diff --git a/common/Cargo.toml b/common/Cargo.toml
index 54dfbe262..89ea63a15 100644
--- a/common/Cargo.toml
+++ b/common/Cargo.toml
@@ -30,7 +30,7 @@ serde = { workspace = true, features = ["derive", "std"] }
 serde_json = { workspace = true }
 sqlx = { workspace = true, optional = true }
 strum = { workspace = true, features = ["derive"] }
-thiserror = { workspace = true, optional = true }
+thiserror = { workspace = true }
 tonic = { workspace = true, optional = true }
 tower = { workspace = true, optional = true }
 tracing = { workspace = true, features = ["std"], optional = true }
@@ -65,7 +65,7 @@ extract_propagation = [
     "tower",
     "tracing-opentelemetry",
 ]
-models = ["async-trait", "reqwest", "service", "thiserror"]
+models = ["async-trait", "reqwest", "service"]
 persist = ["sqlx", "rand"]
 sqlx = ["dep:sqlx", "sqlx/sqlite"]
 service = ["chrono/serde", "display", "tracing", "tracing-subscriber", "uuid"]
diff --git a/common/src/models/error.rs b/common/src/models/error.rs
index 3263c9c5b..f99313c4b 100644
--- a/common/src/models/error.rs
+++ b/common/src/models/error.rs
@@ -30,13 +30,22 @@ impl ApiError {
     }
 
     /// Creates an internal error without exposing sensitive information to the user.
-    pub fn internal_safe(error: impl std::error::Error) -> Self {
-        error!(error = error.to_string(), "");
-
-        Self {
-            message: "Internal server error occured. Please create a ticket to get this fixed."
-                .to_string(),
-            status_code: StatusCode::INTERNAL_SERVER_ERROR.as_u16(),
+    #[inline(always)]
+    pub fn internal_safe<E>(message: &str, error: E) -> Self
+    where
+        E: std::error::Error + 'static,
+    {
+        error!(error = &error as &dyn std::error::Error, "{message}");
+
+        // Return the raw error during debug builds
+        #[cfg(debug_assertions)]
+        {
+            ApiError::internal(&error.to_string())
+        }
+        // Return the safe message during release builds
+        #[cfg(not(debug_assertions))]
+        {
+            ApiError::internal(message)
         }
     }
 
@@ -54,13 +63,6 @@ impl ApiError {
         }
     }
 
-    pub fn not_found(message: impl ToString) -> Self {
-        Self {
-            message: message.to_string(),
-            status_code: StatusCode::NOT_FOUND.as_u16(),
-        }
-    }
-
     pub fn unauthorized() -> Self {
         Self {
             message: "Unauthorized".to_string(),
@@ -80,6 +82,131 @@ impl ApiError {
     }
 }
 
+pub trait ErrorContext<T> {
+    /// Make a new internal server error with the given message.
+    #[inline(always)]
+    fn context_internal_error(self, message: &str) -> Result<T, ApiError>
+    where
+        Self: Sized,
+    {
+        self.with_context_internal_error(move || message.to_string())
+    }
+
+    /// Make a new internal server error using the given function to create the message.
+    fn with_context_internal_error(self, message: impl FnOnce() -> String) -> Result<T, ApiError>;
+
+    /// Make a new bad request error with the given message.
+    #[inline(always)]
+    fn context_bad_request(self, message: &str) -> Result<T, ApiError>
+    where
+        Self: Sized,
+    {
+        self.with_context_bad_request(move || message.to_string())
+    }
+
+    /// Make a new bad request error using the given function to create the message.
+    fn with_context_bad_request(self, message: impl FnOnce() -> String) -> Result<T, ApiError>;
+
+    /// Make a new not found error with the given message.
+    #[inline(always)]
+    fn context_not_found(self, message: &str) -> Result<T, ApiError>
+    where
+        Self: Sized,
+    {
+        self.with_context_not_found(move || message.to_string())
+    }
+
+    /// Make a new not found error using the given function to create the message.
+    fn with_context_not_found(self, message: impl FnOnce() -> String) -> Result<T, ApiError>;
+}
+
+impl<T, E> ErrorContext<T> for Result<T, E>
+where
+    E: std::error::Error + 'static,
+{
+    #[inline(always)]
+    fn with_context_internal_error(self, message: impl FnOnce() -> String) -> Result<T, ApiError> {
+        match self {
+            Ok(value) => Ok(value),
+            Err(error) => Err(ApiError::internal_safe(message().as_ref(), error)),
+        }
+    }
+
+    #[inline(always)]
+    fn with_context_bad_request(self, message: impl FnOnce() -> String) -> Result<T, ApiError> {
+        match self {
+            Ok(value) => Ok(value),
+            Err(error) => Err({
+                let message = message();
+                warn!(
+                    error = &error as &dyn std::error::Error,
+                    "bad request: {message}"
+                );
+
+                ApiError {
+                    message,
+                    status_code: StatusCode::BAD_REQUEST.as_u16(),
+                }
+            }),
+        }
+    }
+
+    #[inline(always)]
+    fn with_context_not_found(self, message: impl FnOnce() -> String) -> Result<T, ApiError> {
+        match self {
+            Ok(value) => Ok(value),
+            Err(error) => Err({
+                let message = message();
+                warn!(
+                    error = &error as &dyn std::error::Error,
+                    "not found: {message}"
+                );
+
+                ApiError {
+                    message,
+                    status_code: StatusCode::NOT_FOUND.as_u16(),
+                }
+            }),
+        }
+    }
+}
+
+impl<T> ErrorContext<T> for Option<T> {
+    #[inline]
+    fn with_context_internal_error(self, message: impl FnOnce() -> String) -> Result<T, ApiError> {
+        match self {
+            Some(value) => Ok(value),
+            None => Err(ApiError::internal(message().as_ref())),
+        }
+    }
+
+    #[inline]
+    fn with_context_bad_request(self, message: impl FnOnce() -> String) -> Result<T, ApiError> {
+        match self {
+            Some(value) => Ok(value),
+            None => Err({
+                ApiError {
+                    message: message(),
+                    status_code: StatusCode::BAD_REQUEST.as_u16(),
+                }
+            }),
+        }
+    }
+
+    #[inline]
+    fn with_context_not_found(self, message: impl FnOnce() -> String) -> Result<T, ApiError> {
+        match self {
+            Some(value) => Ok(value),
+            None => Err({
+                ApiError {
+                    message: message(),
+                    status_code: StatusCode::NOT_FOUND.as_u16(),
+                }
+            }),
+        }
+    }
+}
+
 impl Display for ApiError {
     fn fmt(&self, f: &mut Formatter<'_>) -> std::fmt::Result {
         write!(
diff --git a/common/src/resource.rs b/common/src/resource.rs
index 53931733e..0fdb65d0c 100644
--- a/common/src/resource.rs
+++ b/common/src/resource.rs
@@ -2,6 +2,7 @@ use std::{fmt::Display, str::FromStr};
 
