diff --git a/src/error.rs b/src/error.rs
new file mode 100644
index 00000000..9ccf4925
--- /dev/null
+++ b/src/error.rs
@@ -0,0 +1,64 @@
+//! Error handling facilities
+
+use std::{fmt, iter};
+
+use thiserror::Error;
+
+/// Wraps any [`Error`][e] type so that [`Display`][d] includes its [sources][s]
+///
+/// [e]: std::error::Error
+/// [d]: fmt::Display
+/// [s]: std::error::Error::source
+pub struct Chain<'a>(pub &'a dyn std::error::Error);
+
+impl fmt::Display for Chain<'_> {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        write!(f, "{}", self.0)?;
+
+        let mut source = self.0.source();
+
+        source
+            .into_iter()
+            .chain(iter::from_fn(|| {
+                source = source.and_then(std::error::Error::source);
+                source
+            }))
+            .try_for_each(|source| write!(f, ": {source}"))
+    }
+}
+
+/// Top-level errors
+// Missing docs are allowed here since that kind of information should be
+// encoded in the error messages themselves anyway.
+#[allow(missing_docs)]
+#[derive(Error, Debug)]
+pub enum CliError {
+    #[error(
+        "the `CONDUIT_CONFIG` environment variable must either be set to a configuration file path \
+        or set to an empty string to force configuration through environment variables"
+    )]
+    ConfigPathUnset,
+
+    #[error("invalid configuration")]
+    ConfigInvalid(#[from] figment::Error),
+
+    // Upstream's documentation on what this error means is very sparse
+    #[error("opentelemetry error")]
+    Otel(#[from] opentelemetry::trace::TraceError),
+
+    #[error("invalid log filter syntax")]
+    EnvFilter(#[from] tracing_subscriber::filter::ParseError),
+
+    #[error("failed to install global default tracing subscriber")]
+    SetSubscriber(#[from] tracing::subscriber::SetGlobalDefaultError),
+
+    // Upstream's documentation on what this error means is very sparse
+    #[error("tracing_flame error")]
+    TracingFlame(#[from] tracing_flame::Error),
+
+    #[error("failed to load or create the database")]
+    DatabaseError(#[source] crate::utils::error::Error),
+
+    #[error("failed to serve requests")]
+    Serve(#[source] std::io::Error),
+}
diff --git a/src/lib.rs b/src/lib.rs
index 5a89f805..6ce754eb 100644
--- a/src/lib.rs
+++ b/src/lib.rs
@@ -2,6 +2,7 @@ pub mod api;
 pub mod clap;
 mod config;
 mod database;
+pub mod error;
 mod service;
 mod utils;
 
diff --git a/src/main.rs b/src/main.rs
index 3d66e5ea..94bd6a51 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -48,25 +48,20 @@ async fn main() -> ExitCode {
         return ExitCode::SUCCESS;
     };
 
-    eprintln!("error: {e}");
+    eprintln!("error: {}", error::Chain(&e));
 
     ExitCode::FAILURE
 }
 
 /// Fallible entrypoint
-async fn try_main() -> Result<(), Box<dyn std::error::Error>> {
+async fn try_main() -> Result<(), error::CliError> {
+    use error::CliError as Error;
+
     clap::parse();
 
     // Initialize config
     let raw_config = Figment::new()
-        .merge(
-            Toml::file(Env::var("CONDUIT_CONFIG").ok_or(
-                "the `CONDUIT_CONFIG` environment variable must either be set to a \
-                    configuration file path or set to the empty string to force configuration \
-                    through environment variables",
-            )?)
-            .nested(),
-        )
+        .merge(Toml::file(Env::var("CONDUIT_CONFIG").ok_or(Error::ConfigPathUnset)?).nested())
         .merge(Env::prefixed("CONDUIT_").global());
 
     let config = raw_config.extract::<Config>()?;
@@ -116,11 +111,13 @@ async fn try_main() -> Result<(), Box<dyn std::error::Error>> {
     maximize_fd_limit().expect("should be able to increase the soft limit to the hard limit");
 
     info!("Loading database");
-    KeyValueDatabase::load_or_create(config).await?;
+    KeyValueDatabase::load_or_create(config)
+        .await
+        .map_err(Error::DatabaseError)?;
     let config = &services().globals.config;
 
     info!("Starting server");
-    run_server().await?;
+    run_server().await.map_err(Error::Serve)?;
 
     if config.allow_jaeger {
         opentelemetry::global::shutdown_tracer_provider();