diff --git a/src/main.rs b/src/main.rs
index 856eb18..b1633b3 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -487,15 +487,15 @@ fn main_auto(cli: CliAuto) -> Result<()> {
 fn main_debug_output(cli: CliDebugOutput) -> Result<()> {
     tracing_subscriber::fmt::init();
     tracing::info!("Started tracing");
-    let config = std::fs::read_to_string(&cli.config)?;
-    let config: Config = toml::from_str(&config)?;
+    let config = std::fs::read_to_string(&cli.config).context("Failed to read config file")?;
+    let config: Config = toml::from_str(&config).context("Failed to parse config file")?;
 
-    let data = read_data_from_disk(&config)?;
+    let data = read_data_from_disk(&config).context("Failed to read data from disk")?;
 
     let tz = &config.output.timezone;
     let now = Utc::now().with_timezone(tz);
-    let instances = process_data(&data, &config.output, now)?;
-    output_html(&config.output, &instances, now)?;
+    let instances = process_data(&data, &config.output, now).context("Failed to process data")?;
+    output_html(&config.output, &instances, now).context("Failed to output HTML")?;
 
     Ok(())
 }