From ca6db77a63b8e23607c376674c21334197b256ec Mon Sep 17 00:00:00 2001
From: Ian Manske <ian.manske@pm.me>
Date: Sat, 23 Nov 2024 20:59:39 -0800
Subject: [PATCH] Edit operator type errors

---
 crates/nu-command/src/math/median.rs          |  41 +-
 crates/nu-command/src/math/mode.rs            |  19 +-
 crates/nu-command/src/math/reducers.rs        |  28 +-
 crates/nu-parser/src/type_check.rs            |   7 +-
 crates/nu-protocol/src/errors/shell_error.rs  |  33 +
 crates/nu-protocol/src/value/mod.rs           | 692 ++++++++++--------
 .../src/cool_custom_value.rs                  |  12 +-
 7 files changed, 435 insertions(+), 397 deletions(-)

diff --git a/crates/nu-command/src/math/median.rs b/crates/nu-command/src/math/median.rs
index 653ebb59ba..7b88fab346 100644
--- a/crates/nu-command/src/math/median.rs
+++ b/crates/nu-command/src/math/median.rs
@@ -91,45 +91,26 @@ pub fn median(values: &[Value], span: Span, head: Span) -> Result<Value, ShellEr
         Pick::Median
     };
 
-    let mut sorted = vec![];
-
-    for item in values {
-        sorted.push(item.clone());
-    }
-
-    if let Some(Err(values)) = values
-        .windows(2)
-        .map(|elem| {
-            if elem[0].partial_cmp(&elem[1]).is_none() {
-                return Err(ShellError::OperatorMismatch {
-                    op_span: head,
-                    lhs_ty: elem[0].get_type().to_string(),
-                    lhs_span: elem[0].span(),
-                    rhs_ty: elem[1].get_type().to_string(),
-                    rhs_span: elem[1].span(),
-                });
-            }
-            Ok(elem[0].partial_cmp(&elem[1]).unwrap_or(Ordering::Equal))
-        })
-        .find(|elem| elem.is_err())
-    {
-        return Err(values);
-    }
+    let mut sorted = values
+        .iter()
+        .filter(|x| !x.as_float().is_ok_and(f64::is_nan))
+        .collect::<Vec<_>>();
 
     sorted.sort_by(|a, b| a.partial_cmp(b).unwrap_or(Ordering::Equal));
 
     match take {
         Pick::Median => {
             let idx = (values.len() as f64 / 2.0).floor() as usize;
-            let out = sorted
+            Ok(sorted
                 .get(idx)
                 .ok_or_else(|| ShellError::UnsupportedInput {
                     msg: "Empty input".to_string(),
                     input: "value originates from here".into(),
                     msg_span: head,
                     input_span: span,
-                })?;
-            Ok(out.clone())
+                })?
+                .to_owned()
+                .to_owned())
         }
         Pick::MedianAverage => {
             let idx_end = values.len() / 2;
@@ -143,7 +124,8 @@ pub fn median(values: &[Value], span: Span, head: Span) -> Result<Value, ShellEr
                     msg_span: head,
                     input_span: span,
                 })?
-                .clone();
+                .to_owned()
+                .to_owned();
 
             let right = sorted
                 .get(idx_end)
@@ -153,7 +135,8 @@ pub fn median(values: &[Value], span: Span, head: Span) -> Result<Value, ShellEr
                     msg_span: head,
                     input_span: span,
                 })?
-                .clone();
+                .to_owned()
+                .to_owned();
 
             average(&[left, right], span, head)
         }
diff --git a/crates/nu-command/src/math/mode.rs b/crates/nu-command/src/math/mode.rs
index b89896ca88..56cf274e5b 100644
--- a/crates/nu-command/src/math/mode.rs
+++ b/crates/nu-command/src/math/mode.rs
@@ -111,29 +111,12 @@ impl Command for SubCommand {
 }
 
