diff --git a/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/middleware/errorHandler.ts b/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/middleware/errorHandler.ts
index 4ddc21b6053..d8f08b80fa6 100644
--- a/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/middleware/errorHandler.ts
+++ b/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/middleware/errorHandler.ts
@@ -10,9 +10,17 @@ export const errorHandlerMiddleware = (
   _next: NextFunction
 ) => {
   const error =
-    err instanceof ResponseError ? err : new InternalServerError(String(err))
+    err instanceof ResponseError
+      ? err
+      : new InternalServerError(
+          err instanceof Error ? err.message : String(err)
+        )
   if (!res.headersSent) {
-    res.status(error.status).send({ error: error.name })
+    res
+      .status(error.status)
+      .set('X-Request-ID', res.locals.requestId)
+      .set('Access-Control-Expose-Headers', 'X-Request-ID')
+      .send({ error: error.message })
   }
   // in milliseconds
   const responseTime = new Date().getTime() - res.locals.requestStartTime
diff --git a/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/middleware/locals.ts b/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/middleware/locals.ts
index ca955d27f1f..1b68f1bbdd6 100644
--- a/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/middleware/locals.ts
+++ b/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/middleware/locals.ts
@@ -5,6 +5,7 @@ import { Logger } from 'pino'
 declare global {
   namespace Express {
     interface Locals {
+      requestId: string
       signerUser?: Users
       isSignedByDiscovery?: boolean
       logger: Logger
diff --git a/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/middleware/logging.ts b/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/middleware/logging.ts
index 6452b5c56c6..036239c2e7b 100644
--- a/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/middleware/logging.ts
+++ b/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/middleware/logging.ts
@@ -12,6 +12,7 @@ export const incomingRequestLogger = (
   response.locals.requestStartTime = startTime
   const requestId = uuidv4()
   const { path, method } = request
+  response.locals.requestId = requestId
   response.locals.logger = logger.child({
     requestId,
     path,
diff --git a/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/routes/relay/relay.ts b/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/routes/relay/relay.ts
index 678198f9b5b..5b6e669be4a 100644
--- a/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/routes/relay/relay.ts
+++ b/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/routes/relay/relay.ts
@@ -15,6 +15,7 @@ import {
   sendTransactionWithRetries
 } from '../../utils/transaction'
 
+import { InvalidRelayInstructionError } from './InvalidRelayInstructionError'
 import { assertRelayAllowedInstructions } from './assertRelayAllowedInstructions'
 
 /**
@@ -103,10 +104,20 @@ export const relay = async (
 
     const feePayerKey = decompiled.payerKey
     const feePayerKeyPair = getFeePayerKeyPair(feePayerKey)
-    await assertRelayAllowedInstructions(decompiled.instructions, {
-      user: res.locals.signerUser,
-      feePayer: feePayerKey.toBase58()
-    })
+
+    try {
+      await assertRelayAllowedInstructions(decompiled.instructions, {
+        user: res.locals.signerUser,
+        feePayer: feePayerKey.toBase58()
+      })
+    } catch (e) {
+      if (e instanceof InvalidRelayInstructionError) {
+        res.locals.logger.error(e.toString())
+        throw new BadRequestError('Invalid relay instructions')
+      } else {
+        throw e
+      }
+    }
 
     if (feePayerKeyPair) {
       res.locals.logger.info(
diff --git a/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/utils/transaction.ts b/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/utils/transaction.ts
index 03b1a9ab4cd..abd65f46e1d 100644
--- a/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/utils/transaction.ts
+++ b/packages/discovery-provider/plugins/pedalboard/apps/solana-relay/src/utils/transaction.ts
@@ -17,7 +17,6 @@ import { connections, getConnection } from './connections'
 import { delay } from './delay'
 
 const RETRY_DELAY_MS = 2 * 1000
-const RETRY_TIMEOUT_MS = 60 * 1000
 
 /**
  * Forwards the transaction response to other Solana Relays on other discovery
@@ -66,8 +65,7 @@ const forwardTransaction = async (logger: Logger, transaction: string) => {
 
 /**
  * Sends the transaction repeatedly to all configured RPCs until
- * it's been confirmed with the given commitment level, expires,
- * or times out.
+ * it's been confirmed with the given commitment level or the blockhash expires.
  */
 export const sendTransactionWithRetries = async ({
   transaction,
@@ -103,13 +101,6 @@ export const sendTransactionWithRetries = async ({
     }
   }
 
-  const createTimeoutPromise = async (signal: AbortSignal) => {
-    await delay(RETRY_TIMEOUT_MS)
-    if (!signal.aborted) {
-      logger.error('Timed out sending transaction')
-    }
-  }
-
   const start = Date.now()
   const connection = connections[0]
   const abortController = new AbortController()
@@ -130,12 +121,14 @@ export const sendTransactionWithRetries = async ({
       connection.confirmTransaction(
         { ...confirmationStrategy, abortSignal: abortController.signal },
         commitment
-      ),
-      createTimeoutPromise(abortController.signal)
+      )
     ])
 
-    if (!res || res.value.err) {
-      throw res?.value.err ?? 'Transaction polling timed out.'
+    if (!res) {
+      throw new Error('Failed to get transaction confirmation result')
+    }
+    if (res.value.err) {
+      throw new Error(JSON.stringify(res.value.err))
     }
     logger.info({ commitment }, 'Transaction sent successfully')
     return confirmationStrategy.signature
diff --git a/packages/web/src/store/errors/reportToSentry.ts b/packages/web/src/store/errors/reportToSentry.ts
index 34adc531871..9620889103f 100644
--- a/packages/web/src/store/errors/reportToSentry.ts
+++ b/packages/web/src/store/errors/reportToSentry.ts
@@ -54,6 +54,7 @@ export const reportToSentry = async ({
         additionalInfo = {
           ...additionalInfo,
           response: error.response,
+          requestId: error.response.headers.get('X-Request-ID'),
           responseBody
         }
       }