diff --git a/litellm-rust/Cargo.lock b/litellm-rust/Cargo.lock
index ea4f3d848c4..911cc571df9 100644
--- a/litellm-rust/Cargo.lock
+++ b/litellm-rust/Cargo.lock
@@ -2688,6 +2688,7 @@ dependencies = [
  "rstest",
  "serde",
  "serde_json",
+ "serde_with",
  "tokio",
  "tokio-tungstenite",
 ]
diff --git a/litellm-rust/crates/core-utils/src/serde_compat.rs b/litellm-rust/crates/core-utils/src/serde_compat.rs
index bb2648eb0be..c767c709f50 100644
--- a/litellm-rust/crates/core-utils/src/serde_compat.rs
+++ b/litellm-rust/crates/core-utils/src/serde_compat.rs
@@ -1,33 +1,91 @@
-use serde::{Deserialize, Deserializer, de::Error};
-use serde_json::Value;
+use serde::{
+    Deserializer,
+    de::{Error, Visitor},
+};
 use serde_with::DeserializeAs;
 
 pub struct LaxI64;
 pub struct FiniteF64;
 
+pub fn parse_str_bool(value: &str) -> Option<bool> {
+    let token = value.trim_matches(|character: char| {
+        character.is_whitespace() || matches!(character, '\u{1c}'..='\u{1f}')
+    });
+    if token.eq_ignore_ascii_case("true") {
+        return Some(true);
+    }
+    token.eq_ignore_ascii_case("false").then_some(false)
+}
+
 impl<'de> DeserializeAs<'de, i64> for LaxI64 {
     fn deserialize_as<D: Deserializer<'de>>(deserializer: D) -> Result<i64, D::Error> {
-        match Value::deserialize(deserializer)? {
-            Value::Number(number) if number.is_f64() => number.as_f64().and_then(integral_float),
-            Value::Number(number) => number.as_i64(),
-            Value::String(value) => integer_string(value.trim()),
-            Value::Bool(value) => Some(i64::from(value)),
-            _ => None,
-        }
-        .ok_or_else(|| D::Error::custom("expected an integer in the i64 range"))
+        deserializer.deserialize_any(Self)
+    }
+}
+
+impl<'de> Visitor<'de> for LaxI64 {
+    type Value = i64;
+
+    fn expecting(&self, formatter: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        formatter.write_str("an integer in the i64 range")
+    }
+
+    fn visit_i64<E: Error>(self, value: i64) -> Result<i64, E> {
+        Ok(value)
+    }
+
+    fn visit_u64<E: Error>(self, value: u64) -> Result<i64, E> {
+        i64::try_from(value).map_err(E::custom)
+    }
+
+    fn visit_f64<E: Error>(self, value: f64) -> Result<i64, E> {
+        integral_float(value).ok_or_else(|| E::custom("expected an integer in the i64 range"))
+    }
+
+    fn visit_str<E: Error>(self, value: &str) -> Result<i64, E> {
+        integer_string(value.trim())
+            .ok_or_else(|| E::custom("expected an integer in the i64 range"))
+    }
+
+    fn visit_bool<E: Error>(self, value: bool) -> Result<i64, E> {
+        Ok(i64::from(value))
     }
 }
 
 impl<'de> DeserializeAs<'de, f64> for FiniteF64 {
     fn deserialize_as<D: Deserializer<'de>>(deserializer: D) -> Result<f64, D::Error> {
-        match Value::deserialize(deserializer)? {
-            Value::Number(number) => number.as_f64(),
-            Value::String(value) => value.trim().parse::<f64>().ok(),
-            Value::Bool(value) => Some(f64::from(value)),
-            _ => None,
-        }
-        .filter(|value| value.is_finite())
-        .ok_or_else(|| D::Error::custom("expected a finite number"))
+        deserializer.deserialize_any(Self)
+    }
+}
+
+impl<'de> Visitor<'de> for FiniteF64 {
+    type Value = f64;
+
+    fn expecting(&self, formatter: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        formatter.write_str("a finite number")
+    }
+
+    fn visit_i64<E: Error>(self, value: i64) -> Result<f64, E> {
+        Ok(value as f64)
+    }
+
+    fn visit_u64<E: Error>(self, value: u64) -> Result<f64, E> {
+        Ok(value as f64)
+    }
+
+    fn visit_f64<E: Error>(self, value: f64) -> Result<f64, E> {
+        value
+            .is_finite()
+            .then_some(value)
+            .ok_or_else(|| E::custom("expected a finite number"))
+    }
+
+    fn visit_str<E: Error>(self, value: &str) -> Result<f64, E> {
+        self.visit_f64(value.trim().parse::<f64>().map_err(E::custom)?)
+    }
+
+    fn visit_bool<E: Error>(self, value: bool) -> Result<f64, E> {
+        Ok(f64::from(value))
     }
 }
 
@@ -66,7 +124,7 @@ fn integral_float(value: f64) -> Option<i64> {
 
 #[cfg(test)]
 mod tests {
-    use serde::Serialize;
+    use serde::{Deserialize, Serialize};
     use serde_json::json;
     use serde_with::serde_as;
 