 pub fn mode(values: &[Value], _span: Span, head: Span) -> Result<Value, ShellError> {
-    if let Some(Err(values)) = values
-        .windows(2)
-        .map(|elem| {
-            if elem[0].partial_cmp(&elem[1]).is_none() {
-                return Err(ShellError::OperatorMismatch {
-                    op_span: head,
-                    lhs_ty: elem[0].get_type().to_string(),
-                    lhs_span: elem[0].span(),
-                    rhs_ty: elem[1].get_type().to_string(),
-                    rhs_span: elem[1].span(),
-                });
-            }
-            Ok(elem[0].partial_cmp(&elem[1]).unwrap_or(Ordering::Equal))
-        })
-        .find(|elem| elem.is_err())
-    {
-        return Err(values);
-    }
     //In e-q, Value doesn't implement Hash or Eq, so we have to get the values inside
     // But f64 doesn't implement Hash, so we get the binary representation to use as
     // key in the HashMap
     let hashable_values = values
         .iter()
+        .filter(|x| !x.as_float().is_ok_and(f64::is_nan))
         .map(|val| match val {
             Value::Int { val, .. } => Ok(HashableType::new(val.to_ne_bytes(), NumberTypes::Int)),
             Value::Duration { val, .. } => {
diff --git a/crates/nu-command/src/math/reducers.rs b/crates/nu-command/src/math/reducers.rs
index 86d0f8d7e4..20eeb209b2 100644
--- a/crates/nu-command/src/math/reducers.rs
+++ b/crates/nu-command/src/math/reducers.rs
@@ -32,18 +32,8 @@ pub fn max(data: Vec<Value>, span: Span, head: Span) -> Result<Value, ShellError
         .clone();
 
     for value in &data {
-        if let Some(result) = value.partial_cmp(&biggest) {
-            if result == Ordering::Greater {
-                biggest = value.clone();
-            }
-        } else {
-            return Err(ShellError::OperatorMismatch {
-                op_span: head,
-                lhs_ty: biggest.get_type().to_string(),
-                lhs_span: biggest.span(),
-                rhs_ty: value.get_type().to_string(),
-                rhs_span: value.span(),
-            });
+        if value.partial_cmp(&biggest) == Some(Ordering::Greater) {
+            biggest = value.clone();
         }
     }
     Ok(biggest)
@@ -61,18 +51,8 @@ pub fn min(data: Vec<Value>, span: Span, head: Span) -> Result<Value, ShellError
         .clone();
 
     for value in &data {
-        if let Some(result) = value.partial_cmp(&smallest) {
-            if result == Ordering::Less {
-                smallest = value.clone();
-            }
-        } else {
-            return Err(ShellError::OperatorMismatch {
-                op_span: head,
-                lhs_ty: smallest.get_type().to_string(),
-                lhs_span: smallest.span(),
-                rhs_ty: value.get_type().to_string(),
-                rhs_span: value.span(),
-            });
+        if value.partial_cmp(&smallest) == Some(Ordering::Less) {
+            smallest = value.clone();
         }
     }
     Ok(smallest)
diff --git a/crates/nu-parser/src/type_check.rs b/crates/nu-parser/src/type_check.rs
index 19e0e2d257..ff565e451e 100644
--- a/crates/nu-parser/src/type_check.rs
+++ b/crates/nu-parser/src/type_check.rs
@@ -215,12 +215,7 @@ pub fn math_result_type(
                 type_error("multiplication", op, lhs, rhs, |ty| {
                     matches!(
                         ty,
-                        Type::Int
-                            | Type::Float
-                            | Type::Number
-                            | Type::Date
-                            | Type::Duration
-                            | Type::Filesize,
+                        Type::Int | Type::Float | Type::Number | Type::Duration | Type::Filesize,
                     )
                 })
             }
diff --git a/crates/nu-protocol/src/errors/shell_error.rs b/crates/nu-protocol/src/errors/shell_error.rs
index b4b6c29cee..745cc3b36f 100644
--- a/crates/nu-protocol/src/errors/shell_error.rs
+++ b/crates/nu-protocol/src/errors/shell_error.rs
@@ -17,6 +17,8 @@ pub enum ShellError {
     /// ## Resolution
     ///
     /// Check each argument's type and convert one or both as needed.
+    ///
+    #[deprecated = "use `OperatorUnsupportedType` or `OperatorTypeMismatch` instead"]
     #[error("Type mismatch during operation.")]
     #[diagnostic(code(nu::shell::type_mismatch))]
     OperatorMismatch {
@@ -30,6 +32,37 @@ pub enum ShellError {
         rhs_span: Span,
     },
 
