diff --git a/crates/cli/src/lib.rs b/crates/cli/src/lib.rs
index 2ff15cbc8..860f33662 100644
--- a/crates/cli/src/lib.rs
+++ b/crates/cli/src/lib.rs
@@ -26,28 +26,43 @@ async fn run_commands(cli: Cli) -> Result<()> {
     match &cli.subcommand {
         Subcommands::Init => {
             // init command throws an error if package.json file exist.
-            PackageJson::init(&package_json_path)?;
+            PackageJson::init(&package_json_path).with_context(|| {
+                format!("Failed to initialize package.json at path {:?}", &package_json_path)
+            })?;
         }
         Subcommands::Add(args) => {
-            let mut package_manager = PackageManager::new(package_json_path)?;
+            let mut package_manager =
+                PackageManager::new(&package_json_path).with_context(|| {
+                    format!("Failed to read package.json at path {:?}", &package_json_path)
+                })?;
             // TODO if a package already exists in another dependency group, we don't remove
             // the existing entry.
             package_manager
                 .add(&args.package, args.get_dependency_group(), args.save_exact)
-                .await?;
+                .await
+                .with_context(|| format!("Failed to add package {}", &args.package))?;
         }
         Subcommands::Install(args) => {
-            let mut package_manager = PackageManager::new(package_json_path)?;
-            package_manager.install(args.dev, !args.no_optional).await?;
+            let mut package_manager =
+                PackageManager::new(&package_json_path).with_context(|| {
+                    format!("Failed to read package.json at path {:?}", &package_json_path)
+                })?;
+            package_manager.install(args.dev, !args.no_optional).await.with_context(|| {
+                format!("Failed to install packages on {:?}", package_json_path)
+            })?;
         }
         Subcommands::Test => {
-            let package_json = PackageJson::from_path(&package_json_path)?;
+            let package_json = PackageJson::from_path(&package_json_path).with_context(|| {
+                format!("Failed to read package.json at path {:?}", &package_json_path)
+            })?;
             if let Some(script) = package_json.get_script("test", false)? {
                 execute_shell(script)?;
             }
         }
         Subcommands::Run(args) => {
-            let package_json = PackageJson::from_path(&package_json_path)?;
+            let package_json = PackageJson::from_path(&package_json_path).with_context(|| {
+                format!("Failed to read package.json at path {:?}", &package_json_path)
+            })?;
             if let Some(script) = package_json.get_script(&args.command, args.if_present)? {
                 execute_shell(script)?;
             }
@@ -57,7 +72,9 @@ async fn run_commands(cli: Cli) -> Result<()> {
             // object. If no start property is specified on the scripts object, it will attempt to
             // run node server.js as a default, failing if neither are present.
             // The intended usage of the property is to specify a command that starts your program.
-            let package_json = PackageJson::from_path(&package_json_path)?;
+            let package_json = PackageJson::from_path(&package_json_path).with_context(|| {
+                format!("Failed to read package.json at path {:?}", &package_json_path)
+            })?;
             if let Some(script) = package_json.get_script("start", true)? {
                 execute_shell(script)?;
             } else {
@@ -84,7 +101,6 @@ mod tests {
         env::set_current_dir(parent_folder.path()).unwrap();
         let cli = Cli::parse_from(["", "init"]);
         run_commands(cli).await.unwrap();
-
         assert!(parent_folder.path().join("package.json").exists());
         env::set_current_dir(&current_directory).unwrap();
     }
diff --git a/crates/executor/src/lib.rs b/crates/executor/src/lib.rs
index 57a163e9e..1636d6176 100644
--- a/crates/executor/src/lib.rs
+++ b/crates/executor/src/lib.rs
@@ -5,7 +5,7 @@ use thiserror::Error;
 #[derive(Error, Debug)]
 #[non_exhaustive]
 pub enum ExecutorError {
-    #[error("io error: {0}")]
+    #[error("io error")]
     Io(#[from] std::io::Error),
 }
 
diff --git a/crates/lockfile/src/lib.rs b/crates/lockfile/src/lib.rs
index 18639691c..54e446113 100644
--- a/crates/lockfile/src/lib.rs
+++ b/crates/lockfile/src/lib.rs
@@ -15,9 +15,9 @@ use crate::package::LockfilePackage;
 #[derive(Error, Debug)]
 #[non_exhaustive]
 pub enum LockfileError {
-    #[error("filesystem error: `{0}`")]
+    #[error("filesystem error")]
     FileSystem(#[from] std::io::Error),
-    #[error("serialization error: `{0}")]
+    #[error("serialization error")]
     Serialization(#[from] serde_yaml::Error),
 }
 
diff --git a/crates/package_json/src/error.rs b/crates/package_json/src/error.rs
index 846a073d4..f100b7aa6 100644
--- a/crates/package_json/src/error.rs
+++ b/crates/package_json/src/error.rs
@@ -3,9 +3,9 @@ use thiserror::Error;
 #[derive(Error, Debug)]
 #[non_exhaustive]
 pub enum PackageJsonError {
-    #[error("serialization failed: {0}")]
+    #[error("serialization failed with {0}")]
     Serialization(#[from] serde_json::Error),
-    #[error("io error: `{0}`")]
+    #[error("io error")]
     Io(#[from] std::io::Error),
     #[error("package.json file already exists")]
     AlreadyExist,
diff --git a/crates/package_manager/src/lib.rs b/crates/package_manager/src/lib.rs
index 05137f19a..bcf250c85 100644
--- a/crates/package_manager/src/lib.rs
+++ b/crates/package_manager/src/lib.rs
@@ -12,11 +12,11 @@ pub mod install;
 #[derive(Error, Debug)]
 #[non_exhaustive]
 pub enum PackageManagerError {
-    #[error("tarball error: {0}")]
+    #[error("tarball error")]
     Tarball(#[from] pacquet_tarball::TarballError),
-    #[error("package.json error: {0}")]
+    #[error("package.json error")]
     PackageJson(#[from] pacquet_package_json::error::PackageJsonError),
-    #[error("registry error: {0}")]
+    #[error("registry error")]
     Registry(#[from] pacquet_registry::RegistryError),
 }
 
diff --git a/crates/registry/src/lib.rs b/crates/registry/src/lib.rs
index 208262423..ae10a851a 100644
--- a/crates/registry/src/lib.rs
+++ b/crates/registry/src/lib.rs
@@ -11,19 +11,19 @@ use crate::package::{Package, PackageVersion};
 pub enum RegistryError {
     #[error("missing latest tag on {0}")]
     MissingLatestTag(String),
-    #[error("missing version {0} on package {0}")]
+    #[error("missing version {0} on package {1}")]
     MissingVersionRelease(String, String),
     #[error("network error while fetching {0}")]
     Network(#[from] reqwest::Error),
-    #[error("network middleware error")]
+    #[error("network middleware error with {0}")]
     NetworkMiddleware(#[from] reqwest_middleware::Error),
-    #[error("io error {0}")]
+    #[error("io error with {0}")]
     Io(#[from] std::io::Error),
-    #[error("serialization failed: {0}")]
+    #[error("serialization failed")]
     Serialization(String),
-    #[error("tarball error: {0}")]
+    #[error("tarball error with {0}")]
     Tarball(#[from] pacquet_tarball::TarballError),
-    #[error("package.json error: {0}")]
+    #[error("package.json error")]
     PackageJson(#[from] pacquet_package_json::error::PackageJsonError),
 }