 use serde::{Deserialize, Serialize};
 use serde_json::Value;
+use thiserror::Error;
 
 use crate::{constants::RESOURCE_SCHEMA_VERSION, database};
 
@@ -87,21 +88,32 @@ pub enum Type {
     Container,
 }
 
+#[derive(Debug, Error)]
+pub enum InvalidResourceType {
+    #[error("'{0}' is an unknown database type")]
+    Type(String),
+
+    #[error("{0}")]
+    Database(String),
+}
+
 impl FromStr for Type {
-    type Err = String;
+    type Err = InvalidResourceType;
 
     fn from_str(s: &str) -> Result<Self, Self::Err> {
         if let Some((prefix, rest)) = s.split_once("::") {
             match prefix {
-                "database" => Ok(Self::Database(database::Type::from_str(rest)?)),
-                _ => Err(format!("'{prefix}' is an unknown resource type")),
+                "database" => Ok(Self::Database(
+                    database::Type::from_str(rest).map_err(InvalidResourceType::Database)?,
+                )),
+                _ => Err(InvalidResourceType::Type(prefix.to_string())),
             }
         } else {
             match s {
                 "secrets" => Ok(Self::Secrets),
                 "persist" => Ok(Self::Persist),
                 "container" => Ok(Self::Container),
-                _ => Err(format!("'{s}' is an unknown resource type")),
+                _ => Err(InvalidResourceType::Type(s.to_string())),
             }
         }
     }
diff --git a/resource-recorder/src/dal.rs b/resource-recorder/src/dal.rs
index 9ad8aeb56..78f679a86 100644
--- a/resource-recorder/src/dal.rs
+++ b/resource-recorder/src/dal.rs
@@ -4,7 +4,7 @@ use crate::Error;
 use async_trait::async_trait;
 use chrono::{DateTime, Utc};
 use prost_types::Timestamp;
-use shuttle_common::resource::Type;
+use shuttle_common::resource::{InvalidResourceType, Type};
 use shuttle_proto::resource_recorder::{self, record_request};
 use sqlx::{
     migrate::{MigrateDatabase, Migrator},
@@ -244,7 +244,7 @@ impl FromRow<'_, SqliteRow> for Resource {
 }
 
 impl TryFrom<record_request::Resource> for Resource {
-    type Error = String;
+    type Error = InvalidResourceType;
 
     fn try_from(value: record_request::Resource) -> Result<Self, Self::Error> {
         let r#type = value.r#type.parse()?;
diff --git a/resource-recorder/src/lib.rs b/resource-recorder/src/lib.rs
index 768289e62..1b36894dc 100644
--- a/resource-recorder/src/lib.rs
+++ b/resource-recorder/src/lib.rs
@@ -2,7 +2,10 @@ use async_trait::async_trait;
 use dal::{Dal, DalError, Resource};
 use prost_types::TimestampError;
 use shuttle_backends::{auth::VerifyClaim, client::ServicesApiClient, ClaimExt};
-use shuttle_common::claims::{Claim, Scope};
+use shuttle_common::{
+    claims::{Claim, Scope},
+    resource::InvalidResourceType,
+};
 use shuttle_proto::resource_recorder::{
     self, resource_recorder_server::ResourceRecorder, ProjectResourcesRequest, RecordRequest,
     ResourceIds, ResourceResponse, ResourcesResponse, ResultResponse, ServiceResourcesRequest,
@@ -28,17 +31,13 @@ pub enum Error {
     Dal(#[from] DalError),
 
     #[error("could not parse resource type: {0}")]
-    String(String),
+    ResourceType(#[from] InvalidResourceType),
 
     #[error("could not parse timestamp: {0}")]
     Timestamp(#[from] TimestampError),
-}
 
-// thiserror is not happy to handle a `#[from] String`
-impl From<String> for Error {
-    fn from(value: String) -> Self {
-        Self::String(value)
-    }
+    #[error("{0}")]
+    String(String),
 }
 
 pub struct Service<D> {