywordType::Todo => "todo".to_owned(),
+                    }),
+                title: original
+                    .title
+                    .iter()
+                    .map(|child| {
+                        child
+                            .to_wasm(wasm_context.clone())
+                            .map(Into::<WasmAstNode>::into)
+                    })
+                    .collect::<Result<Vec<_>, _>>()?,
+                priority: original.priority_cookie,
+                is_archived: original.is_archived,
+                is_comment: original.is_comment,
+                raw_value: original.get_raw_value(),
+                is_footnote_section: original.is_footnote_section,
+                scheduled: original
+                    .scheduled
+                    .as_ref()
+                    .map(|child| {
+                        child
+                            .to_wasm(wasm_context.clone())
+                            .map(Into::<WasmAstNode>::into)
+                    })
+                    .map_or(Ok(None), |r| r.map(Some))?
+                    .map(|child| Box::new(child)),
+                deadline: original
+                    .deadline
+                    .as_ref()
+                    .map(|child| {
+                        child
+                            .to_wasm(wasm_context.clone())
+                            .map(Into::<WasmAstNode>::into)
+                    })
+                    .map_or(Ok(None), |r| r.map(Some))?
+                    .map(|child| Box::new(child)),
+                closed: original
+                    .closed
+                    .as_ref()
+                    .map(|child| {
+                        child
+                            .to_wasm(wasm_context.clone())
+                            .map(Into::<WasmAstNode>::into)
+                    })
+                    .map_or(Ok(None), |r| r.map(Some))?
+                    .map(|child| Box::new(child)),
+                pre_blank: 0,
             },
         ))
     }
diff --git a/src/wasm_test/compare.rs b/src/wasm_test/compare.rs
index 20de4eb..8917f2a 100644
--- a/src/wasm_test/compare.rs
+++ b/src/wasm_test/compare.rs
@@ -58,11 +58,36 @@ fn compare_json_value<'b, 's>(
             compare_plain_text(source, e, w)
         }
         (serde_json::Value::Null, Token::Atom("nil")) => Ok(WasmDiffResult::default()),
+        (serde_json::Value::Bool(false), Token::Atom("nil")) => Ok(WasmDiffResult::default()),
+        (serde_json::Value::Bool(true), Token::Atom(e)) if (*e) != "nil" => {
+            Ok(WasmDiffResult::default())
+        }
+        (serde_json::Value::Bool(w), Token::Atom(e)) => {
+            let mut result = WasmDiffResult::default();
+            result.status.push(WasmDiffStatus::Bad(
+                format!(
+                    "Value mismatch. Emacs=({emacs:?}) Wasm=({wasm:?}).",
+                    emacs = e,
+                    wasm = w,
+                )
+                .into(),
+            ));
+            Ok(result)
+        }
+        (serde_json::Value::Number(w), Token::Atom(e)) if w.to_string().as_str() == (*e) => {
+            Ok(WasmDiffResult::default())
+        }
+        (serde_json::Value::Array(w), Token::Atom("nil")) if w.is_empty() => {
+            Ok(WasmDiffResult::default())
+        }
+        (serde_json::Value::String(w), Token::Atom(e)) if w.as_str() == *e => {
+            Ok(WasmDiffResult::default())
+        }
         (serde_json::Value::Null, Token::Atom(_)) => todo!(),
         (serde_json::Value::Null, Token::List(_)) => todo!(),
         (serde_json::Value::Null, Token::TextWithProperties(_)) => todo!(),
         (serde_json::Value::Null, Token::Vector(_)) => todo!(),
-        (serde_json::Value::Bool(_), Token::Atom(_)) => todo!(),
+        // (serde_json::Value::Bool(_), Token::Atom(_)) => todo!(),
         (serde_json::Value::Bool(_), Token::List(_)) => todo!(),
         (serde_json::Value::Bool(_), Token::TextWithProperties(_)) => todo!(),
         (serde_json::Value::Bool(_), Token::Vector(_)) => todo!(),
@@ -70,7 +95,19 @@ fn compare_json_value<'b, 's>(
         (serde_json::Value::Number(_), Token::List(_)) => todo!(),
