diff --git a/zebra-chain/src/amount.rs b/zebra-chain/src/amount.rs
index 0be893bb..28e830f9 100644
--- a/zebra-chain/src/amount.rs
+++ b/zebra-chain/src/amount.rs
@@ -79,7 +79,10 @@ where
     type Output = Result<Amount<C>>;
 
     fn add(self, rhs: Amount<C>) -> Self::Output {
-        let value = self.0 + rhs.0;
+        let value = self
+            .0
+            .checked_add(rhs.0)
+            .expect("adding two constrained Amounts is always within an i64");
         value.try_into()
     }
 }
@@ -125,7 +128,10 @@ where
     type Output = Result<Amount<C>>;
 
     fn sub(self, rhs: Amount<C>) -> Self::Output {
-        let value = self.0 - rhs.0;
+        let value = self
+            .0
+            .checked_sub(rhs.0)
+            .expect("subtracting two constrained Amounts is always within an i64");
         value.try_into()
     }
 }
@@ -172,7 +178,7 @@ impl<C> From<Amount<C>> for i64 {
 
 impl From<Amount<NonNegative>> for u64 {
     fn from(amount: Amount<NonNegative>) -> Self {
-        amount.0 as _
+        amount.0.try_into().expect("non-negative i64 fits in u64")
     }
 }
 
@@ -180,9 +186,14 @@ impl<C> From<Amount<C>> for jubjub::Fr {
     fn from(a: Amount<C>) -> jubjub::Fr {
         // TODO: this isn't constant time -- does that matter?
         if a.0 < 0 {
-            jubjub::Fr::from(a.0.abs() as u64).neg()
+            let abs_amount = i128::from(a.0)
+                .checked_abs()
+                .expect("absolute i64 fits in i128");
+            let abs_amount = u64::try_from(abs_amount).expect("absolute i64 fits in u64");
+
+            jubjub::Fr::from(abs_amount).neg()
         } else {
-            jubjub::Fr::from(a.0 as u64)
+            jubjub::Fr::from(u64::try_from(a.0).expect("non-negative i64 fits in u64"))
         }
     }
 }
@@ -191,13 +202,31 @@ impl<C> From<Amount<C>> for halo2::pasta::pallas::Scalar {
     fn from(a: Amount<C>) -> halo2::pasta::pallas::Scalar {
         // TODO: this isn't constant time -- does that matter?
         if a.0 < 0 {
-            halo2::pasta::pallas::Scalar::from(a.0.abs() as u64).neg()
+            let abs_amount = i128::from(a.0)
+                .checked_abs()
+                .expect("absolute i64 fits in i128");
+            let abs_amount = u64::try_from(abs_amount).expect("absolute i64 fits in u64");
+
+            halo2::pasta::pallas::Scalar::from(abs_amount).neg()
         } else {
-            halo2::pasta::pallas::Scalar::from(a.0 as u64)
+            halo2::pasta::pallas::Scalar::from(
+                u64::try_from(a.0).expect("non-negative i64 fits in u64"),
+            )
         }
     }
 }
 
+impl<C> TryFrom<i32> for Amount<C>
+where
+    C: Constraint,
+{
+    type Error = Error;
+
+    fn try_from(value: i32) -> Result<Self, Self::Error> {
+        C::validate(value.into()).map(|v| Self(v, PhantomData))
+    }
+}
+
 impl<C> TryFrom<i64> for Amount<C>
 where
     C: Constraint,
@@ -209,17 +238,6 @@ where
     }
 }
 
-impl<C> TryFrom<i32> for Amount<C>
-where
-    C: Constraint,
-{
-    type Error = Error;
-
-    fn try_from(value: i32) -> Result<Self, Self::Error> {
-        C::validate(value as _).map(|v| Self(v, PhantomData))
-    }
-}
-
 impl<C> TryFrom<u64> for Amount<C>
 where
     C: Constraint,
@@ -227,6 +245,25 @@ where
     type Error = Error;
 
     fn try_from(value: u64) -> Result<Self, Self::Error> {
+        let value = value.try_into().map_err(|source| Error::Convert {
+            value: value.into(),
+            source,
+        })?;
+
+        C::validate(value).map(|v| Self(v, PhantomData))
+    }
+}
+
+/// Conversion from `i128` to `Amount`.
+///
+/// Used to handle the result of multiplying negative `Amount`s by `u64`.
+impl<C> TryFrom<i128> for Amount<C>
+where
+    C: Constraint,
+{
+    type Error = Error;
+
+    fn try_from(value: i128) -> Result<Self, Self::Error> {
         let value = value
             .try_into()
             .map_err(|source| Error::Convert { value, source })?;
@@ -260,8 +297,7 @@ impl<C> PartialEq<Amount<C>> for i64 {
     }
 }
 