+    /// One or more of the values have types not supported by the operator.
+    #[error("{op} is not supported on values of type {unsupported}.")]
+    #[diagnostic(code(nu::shell::operator_unsupported_type))]
+    OperatorUnsupportedType {
+        op: &'static str,
+        unsupported: Type,
+        #[label = "does support this type"]
+        op_span: Span,
+        #[label("{unsupported}")]
+        unsupported_span: Span,
+        #[help]
+        help: Option<&'static str>,
+    },
+
+    /// The operator supports the types of both values, but not the specific combination of their types.
+    #[error("{op} is not supported between types {lhs} and {rhs}.")]
+    #[diagnostic(code(nu::shell::operator_type_mismatch))]
+    OperatorTypeMismatch {
+        op: &'static str,
+        lhs: Type,
+        rhs: Type,
+        #[label = "does not operate between these two types"]
+        op_span: Span,
+        #[label("{lhs}")]
+        lhs_span: Span,
+        #[label("{rhs}")]
+        rhs_span: Span,
+        #[help]
+        help: Option<&'static str>,
+    },
+
     /// An arithmetic operation's resulting value overflowed its possible size.
     ///
     /// ## Resolution
diff --git a/crates/nu-protocol/src/value/mod.rs b/crates/nu-protocol/src/value/mod.rs
index 28b468a151..3bdad026e9 100644
--- a/crates/nu-protocol/src/value/mod.rs
+++ b/crates/nu-protocol/src/value/mod.rs
@@ -2443,7 +2443,6 @@ impl Value {
             (Value::String { val: lhs, .. }, Value::String { val: rhs, .. }) => {
                 Ok(Value::string(lhs.to_string() + rhs, span))
             }
-
             (Value::Duration { val: lhs, .. }, Value::Date { val: rhs, .. }) => {
                 if let Some(val) = rhs.checked_add_signed(chrono::Duration::nanoseconds(*lhs)) {
                     Ok(Value::date(val, span))
@@ -2488,43 +2487,20 @@ impl Value {
                     })
                 }
             }
-
             (Value::Custom { val: lhs, .. }, rhs) => {
                 lhs.operation(self.span(), Operator::Math(Math::Plus), op, rhs)
             }
-
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
-        }
-    }
-
-    pub fn concat(&self, op: Span, rhs: &Value, span: Span) -> Result<Value, ShellError> {
-        match (self, rhs) {
-            (Value::List { vals: lhs, .. }, Value::List { vals: rhs, .. }) => {
-                Ok(Value::list([lhs.as_slice(), rhs.as_slice()].concat(), span))
-            }
-            (Value::String { val: lhs, .. }, Value::String { val: rhs, .. }) => {
-                Ok(Value::string([lhs.as_str(), rhs.as_str()].join(""), span))
-            }
-            (Value::Binary { val: lhs, .. }, Value::Binary { val: rhs, .. }) => Ok(Value::binary(
-                [lhs.as_slice(), rhs.as_slice()].concat(),
-                span,
-            )),
-            (Value::Custom { val: lhs, .. }, rhs) => {
-                lhs.operation(self.span(), Operator::Math(Math::Concat), op, rhs)
-            }
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
+            _ => Err(operator_type_error("addition", op, self, rhs, |val| {
+                matches!(
+                    val,
+                    Value::Int { .. }
+                        | Value::Float { .. }
+                        | Value::String { .. }
+                        | Value::Date { .. }
+                        | Value::Duration { .. }
+                        | Value::Filesize { .. },
+                )
+            })),
         }
     }
 
@@ -2552,7 +2528,6 @@ impl Value {
             }
             (Value::Date { val: lhs, .. }, Value::Date { val: rhs, .. }) => {
                 let result = lhs.signed_duration_since(*rhs);
-
                 if let Some(v) = result.num_nanoseconds() {
                     Ok(Value::duration(v, span))
                 } else {
@@ -2595,18 +2570,19 @@ impl Value {
                     })
                 }
             }
-
             (Value::Custom { val: lhs, .. }, rhs) => {
                 lhs.operation(self.span(), Operator::Math(Math::Minus), op, rhs)
             }
-
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
+            _ => Err(operator_type_error("subtraction", op, self, rhs, |val| {
+                matches!(
+                    val,
+                    Value::Int { .. }
+                        | Value::Float { .. }
+                        | Value::Date { .. }
+                        | Value::Duration { .. }
+                        | Value::Filesize { .. },
+                )
+            })),
         }
     }
 
