diff --git a/lib/rails_ext/active_storage_analyze_job_retries.rb b/lib/rails_ext/active_storage_analyze_job_retries.rb
new file mode 100644
index 000000000..1d9f2c9b8
--- /dev/null
+++ b/lib/rails_ext/active_storage_analyze_job_retries.rb
@@ -0,0 +1,23 @@
+# Avoid sporadic ActiveStorage::FileNotFoundError errors
+#
+# Our direct-uploads aren't really direct. They first get buffered by CloudFlare
+# and then get sent to our storage servers. This can lead to situations where
+# a form was submitted, and ActiveStorage::Attachment created, and an
+# AnalyzeJob enqueued, but the file associated with the Blob doesn't yet exist
+# in our storage service.
+#
+# A simple olution ot this problem is just to retry the job a few times with
+# some backoff.
+#
+# Discussion: https://app.fizzy.do/5986089/cards/3056
+module ActiveStorageAnalyzeJobRetires
+  extend ActiveSupport::Concern
+
+  included do
+    retry_on ActiveStorage::FileNotFoundError, attempts: 15, wait: 2.seconds
+  end
+end
+
+ActiveSupport.on_load :active_storage_blob do
+  ActiveStorage::AnalyzeJob.prepend ActiveStorageAnalyzeJobRetires
+end