diff --git a/src/bin/enqueue-job.rs b/src/bin/enqueue-job.rs
index 42a59d41b28..94db422c14f 100644
--- a/src/bin/enqueue-job.rs
+++ b/src/bin/enqueue-job.rs
@@ -1,6 +1,8 @@
 #![deny(clippy::all)]
 
 use cargo_registry::{db, env, tasks, util::Error};
+use diesel::prelude::*;
+use swirl::schema::background_jobs::dsl::*;
 use swirl::Job;
 
 fn main() -> Result<(), Error> {
@@ -11,7 +13,20 @@ fn main() -> Result<(), Error> {
     println!("Enqueueing background job: {}", job);
 
     match &*job {
-        "update_downloads" => Ok(tasks::update_downloads().enqueue(&conn)?),
+        "update_downloads" => {
+            let count: i64 = background_jobs
+                .filter(job_type.eq("update_downloads"))
+                .count()
+                .get_result(&conn)
+                .unwrap();
+
+            if count > 0 {
+                println!("Did not enqueue update_downloads, existing job already in progress");
+                Ok(())
+            } else {
+                Ok(tasks::update_downloads().enqueue(&conn)?)
+            }
+        }
         "dump_db" => {
             let database_url = args.next().unwrap_or_else(|| env("READ_ONLY_REPLICA_URL"));
             let target_name = args
diff --git a/src/bin/monitor.rs b/src/bin/monitor.rs
index 1e2f550172a..aa55ac233da 100644
--- a/src/bin/monitor.rs
+++ b/src/bin/monitor.rs
@@ -14,20 +14,30 @@ use diesel::prelude::*;
 fn main() -> Result<(), Error> {
     let conn = db::connect_now()?;
 
-    check_stalled_background_jobs(&conn)?;
+    check_failing_background_jobs(&conn)?;
+    check_stalled_update_downloads(&conn)?;
     check_spam_attack(&conn)?;
     Ok(())
 }
 
-fn check_stalled_background_jobs(conn: &PgConnection) -> Result<(), Error> {
+/// Check for old background jobs that are not currently running.
+///
+/// This check includes `skip_locked` in the query and will only trigger on
+/// enqueued jobs that have attempted to run and have failed (and are in the
+/// queue awaiting a retry).
+///
+/// Within the default 15 minute time, a job should have already had several
+/// failed retry attempts.
+fn check_failing_background_jobs(conn: &PgConnection) -> Result<(), Error> {
     use cargo_registry::schema::background_jobs::dsl::*;
     use diesel::dsl::*;
     use diesel::sql_types::Integer;
 
     const EVENT_KEY: &str = "background_jobs";
 
-    println!("Checking for stalled background jobs");
+    println!("Checking for failed background jobs");
 
+    // Max job execution time in minutes
     let max_job_time = dotenv::var("MAX_JOB_TIME")
         .map(|s| s.parse::<i32>().unwrap())
         .unwrap_or(15);
@@ -59,6 +69,44 @@ fn check_stalled_background_jobs(conn: &PgConnection) -> Result<(), Error> {
     Ok(())
 }
 
+/// Check for an `update_downloads` job that has run longer than expected
+fn check_stalled_update_downloads(conn: &PgConnection) -> Result<(), Error> {
+    use cargo_registry::schema::background_jobs::dsl::*;
+    use chrono::{DateTime, NaiveDateTime, Utc};
+
+    const EVENT_KEY: &str = "update_downloads_stalled";
+
+    println!("Checking for stalled background jobs");
+
+    // Max job execution time in minutes
+    let max_job_time = dotenv::var("MONITOR_MAX_UPDATE_DOWNLOADS_TIME")
+        .map(|s| s.parse::<u32>().unwrap() as i64)
+        .unwrap_or(120);
+
+    let start_time = background_jobs
+        .filter(job_type.eq("update_downloads"))
+        .select(created_at)
+        .first::<NaiveDateTime>(conn);
+
+    if let Ok(start_time) = start_time {
+        let start_time = DateTime::<Utc>::from_utc(start_time, Utc);
+        let minutes = Utc::now().signed_duration_since(start_time).num_minutes();
+
+        if minutes > max_job_time {
+            return log_and_trigger_event(on_call::Event::Trigger {
+                incident_key: Some(EVENT_KEY.into()),
+                description: format!("update_downloads job running for {} minutes", minutes),
+            });
+        }
+    };
+
+    log_and_trigger_event(on_call::Event::Resolve {
+        incident_key: EVENT_KEY.into(),
+        description: Some("No stalled update_downloads job".into()),
+    })
+}
+
+/// Check for known spam patterns
 fn check_spam_attack(conn: &PgConnection) -> Result<(), Error> {
     use cargo_registry::models::krate::canon_crate_name;
     use diesel::dsl::*;