From 8ddea11599c7d0f12c8acdcbc9d6237b06b12a1f Mon Sep 17 00:00:00 2001
From: "copilot-swe-agent[bot]" <198982749+Copilot@users.noreply.github.com>
Date: Tue, 24 Mar 2026 13:57:08 +0000
Subject: [PATCH] Tighten retry exhaustion state handling

Co-authored-by: jjmata <187772+jjmata@users.noreply.github.com>
Agent-Logs-Url: https://github.com/we-promise/sure/sessions/ea7a06f4-8344-4a00-877a-eda8cdfdc16a
---
 app/models/sync.rb       |  5 +++--
 test/models/sync_test.rb | 12 ++++++++++++
 2 files changed, 15 insertions(+), 2 deletions(-)

diff --git a/app/models/sync.rb b/app/models/sync.rb
index ba19bac01..faccac42b 100644
--- a/app/models/sync.rb
+++ b/app/models/sync.rb
@@ -108,7 +108,7 @@ class Sync < ApplicationRecord
       # Retry exhaustion can leave the sync in `pending` because we reset it
       # after each rate-limit error to make the next ActiveJob retry retryable.
       start! if pending?
-      fail! if may_fail?
+      fail!
       update!(error: error_message)
     end
 
@@ -167,7 +167,8 @@ class Sync < ApplicationRecord
     def reset_for_retry!
       # We intentionally bypass callbacks/state events here so the same sync record
       # can become retryable again without firing post-sync hooks or extra
-      # transition side effects while the job is being retried.
+      # transition side effects while the TwelveData rate-limit error is being
+      # re-raised back to `SyncJob.retry_on`.
       update_columns(
         status: "pending",
         error: nil,
diff --git a/test/models/sync_test.rb b/test/models/sync_test.rb
index ecb78f816..ae9c515a9 100644
--- a/test/models/sync_test.rb
+++ b/test/models/sync_test.rb
@@ -76,6 +76,18 @@ class SyncTest < ActiveSupport::TestCase
     assert_not_nil sync.failed_at
   end
 
+  test "fail_for_retry_exhaustion! marks syncing sync as failed" do
+    sync = Sync.create!(syncable: accounts(:depository))
+    sync.start!
+
+    sync.fail_for_retry_exhaustion!("rate limited too many times")
+
+    sync.reload
+    assert_equal "failed", sync.status
+    assert_equal "rate limited too many times", sync.error
+    assert_not_nil sync.failed_at
+  end
+
   test "can run nested syncs that alert the parent when complete" do
     family = families(:dylan_family)
     plaid_item = plaid_items(:one)