diff --git a/apps/web/src/lib/bot/agent-runner.ts b/apps/web/src/lib/bot/agent-runner.ts
index 4b614bdcb..9367d60a5 100644
--- a/apps/web/src/lib/bot/agent-runner.ts
+++ b/apps/web/src/lib/bot/agent-runner.ts
@@ -23,6 +23,7 @@ import { buildSessionUrl } from '@/lib/cloud-agent-next/session-url';
 import { APP_URL } from '@/lib/constants';
 import { FEATURE_HEADER } from '@/lib/feature-detection';
 import { ownerFromIntegration } from '@/lib/integrations/core/owner';
+import type { Images } from '@/lib/images-schema';
 import {
   formatGitHubRepositoriesForPrompt,
   getGitHubRepositoryContext,
@@ -60,6 +61,8 @@ type RunBotAgentParams = {
   user: User;
   botRequestId: string | undefined;
   prompt: string;
+  /** Pre-uploaded image attachments from the user's message (already in R2). */
+  images?: Images;
   completedStepCount?: number;
   initialSteps?: BotRequestStep[];
   onSessionReady?: (params: {
@@ -262,6 +265,8 @@ export async function runBotAgent(params: RunBotAgentParams): Promise<BotAgentCo
       spawnCloudAgentSession: tool({
         description: `Spawn a Cloud Agent session to perform coding tasks on a GitHub repository or GitLab project. The agent can make code changes, fix bugs, implement features, review/analyze code, run tests, or open PRs/MRs. Do NOT use it for questions you can answer directly.
 
+If the user attached images to their message, those images are automatically forwarded to the Cloud Agent session — you do not need to describe or re-upload them. Reference them in the prompt if relevant (e.g. "implement the design shown in the attached screenshot").
+
 This tool returns an acknowledgement immediately. The final Cloud Agent result will be posted later in the same thread after the async session completes.`,
         inputSchema: spawnCloudAgentInputSchema,
         execute: async args => {
@@ -298,6 +303,7 @@ This tool returns an acknowledgement immediately. The final Cloud Agent result w
               prSignature,
               chatPlatform,
               currentStep,
+              images: params.images,
             }
           );
 
@@ -332,7 +338,13 @@ This tool returns an acknowledgement immediately. The final Cloud Agent result w
     },
   });
 
-  const result = await agent.generate({ prompt: params.prompt });
+  const imageCount = params.images?.files.length ?? 0;
+  const promptWithImageContext =
+    imageCount > 0
+      ? `${params.prompt}\n\n[The user attached ${imageCount} image${imageCount > 1 ? 's' : ''} to this message. The image${imageCount > 1 ? 's are' : ' is'} automatically forwarded to any Cloud Agent session you spawn.]`
+      : params.prompt;
+
+  const result = await agent.generate({ prompt: promptWithImageContext });
 
   return {
     finalText: result.text,
diff --git a/apps/web/src/lib/bot/images.ts b/apps/web/src/lib/bot/images.ts
new file mode 100644
index 000000000..5d88b0882
--- /dev/null
+++ b/apps/web/src/lib/bot/images.ts
@@ -0,0 +1,101 @@
+import { PutObjectCommand } from '@aws-sdk/client-s3';
+import {
+  CLOUD_AGENT_IMAGE_ALLOWED_TYPES,
+  CLOUD_AGENT_IMAGE_MAX_COUNT,
+  CLOUD_AGENT_IMAGE_MAX_SIZE_BYTES,
+  CLOUD_AGENT_IMAGE_MIME_TO_EXTENSION,
+  type CloudAgentImageAllowedType,
+} from '@/lib/cloud-agent/constants';
+import type { Images } from '@/lib/images-schema';
+import { r2Client, r2CloudAgentAttachmentsBucketName } from '@/lib/r2/client';
+import { captureException } from '@sentry/nextjs';
+import type { Attachment, Message } from 'chat';
+import { randomUUID } from 'crypto';
+
+const ALLOWED_TYPES_SET = new Set<string>(CLOUD_AGENT_IMAGE_ALLOWED_TYPES);
+
+function isAllowedImageType(mimeType: string): mimeType is CloudAgentImageAllowedType {
+  return ALLOWED_TYPES_SET.has(mimeType);
+}
+
+/**
+ * Extract image attachments from a chat Message, download them via the
+ * adapter's authenticated `fetchData()`, upload to R2, and return an
+ * `Images` reference that can be passed to the Cloud Agent API.
+ *
+ * Returns `undefined` when the message has no usable image attachments.
+ */
+export async function extractAndUploadImages(
+  message: Message,
+  userId: string
+): Promise<Images | undefined> {
+  const imageAttachments = message.attachments.filter(
+    (a): a is Attachment & { mimeType: string; fetchData: () => Promise<Buffer> } =>
+      a.type === 'image' &&
+      typeof a.mimeType === 'string' &&
+      isAllowedImageType(a.mimeType) &&
+      typeof a.fetchData === 'function'
+  );
+
+  if (imageAttachments.length === 0) return undefined;
+
+  // Respect the Cloud Agent's per-message image limit
+  const toProcess = imageAttachments.slice(0, CLOUD_AGENT_IMAGE_MAX_COUNT);
+
+  const messageUuid = randomUUID();
+  const uploadResults = await Promise.allSettled(
+    toProcess.map(async attachment => {
+      const imageId = randomUUID();
+      const ext =
+        CLOUD_AGENT_IMAGE_MIME_TO_EXTENSION[attachment.mimeType as CloudAgentImageAllowedType];
+      const filename = `${imageId}.${ext}`;
+      const r2Key = `${userId}/cloud-agent/${messageUuid}/${filename}`;
+
+      if (
+        typeof attachment.size === 'number' &&
+        attachment.size > CLOUD_AGENT_IMAGE_MAX_SIZE_BYTES
+      ) {
+        throw new Error(
+          `Image ${attachment.name ?? filename} exceeds ${CLOUD_AGENT_IMAGE_MAX_SIZE_BYTES / (1024 * 1024)}MB limit (${(attachment.size / (1024 * 1024)).toFixed(1)}MB)`
+        );
+      }
+
+      const data = await attachment.fetchData();
+
+      if (data.byteLength > CLOUD_AGENT_IMAGE_MAX_SIZE_BYTES) {
+        throw new Error(
+          `Image ${attachment.name ?? filename} exceeds ${CLOUD_AGENT_IMAGE_MAX_SIZE_BYTES / (1024 * 1024)}MB limit (${(data.byteLength / (1024 * 1024)).toFixed(1)}MB)`
+        );
+      }
+
+      await r2Client.send(
+        new PutObjectCommand({
+          Bucket: r2CloudAgentAttachmentsBucketName,
+          Key: r2Key,
+          Body: data,
+          ContentType: attachment.mimeType,
+          ContentLength: data.byteLength,
+          Metadata: { userId, messageUuid, imageId },
+        })
+      );
+
+      return filename;
+    })
+  );
+
+  const filenames: string[] = [];
+  for (const result of uploadResults) {
+    if (result.status === 'fulfilled') {
+      filenames.push(result.value);
+    } else {
+      console.error('[KiloBot] Failed to upload image attachment:', result.reason);
+      captureException(result.reason, {
+        tags: { component: 'kilo-bot', op: 'upload-slack-image' },
+      });
+    }
+  }
+
+  if (filenames.length === 0) return undefined;
+
+  return { path: messageUuid, files: filenames };
+}
diff --git a/apps/web/src/lib/bot/run.ts b/apps/web/src/lib/bot/run.ts
index 2c3873764..bf7e57f03 100644
--- a/apps/web/src/lib/bot/run.ts
+++ b/apps/web/src/lib/bot/run.ts
@@ -1,8 +1,10 @@
 import { updateBotRequest } from '@/lib/bot/request-logging';
 import { runBotAgent } from '@/lib/bot/agent-runner';
+import { extractAndUploadImages } from '@/lib/bot/images';
 import type { PlatformIntegration, User } from '@kilocode/db';
 import type { Message, Thread } from 'chat';
 import { emoji } from 'chat';
+import { captureException } from '@sentry/nextjs';
 