@@ -81,6 +139,22 @@ mod tests {
         float: Option<f64>,
     }
 
+    #[test]
+    fn boolean_tokens_follow_python_string_trimming_without_redis_tokens() {
+        for (input, expected) in [
+            (" True ", Some(true)),
+            ("\u{1c}TRUE\u{1f}", Some(true)),
+            ("\u{a0}False\u{2003}", Some(false)),
+            ("true\u{200b}", None),
+            ("yes", None),
+            ("1", None),
+            ("", None),
+            ("unknown", None),
+        ] {
+            assert_eq!(parse_str_bool(input), expected, "{input:?}");
+        }
+    }
+
     #[test]
     fn adapters_compose_and_serialize_as_numbers() {
         let numbers: Numbers = serde_json::from_value(json!({
diff --git a/litellm-rust/crates/host-python/src/marshal.rs b/litellm-rust/crates/host-python/src/marshal.rs
index 881ad0e0389..8f284abf9dd 100644
--- a/litellm-rust/crates/host-python/src/marshal.rs
+++ b/litellm-rust/crates/host-python/src/marshal.rs
@@ -45,7 +45,7 @@ where
     fn into_pyobject(self, py: Python<'py>) -> PyResult<Self::Output> {
         catch_unwind(AssertUnwindSafe(|| pythonize::pythonize(py, &self.0)))
             .map_err(panic_to_pyerr)?
-            .map_err(|error| PyValueError::new_err(error.to_string()))
+            .map_err(PyErr::from)
     }
 }
 
@@ -87,6 +87,19 @@ mod tests {
         });
     }
 
+    #[test]
+    fn pythonized_preserves_python_serialization_error_types() {
+        crate::initialize_python();
+        Python::attach(|py| {
+            let value = std::collections::BTreeMap::from([(vec![1], "value")]);
+            let direct = to_py(py, &value).unwrap_err();
+            let wrapped = Pythonized(value).into_pyobject(py).unwrap_err();
+            assert!(direct.is_instance_of::<pyo3::exceptions::PyTypeError>(py));
+            assert!(wrapped.is_instance_of::<pyo3::exceptions::PyTypeError>(py));
+            assert_eq!(wrapped.to_string(), direct.to_string());
+        });
+    }
+
     #[test]
     fn pythonized_maps_serializer_panics_to_a_base_exception() {
         crate::initialize_python();
diff --git a/litellm-rust/crates/python-bridge/Cargo.toml b/litellm-rust/crates/python-bridge/Cargo.toml
index 1eb2ec28036..1bba83922f9 100644
--- a/litellm-rust/crates/python-bridge/Cargo.toml
+++ b/litellm-rust/crates/python-bridge/Cargo.toml
@@ -41,6 +41,8 @@ serde_json.workspace = true
 tokio = { workspace = true, features = ["sync"] }
 
 [dev-dependencies]
+serde.workspace = true
+serde_with.workspace = true
 criterion.workspace = true
 futures-util.workspace = true
 rstest.workspace = true
diff --git a/litellm-rust/crates/python-bridge/src/marshal.rs b/litellm-rust/crates/python-bridge/src/marshal.rs
index 2aba51cc4ff..fe5d551a931 100644
--- a/litellm-rust/crates/python-bridge/src/marshal.rs
+++ b/litellm-rust/crates/python-bridge/src/marshal.rs
@@ -172,6 +172,60 @@ mod tests {
         request_input_sources(&kwargs, names.iter().copied())
     }
 
+    #[serde_with::serde_as]
+    #[derive(Debug, serde::Deserialize, serde::Serialize, PartialEq)]
+    struct Numbers {
+        #[serde_as(deserialize_as = "Option<Vec<litellm_core_utils::serde_compat::LaxI64>>")]
+        integers: Option<Vec<i64>>,
+        #[serde_as(deserialize_as = "Option<litellm_core_utils::serde_compat::FiniteF64>")]
+        float: Option<f64>,
+    }
+
+    #[test]
+    fn numeric_adapters_agree_across_json_and_python_boundaries() {
+        Python::initialize();
+        Python::attach(|py| {
+            for input in [
+                json!({}),
+                json!({"integers": null, "float": null}),
+                json!({"integers": [i64::MIN, i64::MAX, "9007199254740993.0", " +1_000.00 ", true, 3.0], "float": " 1.25 "}),
+                json!({"integers": [u64::MAX]}),
+                json!({"integers": ["1.0000000000000001"]}),
+                json!({"integers": [2.5]}),
+                json!({"float": "NaN"}),
+                json!({"float": "inf"}),
+                json!({"float": "1e999"}),
+                json!({"float": true}),
+                json!({"float": u64::MAX}),
+            ] {
+                let expected = serde_json::from_value::<Numbers>(input.clone());
+                let python = litellm_host_python::to_py(py, &input).unwrap();
+                let actual = from_py::<Numbers>(python.bind(py));
+                match (expected, actual) {
+                    (Ok(expected), Ok(actual)) => {
+                        assert_eq!(actual, expected);
+                        let serialized = litellm_host_python::to_py(py, &actual).unwrap();
+                        assert_eq!(
+                            from_py::<Value>(serialized.bind(py)).unwrap(),
+                            serde_json::to_value(expected).unwrap()
+                        );
+                    }
+                    (Err(_), Err(_)) => {}
+                    mismatch => panic!("boundary mismatch for {input}: {mismatch:?}"),
+                }
+            }
+            for source in [
+                c"{'float': float('nan')}",
+                c"{'float': float('inf')}",
+                c"{'integers': [float('inf')]}",
+                c"{'integers': [2 ** 100]}",
+            ] {
+                let value = py.eval(source, None, None).unwrap();
+                assert!(from_py::<Numbers>(&value).is_err());
+            }
+        });
+    }
+
     #[test]
     fn argument_converters_keep_nested_values_and_accept_explicit_none() {
         Python::initialize();