         (serde_json::Value::Number(_), Token::TextWithProperties(_)) => todo!(),
         (serde_json::Value::Number(_), Token::Vector(_)) => todo!(),
-        (serde_json::Value::String(_), Token::Atom(_)) => todo!(),
+        // (serde_json::Value::String(_), Token::Atom(_)) => todo!(),
+        (serde_json::Value::String(w), Token::Atom(e)) => {
+            let mut result = WasmDiffResult::default();
+            result.status.push(WasmDiffStatus::Bad(
+                format!(
+                    "Value mismatch. Emacs=({emacs:?}) Wasm=({wasm:?}).",
+                    emacs = e,
+                    wasm = w,
+                )
+                .into(),
+            ));
+            Ok(result)
+        }
         (serde_json::Value::String(_), Token::List(_)) => todo!(),
         (serde_json::Value::String(_), Token::TextWithProperties(_)) => todo!(),
         (serde_json::Value::String(_), Token::Vector(_)) => todo!(),
@@ -85,6 +122,31 @@ fn compare_json_value<'b, 's>(
     }
 }
 
+fn compare_optional_json_value<'b, 's>(
+    source: &'s str,
+    emacs: Option<&'b Token<'s>>,
+    wasm: Option<&serde_json::Value>,
+) -> Result<WasmDiffResult<'s>, Box<dyn std::error::Error>> {
+    match (emacs, wasm) {
+        (None, None) | (None, Some(serde_json::Value::Null)) | (Some(Token::Atom("nil")), None) => {
+            Ok(WasmDiffResult::default())
+        }
+        (Some(e), Some(w)) => compare_json_value(source, e, w),
+        _ => Ok(WasmDiffResult {
+            status: vec![WasmDiffStatus::Bad(
+                format!(
+                    "Nullness mismatch. Emacs=({emacs:?}) Wasm=({wasm:?}).",
+                    emacs = emacs,
+                    wasm = wasm
+                )
+                .into(),
+            )],
+            children: Vec::new(),
+            name: "".into(),
+        }),
+    }
+}
+
 fn compare_ast_node<'e, 's, 'w>(
     source: &'s str,
     emacs: &'e Vec<Token<'s>>,
@@ -137,12 +199,21 @@ fn compare_ast_node<'e, 's, 'w>(
             .keys()
             .map(|s| (*s).to_owned())
             .collect();
+        // wasm_attributes_map.iter().filter_map(|(k,v)| if matches!(v, serde_json::Value::Null) {None} else {Some(k)}).map(wasm_key_to_emacs_key)
         let wasm_keys: std::collections::BTreeSet<String> =
             std::iter::once(":standard-properties".to_owned())
                 .chain(wasm_attributes_map.keys().map(wasm_key_to_emacs_key))
                 .collect();
         let emacs_only_attributes: Vec<&String> = emacs_keys.difference(&wasm_keys).collect();
-        let wasm_only_attributes: Vec<&String> = wasm_keys.difference(&emacs_keys).collect();
+        let wasm_only_attributes: Vec<&String> = wasm_keys
+            .difference(&emacs_keys)
+            .filter(|attribute| {
+                emacs_attributes_map
+                    .get(attribute.as_str())
+                    .map(|token| !matches!(token, Token::Atom("nil")))
+                    .unwrap_or(false)
+            })
+            .collect();
         if !emacs_only_attributes.is_empty() {
             result.status.push(WasmDiffStatus::Bad(
                 format!(
@@ -180,14 +251,10 @@ fn compare_ast_node<'e, 's, 'w>(
         for attribute_name in wasm_attributes_map.keys() {
             let mut layer = WasmDiffResult::default();
             layer.name = Cow::Owned(attribute_name.clone());
-            let wasm_attribute_value = wasm_attributes_map
-                .get(attribute_name)
-                .ok_or("Key should exist in both wasm and elisp at this point.")?;
+            let wasm_attribute_value = wasm_attributes_map.get(attribute_name);
             let emacs_key = wasm_key_to_emacs_key(attribute_name);
-            let emacs_attribute_value = *emacs_attributes_map
-                .get(emacs_key.as_str())
-                .ok_or("Key should exist in both wasm and elisp at this point.")?;
-            layer.extend(compare_json_value(
+            let emacs_attribute_value = emacs_attributes_map.get(emacs_key.as_str()).map(|e| *e);
+            layer.extend(compare_optional_json_value(
                 source,
                 emacs_attribute_value,
                 wasm_attribute_value,