Evaluating Webhook Infrastructure for Sending Webhooks

Webhook infrastructure sounds simple. Your platform has users, so when something important happens—a payment processes, a message arrives, a record updates—you need to notify them. Webhooks are the obvious solution: send an HTTP POST to their endpoint. But as any team that's shipped webhooks to production knows, the devil is in the details. One webhook silently failing could mean big problems for a customer: a payment gets missed, a CI task fails to run, or an order doesn't get processed.

The difference between a basic webhook implementation and one that reliably delivers events at scale involves navigating authentication, retry logic, monitoring, security, and operational overhead that most teams underestimate. This is why many platforms are moving beyond building custom webhook systems and instead evaluating managed, purpose-built solutions.

This guide walks you through the key considerations for evaluating webhook infrastructure, the critical features that matter most, and how to align your selection with your team's priorities and constraints.

The Hidden Complexity of Sending Webhooks

Before evaluating solutions, it's important to understand why webhooks require more engineering investment than you might expect.

Webhooks fail for a number of reasons that rarely surface during development or testing. Whether there's a network error, a server goes down, or a request simply times out. Yet, they have a high bar for reliability. In order for webhooks to be useful to customers, you can't drop a webhook here and there - they need to fire (and get delivered) every time. Since customers have no control over webhooks - they just arrive - they have no way of knowing if they've missed one or not. Plus, they need to be timely. Depending on the use-case, even a delay of several seconds could render the notification useless.

Given that customers don't control them, a portal for them to add and remove endpoints, inspect logs and test, inspect and replay their webhooks becomes essential to scaling your offering (if you don't want to drown in support requests).

You don't control the recipient's endpoints, either. HTTP servers each have their own quirks and differences, which you'll need to work around. And they'll fail or not respond more often than you expect, too.

Plus, webhooks come with a number of security concerns, from SSRF to replay attacks, and you'll want to sign requests so customers can ensure their authenticity.

With these challenges in mind, you need to think seriously about the system you'll use to send webhooks.

Why Use a Purpose-built Tool?

The traditional approach to sending webhooks involves a stack of tools: message queues (Kafka, RabbitMQ, AWS SQS), consumer runtimes (Lambda, Kubernetes), storage (Postgres, DynamoDB), alerting (Datadog, New Relic), and custom scripts for retries and troubleshooting. This works, but it's expensive to build, maintain, and operate.

The burden falls on your team:

• Maintaining multiple tools from different vendors
• No standardized workflow
• Quality directly proportional to your team's webhook expertise
• Onboarding challenges for new engineers
• Best-effort resiliency (often suboptimal)
• Coordination overhead when vendors introduce breaking changes

The alternative is managed webhook infrastructure—a single, focused solution designed specifically for reliable event delivery. This shifts the burden from your team to a specialized platform. But which is the right fit for you and your team?

Key Priorities for Evaluating Webhook Infrastructure

Let's take a look at the key functionality you should expect from a webhook sending solution.

1. Reliability and Delivery Guarantees

The requirement: Your webhook infrastructure must guarantee at-least-once delivery. Events should never be lost.

What to look for:

• At-least-once delivery guarantee: The platform explicitly commits to never losing an event, even during system failures.
• Automatic retry logic with exponential backoff: Retries should be configurable but sensible by default. Exponential backoff prevents overwhelming customers' endpoints.
• Failure handling: When a destination consistently fails, the system should automatically disable it and alert you, preventing endless retry storms.
• Transparent delivery status tracking: You should see exactly what happened to each event: was it delivered? Did it timeout? Did the customer's endpoint return an error?

Why it matters: A single lost event can break customer workflows, trigger support tickets, and damage trust. Reliability is a must.

2. Observability and Monitoring

The requirement: Webhooks operate across your infrastructure and your customers' infrastructure. When something breaks, you need visibility.

What to look for:

• Detailed delivery logs: View each delivery attempt, including request payloads, status codes, and error messages.
• Event inspection and replay: Manually trigger retries for specific events. Inspect the payload that was sent. This is essential for debugging customer issues.
• OpenTelemetry integration: For teams using observability platforms, native OTel support enables correlation with your existing monitoring stack.

Why it matters: Observability and alerting about delivery failures or auto-disabled destinations can mean the difference between you catching an issue, or your customer spotting it first.

3. Multi-Tenant Support and Per-Customer Configuration

The requirement: Different customers have different needs. Some want webhooks only. Others need to push events into their AWS SQS queues. Some require custom retry policies or payload transformations.

What to look for:

• Native multi-tenant support: The platform should handle multiple tenants on a single deployment without cross-tenant leakage.
• Flexible destination types: Support for webhooks, but also AWS SQS, RabbitMQ, Kafka, Amazon EventBridge, GCP Pub/Sub, and others. This is critical because it reduces your customers' operational burden.
• Topic-based subscriptions: Let customers subscribe only to the events they care about, reducing noise and payload sizes.
• Destination-level filtering: Customers should be able to filter events by payload content before they're delivered (e.g., "only send me webhook events where the status is 'completed'").
• Configurable retry policies: Some customers need aggressive retries; others prefer faster failure detection. Per-destination configuration matters.

Why it matters: The more flexibility you offer customers, the more use cases you can support. Customers increasingly expect event delivery to their infrastructure of choice, not just webhooks.

