diff --git a/crates/service/plugins/billing/src/stripe/http_endpoints/webhook/stripe_webhook_handler.rs b/crates/service/plugins/billing/src/stripe/http_endpoints/webhook/stripe_webhook_handler.rs
index 02a0b6d5b3..90fbbefba8 100644
--- a/crates/service/plugins/billing/src/stripe/http_endpoints/webhook/stripe_webhook_handler.rs
+++ b/crates/service/plugins/billing/src/stripe/http_endpoints/webhook/stripe_webhook_handler.rs
@@ -43,8 +43,9 @@ pub async fn stripe_webhook_handler(
 {
   verify_stripe_webhook_ip_address(&http_request)
       .map_err(|e| {
-        error!("Improper client IP address. Error: {:?}", e);
-        StripeWebhookError::BadRequest
+        let reason = format!("Improper client IP address. Error: {:?}", e);
+        error!("{}", &reason);
+        StripeWebhookError::BadRequest(reason)
       })?;
 
   let secret_signing_key = &stripe_config.secrets.secret_webhook_signing_key;
@@ -55,14 +56,16 @@ pub async fn stripe_webhook_handler(
   // NB: Treat the request payload as unstructured and defer to Stripe libraries.
   let webhook_payload = String::from_utf8(request_body_bytes.to_vec())
       .map_err(|err| {
-        error!("Could not decode request body to stripe webhook!");
-        StripeWebhookError::BadRequest
+        let reason = format!("Could not decode request body to UTF-8: {:?}", err);
+        error!("{}", &reason);
+        StripeWebhookError::BadRequest(reason)
       })?;
 
   let webhook_payload = Webhook::construct_event(&webhook_payload, &stripe_signature, secret_signing_key)
       .map_err(|e| {
-        error!("Could not decode stripe webhook: {:?}", e);
-        StripeWebhookError::BadRequest
+        let reason = format!("Could not construct Stripe webhook event: {:?}", e);
+        error!("{}", &reason);
+        StripeWebhookError::BadRequest(reason)
       })?;
 
   // Events can be re-sent, so we need to make handling them idempotent.
@@ -73,8 +76,9 @@ pub async fn stripe_webhook_handler(
   let stripe_event_type = serde_json::to_string(&webhook_payload.type_)
       .map(|s| s.replace("\"", ""))
       .map_err(|err| {
-        error!("Could not deserialize webhook type: {:?}", err);
-        StripeWebhookError::BadRequest
+        let reason = format!("Could not serialize webhook type: {:?}", err);
+        error!("{}", &reason);
+        StripeWebhookError::BadRequest(reason)
       })?;
 
   // NB: Whether this was test data or live data
@@ -90,8 +94,9 @@ pub async fn stripe_webhook_handler(
   let maybe_previously_played_event = get_stripe_webhook_event_log_by_id(&stripe_event_id, &mysql_pool)
       .await
       .map_err(|err| {
-        error!("Could not query previous event by ID ({}): {:?}", &stripe_event_id, err);
-        StripeWebhookError::ServerError
+        let reason = format!("Could not query previous event by ID ({}): {:?}", &stripe_event_id, err);
+        error!("{}", &reason);
+        StripeWebhookError::ServerError(reason)
       })?;
 
   if let Some(event) = maybe_previously_played_event {
@@ -327,8 +332,9 @@ pub async fn stripe_webhook_handler(
   query.insert(&mysql_pool)
       .await
       .map_err(|err| {
-        error!("Failure to record event: {:?}", err);
-        StripeWebhookError::ServerError
+        let reason = format!("Could not insert Stripe webhook event log: {:?}", err);
+        error!("{}", &reason);
+        StripeWebhookError::ServerError(reason)
       })?;
 
   report_success()
@@ -341,7 +347,7 @@ fn report_success() -> Result<HttpResponse, StripeWebhookError> {
   };
 
   let body = serde_json::to_string(&response)
-      .map_err(|_e| StripeWebhookError::ServerError)?;
+      .map_err(|_e| StripeWebhookError::ServerError(_e.to_string()))?;
 
   Ok(HttpResponse::Ok()
       .content_type("application/json")
diff --git a/crates/service/plugins/billing/src/stripe/http_endpoints/webhook/webhook_event_handlers/stripe_webhook_error.rs b/crates/service/plugins/billing/src/stripe/http_endpoints/webhook/webhook_event_handlers/stripe_webhook_error.rs
index 9367fd1be8..97922ebfe7 100644
--- a/crates/service/plugins/billing/src/stripe/http_endpoints/webhook/webhook_event_handlers/stripe_webhook_error.rs
+++ b/crates/service/plugins/billing/src/stripe/http_endpoints/webhook/webhook_event_handlers/stripe_webhook_error.rs
@@ -9,15 +9,15 @@ use http_server_common::response::serialize_as_json_error::serialize_as_json_err
 
 #[derive(Debug, Serialize)]
 pub enum StripeWebhookError {
-  BadRequest,
-  ServerError,
+  BadRequest(String),
+  ServerError(String),
 }
 
 impl ResponseError for StripeWebhookError {
   fn status_code(&self) -> StatusCode {
-    match *self {
-      StripeWebhookError::BadRequest => StatusCode::BAD_REQUEST,
-      StripeWebhookError::ServerError => StatusCode::INTERNAL_SERVER_ERROR,
+    match self {
+      StripeWebhookError::BadRequest(String) => StatusCode::BAD_REQUEST,
+      StripeWebhookError::ServerError(String) => StatusCode::INTERNAL_SERVER_ERROR,
     }
   }