diff --git a/src/background_jobs.rs b/src/background_jobs.rs
index 5f011150824..deef5340a11 100644
--- a/src/background_jobs.rs
+++ b/src/background_jobs.rs
@@ -1,5 +1,5 @@
 use std::panic::AssertUnwindSafe;
-use std::sync::{Mutex, MutexGuard, PoisonError};
+use std::sync::{Arc, Mutex, MutexGuard, PoisonError};
 use swirl::PerformError;
 
 use crate::db::{DieselPool, DieselPooledConn};
@@ -21,7 +21,7 @@ impl swirl::db::DieselPool for DieselPool {
 
 #[allow(missing_debug_implementations)]
 pub struct Environment {
-    index: Mutex<Repository>,
+    index: Arc<Mutex<Repository>>,
     pub credentials: Option<(String, String)>,
     // FIXME: https://github.com/sfackler/r2d2/pull/70
     pub connection_pool: AssertUnwindSafe<DieselPool>,
@@ -29,6 +29,20 @@ pub struct Environment {
     http_client: AssertUnwindSafe<reqwest::Client>,
 }
 
+// FIXME: AssertUnwindSafe should be `Clone`, this can be replaced with
+// `#[derive(Clone)]` if that is fixed in the standard lib
+impl Clone for Environment {
+    fn clone(&self) -> Self {
+        Self {
+            index: self.index.clone(),
+            credentials: self.credentials.clone(),
+            connection_pool: AssertUnwindSafe(self.connection_pool.0.clone()),
+            uploader: self.uploader.clone(),
+            http_client: AssertUnwindSafe(self.http_client.0.clone()),
+        }
+    }
+}
+
 impl Environment {
     pub fn new(
         index: Repository,
@@ -38,7 +52,7 @@ impl Environment {
         http_client: reqwest::Client,
     ) -> Self {
         Self {
-            index: Mutex::new(index),
+            index: Arc::new(Mutex::new(index)),
             credentials,
             connection_pool: AssertUnwindSafe(connection_pool),
             uploader,
diff --git a/src/bin/background-worker.rs b/src/bin/background-worker.rs
index 5caf09d5644..a1350263845 100644
--- a/src/bin/background-worker.rs
+++ b/src/bin/background-worker.rs
@@ -1,11 +1,14 @@
-// Runs enqueued background jobs
-//
-// This binary will loop until interrupted. Every second, it will attempt to
-// run any jobs in the background queue. Panics if attempting to count
-// available jobs fails.
-//
-// Usage:
-//      cargo run --bin background-worker
+//! Runs enqueued background jobs
+//!
+//! This binary will loop until interrupted. It will run all jobs in the
+//! background queue, sleeping for 1 second whenever the queue is empty. If we
+//! are unable to spawn workers to run jobs (either because we couldn't connect
+//! to the DB, an error occurred while loading, or we just never heard back from
+//! the worker thread), we will rebuild the runner and try again up to 5 times.
+//! After the 5th occurrance, we will panic.
+//!
+//! Usage:
+//!      cargo run --bin background-worker
 
 #![deny(warnings, clippy::all, rust_2018_idioms)]
 
@@ -20,8 +23,13 @@ fn main() {
 
     let config = cargo_registry::Config::default();
 
-    // We're only using 1 thread, so we only need 2 connections
-    let db_config = r2d2::Pool::builder().max_size(2);
+    // 2x the thread pool size -- not all our jobs need a DB connection,
+    // but we want to always be able to run our jobs in parallel, rather
+    // than adjusting based on how many concurrent jobs need a connection.
+    // Eventually swirl will do this for us, and this will be the default
+    // -- we should just let it do a thread pool size of CPU count, and a
+    // a connection pool size of 2x that when that lands.
+    let db_config = r2d2::Pool::builder().max_size(4);
     let db_pool = db::diesel_pool(&config.db_url, config.env, db_config);
 
     let username = dotenv::var("GIT_HTTP_USER");
@@ -31,6 +39,11 @@ fn main() {
         _ => None,
     };
 
+    let job_start_timeout = dotenv::var("BACKGROUND_JOB_TIMEOUT")
+        .unwrap_or_else(|_| "30".into())
+        .parse()
+        .expect("Invalid value for `BACKGROUND_JOB_TIMEOUT`");
+
     println!("Cloning index");
 
     let repository = Repository::open(&config.index_location).expect("Failed to clone index");
@@ -43,17 +56,31 @@ fn main() {
         reqwest::Client::new(),
     );
 
-    let runner = swirl::Runner::builder(db_pool, environment)
-        .thread_count(1)
-        .job_start_timeout(Duration::from_secs(10))
-        .build();
+    let build_runner = || {
+        swirl::Runner::builder(db_pool.clone(), environment.clone())
+            .thread_count(2)
+            .job_start_timeout(Duration::from_secs(job_start_timeout))
+            .build()
+    };
+    let mut runner = build_runner();
 
     println!("Runner booted, running jobs");
 
+    let mut failure_count = 0;
+
     loop {
-        runner
-            .run_all_pending_jobs()
-            .expect("Could not begin running jobs");
+        if let Err(e) = runner.run_all_pending_jobs() {
+            failure_count += 1;
+            if failure_count < 5 {
+                eprintln!(
+                    "Error running jobs (n = {}) -- retrying: {:?}",
+                    failure_count, e,
+                );
+                runner = build_runner();
+            } else {
+                panic!("Failed to begin running jobs 5 times. Restarting the process");
+            }
+        }
         sleep(Duration::from_secs(1));
     }
 }