diff --git a/src/bot/commands/gcal.rs b/src/bot/commands/gcal.rs
index aadb86f..f73fd7b 100644
--- a/src/bot/commands/gcal.rs
+++ b/src/bot/commands/gcal.rs
@@ -80,7 +80,19 @@ pub async fn gcal(
     let response: Vec<LinkDetail> = match meeting_times.len() {
         0 => Err(anyhow::anyhow!("No meeting times found for this course.")),
         1.. => {
-            let links = meeting_times
+            // Sort meeting times by start time of their TimeRange
+            let mut sorted_meeting_times = meeting_times.to_vec();
+            sorted_meeting_times.sort_unstable_by(|a, b| {
+                // Primary sort: by start time
+                match (&a.time_range, &b.time_range) {
+                    (Some(a_time), Some(b_time)) => a_time.start.cmp(&b_time.start),
+                    (Some(_), None) => std::cmp::Ordering::Less,
+                    (None, Some(_)) => std::cmp::Ordering::Greater,
+                    (None, None) => a.days.bits().cmp(&b.days.bits()),
+                }
+            });
+
+            let links = sorted_meeting_times
                 .iter()
                 .map(|m| {
                     let link = generate_gcal_url(&course, m)?;
diff --git a/src/main.rs b/src/main.rs
index 0348c29..b0b13a2 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -1,6 +1,6 @@
 use serenity::all::{ClientBuilder, GatewayIntents};
 use tokio::signal;
-use tracing::{error, info, warn};
+use tracing::{debug, error, info, warn};
 use tracing_subscriber::{EnvFilter, FmtSubscriber};
 
 use crate::app_state::AppState;
@@ -132,7 +132,7 @@ async fn main() {
             // Shutdown remaining services
             match service_manager.shutdown(shutdown_timeout).await {
                 Ok(()) => {
-                    info!("Graceful shutdown complete");
+                    debug!("Graceful shutdown complete");
                 }
                 Err(pending_services) => {
                     warn!(
@@ -147,7 +147,7 @@ async fn main() {
             // User requested shutdown
             match service_manager.shutdown(shutdown_timeout).await {
                 Ok(()) => {
-                    info!("Graceful shutdown complete");
+                    debug!("Graceful shutdown complete");
                 }
                 Err(pending_services) => {
                     warn!(
@@ -160,6 +160,6 @@ async fn main() {
         }
     }
 
-    info!("Application shutdown complete (exit code: {})", exit_code);
+    info!(exit_code = exit_code, "Shutdown complete");
     std::process::exit(exit_code);
 }