-impl Eq for Amount<NegativeAllowed> {}
-impl Eq for Amount<NonNegative> {}
+impl<C> Eq for Amount<C> {}
 
 impl<C1, C2> PartialOrd<Amount<C2>> for Amount<C1> {
     fn partial_cmp(&self, other: &Amount<C2>) -> Option<Ordering> {
@@ -269,47 +305,54 @@ impl<C1, C2> PartialOrd<Amount<C2>> for Amount<C1> {
     }
 }
 
-impl Ord for Amount<NegativeAllowed> {
-    fn cmp(&self, other: &Amount<NegativeAllowed>) -> Ordering {
+impl<C> Ord for Amount<C> {
+    fn cmp(&self, other: &Amount<C>) -> Ordering {
         self.0.cmp(&other.0)
     }
 }
 
-impl Ord for Amount<NonNegative> {
-    fn cmp(&self, other: &Amount<NonNegative>) -> Ordering {
-        self.0.cmp(&other.0)
-    }
-}
-
-impl std::ops::Mul<u64> for Amount<NonNegative> {
-    type Output = Result<Amount<NonNegative>>;
+impl<C> std::ops::Mul<u64> for Amount<C>
+where
+    C: Constraint,
+{
+    type Output = Result<Amount<C>>;
 
     fn mul(self, rhs: u64) -> Self::Output {
-        let value = (self.0 as u64)
-            .checked_mul(rhs)
-            .ok_or(Error::MultiplicationOverflow {
-                amount: self.0,
-                multiplier: rhs,
-            })?;
-        value.try_into()
+        // use i128 for multiplication, so we can handle negative Amounts
+        let value = i128::from(self.0)
+            .checked_mul(i128::from(rhs))
+            .expect("multiplying i64 by u64 can't overflow i128");
+
+        value.try_into().map_err(|_| Error::MultiplicationOverflow {
+            amount: self.0,
+            multiplier: rhs,
+            overflowing_result: value,
+        })
     }
 }
 
-impl std::ops::Mul<Amount<NonNegative>> for u64 {
-    type Output = Result<Amount<NonNegative>>;
+impl<C> std::ops::Mul<Amount<C>> for u64
+where
+    C: Constraint,
+{
+    type Output = Result<Amount<C>>;
 
-    fn mul(self, rhs: Amount<NonNegative>) -> Self::Output {
+    fn mul(self, rhs: Amount<C>) -> Self::Output {
         rhs.mul(self)
     }
 }
 
-impl std::ops::Div<u64> for Amount<NonNegative> {
-    type Output = Result<Amount<NonNegative>>;
+impl<C> std::ops::Div<u64> for Amount<C>
+where
+    C: Constraint,
+{
+    type Output = Result<Amount<C>>;
 
     fn div(self, rhs: u64) -> Self::Output {
-        let quotient = (self.0 as u64)
-            .checked_div(rhs)
+        let quotient = i128::from(self.0)
+            .checked_div(i128::from(rhs))
             .ok_or(Error::DivideByZero { amount: self.0 })?;
+
         Ok(quotient
             .try_into()
             .expect("division by a positive integer always stays within the constraint"))
@@ -320,14 +363,16 @@ impl<C> std::iter::Sum<Amount<C>> for Result<Amount<C>>
 where
     C: Constraint,
 {
-    fn sum<I: Iterator<Item = Amount<C>>>(iter: I) -> Self {
-        let sum = iter
-            .map(|a| a.0)
-            .try_fold(0i64, |acc, amount| acc.checked_add(amount));
+    fn sum<I: Iterator<Item = Amount<C>>>(mut iter: I) -> Self {
+        let sum = iter.try_fold(Amount::zero(), |acc, amount| acc + amount);
 
         match sum {
-            Some(sum) => Amount::try_from(sum),
-            None => Err(Error::SumOverflow),
+            Ok(sum) => Ok(sum),
+            Err(Error::Constraint { value, .. }) => Err(Error::SumOverflow {
+                partial_sum: value,
+                remaining_items: iter.count(),
+            }),
+            Err(unexpected_error) => unreachable!("unexpected Add error: {:?}", unexpected_error),
         }
     }
 }
@@ -352,27 +397,37 @@ where
     }
 }
 