@@ -2659,13 +2635,21 @@ impl Value {
             (Value::Custom { val: lhs, .. }, rhs) => {
                 lhs.operation(self.span(), Operator::Math(Math::Multiply), op, rhs)
             }
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
+            _ => Err(operator_type_error(
+                "multiplication",
+                op,
+                self,
+                rhs,
+                |val| {
+                    matches!(
+                        val,
+                        Value::Int { .. }
+                            | Value::Float { .. }
+                            | Value::Duration { .. }
+                            | Value::Filesize { .. },
+                    )
+                },
+            )),
         }
     }
 
@@ -2774,14 +2758,15 @@ impl Value {
             (Value::Custom { val: lhs, .. }, rhs) => {
                 lhs.operation(self.span(), Operator::Math(Math::Divide), op, rhs)
             }
-
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
+            _ => Err(operator_type_error("division", op, self, rhs, |val| {
+                matches!(
+                    val,
+                    Value::Int { .. }
+                        | Value::Float { .. }
+                        | Value::Duration { .. }
+                        | Value::Filesize { .. },
+                )
+            })),
         }
     }
 
@@ -2931,14 +2916,15 @@ impl Value {
             (Value::Custom { val: lhs, .. }, rhs) => {
                 lhs.operation(span, Operator::Math(Math::Modulo), op, rhs)
             }
-
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
+            _ => Err(operator_type_error("modulo", op, self, rhs, |val| {
+                matches!(
+                    val,
+                    Value::Int { .. }
+                        | Value::Float { .. }
+                        | Value::Duration { .. }
+                        | Value::Filesize { .. },
+                )
+            })),
         }
     }
 
@@ -3087,13 +3073,51 @@ impl Value {
             (Value::Custom { val: lhs, .. }, rhs) => {
                 lhs.operation(self.span(), Operator::Math(Math::Divide), op, rhs)
             }
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
+            _ => Err(operator_type_error(
+                "floor division",
+                op,
+                self,
+                rhs,
+                |val| {
+                    matches!(
+                        val,
+                        Value::Int { .. }
+                            | Value::Float { .. }
+                            | Value::Duration { .. }
+                            | Value::Filesize { .. },
+                    )
+                },
+            )),
+        }
+    }
+
+    pub fn concat(&self, op: Span, rhs: &Value, span: Span) -> Result<Value, ShellError> {
+        match (self, rhs) {
+            (Value::List { vals: lhs, .. }, Value::List { vals: rhs, .. }) => {
+                Ok(Value::list([lhs.as_slice(), rhs.as_slice()].concat(), span))
+            }
+            (Value::String { val: lhs, .. }, Value::String { val: rhs, .. }) => {
+                Ok(Value::string([lhs.as_str(), rhs.as_str()].join(""), span))
+            }
+            (Value::Binary { val: lhs, .. }, Value::Binary { val: rhs, .. }) => Ok(Value::binary(
+                [lhs.as_slice(), rhs.as_slice()].concat(),
+                span,
+            )),
+            (Value::Custom { val: lhs, .. }, rhs) => {
+                lhs.operation(self.span(), Operator::Math(Math::Concat), op, rhs)
+            }
+            _ => Err(operator_type_error(
+                "concatentation",
+                op,
+                self,
+                rhs,
+                |val| {
+                    matches!(
+                        val,
+                        Value::List { .. } | Value::String { .. } | Value::Binary { .. },
+                    )
+                },
+            )),
         }
     }
 
@@ -3111,30 +3135,32 @@ impl Value {
             return Ok(Value::nothing(span));
         }
 
-        if !type_compatible(self.get_type(), rhs.get_type())
-            && (self.get_type() != Type::Any)
-            && (rhs.get_type() != Type::Any)
-        {
-            return Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            });
+        if !type_compatible(self.get_type(), rhs.get_type()) {
+            return Err(operator_type_error(
+                "less than comparison",
+                op,
+                self,
+                rhs,
+                |val| {
+                    matches!(
+                        val,
+                        Value::Int { .. }
+                            | Value::Float { .. }
+                            | Value::String { .. }
+                            | Value::Filesize { .. }
+                            | Value::Duration { .. }
+                            | Value::Date { .. }
+                            | Value::Bool { .. }
+                            | Value::Nothing { .. }
+                    )
+                },
+            ));
         }
 
