Stripe Changes, File Upload Quirks, Scaling Sidekiq

Chris and Andrew catch up after Andrew’s whirlwind “vacation-ish” road trip before diving into Stripe’s latest announcements, usage-based billing, merchant-of-record pricing, Rails file upload quirks, Active Storage image handling, Sidekiq queue strategy, and the future of RubyGems. They also discuss browser form behavior, preserving and deleting attachments, image variant performance, and how to think more clearly about background job priorities. Hit download now to hear more!

Links

• Judoscale- Remote Ruby listener gift
• Dungeon Crawler Carl
• Everything we announced at Sessions 2026 (Stripe Blog)
• Scaling Sidekiq at Gusto (Medium)
• Scaling-Sidekiq -GitHub
• Nate Berkopec post on LinkedIn-Running Containers

• Chris Oliver X/Twitter
• Andrew Mason X/Twitter
• Jason Charnes X/Twitter