-#[derive(thiserror::Error, Debug, displaydoc::Display, Clone, PartialEq)]
+#[derive(thiserror::Error, Debug, displaydoc::Display, Clone, PartialEq, Eq)]
 #[allow(missing_docs)]
 /// Errors that can be returned when validating `Amount`s
 pub enum Error {
     /// input {value} is outside of valid range for zatoshi Amount, valid_range={range:?}
-    Contains {
-        range: RangeInclusive<i64>,
+    Constraint {
         value: i64,
+        range: RangeInclusive<i64>,
     },
-    /// u64 {value} could not be converted to an i64 Amount
+
+    /// {value} could not be converted to an i64 Amount
     Convert {
-        value: u64,
+        value: i128,
         source: std::num::TryFromIntError,
     },
-    /// i64 overflow when multiplying i64 non-negative amount {amount} by u64 {multiplier}
-    MultiplicationOverflow { amount: i64, multiplier: u64 },
+
+    /// i64 overflow when multiplying i64 amount {amount} by u64 {multiplier}, overflowing result {overflowing_result}
+    MultiplicationOverflow {
+        amount: i64,
+        multiplier: u64,
+        overflowing_result: i128,
+    },
+
     /// cannot divide amount {amount} by zero
     DivideByZero { amount: i64 },
 
-    /// i64 overflow when summing i64 amounts
-    SumOverflow,
+    /// i64 overflow when summing i64 amounts, partial_sum: {partial_sum}, remaining items: {remaining_items}
+    SumOverflow {
+        partial_sum: i64,
+        remaining_items: usize,
+    },
 }
 
 /// Marker type for `Amount` that allows negative values.
@@ -427,7 +482,7 @@ pub trait Constraint {
         let range = Self::valid_range();
 
         if !range.contains(&value) {
-            Err(Error::Contains { range, value })
+            Err(Error::Constraint { value, range })
         } else {
             Ok(value)
         }
@@ -778,9 +833,9 @@ mod test {
         assert_eq!(sum_ref, sum_value);
         assert_eq!(
             sum_ref,
-            Err(Error::Contains {
-                range: -MAX_MONEY..=MAX_MONEY,
-                value: integer_sum,
+            Err(Error::SumOverflow {
+                partial_sum: integer_sum,
+                remaining_items: 0
             })
         );
 
@@ -795,9 +850,9 @@ mod test {
         assert_eq!(sum_ref, sum_value);
         assert_eq!(
             sum_ref,
-            Err(Error::Contains {
-                range: -MAX_MONEY..=MAX_MONEY,
-                value: integer_sum,
+            Err(Error::SumOverflow {
+                partial_sum: integer_sum,
+                remaining_items: 0
             })
         );
 
@@ -813,7 +868,13 @@ mod test {
         let sum_value = amounts.into_iter().sum::<Result<Amount, Error>>();
 
         assert_eq!(sum_ref, sum_value);
-        assert_eq!(sum_ref, Err(Error::SumOverflow));
+        assert_eq!(
+            sum_ref,
+            Err(Error::SumOverflow {
+                partial_sum: 4200000000000000,
+                remaining_items: 4391
+            })
+        );
 
         // below min of i64 overflow
         let times: usize = (i64::MAX / MAX_MONEY)
@@ -827,7 +888,13 @@ mod test {
         let sum_value = amounts.into_iter().sum::<Result<Amount, Error>>();
 
         assert_eq!(sum_ref, sum_value);
-        assert_eq!(sum_ref, Err(Error::SumOverflow));
+        assert_eq!(
+            sum_ref,
+            Err(Error::SumOverflow {
+                partial_sum: -4200000000000000,
+                remaining_items: 4391
+            })
+        );
 
         Ok(())
     }
diff --git a/zebra-chain/src/value_balance.rs b/zebra-chain/src/value_balance.rs
index 834b4458..bfaf17cb 100644
--- a/zebra-chain/src/value_balance.rs
+++ b/zebra-chain/src/value_balance.rs
@@ -1,6 +1,6 @@
 //! A type that can hold the four types of Zcash value pools.
 
