diff --git a/CHANGELOG.md b/CHANGELOG.md
index 49f6d2f09..35514d558 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,4 +1,6 @@
 # Unreleased
+* (bugfix) Retry GitHub server errors in background jobs with polynomial backoff for ten attempts
+  (about 4.3 hours plus jitter), retaining error reporting when retries are exhausted.
 
 # 0.45.5
 * (bugfix) Update existing check runs without first attempting a duplicate insert. Concurrent
diff --git a/app/jobs/shipit/background_job.rb b/app/jobs/shipit/background_job.rb
index cef3c3cff..3a14093a1 100644
--- a/app/jobs/shipit/background_job.rb
+++ b/app/jobs/shipit/background_job.rb
@@ -8,8 +8,8 @@ class << self
 
     DEFAULT_RETRY_TIME_IN_SECONDS = 30
 
-    # Write actions can sometimes fail intermittently, particulary for large and/or busy repositories
-    retry_on(Octokit::ServerError)
+    # Allow hours for GitHub outages to recover while still raising after the last attempt.
+    retry_on(Octokit::ServerError, wait: :polynomially_longer, attempts: 10)
 
     rescue_from(Octokit::TooManyRequests, Octokit::AbuseDetected) do |exception|
       retry_job wait: exception.response_headers.fetch("Retry-After", DEFAULT_RETRY_TIME_IN_SECONDS).to_i.seconds
diff --git a/test/jobs/shipit/background_job_test.rb b/test/jobs/shipit/background_job_test.rb
index d1e5ddfaa..daa313755 100644
--- a/test/jobs/shipit/background_job_test.rb
+++ b/test/jobs/shipit/background_job_test.rb
@@ -24,8 +24,29 @@ class BackgroundJobTest < ActiveSupport::TestCase
       end
     end
 
+    test "#perform backs off GitHub server errors and re-raises after ten attempts" do
+      Shipit.github.api.expects(:user).with(@user.github_id).times(10).raises(Octokit::InternalServerError)
+      job = BackgroundStubJob.new(@user).serialize
+
+      freeze_time do
+        (1..9).each do |execution|
+          clear_enqueued_jobs
+          assert_enqueued_with(job: BackgroundStubJob, at: Time.now + (execution**4 + 2).seconds) do
+            ActiveJob::Base.execute(job)
+          end
+          job = enqueued_jobs.last
+        end
+
+        clear_enqueued_jobs
+        assert_no_enqueued_jobs do
+          assert_raises(Octokit::InternalServerError) { ActiveJob::Base.execute(job) }
+        end
+      end
+    end
+
     class BackgroundStubJob < BackgroundJob
       queue_as :default
+      self.retry_jitter = 0.0
 
       def perform(user)
         Shipit.github.api.user(user.github_id)
diff --git a/test/jobs/shipit/create_on_github_job_test.rb b/test/jobs/shipit/create_on_github_job_test.rb
index 907b409b8..8937f408e 100644
--- a/test/jobs/shipit/create_on_github_job_test.rb
+++ b/test/jobs/shipit/create_on_github_job_test.rb
@@ -25,5 +25,37 @@ class CreateOnGithubJobTest < ActiveSupport::TestCase
 
       assert_nothing_raised { job.perform_now }
     end
+
+    test "#perform retries failed deployment statuses without recreating published records" do
+      status = shipit_commit_deployment_statuses(:shipit2_deploy_third_in_progress)
+      deployment = status.commit_deployment
+      shipit_commit_deployment_statuses(:shipit2_deploy_third_failure).update!(github_id: 43)
+      response = stub(id: 44, url: "#{deployment.api_url}/statuses/44")
+      client_class = deployment.stack.github_api.class
+      client_class.any_instance.expects(:create_deployment).never
+      client_class.any_instance.expects(:create_deployment_status)
+                  .with(deployment.api_url, 'in_progress', anything).twice
+                  .raises(Octokit::InternalServerError).then.returns(response)
+
+      assert_enqueued_with(job: CreateOnGithubJob) { CreateOnGithubJob.perform_now(deployment) }
+      assert_nil status.reload.github_id
+
+      retry_job = enqueued_jobs.last
+      clear_enqueued_jobs
+      assert_no_enqueued_jobs { ActiveJob::Base.execute(retry_job) }
+
+      assert_equal response.id, status.reload.github_id
+      assert_equal response.url, status.api_url
+    end
+
+    test "#perform re-raises after exhausting GitHub server error retries" do
+      CommitDeployment.any_instance.stubs(:create_on_github!).raises(Octokit::InternalServerError)
+      job = CreateOnGithubJob.new(@deployment)
+      job.exception_executions = { "[Octokit::ServerError]" => 9 }
+
+      assert_no_enqueued_jobs do
+        assert_raises(Octokit::InternalServerError) { job.perform_now }
+      end
+    end
   end
 end
diff --git a/test/jobs/shipit/refresh_check_runs_job_test.rb b/test/jobs/shipit/refresh_check_runs_job_test.rb
new file mode 100644
index 000000000..d8116cf4e
--- /dev/null
+++ b/test/jobs/shipit/refresh_check_runs_job_test.rb
@@ -0,0 +1,18 @@
+# frozen_string_literal: true
+
+require 'test_helper'
+
+module Shipit
+  class RefreshCheckRunsJobTest < ActiveSupport::TestCase
+    test "#perform backs off GitHub server errors" do
+      Commit.any_instance.stubs(:refresh_check_runs!).raises(Octokit::InternalServerError)
+      job = RefreshCheckRunsJob.new(commit_id: shipit_commits(:first).id)
+      job.exception_executions = { "[Octokit::ServerError]" => 1 }
+
+      freeze_time do
+        retry_time = ->(at) { (18.seconds.from_now..20.4.seconds.from_now).cover?(at) }
+        assert_enqueued_with(job: RefreshCheckRunsJob, at: retry_time) { job.perform_now }
+      end
+    end
+  end
+end