 export async function processMessage({
   thread,
@@ -19,6 +21,19 @@ export async function processMessage({
 }) {
   const startedAt = Date.now();
 
+  // Extract and upload any image attachments from the Slack message to R2.
+  // This runs before the agent loop so the images are ready when a Cloud Agent
+  // session is spawned. Failures are non-fatal — we log and continue without images.
+  let images: Awaited<ReturnType<typeof extractAndUploadImages>>;
+  try {
+    images = await extractAndUploadImages(message, user.id);
+  } catch (error) {
+    console.error('[KiloBot] Failed to extract/upload images, continuing without them:', error);
+    captureException(error, {
+      tags: { component: 'kilo-bot', op: 'extract-upload-images' },
+    });
+  }
+
   try {
     const result = await runBotAgent({
       thread,
@@ -28,6 +43,7 @@ export async function processMessage({
       user,
       botRequestId,
       prompt: message.text,
+      images,
     });
 
     if (botRequestId) {
diff --git a/apps/web/src/lib/bot/tools/spawn-cloud-agent-session.ts b/apps/web/src/lib/bot/tools/spawn-cloud-agent-session.ts
index 46d9d2705..4fd7f8e5d 100644
--- a/apps/web/src/lib/bot/tools/spawn-cloud-agent-session.ts
+++ b/apps/web/src/lib/bot/tools/spawn-cloud-agent-session.ts
@@ -15,6 +15,7 @@ import {
   getGitLabInstanceUrlForUser,
   buildGitLabCloneUrl,
 } from '@/lib/cloud-agent/gitlab-integration-helpers';
+import type { Images } from '@/lib/images-schema';
 import { APP_URL } from '@/lib/constants';
 import { INTERNAL_API_SECRET } from '@/lib/config.server';
 import { parseBotCallbackStep } from '@/lib/bot/step-budget';
@@ -94,7 +95,7 @@ export default async function spawnCloudAgentSession(
   ticketUserId: string,
   botRequestId: string | undefined,
   onSessionReady?: RunSessionInput['onSessionReady'],
-  options?: { prSignature?: string; chatPlatform?: string; currentStep?: number }
+  options?: { prSignature?: string; chatPlatform?: string; currentStep?: number; images?: Images }
 ): Promise<SpawnCloudAgentResult> {
   console.log('[KiloBot] spawnCloudAgentSession called with args:', JSON.stringify(args, null, 2));
 
@@ -172,6 +173,7 @@ export default async function spawnCloudAgentSession(
       kilocodeOrganizationId,
       createdOnPlatform: chatPlatform,
       callbackTarget,
+      images: options?.images,
       envVars: profileConfig.envVars,
       encryptedSecrets: profileConfig.encryptedSecrets,
       setupCommands: profileConfig.setupCommands,
@@ -200,6 +202,7 @@ export default async function spawnCloudAgentSession(
       kilocodeOrganizationId,
       createdOnPlatform: chatPlatform,
       callbackTarget,
+      images: options?.images,
       envVars: profileConfig.envVars,
       encryptedSecrets: profileConfig.encryptedSecrets,
       setupCommands: profileConfig.setupCommands,