diff --git a/apps/api/src/app/agents/services/chat-sdk.service.ts b/apps/api/src/app/agents/services/chat-sdk.service.ts
index 884d3eaeab0..aa5c976d880 100644
--- a/apps/api/src/app/agents/services/chat-sdk.service.ts
+++ b/apps/api/src/app/agents/services/chat-sdk.service.ts
@@ -1,4 +1,4 @@
-import { BadRequestException, Injectable, OnModuleDestroy } from '@nestjs/common';
+import { BadGatewayException, BadRequestException, Injectable, OnModuleDestroy } from '@nestjs/common';
 import { CacheService, decryptCredentials, MailFactory, PinoLogger } from '@novu/application-generic';
 import { IntegrationRepository } from '@novu/dal';
 import type { SentMessageInfo } from '@novu/framework';
@@ -14,6 +14,16 @@ import { sendWebResponse, toWebRequest } from '../utils/express-to-web-request';
 import { AgentConfigResolver, ResolvedAgentConfig } from './agent-config-resolver.service';
 import { AgentInboundHandler } from './agent-inbound-handler.service';
 
+function toDeliveryError(err: unknown): never {
+  const base = err instanceof Error ? err.message : String(err);
+  const body = (err as any)?.response?.body;
+  const detail = Array.isArray(body?.errors) ? body.errors[0]?.message : body?.message;
+  throw new BadGatewayException({
+    error: 'delivery_failed',
+    message: detail ? `${base}: ${detail}` : base,
+  });
+}
+
 /** Ensure a Message-ID value is wrapped in RFC 5322 angle brackets. */
 function wrapMsgId(id: string): string {
   const trimmed = id.trim();
@@ -134,15 +144,17 @@ export class ChatSdkService implements OnModuleDestroy {
     const adapter = chat.getAdapter(platform);
     const thread = ThreadImpl.fromJSON(serializedThread, adapter);
 
-    let sent: { id: string; threadId: string };
+    let postPromise: Promise<{ id: string; threadId: string }>;
     if (content.card) {
-      sent = await thread.post(content.card);
+      postPromise = thread.post(content.card);
     } else if (content.markdown !== undefined) {
-      sent = await thread.post({ markdown: content.markdown, files: content.files });
+      postPromise = thread.post({ markdown: content.markdown, files: content.files });
     } else {
-      sent = await thread.post(content.text ?? '');
+      postPromise = thread.post(content.text ?? '');
     }
 
+    const sent = await postPromise.catch(toDeliveryError);
+
     return { messageId: sent.id, platformThreadId: sent.threadId };
   }
 
@@ -163,22 +175,24 @@ export class ChatSdkService implements OnModuleDestroy {
       throw new BadRequestException(`Platform ${platform} does not support editing messages`);
     }
 
-    let edited: { id: string; threadId: string };
+    let editPromise: Promise<{ id: string; threadId: string }>;
     if (content.card) {
-      edited = await adapter.editMessage(
+      editPromise = adapter.editMessage(
         platformThreadId,
         platformMessageId,
         content.card as unknown as AdapterPostableMessage
       );
     } else if (content.markdown !== undefined) {
-      edited = await adapter.editMessage(platformThreadId, platformMessageId, {
+      editPromise = adapter.editMessage(platformThreadId, platformMessageId, {
         markdown: content.markdown,
         files: content.files,
       } as unknown as AdapterPostableMessage);
     } else {
-      edited = await adapter.editMessage(platformThreadId, platformMessageId, content.text ?? '');
+      editPromise = adapter.editMessage(platformThreadId, platformMessageId, content.text ?? '');
     }
 
+    const edited = await editPromise.catch(toDeliveryError);
+
     return { messageId: edited.id, platformThreadId: edited.threadId };
   }
 
@@ -419,7 +433,7 @@ export class ChatSdkService implements OnModuleDestroy {
         },
       };
 
-      const result = await handler.send(mailOptions);
+      const result = await handler.send(mailOptions).catch(toDeliveryError);
 
       return { messageId: result?.id || params.messageId || '' };
     };
diff --git a/apps/api/src/app/agents/usecases/send-agent-test-email/send-agent-test-email.usecase.ts b/apps/api/src/app/agents/usecases/send-agent-test-email/send-agent-test-email.usecase.ts
index 49b6878928c..06e02d9c80a 100644
--- a/apps/api/src/app/agents/usecases/send-agent-test-email/send-agent-test-email.usecase.ts
+++ b/apps/api/src/app/agents/usecases/send-agent-test-email/send-agent-test-email.usecase.ts
@@ -1,4 +1,4 @@
-import { BadRequestException, Injectable, NotFoundException } from '@nestjs/common';
+import { BadGatewayException, BadRequestException, Injectable, NotFoundException } from '@nestjs/common';
 import { decryptCredentials, InstrumentUsecase, MailFactory } from '@novu/application-generic';
 import { AgentIntegrationRepository, AgentRepository, IntegrationRepository } from '@novu/dal';
 import { ChannelTypeEnum, EmailProviderIdEnum, IEmailOptions } from '@novu/shared';
@@ -85,7 +85,15 @@ export class SendAgentTestEmail {
       senderName: (senderIntegration.credentials?.senderName as string) || 'Novu',
     };
 
