diff --git a/src/error.rs b/src/error.rs
new file mode 100644
index 00000000..dd50fee0
--- /dev/null
+++ b/src/error.rs
@@ -0,0 +1,70 @@
+//! Error handling facilities
+
+use std::{fmt, iter};
+
+use thiserror::Error;
+
+/// Formats an [`Error`][0] and its [`source`][1]s with a separator
+///
+/// [0]: std::error::Error
+/// [1]: std::error::Error::source
+pub(crate) struct DisplayWithSources<'a> {
+    /// The error (and its sources) to write
+    pub(crate) error: &'a dyn std::error::Error,
+
+    /// Separator to write between the original error and subsequent sources
+    pub(crate) infix: &'static str,
+}
+
+impl fmt::Display for DisplayWithSources<'_> {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        write!(f, "{}", self.error)?;
+
+        let mut source = self.error.source();
+
+        source
+            .into_iter()
+            .chain(iter::from_fn(|| {
+                source = source.and_then(std::error::Error::source);
+                source
+            }))
+            .try_for_each(|source| write!(f, "{}{source}", self.infix))
+    }
+}
+
+/// 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(crate) enum Main {
+    #[error(
+        "the `{0}` environment variable must either be set to a configuration \
+         file path or set to an empty string to force configuration through \
+         environment variables"
+    )]
+    ConfigPathUnset(&'static str),
+
+    #[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/main.rs b/src/main.rs
index c8abc651..b9d165be 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -45,6 +45,7 @@ pub(crate) mod api;
 pub(crate) mod clap;
 mod config;
 mod database;
+mod error;
 mod service;
 mod utils;
 
@@ -92,23 +93,30 @@ async fn main() -> ExitCode {
         return ExitCode::SUCCESS;
     };
 
-    eprintln!("error: {e}");
+    eprintln!(
+        "Error: {}",
+        error::DisplayWithSources {
+            error: &e,
+            infix: "\n    Caused by: "
+        }
+    );
 
     ExitCode::FAILURE
 }
 
 /// Fallible entrypoint
-async fn try_main() -> Result<(), Box<dyn std::error::Error>> {
+async fn try_main() -> Result<(), error::Main> {
+    use error::Main as Error;
+
     clap::parse();
 
     // Initialize config
     let raw_config = Figment::new()
         .merge(
-            Toml::file(Env::var("GRAPEVINE_CONFIG").ok_or(
-                "the `GRAPEVINE_CONFIG` environment variable must either be \
-                 set to a configuration file path or set to the empty string \
-                 to force configuration through environment variables",
-            )?)
+            Toml::file({
+                let name = "GRAPEVINE_CONFIG";
+                Env::var(name).ok_or(Error::ConfigPathUnset(name))?
+            })
             .nested(),
         )
         .merge(Env::prefixed("GRAPEVINE_").global());
@@ -164,11 +172,13 @@ async fn try_main() -> Result<(), Box<dyn std::error::Error>> {
         .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();