diff --git a/atuin-client/src/settings.rs b/atuin-client/src/settings.rs
index 407013f..8793b73 100644
--- a/atuin-client/src/settings.rs
+++ b/atuin-client/src/settings.rs
@@ -5,7 +5,7 @@ use std::path::{Path, PathBuf};
 use chrono::prelude::*;
 use chrono::Utc;
 use config::{Config, Environment, File as ConfigFile};
-use eyre::{eyre, Result};
+use eyre::{eyre, Context, Result};
 use parse_duration::parse;
 
 pub const HISTORY_PAGE_SIZE: i64 = 100;
@@ -105,8 +105,10 @@ impl Settings {
 
         let data_dir = atuin_common::utils::data_dir();
 
-        create_dir_all(&config_dir)?;
-        create_dir_all(&data_dir)?;
+        create_dir_all(&config_dir)
+            .wrap_err_with(|| format!("could not create dir {:?}", config_dir))?;
+        create_dir_all(&data_dir)
+            .wrap_err_with(|| format!("could not create dir {:?}", data_dir))?;
 
         let mut config_file = if let Ok(p) = std::env::var("ATUIN_CONFIG_DIR") {
             PathBuf::from(p)
@@ -134,14 +136,17 @@ impl Settings {
         s.set_default("search_mode", "prefix")?;
 
         if config_file.exists() {
-            s.merge(ConfigFile::with_name(config_file.to_str().unwrap()))?;
+            s.merge(ConfigFile::with_name(config_file.to_str().unwrap()))
+                .wrap_err_with(|| format!("could not load config file {:?}", config_file))?;
         } else {
             let example_config = include_bytes!("../config.toml");
-            let mut file = File::create(config_file)?;
-            file.write_all(example_config)?;
+            let mut file = File::create(config_file).wrap_err("could not create config file")?;
+            file.write_all(example_config)
+                .wrap_err("could not write default config file")?;
         }
 
-        s.merge(Environment::with_prefix("atuin").separator("_"))?;
+        s.merge(Environment::with_prefix("atuin").separator("_"))
+            .wrap_err("could not load environment")?;
 
         // all paths should be expanded
         let db_path = s.get_str("db_path")?;
diff --git a/src/command/mod.rs b/src/command/mod.rs
index 6a79a32..0295036 100644
--- a/src/command/mod.rs
+++ b/src/command/mod.rs
@@ -1,6 +1,6 @@
 use std::path::PathBuf;
 
-use eyre::Result;
+use eyre::{Result, WrapErr};
 use structopt::StructOpt;
 
 use atuin_client::database::Sqlite;
@@ -96,8 +96,8 @@ pub enum AtuinCmd {
 
 impl AtuinCmd {
     pub async fn run(self) -> Result<()> {
-        let client_settings = ClientSettings::new()?;
-        let server_settings = ServerSettings::new()?;
+        let client_settings = ClientSettings::new().wrap_err("could not load client settings")?;
+        let server_settings = ServerSettings::new().wrap_err("could not load server settings")?;
 
         let db_path = PathBuf::from(client_settings.db_path.as_str());
 
@@ -151,8 +151,10 @@ impl AtuinCmd {
                 register::run(&client_settings, &r.username, &r.email, &r.password)
             }
             Self::Key => {
-                let key = atuin_client::encryption::load_key(&client_settings)?;
-                println!("{}", atuin_client::encryption::encode_key(key)?);
+                use atuin_client::encryption::{encode_key, load_key};
+                let key = load_key(&client_settings).wrap_err("could not load encryption key")?;
+                let encode = encode_key(key).wrap_err("could not encode encryption key")?;
+                println!("{}", encode);
                 Ok(())
             }