-        if let Some(ordering) = self.partial_cmp(rhs) {
-            Ok(Value::bool(matches!(ordering, Ordering::Less), span))
-        } else {
-            Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            })
-        }
+        Ok(Value::bool(
+            matches!(self.partial_cmp(rhs), Some(Ordering::Less)),
+            span,
+        ))
     }
 
     pub fn lte(&self, op: Span, rhs: &Value, span: Span) -> Result<Value, ShellError> {
@@ -3151,28 +3177,35 @@ impl Value {
             return Ok(Value::nothing(span));
         }
 
-        if !type_compatible(self.get_type(), rhs.get_type())
-            && (self.get_type() != Type::Any)
-            && (rhs.get_type() != Type::Any)
-        {
-            return Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            });
+        if !type_compatible(self.get_type(), rhs.get_type()) {
+            return Err(operator_type_error(
+                "less than or equal to comparison",
+                op,
+                self,
+                rhs,
+                |val| {
+                    matches!(
+                        val,
+                        Value::Int { .. }
+                            | Value::Float { .. }
+                            | Value::String { .. }
+                            | Value::Filesize { .. }
+                            | Value::Duration { .. }
+                            | Value::Date { .. }
+                            | Value::Bool { .. }
+                            | Value::Nothing { .. }
+                    )
+                },
+            ));
         }
 
-        self.partial_cmp(rhs)
-            .map(|ordering| Value::bool(matches!(ordering, Ordering::Less | Ordering::Equal), span))
-            .ok_or(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            })
+        Ok(Value::bool(
+            matches!(
+                self.partial_cmp(rhs),
+                Some(Ordering::Less | Ordering::Equal)
+            ),
+            span,
+        ))
     }
 
     pub fn gt(&self, op: Span, rhs: &Value, span: Span) -> Result<Value, ShellError> {
@@ -3189,28 +3222,32 @@ impl Value {
             return Ok(Value::nothing(span));
         }
 
-        if !type_compatible(self.get_type(), rhs.get_type())
-            && (self.get_type() != Type::Any)
-            && (rhs.get_type() != Type::Any)
-        {
-            return Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            });
+        if !type_compatible(self.get_type(), rhs.get_type()) {
+            return Err(operator_type_error(
+                "greater than comparison",
+                op,
+                self,
+                rhs,
+                |val| {
+                    matches!(
+                        val,
+                        Value::Int { .. }
+                            | Value::Float { .. }
+                            | Value::String { .. }
+                            | Value::Filesize { .. }
+                            | Value::Duration { .. }
+                            | Value::Date { .. }
+                            | Value::Bool { .. }
+                            | Value::Nothing { .. }
+                    )
+                },
+            ));
         }
 
-        self.partial_cmp(rhs)
-            .map(|ordering| Value::bool(matches!(ordering, Ordering::Greater), span))
-            .ok_or(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            })
+        Ok(Value::bool(
+            matches!(self.partial_cmp(rhs), Some(Ordering::Greater)),
+            span,
+        ))
     }
 
     pub fn gte(&self, op: Span, rhs: &Value, span: Span) -> Result<Value, ShellError> {
@@ -3227,32 +3264,35 @@ impl Value {
             return Ok(Value::nothing(span));
         }
 
-        if !type_compatible(self.get_type(), rhs.get_type())
-            && (self.get_type() != Type::Any)
-            && (rhs.get_type() != Type::Any)
-        {
-            return Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            });
+        if !type_compatible(self.get_type(), rhs.get_type()) {
+            return Err(operator_type_error(
+                "greater than or equal to comparison",
+                op,
+                self,
+                rhs,
+                |val| {
+                    matches!(
+                        val,
+                        Value::Int { .. }
+                            | Value::Float { .. }
+                            | Value::String { .. }
+                            | Value::Filesize { .. }
+                            | Value::Duration { .. }
+                            | Value::Date { .. }
+                            | Value::Bool { .. }
+                            | Value::Nothing { .. }
+                    )
+                },
+            ));
         }
 
-        match self.partial_cmp(rhs) {
-            Some(ordering) => Ok(Value::bool(
-                matches!(ordering, Ordering::Greater | Ordering::Equal),
-                span,
-            )),
-            None => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
-        }
+        Ok(Value::bool(
+            matches!(
+                self.partial_cmp(rhs),
+                Some(Ordering::Greater | Ordering::Equal)
+            ),
+            span,
+        ))
     }
 
     pub fn eq(&self, op: Span, rhs: &Value, span: Span) -> Result<Value, ShellError> {
@@ -3265,22 +3305,10 @@ impl Value {
             );
         }
 