-use crate::amount::{Amount, Constraint, Error, NonNegative};
+use crate::amount::{Amount, Constraint, Error, NegativeAllowed, NonNegative};
 
 use std::convert::TryInto;
 
@@ -10,8 +10,10 @@ mod arbitrary;
 #[cfg(test)]
 mod tests;
 
+use ValueBalanceError::*;
+
 /// An amount spread between different Zcash pools.
-#[derive(Clone, Copy, Debug, PartialEq)]
+#[derive(Clone, Copy, Debug, PartialEq, Eq)]
 pub struct ValueBalance<C> {
     transparent: Amount<C>,
     sprout: Amount<C>,
@@ -131,6 +133,20 @@ where
         }
     }
 
+    /// Convert this value balance to a different ValueBalance type,
+    /// if it satisfies the new constraint
+    pub fn constrain<C2>(self) -> Result<ValueBalance<C2>, ValueBalanceError>
+    where
+        C2: Constraint,
+    {
+        Ok(ValueBalance::<C2> {
+            transparent: self.transparent.constrain().map_err(Transparent)?,
+            sprout: self.sprout.constrain().map_err(Sprout)?,
+            sapling: self.sapling.constrain().map_err(Sapling)?,
+            orchard: self.orchard.constrain().map_err(Orchard)?,
+        })
+    }
+
     /// To byte array
     pub fn to_bytes(self) -> [u8; 32] {
         let transparent = self.transparent.to_bytes();
@@ -151,22 +167,29 @@ where
             bytes[0..8]
                 .try_into()
                 .expect("Extracting the first quarter of a [u8; 32] should always succeed"),
-        )?;
+        )
+        .map_err(Transparent)?;
+
         let sprout = Amount::from_bytes(
             bytes[8..16]
                 .try_into()
                 .expect("Extracting the second quarter of a [u8; 32] should always succeed"),
-        )?;
+        )
+        .map_err(Sprout)?;
+
         let sapling = Amount::from_bytes(
             bytes[16..24]
                 .try_into()
                 .expect("Extracting the third quarter of a [u8; 32] should always succeed"),
-        )?;
+        )
+        .map_err(Sapling)?;
+
         let orchard = Amount::from_bytes(
             bytes[24..32]
                 .try_into()
                 .expect("Extracting the last quarter of a [u8; 32] should always succeed"),
-        )?;
+        )
+        .map_err(Orchard)?;
 
         Ok(ValueBalance {
             transparent,
@@ -177,12 +200,20 @@ where
     }
 }
 
-#[derive(thiserror::Error, Debug, Clone, PartialEq)]
-/// Errors that can be returned when validating a [`ValueBalance`].
+#[derive(thiserror::Error, Debug, displaydoc::Display, Clone, PartialEq, Eq)]
+/// Errors that can be returned when validating a [`ValueBalance`]
 pub enum ValueBalanceError {
-    #[error("value balance contains invalid amounts")]
-    /// Any error related to [`Amount`]s inside the [`ValueBalance`]
-    AmountError(#[from] Error),
+    /// transparent amount error {0}
+    Transparent(Error),
+
+    /// sprout amount error {0}
+    Sprout(Error),
+
+    /// sapling amount error {0}
+    Sapling(Error),
+
+    /// orchard amount error {0}
+    Orchard(Error),
 }
 