4. Security and Best Practices

The requirement: Secure by default, but not complex. Many implementations get this wrong.

What to look for:

• Header customization: Control which headers are sent, including authentication headers, timestamps, and signatures.
• Signature verification: The platform should automatically sign webhooks using HMAC or similar cryptographic methods.
• Signature rotation: Support for rolling out new signing keys without invalidating existing ones.
• Idempotency headers: Include unique identifiers in each delivery attempt so customers can deduplicate if the same event is delivered twice.
• Timestamps: Include delivery timestamps so customers can detect stale events.
• SSRF and security hardening: The platform should protect against SSRF attacks and other webhook-specific vulnerabilities.
• Event Destination security requirement support: For some event destination types, security isn't opt-in; it's required. Make sure security measures for the event destinations you need are supported.

Why it matters: Webhook security isn't an afterthought. Platforms that handle this out-of-the-box eliminate entire classes of vulnerabilities.

5. Customer and Developer Experience

The requirement: Your customers need to see what's happening with their webhooks and your developers need to work with the platform you choose.

What to look for:

• Tenant user portal: A UI where customers can register webhook URLs, view delivery history, manually replay events, and inspect logs.
• Clear documentation and examples: Comprehensive guides for common use cases and tutorials for working with the platform.
• SDK support: SDKs that help you integrate your applications with your webhook sending solution.

Why it matters: Good CX reduces your support burden and improves customer adoption, while great DX accelerates time-to-integration and reduces operational overhead.

Beyond Webhooks: Supporting Event Destinations

Another consideration is whether supporting just webhooks is enough. A critical evolution is happening in the webhook and event delivery space. Leading platforms like Stripe, Shopify, and Twilio are moving beyond webhooks-only solutions toward Event Destinations.

What Are Event Destinations?

Event Destinations allow customers to choose where their events are delivered:

• Traditional webhooks for reach and compatibility
• Message queues (AWS SQS, RabbitMQ, Kafka) for customers who want to decouple event consumption
• Event buses (Amazon EventBridge) for customers building event-driven architectures
• Managed services (Hookdeck Event Gateway, GCP Pub/Sub) for customers who want managed reliability

This matters because webhooks have fundamental limitations:

• Webhooks require customers to run and maintain HTTP endpoints
• They lack standardization in retries, timeouts, and security
• They're suboptimal for high-throughput scenarios
• Failure rates are high due to endpoint variability

By supporting Event Destinations, you eliminate these problems. Customers can push events directly to their infrastructure, bypassing HTTP overhead entirely.

Why Consider Event Destinations Support?

For your customers:

• Reduced operational overhead: No need to maintain HTTP endpoints
• Improved reliability: Direct integration to message queues and event buses is more reliable than HTTP
• Better developer experience: Use familiar tools and patterns from their infrastructure
• Built-in scalability: Message queues handle buffering and scaling automatically

For your platform:

• Lower failure rates: Message queues don't timeout or hang like HTTP endpoints
• Reduced retries and costs: Fewer failed deliveries means lower operational costs
• Extensibility: Support more customer use cases without custom code
• Future-proofing: Align with industry evolution toward event-driven architectures

If you're evaluating webhook infrastructure, ask whether the solution supports Event Destinations or provides a path toward supporting them.

Self-Hosted vs. Managed Solutions

Your choice between self-hosted and managed webhook infrastructure depends on your constraints and priorities.

Self-Hosted Solutions (e.g. Outpost)

Pros:

• Full control: Your infrastructure, your compliance rules, your data residency.
• Cost efficiency at scale: No per-event pricing; you pay for compute and storage.
• Privacy: Events never leave your infrastructure.
• Customization: Extend the system to meet bespoke requirements.

Cons:

• Operational burden: You maintain the deployment, updates, and monitoring.
• Initial complexity: Setup, configuration, and integration require engineering time.
• Scaling responsibility: As volume grows, you manage scaling decisions.

When to choose self-hosted: You have infrastructure expertise, strict data residency requirements, or high event volumes where per-event pricing becomes prohibitive.

Managed Services (e.g. Hookdeck Outpost)

Pros:

• Minimal operational overhead: The vendor handles infrastructure, scaling, and maintenance.
• Faster time-to-value: Integration is usually quicker.
• Vendor support: Dedicated support teams help troubleshoot issues.

Cons:

• Vendor lock-in: Your webhooks depend on the platform's uptime and roadmap.
• Per-event pricing: Costs scale with event volume.
• Data sensitivity: Events transit through or are stored by an external vendor.

When to choose managed: You prioritize time-to-market, have limited infrastructure expertise, or don't want operational responsibility.

Why not both?

Perhaps your solution needs both a managed and self-hosted option, for example, if your customers need on-prem deployments. Then you should look for solutions which have parity between their managed and self-hosted options, like Hookdeck Outpost, for example. No private forks or proprietary versions—it's the same Outpost.

Conclusion: Choosing Webhook Infrastructure

Webhook infrastructure is no longer something every platform needs to build from scratch. The maturity of managed solutions and open-source tools like Outpost means you can focus on your product while offloading the complexity of reliable event delivery.

There's no single right answer as to which option is best for you. But by evaluating solutions against your team's constraints, use case complexity, and infrastructure maturity, you'll make a decision that serves your platform and customers well.