-        if let Some(ordering) = self.partial_cmp(rhs) {
-            Ok(Value::bool(matches!(ordering, Ordering::Equal), span))
-        } else {
-            match (self, rhs) {
-                (Value::Nothing { .. }, _) | (_, Value::Nothing { .. }) => {
-                    Ok(Value::bool(false, span))
-                }
-                _ => Err(ShellError::OperatorMismatch {
-                    op_span: op,
-                    lhs_ty: self.get_type().to_string(),
-                    lhs_span: self.span(),
-                    rhs_ty: rhs.get_type().to_string(),
-                    rhs_span: rhs.span(),
-                }),
-            }
-        }
+        Ok(Value::bool(
+            matches!(self.partial_cmp(rhs), Some(Ordering::Equal)),
+            span,
+        ))
     }
 
     pub fn ne(&self, op: Span, rhs: &Value, span: Span) -> Result<Value, ShellError> {
@@ -3293,22 +3321,10 @@ impl Value {
             );
         }
 
-        if let Some(ordering) = self.partial_cmp(rhs) {
-            Ok(Value::bool(!matches!(ordering, Ordering::Equal), span))
-        } else {
-            match (self, rhs) {
-                (Value::Nothing { .. }, _) | (_, Value::Nothing { .. }) => {
-                    Ok(Value::bool(true, span))
-                }
-                _ => Err(ShellError::OperatorMismatch {
-                    op_span: op,
-                    lhs_ty: self.get_type().to_string(),
-                    lhs_span: self.span(),
-                    rhs_ty: rhs.get_type().to_string(),
-                    rhs_span: rhs.span(),
-                }),
-            }
-        }
+        Ok(Value::bool(
+            !matches!(self.partial_cmp(rhs), Some(Ordering::Equal)),
+            span,
+        ))
     }
 
     pub fn r#in(&self, op: Span, rhs: &Value, span: Span) -> Result<Value, ShellError> {
@@ -3349,13 +3365,34 @@ impl Value {
             (Value::Custom { val: lhs, .. }, rhs) => {
                 lhs.operation(self.span(), Operator::Comparison(Comparison::In), op, rhs)
             }
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
+            (lhs, rhs) => Err(
+                if matches!(
+                    rhs,
+                    Value::List { .. }
+                        | Value::Range { .. }
+                        | Value::String { .. }
+                        | Value::Record { .. }
+                        | Value::Custom { .. }
+                ) {
+                    ShellError::OperatorTypeMismatch {
+                        op: "'in' comparison",
+                        lhs: lhs.get_type(),
+                        rhs: rhs.get_type(),
+                        op_span: op,
+                        lhs_span: lhs.span(),
+                        rhs_span: rhs.span(),
+                        help: None,
+                    }
+                } else {
+                    ShellError::OperatorUnsupportedType {
+                        op: "'in' comparison",
+                        unsupported: rhs.get_type(),
+                        op_span: op,
+                        unsupported_span: rhs.span(),
+                        help: None,
+                    }
+                },
+            ),
         }
     }
 
@@ -3400,13 +3437,34 @@ impl Value {
                 op,
                 rhs,
             ),
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
+            (lhs, rhs) => Err(
+                if matches!(
+                    rhs,
+                    Value::List { .. }
+                        | Value::Range { .. }
+                        | Value::String { .. }
+                        | Value::Record { .. }
+                        | Value::Custom { .. }
+                ) {
+                    ShellError::OperatorTypeMismatch {
+                        op: "'not-in' comparison",
+                        lhs: lhs.get_type(),
+                        rhs: rhs.get_type(),
+                        op_span: op,
+                        lhs_span: lhs.span(),
+                        rhs_span: rhs.span(),
+                        help: None,
+                    }
+                } else {
+                    ShellError::OperatorUnsupportedType {
+                        op: "'not-in' comparison",
+                        unsupported: rhs.get_type(),
+                        op_span: op,
+                        unsupported_span: rhs.span(),
+                        help: None,
+                    }
+                },
+            ),
         }
     }
 
@@ -3468,13 +3526,9 @@ impl Value {
                 op,
                 rhs,
             ),
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
+            _ => Err(operator_type_error("regex match", op, self, rhs, |val| {
+                matches!(val, Value::String { .. })
+            })),
         }
     }
 
