diff --git a/arbitrary-value/src/arbitrary.rs b/arbitrary-value/src/arbitrary.rs
index 63bc962..e130b89 100644
--- a/arbitrary-value/src/arbitrary.rs
+++ b/arbitrary-value/src/arbitrary.rs
@@ -3,11 +3,13 @@ use chrono_tz::Tz;
 use ijson::{IArray, INumber, IObject, IString, IValue};
 #[cfg(feature = "pyo3")]
 use pyo3::{
-    exceptions::{PyTypeError, PyValueError},
+    exceptions::{PyException, PyTypeError, PyValueError},
     prelude::*,
     types::{PyList, PyNone},
 };
-use snafu::Snafu;
+use snafu::{ResultExt, Snafu};
+
+use crate::finite_f64::NotFinite;
 
 use super::{finite_f64::FiniteF64, map::Map, map_key::MapKey};
 
@@ -73,22 +75,64 @@ impl From<Arbitrary> for IValue {
 }
 
 #[cfg(feature = "pyo3")]
-impl<'py> FromPyObject<'py> for Arbitrary {
-    fn extract_bound(ob: &Bound<'py, PyAny>) -> PyResult<Self> {
+#[derive(Debug, Snafu)]
+pub enum ExtractArbitraryError {
+    /// error getting the qualified type name when trying to report
+    /// that an instance of this type cannot be extracted as an [`Arbitrary`]
+    GetTypeNameError { source: PyErr },
+
+    /// error extracting the (successfully retrieved) fully qualified type name as a [`String`]
+    ExtractTypeNameError { source: PyErr },
+
+    /// the float trying to be extracted is not finite, which isn't supported
+    FloatNotFinite { source: NotFinite },
+
+    /// can't extract an arbitrary from a {type_name}
+    UnsupportedType { type_name: String },
+}
+
+#[cfg(feature = "pyo3")]
+impl From<ExtractArbitraryError> for PyErr {
+    fn from(error: ExtractArbitraryError) -> Self {
+        match &error {
+            ExtractArbitraryError::GetTypeNameError { .. } => {
+                PyException::new_err(error.to_string())
+            }
+            ExtractArbitraryError::ExtractTypeNameError { .. } => {
+                PyException::new_err(error.to_string())
+            }
+            ExtractArbitraryError::FloatNotFinite { .. } => {
+                PyValueError::new_err(error.to_string())
+            }
+            ExtractArbitraryError::UnsupportedType { .. } => {
+                PyTypeError::new_err(error.to_string())
+            }
+        }
+    }
+}
+
+#[cfg(feature = "pyo3")]
+impl<'a, 'py> FromPyObject<'a, 'py> for Arbitrary {
+    type Error = ExtractArbitraryError;
+
+    fn extract(ob: Borrowed<'a, 'py, PyAny>) -> Result<Self, Self::Error> {
         if let Ok(map_key) = ob.extract::<MapKey>() {
             Ok(map_key.into())
         } else if let Ok(map) = ob.extract() {
             Ok(Self::Map(map))
         } else if let Ok(f) = ob.extract::<f64>() {
-            let f = FiniteF64::try_from(f).map_err(|err| PyValueError::new_err(err.to_string()))?;
+            let f = FiniteF64::try_from(f).context(FloatNotFiniteSnafu)?;
             Ok(Self::Float(f))
         } else if let Ok(vec) = ob.extract() {
             Ok(Self::Array(vec))
         } else {
-            let type_name = ob.get_type().fully_qualified_name()?;
-            Err(PyTypeError::new_err(format!(
-                "can't extract an arbitrary from a {type_name}"
-            )))
+            let type_name = ob
+                .get_type()
+                .fully_qualified_name()
+                .context(GetTypeNameSnafu)?
+                .extract()
+                .context(ExtractTypeNameSnafu)?;
+            Err(ExtractArbitraryError::UnsupportedType { type_name })
         }
     }
 }
diff --git a/arbitrary-value/src/map_key.rs b/arbitrary-value/src/map_key.rs
index 4f593f2..de6c42f 100644
--- a/arbitrary-value/src/map_key.rs
+++ b/arbitrary-value/src/map_key.rs
@@ -10,6 +10,7 @@ use pyo3::{
     prelude::*,
     types::{PyNone, PyTuple},
 };
+use snafu::{ResultExt, Snafu};
 
 use super::arbitrary::{Arbitrary, MapKeyFromArbitraryError};
 
@@ -43,9 +44,40 @@ impl Display for MapKey {
 }
 
 #[cfg(feature = "pyo3")]
-impl<'py> FromPyObject<'py> for MapKey {
-    fn extract_bound(ob: &Bound<'py, PyAny>) -> PyResult<Self> {
-        if let Ok(_none) = ob.downcast::<PyNone>() {
+#[derive(Debug, Snafu)]
+pub enum ExtractMapKeyError {
+    /// error getting the qualified type name when trying to report
+    /// that an instance of this type cannot be extracted as an [`Arbitrary`]
+    GetTypeNameError { source: PyErr },
+
+    /// error extracting the (successfully retrieved) fully qualified type name as a [`String`]
+    ExtractTypeNameError { source: PyErr },
+
+    /// can't extract a map key from a {type_name}
+    UnsupportedType { type_name: String },
+}
+
+#[cfg(feature = "pyo3")]
+impl From<ExtractMapKeyError> for PyErr {
+    fn from(error: ExtractMapKeyError) -> Self {
+        use pyo3::exceptions::PyException;
+
+        match &error {
+            ExtractMapKeyError::GetTypeNameError { .. } => PyException::new_err(error.to_string()),
+            ExtractMapKeyError::ExtractTypeNameError { .. } => {
+                PyException::new_err(error.to_string())
+            }
+            ExtractMapKeyError::UnsupportedType { .. } => PyTypeError::new_err(error.to_string()),
+        }
+    }
+}
+
+#[cfg(feature = "pyo3")]
+impl<'a, 'py> FromPyObject<'a, 'py> for MapKey {
+    type Error = ExtractMapKeyError;
+
+    fn extract(ob: Borrowed<'a, 'py, PyAny>) -> Result<Self, Self::Error> {
+        if let Ok(_none) = ob.cast::<PyNone>() {
             Ok(Self::Null)
         } else if let Ok(b) = ob.extract() {
             Ok(Self::Bool(b))
@@ -56,10 +88,13 @@ impl<'py> FromPyObject<'py> for MapKey {
         } else if let Ok(tuple) = ob.extract() {
             Ok(Self::Tuple(tuple))
         } else {
-            let type_name = ob.get_type().fully_qualified_name()?;
-            Err(PyTypeError::new_err(format!(
-                "can't extract a map key from a {type_name}"
-            )))
+            let type_name = ob
+                .get_type()
+                .fully_qualified_name()
+                .context(GetTypeNameSnafu)?
+                .extract()
+                .context(ExtractTypeNameSnafu)?;
+            Err(ExtractMapKeyError::UnsupportedType { type_name })
         }
     }
 }