 impl<C> std::ops::Add for ValueBalance<C>
@@ -192,10 +223,10 @@ where
     type Output = Result<ValueBalance<C>, ValueBalanceError>;
     fn add(self, rhs: ValueBalance<C>) -> Self::Output {
         Ok(ValueBalance::<C> {
-            transparent: (self.transparent + rhs.transparent)?,
-            sprout: (self.sprout + rhs.sprout)?,
-            sapling: (self.sapling + rhs.sapling)?,
-            orchard: (self.orchard + rhs.orchard)?,
+            transparent: (self.transparent + rhs.transparent).map_err(Transparent)?,
+            sprout: (self.sprout + rhs.sprout).map_err(Sprout)?,
+            sapling: (self.sapling + rhs.sapling).map_err(Sapling)?,
+            orchard: (self.orchard + rhs.orchard).map_err(Orchard)?,
         })
     }
 }
@@ -216,10 +247,10 @@ where
     type Output = Result<ValueBalance<C>, ValueBalanceError>;
     fn sub(self, rhs: ValueBalance<C>) -> Self::Output {
         Ok(ValueBalance::<C> {
-            transparent: (self.transparent - rhs.transparent)?,
-            sprout: (self.sprout - rhs.sprout)?,
-            sapling: (self.sapling - rhs.sapling)?,
-            orchard: (self.orchard - rhs.orchard)?,
+            transparent: (self.transparent - rhs.transparent).map_err(Transparent)?,
+            sprout: (self.sprout - rhs.sprout).map_err(Sprout)?,
+            sapling: (self.sapling - rhs.sapling).map_err(Sapling)?,
+            orchard: (self.orchard - rhs.orchard).map_err(Orchard)?,
         })
     }
 }
@@ -239,12 +270,7 @@ where
 {
     fn sum<I: Iterator<Item = ValueBalance<C>>>(mut iter: I) -> Self {
         iter.try_fold(ValueBalance::zero(), |acc, value_balance| {
-            Ok(ValueBalance {
-                transparent: (acc.transparent + value_balance.transparent)?,
-                sprout: (acc.sprout + value_balance.sprout)?,
-                sapling: (acc.sapling + value_balance.sapling)?,
-                orchard: (acc.orchard + value_balance.orchard)?,
-            })
+            acc + value_balance
         })
     }
 }
@@ -257,3 +283,19 @@ where
         iter.copied().sum()
     }
 }
+
+impl<C> std::ops::Neg for ValueBalance<C>
+where
+    C: Constraint,
+{
+    type Output = ValueBalance<NegativeAllowed>;
+
+    fn neg(self) -> Self::Output {
+        ValueBalance::<NegativeAllowed> {
+            transparent: self.transparent.neg(),
+            sprout: self.sprout.neg(),
+            sapling: self.sapling.neg(),
+            orchard: self.orchard.neg(),
+        }
+    }
+}
diff --git a/zebra-chain/src/value_balance/tests/prop.rs b/zebra-chain/src/value_balance/tests/prop.rs
index 9806d431..f55b22d4 100644
--- a/zebra-chain/src/value_balance/tests/prop.rs
+++ b/zebra-chain/src/value_balance/tests/prop.rs
@@ -29,7 +29,11 @@ proptest! {
             ),
             _ => prop_assert!(
                 matches!(
-                    value_balance1 + value_balance2, Err(ValueBalanceError::AmountError(_))
+                    value_balance1 + value_balance2,
+                    Err(ValueBalanceError::Transparent(_)
+                        | ValueBalanceError::Sprout(_)
+                        | ValueBalanceError::Sapling(_)
+                        | ValueBalanceError::Orchard(_))
                 )
             ),
         }
@@ -58,7 +62,11 @@ proptest! {
             ),
             _ => prop_assert!(
                 matches!(
-                    value_balance1 - value_balance2, Err(ValueBalanceError::AmountError(_))
+                    value_balance1 - value_balance2,
+                    Err(ValueBalanceError::Transparent(_)
+                        | ValueBalanceError::Sprout(_)
+                        | ValueBalanceError::Sapling(_)
+                        | ValueBalanceError::Orchard(_))
                 )
             ),
         }
@@ -88,7 +96,12 @@ proptest! {
                     orchard,
                 })
             ),
-            _ => prop_assert!(matches!(collection.iter().sum(), Err(ValueBalanceError::AmountError(_))))
+            _ => prop_assert!(matches!(collection.iter().sum(),
+                                       Err(ValueBalanceError::Transparent(_)
+                                           | ValueBalanceError::Sprout(_)
+                                           | ValueBalanceError::Sapling(_)
+                                           | ValueBalanceError::Orchard(_))
+            ))
         }
     }