@@ -3489,13 +3543,13 @@ impl Value {
                 op,
                 rhs,
             ),
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
+            _ => Err(operator_type_error(
+                "starts-with comparison",
+                op,
+                self,
+                rhs,
+                |val| matches!(val, Value::String { .. }),
+            )),
         }
     }
 
@@ -3510,13 +3564,13 @@ impl Value {
                 op,
                 rhs,
             ),
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
+            _ => Err(operator_type_error(
+                "ends-with comparison",
+                op,
+                self,
+                rhs,
+                |val| matches!(val, Value::String { .. }),
+            )),
         }
     }
 
@@ -3539,13 +3593,13 @@ impl Value {
             (Value::Custom { val: lhs, .. }, rhs) => {
                 lhs.operation(span, Operator::Bits(Bits::ShiftLeft), op, rhs)
             }
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
+            _ => Err(operator_type_error(
+                "bit left shift",
+                op,
+                self,
+                rhs,
+                |val| matches!(val, Value::Int { .. }),
+            )),
         }
     }
 
@@ -3568,49 +3622,13 @@ impl Value {
             (Value::Custom { val: lhs, .. }, rhs) => {
                 lhs.operation(span, Operator::Bits(Bits::ShiftRight), op, rhs)
             }
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
-        }
-    }
-
-    pub fn bit_or(&self, op: Span, rhs: &Value, span: Span) -> Result<Value, ShellError> {
-        match (self, rhs) {
-            (Value::Int { val: lhs, .. }, Value::Int { val: rhs, .. }) => {
-                Ok(Value::int(*lhs | rhs, span))
-            }
-            (Value::Custom { val: lhs, .. }, rhs) => {
-                lhs.operation(span, Operator::Bits(Bits::BitOr), op, rhs)
-            }
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
-        }
-    }
-
-    pub fn bit_xor(&self, op: Span, rhs: &Value, span: Span) -> Result<Value, ShellError> {
-        match (self, rhs) {
-            (Value::Int { val: lhs, .. }, Value::Int { val: rhs, .. }) => {
-                Ok(Value::int(*lhs ^ rhs, span))
-            }
-            (Value::Custom { val: lhs, .. }, rhs) => {
-                lhs.operation(span, Operator::Bits(Bits::BitXor), op, rhs)
-            }
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
+            _ => Err(operator_type_error(
+                "bit right shift",
+                op,
+                self,
+                rhs,
+                |val| matches!(val, Value::Int { .. }),
+            )),
         }
     }
 
@@ -3622,13 +3640,37 @@ impl Value {
             (Value::Custom { val: lhs, .. }, rhs) => {
                 lhs.operation(span, Operator::Bits(Bits::BitAnd), op, rhs)
             }
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
+            _ => Err(operator_type_error("bitwise and", op, self, rhs, |val| {
+                matches!(val, Value::Int { .. })
+            })),
+        }
+    }
+
+    pub fn bit_or(&self, op: Span, rhs: &Value, span: Span) -> Result<Value, ShellError> {
+        match (self, rhs) {
+            (Value::Int { val: lhs, .. }, Value::Int { val: rhs, .. }) => {
+                Ok(Value::int(*lhs | rhs, span))
+            }
+            (Value::Custom { val: lhs, .. }, rhs) => {
+                lhs.operation(span, Operator::Bits(Bits::BitOr), op, rhs)
+            }
+            _ => Err(operator_type_error("bitwise or", op, self, rhs, |val| {
+                matches!(val, Value::Int { .. })
+            })),
+        }
+    }
+
+    pub fn bit_xor(&self, op: Span, rhs: &Value, span: Span) -> Result<Value, ShellError> {
+        match (self, rhs) {
+            (Value::Int { val: lhs, .. }, Value::Int { val: rhs, .. }) => {
+                Ok(Value::int(*lhs ^ rhs, span))
+            }
+            (Value::Custom { val: lhs, .. }, rhs) => {
+                lhs.operation(span, Operator::Bits(Bits::BitXor), op, rhs)
+            }
+            _ => Err(operator_type_error("bitwise xor", op, self, rhs, |val| {
+                matches!(val, Value::Int { .. })
+            })),
         }
     }
 
