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Buttondown's blog

Email could have been X.400 times better The physicists who convinced Fermilab to send Brazil's emails Better in-app previews Analytics 3.0 Subscriber ID variables Comments! Send latest premium action Automation filtering Free API subscribers Surveys in automations Reply to replies Labels for RSS feeds How Jeremy Singer-Vine curates curious datasets for readers 2023 (and what's next) Email vs web content Sort by engagement Better gift subscriptions How Andy Dehnart built a career reviewing television New email template Email-based automations Opt-in reply tracking Automatic alt text More social network integrations Sort by metadata Overlarge image warnings Automation tag actions Pause emails mid-flight Search tags and automations Gift via automations Subscriber-driving emails Programmatic webhooks Email page views Tag statistics Discord webhook formatting Automatic subscriber cleanup RSS subscriber count Weekly subscriber reports More list columns Customizable list views How Max Voltar turned a side gig into a trusted keyboard resource How Nick Disabato runs two newsletters from one design consultancy Made-for-you share images Automation improvements End-of-email surveys Filter by date Survey-triggered automations More automation functionality New webhooks How France Insider built a news service with paid subscribers Email as primary key How John Willshire unites two businesses in one newsletter Confirmation reminders Email churned subscribers Email-to-draft Subscriber metadata columns ChatGPT integration Faster web archives Referral program Better search results TikTok embeds Subscriber timeline Spotify embeds Improved RSS-to-email Subscribe page OG image New analytics page Google Tag Manager Even more subscriber types Integrating Duda with Buttondown Linktree integration guide Advanced and enterprise plans Framer integration guide API requests page Team collaboration In-email surveys Better CSS settings Better RSS automation fetching! Editor toolbar improvements Smart filters Faster emails page RSS automations Faster email analytics Zapier error codes Image accessibility checks Tags vs newsletters OG image picker Image editor improvements API bulk actions Improved OpenAPI spec Mastodon support Better subscriber filtering Better subscriber validation Hotkey support! Programmatic access to analytics Stronger bulk actions Faster archive page Custom canonical URLs Email slug and metadata Improved writing interface Generating a Typescript router in Django Filter emails by source
Public postmortem: email timeouts
Justin Duke · 2025-03-14 · via Buttondown's blog

Here is the not-so-fun thing about running an email service provider: you get malicious actors trying to use your infrastructure for, well, malice — phishing, spoofing, et cetera.

We have a lot of defenses in place for this, but we detected someone with a relatively novel approach of trying to pass in problematic URLs which we weren't catching. Our other various systems did catch and apprehend this user before they were able to send any emails, but in our haste to push forward a solution quickly we didn't backtest the performance of this solution — in particular, it added a very serious lag to particularly long emails, causing some of them to time out when you went to go and send them (either via the UI or the API.)

Normally, when something like this happens we just roll back to stem the bleeding; because this was also a bit of a security/fraud issue, we opted to roll forward and try and fix it live. We are all set now, but apologies if you had issues sending over the last 24 hours; we take that critical path seriously, and hope you understand (and forgive) the interruption.