Attack Chain

1. Initial Access: An attacker identifies a Rails application utilizing the Pay gem (version <= 11.6.1) and exposing the POST /pay/webhooks/paddle_billing endpoint, which is publicly accessible for Paddle to deliver webhook events.
2. Information Gathering / Reconnaissance: The attacker crafts a series of requests to the exposed webhook endpoint, supplying a valid timestamp (ts=<now>) and a systematically varying guessed HMAC signature (h1=<guess>) within the Paddle-Signature header.
3. Exploitation (Timing Side Channel): The vulnerable application processes each request, internally calculating the true HMAC for the raw post data and comparing it to the attacker's h1 guess using Ruby's String#==. Due to the non-constant-time nature of this comparison, the server's response time varies subtly based on how many leading characters of the h1 guess match the true HMAC.
4. Credential Access (HMAC Key Recovery): By sending a large number of requests and precisely measuring and analyzing the response times for each attempt, the attacker can use this timing oracle to accurately reconstruct the full 64-character hex-encoded SHA-256 HMAC, byte by byte, for a known payload.
5. Forging Webhooks: Once the HMAC signing secret is effectively known (as the HMAC for any given payload can be computed), the attacker can generate valid Paddle-Signature headers for arbitrary Paddle Billing webhook payloads that they construct.
6. Impact (Business Logic Abuse): The attacker then delivers these forged webhook events (e.g., subscription.created, transaction.completed, invoice.paid) to the /pay/webhooks/paddle_billing endpoint. The vulnerable application processes these forged events as legitimate, leading to unauthorized actions such as provisioning premium features for free, initiating fraudulent refunds, or triggering false customer notifications and database updates.

Impact

This vulnerability (CWE-208: Observable Timing Discrepancy) allows an unauthenticated attacker to fully compromise the integrity of Paddle Billing webhook events. By recovering the HMAC signing secret through a timing side-channel, attackers can forge any webhook event, effectively tricking the application into believing Paddle Billing sent it. This can lead to significant financial losses through fraudulent transactions (e.g., free access to paid features, unauthorized refunds), customer confusion from incorrect notifications, or data integrity issues due to malicious updates to billing states. Since the webhook endpoint must be internet-reachable by design, all Pay gem installations integrating with Paddle Billing are exposed to this risk. No specific victim counts or sectors were identified in the source, but any organization using the affected Pay gem version is at risk.

Recommendation

• Immediately update the pay gem to a version greater than 11.6.1 to apply the fix that replaces the non-constant-time String#== comparison with ActiveSupport::SecurityUtils.secure_compare.
• Review application logs for the /pay/webhooks/paddle_billing endpoint for unusually high request volumes from single IP addresses or abnormal response time distributions, which could indicate attempts at timing side-channel exploitation.
• Review application-level audit logs for the Pay gem for any anomalous subscription.created, transaction.completed, or other financial event entries around the time of the vulnerability disclosure or patch deployment, as these could indicate forged events delivered by an attacker.