WooCommerce webhooks are disabled after 5 failed retries—with no notification to the store owner. That means critical orders can silently fail to reach your CRM, Klaviyo, or fulfillment system. You don’t know it’s broken until you notice the data stopped flowing.

This isn’t a bug you can fix with configuration. It’s how webhook architecture fundamentally works: WooCommerce attempts to deliver an event, and if the receiving system can’t accept it five times, WooCommerce gives up. Silently.

The reliability problem has been documented in GitHub issues since 2017. Store owners keep discovering their integrations broke weeks ago.

Why WooCommerce Webhooks Fail Intermittently

WooCommerce webhooks use wp_remote_post to send HTTP requests to external endpoints. This architecture depends on multiple things going right simultaneously:

• Your WordPress server must successfully initiate the request
• The receiving endpoint must be available and respond quickly
• No firewall or security plugin can interfere with the connection
• WordPress cron must run to process the Action Scheduler queue

When any link in this chain breaks, the webhook fails. And the failure modes are numerous.

Definition: Action Scheduler is WooCommerce’s background processing system that queues webhook deliveries. It depends on WordPress cron, which only runs when someone visits the site. During low-traffic periods, webhook deliveries can be delayed or missed entirely.

A developer debugging webhook reliability on GitHub noted: “Every now and then the webhook is not added to the table that is read in and then fired by the CRON job” (GitHub WooCommerce Issues, 2017). This intermittent behavior makes the problem particularly difficult to diagnose—webhooks work most of the time, then randomly fail.

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The 5-Retry Silent Disable Problem

According to WooCommerce Developer Documentation, webhooks are disabled after 5 retries by default if the delivery URL returns an unsuccessful status such as 404 or 5xx. There’s no email. No dashboard alert. No indication anything is wrong.

You find out when you realize your Klaviyo segments stopped updating three weeks ago.

Common causes of webhook delivery failures:

• Cloudflare or security plugins blocking incoming webhook requests
• Temporary endpoint unavailability during platform maintenance
• Rate limiting from the receiving platform
• Action Scheduler delays causing timeout on the receiving end
• WordPress cron not firing during low-traffic periods

WooCommerce 10.4.3 in December 2025 had to fix an issue where HPOS sync-on-read could trigger an infinite loop of webhooks and Analytics events (WooCommerce Developer Blog, 2025). When webhook architecture can cause infinite loops that require emergency patches, reliability concerns aren’t theoretical.

The Architecture Problem: Push vs. Pull

Webhooks are fundamentally a “push and hope” architecture. WooCommerce pushes an event and hopes the external system receives it. If the external system is busy, rate-limiting, or temporarily down, the event fails.

Definition: Server-Side Event Processing is an architecture where your server actively pushes events to destinations rather than waiting for external systems to receive webhooks. You control the transmission timing, reliability, and retry logic.

The difference matters:

• Webhook architecture: External system must be available when WooCommerce delivers
• Server-side event processing: Events queue locally, deliver when destination is ready

When Klaviyo has a 10-minute outage, webhook architecture loses events. Server-side event processing queues them and delivers when Klaviyo comes back.

Some events can be delayed for processing by up to 2 hours when using fallback polling mechanisms to recover failed webhooks (WooCommerce Payments webhook reliability solution, 2025). That’s assuming you have a fallback mechanism at all. Most WooCommerce stores don’t.

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Real Support Forum Reports

WordPress.org support forums document the pattern repeatedly:

“Webhooks work perfectly on our other WooCommerce stores but not on this one. Order-related webhook events are missing or not firing despite receiving HTTP 200 OK status from our webhook endpoint” (WordPress.org Support Forums, June 2025).

The frustrating part: intermittent failures are nearly impossible to debug. The webhook works for 50 orders, fails for 1, works for 30 more, fails for 2. By the time you notice, multiple orders have fallen through the cracks.

And the silent disable means you might not notice for weeks—until someone asks why their email sequence stopped or why orders aren’t reaching fulfillment.

Server-Side Event Processing: The Architectural Alternative

Server-side event processing inverts the reliability equation. Instead of hoping external systems receive your webhooks, your server controls the entire transmission chain.

Here’s how it works:

• Events captured from WooCommerce hooks (order created, payment complete, etc.)
• Queued locally on your server with controlled retry logic
• Pushed to destinations when those destinations are available
• Status logged for every event delivery attempt

If GA4’s Measurement Protocol rate limits you, events buffer and retry. If Klaviyo is down for maintenance, events queue and deliver when it comes back. If Facebook CAPI returns a temporary error, your server retries until success.

No silent failures. No 5-retry disable. Complete visibility into what went where and when.

Transmute Engine™ is a first-party Node.js server that runs on your subdomain (like data.yourstore.com). The inPIPE WordPress plugin captures events from WooCommerce hooks and sends them via API to your Transmute Engine server, which formats, enhances, and routes them to all configured destinations—GA4, Facebook CAPI, Klaviyo, BigQuery—with retry logic you control.

The difference isn’t just reliability. It’s visibility. Every event shows its delivery status in your dashboard. You know what succeeded, what’s queued, and what needs attention. No more discovering three weeks later that your integration silently broke.

Key Takeaways

• WooCommerce webhooks disable after 5 failed retries—with no notification to store owners
• Webhook architecture depends on external systems being available at the exact delivery moment
• GitHub issues document intermittent failures going back to 2017—this isn’t a new problem
• Action Scheduler + WordPress cron dependencies add additional failure points
• Server-side event processing inverts reliability—your server controls retry logic instead of hoping webhooks land

Ready for reliable event delivery? See how Transmute Engine handles event processing.