diff --git a/src/bin/background-worker.rs b/src/bin/background-worker.rs
index ada1edfd123..2a503748c19 100644
--- a/src/bin/background-worker.rs
+++ b/src/bin/background-worker.rs
@@ -41,6 +41,7 @@ fn main() {
 
     let repository_config = RepositoryConfig::from_environment();
     let repository = Repository::open(&repository_config).expect("Failed to clone index");
+    println!("Index cloned");
 
     let environment = Environment::new(
         repository,
diff --git a/src/bin/enqueue-job.rs b/src/bin/enqueue-job.rs
index f5df8b7cc3c..568efc72811 100644
--- a/src/bin/enqueue-job.rs
+++ b/src/bin/enqueue-job.rs
@@ -5,7 +5,11 @@ use diesel::PgConnection;
 fn main() -> AppResult<()> {
     let conn = db::connect_now()?;
     let mut args = std::env::args().skip(1);
-    match &*args.next().unwrap_or_default() {
+
+    let job = args.next().unwrap_or_default();
+    println!("Enqueueing background job: {}", job);
+
+    match &*job {
         "update_downloads" => tasks::update_downloads().enqueue(&conn),
         "dump_db" => {
             let database_url = args.next().unwrap_or_else(|| env("DATABASE_URL"));
diff --git a/src/tasks/dump_db.rs b/src/tasks/dump_db.rs
index 8d64d1bf184..41d0e2a11d1 100644
--- a/src/tasks/dump_db.rs
+++ b/src/tasks/dump_db.rs
@@ -16,10 +16,16 @@ pub fn dump_db(
     target_name: String,
 ) -> Result<(), PerformError> {
     let directory = DumpDirectory::create()?;
+
+    println!("Begin exporting database");
     directory.populate(&database_url)?;
+
+    println!("Creating tarball");
     let tarball = DumpTarball::create(&directory.export_dir)?;
-    tarball.upload(&target_name, &env.uploader)?;
-    println!("Database dump uploaded to {}.", &target_name);
+
+    println!("Uploading tarball");
+    let size = tarball.upload(&target_name, &env.uploader)?;
+    println!("Database dump uploaded {} bytes to {}.", size, &target_name);
     Ok(())
 }
 
@@ -145,7 +151,7 @@ impl DumpTarball {
         Ok(result)
     }
 
-    fn upload(&self, target_name: &str, uploader: &Uploader) -> Result<(), PerformError> {
+    fn upload(&self, target_name: &str, uploader: &Uploader) -> Result<u64, PerformError> {
         let client = reqwest::Client::new();
         let tarfile = File::open(&self.tarball_path)?;
         let content_length = tarfile.metadata()?.len();
@@ -160,7 +166,7 @@ impl DumpTarball {
                 header::HeaderMap::new(),
             )
             .map_err(std_error_no_send)?;
-        Ok(())
+        Ok(content_length)
     }
 }
 
diff --git a/src/tasks/update_downloads.rs b/src/tasks/update_downloads.rs
index 6feb218b3dc..b59de4b032b 100644
--- a/src/tasks/update_downloads.rs
+++ b/src/tasks/update_downloads.rs
@@ -23,7 +23,10 @@ fn update(conn: &PgConnection) -> QueryResult<()> {
         .filter(processed.eq(false))
         .filter(downloads.ne(counted))
         .load(conn)?;
+
+    println!("Updating {} versions", rows.len());
     collect(conn, &rows)?;
+    println!("Finished updating versions");
 
     // Anything older than 24 hours ago will be frozen and will not be queried
     // against again.
@@ -33,17 +36,18 @@ fn update(conn: &PgConnection) -> QueryResult<()> {
         .filter(downloads.eq(counted))
         .filter(processed.eq(false))
         .execute(conn)?;
+    println!("Finished freezing old version_downloads");
 
     no_arg_sql_function!(refresh_recent_crate_downloads, ());
     select(refresh_recent_crate_downloads).execute(conn)?;
+    println!("Finished running refresh_recent_crate_downloads");
+
     Ok(())
 }
 
 fn collect(conn: &PgConnection, rows: &[VersionDownload]) -> QueryResult<()> {
     use diesel::update;
 
-    println!("updating {} versions", rows.len());
-
     for download in rows {
         let amt = download.downloads - download.counted;