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文章列表

Compulsive curiosity, or, how I built an infinite idea machine Gift details on the subscriber portal Portal link in the archive nav First, add no friction: How micropayments lost and subscriptions won Filter subscribers and automations by source Automations, rebuilt What email will look like in the future Filter subscribers by bounce date and reason Email could have been X.400 times better Three features are moving behind the paywall Firewall changes and improvements Put your name and voice into your company newsletter Subscription wall Simplified email address settings Inboxes were overwhelming before we'd even named them The US government tried really hard to screw up email Public postmortem: database connection exhaustion Ask a nerd: what is the best way to unsubscribe from newsletters? Bookshop.org embeds Email was into agents before they were cool Passwordless login Rename metadata keys in bulk A spring cleaning for our legal docs Ask a nerd: what happens when you click the spam button? Passkey support for two-factor authentication How Buttondown's API versioning works Safer defaults for the email creation API How to send email to space How we enabled Content Security Policy for everyone Recovery codes for two-factor authentication Filter sent emails by engagement rate How we migrated to TypeIDs without breaking clients Should we bring back email exploders? Use newsletter metadata in your emails Sort and filter by open and click rates Custom click tracking domains More newsletter settings in the API Revamped replies Custom email templates for everyone Simplified cancellation Ask a Nerd: Does email length affect deliverability? The changelog, reborn Swedish localization Forwarding an email is not always straightforward
How we check every link in your email
Justin Duke · 2026-02-28 · via

One of the scariest parts about hitting "send" on an email is the feeling that there's no takesies-backsies. As soon as it starts hitting people's inboxes, you are left without a mechanism to fix any mistakes. A broken link in a blog post is a minor embarrassment; a broken link in an email to ten thousand subscribers is a small catastrophe.

This is why Buttondown checks every link in your email before you send it, and why the machinery behind that check is more involved than you might expect.

Our link checking infrastructure makes the most sense viewed through the lens of its development: just like in so many things, we started naively and grew increasingly robust over time.

---
config:
  layout: elk
  elk:
    mergeEdges: true
    nodePlacementStrategy: LINEAR_SEGMENTS
---

flowchart-elk
    A["Extract URLs from email body"] --> B{"Malformed?"}

    B -- "Yes" --> WARN
    B -- "No" --> D{"Cached?"}

    D -- "Hit (safe)" --> SAFE
    D -- "Hit (warn)" --> WARN
    D -- "Hit (block)" --> BLOCK
    D -- "Miss" --> F["HEAD https://foo.com"]

    F --> G{"2xx?"}
    G -- "Yes" --> L
    G -- "No (404/405)" --> I["GET https://foo.com"]
    I --> J{"2xx?"}
    J -- "Yes" --> L
    J -- "No / Timeout" --> WARN



    L["Check external services (Google Web Risk, SURBL, Spamhaus)"] --> M{"Flagged?"}
    M -- "No" --> SAFE
    M -- "Yes" --> BLOCK

    SAFE["Safe to send"] --> P
    WARN["Broken link warning"] --> P
    BLOCK["Block send"] --> P

    P[("Cache result (client + server)")]

    subgraph Client-Side
        A
        B
        D
    end

    subgraph Server-Side
        F
        G
        I
        J
        L
        M
    end

    classDef reject fill:#dc2626,stroke:#991b1b,color:#fff
    classDef success fill:#16a34a,stroke:#166534,color:#fff
    classDef warn fill:#ca8a04,stroke:#854d0e,color:#fff
    classDef process fill:#2563eb,stroke:#1e40af,color:#fff
    classDef cache fill:#9333ea,stroke:#6b21a8,color:#fff

    class BLOCK reject
    class SAFE success
    class WARN warn
    class F,I,L process
    class P cache

You might be wondering what actually processes the asynchronous work mentioned above. We used to use RQ exclusively (and still do in a handful of places), but this and other workloads have moved to AsynchronousAction, our home-built Postgres-based task runner. We'll write more about it soon!