feat(slack): add logging for Slack webhook middleware (#2366)

Author: ComputelessComputer

apps/api/src/middleware/slack.ts

@@ -9,23 +9,32 @@ export const verifySlackWebhook = createMiddleware<{
     slackTimestamp: string;
   };
 }>(async (c, next) => {
+  console.log("[slack middleware] Starting verification");
+
   if (!env.SLACK_SIGNING_SECRET) {
+    console.log("[slack middleware] SLACK_SIGNING_SECRET not configured");
     return c.text("slack_signing_secret_not_configured", 500);
   }
 
   const signature = c.req.header("X-Slack-Signature");
   const timestamp = c.req.header("X-Slack-Request-Timestamp");
 
+  console.log("[slack middleware] signature:", signature);
+  console.log("[slack middleware] timestamp:", timestamp);
+
   if (!signature || !timestamp) {
+    console.log("[slack middleware] Missing signature or timestamp");
     return c.text("missing_slack_signature", 400);
   }
 
   const fiveMinutesAgo = Math.floor(Date.now() / 1000) - 60 * 5;
   if (Number.parseInt(timestamp) < fiveMinutesAgo) {
+    console.log("[slack middleware] Request too old, timestamp:", timestamp);
     return c.text("slack_request_too_old", 400);
   }
 
   const body = await c.req.text();
+  console.log("[slack middleware] Request body:", body);
 
   try {
     const sigBaseString = `v0:${timestamp}:${body}`;
@@ -46,14 +55,20 @@ export const verifySlackWebhook = createMiddleware<{
       .map((b) => b.toString(16).padStart(2, "0"))
       .join("")}`;
 
+    console.log("[slack middleware] computedSignature:", computedSignature);
+    console.log("[slack middleware] receivedSignature:", signature);
+
     if (computedSignature !== signature) {
+      console.log("[slack middleware] Signature mismatch!");
       return c.text("invalid_slack_signature", 400);
     }
 
+    console.log("[slack middleware] Signature verified, proceeding");
     c.set("slackRawBody", body);
     c.set("slackTimestamp", timestamp);
     await next();
   } catch (err) {
+    console.log("[slack middleware] Error during verification:", err);
     Sentry.captureException(err, {
       tags: { webhook: "slack", step: "signature_verification" },
     });

apps/api/src/routes/webhook.ts

@@ -146,14 +146,20 @@ webhook.post(
     const rawBody = c.get("slackRawBody");
     const span = c.get("sentrySpan");
 
+    console.log("[slack/events] Received request, rawBody:", rawBody);
+
     let payload: z.infer<typeof SlackEventSchema>;
     try {
       payload = SlackEventSchema.parse(JSON.parse(rawBody));
-    } catch {
+    } catch (e) {
+      console.log("[slack/events] Failed to parse payload:", e);
       return c.json({ error: "invalid_payload" }, 400);
     }
 
+    console.log("[slack/events] Parsed payload type:", payload.type);
+
     if (payload.type === "url_verification" && payload.challenge) {
+      console.log("[slack/events] URL verification, returning challenge");
       return c.json({ challenge: payload.challenge }, 200);
     }