-    await handler.send(mailOptions);
+    await handler.send(mailOptions).catch((err) => {
+      const base = err instanceof Error ? err.message : String(err);
+      const body = (err as any)?.response?.body;
+      const detail = Array.isArray(body?.errors) ? body.errors[0]?.message : body?.message;
+      throw new BadGatewayException({
+        error: 'delivery_failed',
+        message: detail ? `${base}: ${detail}` : base,
+      });
+    });
 
     return { success: true };
   }
diff --git a/packages/framework/src/index.ts b/packages/framework/src/index.ts
index d584f80910e..fc76897d05b 100644
--- a/packages/framework/src/index.ts
+++ b/packages/framework/src/index.ts
@@ -30,6 +30,7 @@ export type {
 } from './resources';
 export {
   Actions,
+  AgentDeliveryError,
   AgentEventEnum,
   agent,
   Button,
diff --git a/packages/framework/src/resources/agent/agent.context.ts b/packages/framework/src/resources/agent/agent.context.ts
index d40d25533e1..deb261c78c5 100644
--- a/packages/framework/src/resources/agent/agent.context.ts
+++ b/packages/framework/src/resources/agent/agent.context.ts
@@ -1,4 +1,5 @@
 import { isJSX, toCardElement } from 'chat/jsx-runtime';
+import { AgentDeliveryError } from './agent.errors';
 import type {
   AgentAction,
   AgentBridgeRequest,
@@ -216,6 +217,18 @@ export class AgentContextImpl implements AgentContext {
 
     if (!response.ok) {
       const text = await response.text().catch(() => '');
+
+      if (response.status === 502) {
+        let message = text;
+        try {
+          const parsed = JSON.parse(text) as { message?: string };
+          if (parsed.message) message = parsed.message;
+        } catch {
+          // use raw text if JSON parsing fails
+        }
+        throw new AgentDeliveryError(502, message);
+      }
+
       throw new Error(`Agent reply failed (${response.status}): ${text}`);
     }
 
diff --git a/packages/framework/src/resources/agent/agent.errors.ts b/packages/framework/src/resources/agent/agent.errors.ts
new file mode 100644
index 00000000000..349955594b1
--- /dev/null
+++ b/packages/framework/src/resources/agent/agent.errors.ts
@@ -0,0 +1,32 @@
+/**
+ * Thrown by `ctx.reply()` and `handle.edit()` when the upstream message delivery
+ * fails — e.g. the configured email provider returns 401, Slack rejects the token,
+ * or Teams rejects the request.
+ *
+ * The `message` property contains the original provider error text
+ *
+ * @example
+ * ```ts
+ * import { AgentDeliveryError } from '@novu/framework';
+ *
+ * try {
+ *   await ctx.reply('Hello!');
+ * } catch (err) {
+ *   if (err instanceof AgentDeliveryError) {
+ *     // Delivery failed (misconfigured provider, rate limit, etc.)
+ *     console.error('Delivery failed:', err.message);
+ *     return;
+ *   }
+ *   throw err;
+ * }
+ * ```
+ */
+export class AgentDeliveryError extends Error {
+  readonly statusCode: number;
+
+  constructor(statusCode: number, message: string) {
+    super(message);
+    this.name = 'AgentDeliveryError';
+    this.statusCode = statusCode;
+  }
+}
diff --git a/packages/framework/src/resources/agent/index.ts b/packages/framework/src/resources/agent/index.ts
index 7fd2a81445f..3b6edfbc3b4 100644
--- a/packages/framework/src/resources/agent/index.ts
+++ b/packages/framework/src/resources/agent/index.ts
@@ -12,6 +12,7 @@ export type {
 } from 'chat';
 export { Actions, Button, Card, CardLink, CardText, Divider, Select, SelectOption, TextInput } from 'chat';
 export { AgentContextImpl } from './agent.context';
+export { AgentDeliveryError } from './agent.errors';
 export { agent } from './agent.resource';
 export type {
   Agent,