@@ -3640,13 +3682,9 @@ impl Value {
             (Value::Custom { val: lhs, .. }, rhs) => {
                 lhs.operation(span, Operator::Boolean(Boolean::And), op, rhs)
             }
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
+            _ => Err(operator_type_error("boolean and", op, self, rhs, |val| {
+                matches!(val, Value::Bool { .. })
+            })),
         }
     }
 
@@ -3658,13 +3696,9 @@ impl Value {
             (Value::Custom { val: lhs, .. }, rhs) => {
                 lhs.operation(span, Operator::Boolean(Boolean::Or), op, rhs)
             }
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
+            _ => Err(operator_type_error("boolean or", op, self, rhs, |val| {
+                matches!(val, Value::Bool { .. })
+            })),
         }
     }
 
@@ -3676,13 +3710,9 @@ impl Value {
             (Value::Custom { val: lhs, .. }, rhs) => {
                 lhs.operation(span, Operator::Boolean(Boolean::Xor), op, rhs)
             }
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
+            _ => Err(operator_type_error("boolean xor", op, self, rhs, |val| {
+                matches!(val, Value::Bool { .. })
+            })),
         }
     }
 
@@ -3711,14 +3741,13 @@ impl Value {
             (Value::Custom { val: lhs, .. }, rhs) => {
                 lhs.operation(span, Operator::Math(Math::Pow), op, rhs)
             }
-
-            _ => Err(ShellError::OperatorMismatch {
-                op_span: op,
-                lhs_ty: self.get_type().to_string(),
-                lhs_span: self.span(),
-                rhs_ty: rhs.get_type().to_string(),
-                rhs_span: rhs.span(),
-            }),
+            _ => Err(operator_type_error(
+                "exponentiation",
+                op,
+                self,
+                rhs,
+                |val| matches!(val, Value::Int { .. } | Value::Float { .. }),
+            )),
         }
     }
 }
@@ -3733,6 +3762,41 @@ fn type_compatible(a: Type, b: Type) -> bool {
     matches!((a, b), (Type::Int, Type::Float) | (Type::Float, Type::Int))
 }
 
+fn operator_type_error(
+    op_name: &'static str,
+    op_span: Span,
+    lhs: &Value,
+    rhs: &Value,
+    is_supported: fn(&Value) -> bool,
+) -> ShellError {
+    let is_supported = |val| is_supported(val) || matches!(val, Value::Custom { .. });
+    match (is_supported(lhs), is_supported(rhs)) {
+        (true, true) => ShellError::OperatorTypeMismatch {
+            op: op_name,
+            lhs: lhs.get_type(),
+            rhs: rhs.get_type(),
+            op_span,
+            lhs_span: lhs.span(),
+            rhs_span: rhs.span(),
+            help: None,
+        },
+        (true, false) => ShellError::OperatorUnsupportedType {
+            op: op_name,
+            unsupported: rhs.get_type(),
+            op_span,
+            unsupported_span: rhs.span(),
+            help: None,
+        },
+        (false, _) => ShellError::OperatorUnsupportedType {
+            op: op_name,
+            unsupported: lhs.get_type(),
+            op_span,
+            unsupported_span: lhs.span(),
+            help: None,
+        },
+    }
+}
+
 #[cfg(test)]
 mod tests {
     use super::{Record, Value};
diff --git a/crates/nu_plugin_custom_values/src/cool_custom_value.rs b/crates/nu_plugin_custom_values/src/cool_custom_value.rs
index cd160e0d0c..144091ced0 100644
--- a/crates/nu_plugin_custom_values/src/cool_custom_value.rs
+++ b/crates/nu_plugin_custom_values/src/cool_custom_value.rs
@@ -105,7 +105,7 @@ impl CustomValue for CoolCustomValue {
 
     fn operation(
         &self,
-        lhs_span: Span,
+        _lhs_span: Span,
         operator: ast::Operator,
         op_span: Span,
         right: &Value,
@@ -125,12 +125,12 @@ impl CustomValue for CoolCustomValue {
                         op_span,
                     ))
                 } else {
-                    Err(ShellError::OperatorMismatch {
+                    Err(ShellError::OperatorUnsupportedType {
+                        op: "concatenation",
+                        unsupported: right.get_type(),
                         op_span,
-                        lhs_ty: self.typetag_name().into(),
-                        lhs_span,
-                        rhs_ty: right.get_type().to_string(),
-                        rhs_span: right.span(),
+                        unsupported_span: right.span(),
+                        help: None,
                     })
                 }
             }