diff --git a/engine/baml-lib/jsonish/src/deserializer/coercer/coerce_primitive.rs b/engine/baml-lib/jsonish/src/deserializer/coercer/coerce_primitive.rs
index a520221cb..0041652c2 100644
--- a/engine/baml-lib/jsonish/src/deserializer/coercer/coerce_primitive.rs
+++ b/engine/baml-lib/jsonish/src/deserializer/coercer/coerce_primitive.rs
@@ -236,8 +236,11 @@ pub(super) fn coerce_bool(
                         target,
                         Some(value),
                         &[
-                            ("true", vec!["true".into()]),
-                            ("false", vec!["false".into()]),
+                            ("true", vec!["true".into(), "True".into(), "TRUE".into()]),
+                            (
+                                "false",
+                                vec!["false".into(), "False".into(), "FALSE".into()],
+                            ),
                         ],
                     ) {
                         Ok(val) => match val.value().as_str() {
diff --git a/engine/baml-lib/jsonish/src/deserializer/coercer/match_string.rs b/engine/baml-lib/jsonish/src/deserializer/coercer/match_string.rs
index 44274ede0..a5475642d 100644
--- a/engine/baml-lib/jsonish/src/deserializer/coercer/match_string.rs
+++ b/engine/baml-lib/jsonish/src/deserializer/coercer/match_string.rs
@@ -18,6 +18,7 @@ use crate::{
 
 use super::ParsingContext;
 
+/// Heuristic match of different possible values against an input string.
 pub(super) fn match_string(
     parsing_context: &ParsingContext,
     target: &FieldType,
@@ -35,6 +36,7 @@ pub(super) fn match_string(
 
     let mut flags = DeserializerConditions::new();
 
+    // Grab context.
     let jsonish_string = match value {
         jsonish::Value::String(s) => s.clone(),
         jsonish::Value::AnyOf(_, s) => {
@@ -47,8 +49,10 @@ pub(super) fn match_string(
         }
     };
 
+    // Trim whitespaces.
     let match_context = jsonish_string.trim();
 
+    // First attempt, case sensitive match ignoring possible pucntuation.
     if let Some(string_match) = string_match_strategy(&match_context, &candidates, &mut flags) {
         return try_match_only_once(parsing_context, target, string_match, flags);
     }
@@ -56,16 +60,31 @@ pub(super) fn match_string(
     // Strip punctuation and try again.
     let match_context = strip_punctuation(match_context);
 
-    let candidates = candidates
-        .iter()
-        .map(|(candidate, valid_values)| {
-            (
-                *candidate,
-                valid_values.iter().map(|v| strip_punctuation(v)).collect(),
-            )
-        })
-        .collect::<Vec<_>>();
+    // TODO: If the candidates don't contain any punctuation themselves there's
+    // no point in removing the punctuation from the input string and running
+    // the entire algorithm again because it should've already matched the
+    // substrings in the previous attempt. This can be optimized.
+    let mut candidates = Vec::from_iter(candidates.iter().map(|(candidate, valid_values)| {
+        let stripped_valid_values = valid_values.iter().map(|v| strip_punctuation(v)).collect();
+        (*candidate, stripped_valid_values)
+    }));
+
+    // Second attempt, case sensitive match without punctuation.
+    if let Some(string_match) = string_match_strategy(&match_context, &candidates, &mut flags) {
+        return try_match_only_once(parsing_context, target, string_match, flags);
+    }
 
+    // Last hope, case insensitive match without punctuation. This could yield
+    // wrong results since the name of a candidate could appear as a "normal"
+    // word used by the LLM to explain the output.
+    let match_context = match_context.to_lowercase();
+
+    // TODO: Consider adding a flag for case insensitive match.
+    candidates.iter_mut().for_each(|(_, valid_values)| {
+        valid_values.iter_mut().for_each(|v| *v = v.to_lowercase());
+    });
+
+    // There goes our last hope :)
     if let Some(string_match) = string_match_strategy(&match_context, &candidates, &mut flags) {
         return try_match_only_once(parsing_context, target, string_match, flags);
     }
@@ -79,6 +98,9 @@ fn strip_punctuation(s: &str) -> String {
         .collect::<String>()
 }
 
+/// Helper function to return a single string match result.
+///
+/// Multiple results will yield an error.
 fn try_match_only_once(
     parsing_context: &ParsingContext<'_>,
     target: &FieldType,
@@ -100,6 +122,13 @@ fn try_match_only_once(
     Ok((string_match.to_string(), flags).into())
 }
 
+/// Heuristic string match algorithm.
+///
+/// The algorithm is case sensitive so for case insensitive matches it must
+/// recieve lowercase strings. This algorithm will first try to look for exact
+/// matches in the input string, if it doesn't find any it will look for
+/// substring matches and return the one with the most matches. Whether that is
+/// an ambigous match or not is up to the caller to decide.
 fn string_match_strategy<'c>(
     value_str: &str,
     candidates: &'c [(&'c str, Vec<String>)],
@@ -107,30 +136,20 @@ fn string_match_strategy<'c>(
 ) -> Option<&'c str> {
     // Try and look for an exact match against valid values.
     for (candidate, valid_values) in candidates {
-        // Consider adding a flag for case insensitive match.
-        if valid_values
-            .iter()
-            .any(|v| v.eq_ignore_ascii_case(value_str))
-        {
+        if valid_values.iter().any(|v| v == value_str) {
             // We did nothing fancy, so no extra flags.
             return Some(candidate);
         }
     }
 
-    // We'll match evetything using lower case and then return the original
-    // variants.
-    let case_insensitive_str = value_str.to_lowercase();
-
     // Now find all the candidates which occur in the value, by frequency.
     let mut result = Vec::from_iter(candidates.iter().filter_map(|(variant, valid_names)| {
         // Check how many counts of the variant are in the value.
         let match_count_pos = valid_names
             .iter()
             .filter_map(|valid_name| {
-                // Convert to lower.
-                let case_insensitive_name = valid_name.to_lowercase();
-                // Match against full lower case input.
-                let matches = case_insensitive_str.match_indices(&case_insensitive_name);
+                // Match ocurrences of valid name.
+                let matches = value_str.match_indices(valid_name);
                 // Return (count, first_idx)
                 matches.fold(None, |acc, (idx, _)| match acc {
                     Some((count, prev_idx)) => Some((count + 1, prev_idx)),
diff --git a/engine/baml-lib/jsonish/src/tests/test_enum.rs b/engine/baml-lib/jsonish/src/tests/test_enum.rs
index ab124ea97..6e97cffa4 100644
--- a/engine/baml-lib/jsonish/src/tests/test_enum.rs
+++ b/engine/baml-lib/jsonish/src/tests/test_enum.rs
@@ -96,6 +96,21 @@ test_deserializer!(
     "ONE"
 );
 
+test_deserializer!(
+    case_sensitive_non_ambiguous_match,
+    ENUM_FILE,
+    r#"TWO" is one of the correct answers."#,
+    FieldType::Enum("Category".to_string()),
+    "TWO"
+);
+
+test_failing_deserializer!(
+    case_insensitive_ambiguous_match,
+    ENUM_FILE,
+    r#"Two" is one of the correct answers."#,
+    FieldType::Enum("Category".to_string())
+);
+
 test_failing_deserializer!(
     from_string_with_extra_text_after_3,
     ENUM_FILE,