diff --git a/services/kiloclaw/plugins/kilo-chat/src/channel.ts b/services/kiloclaw/plugins/kilo-chat/src/channel.ts
index 1d80a18564..33173d7729 100644
--- a/services/kiloclaw/plugins/kilo-chat/src/channel.ts
+++ b/services/kiloclaw/plugins/kilo-chat/src/channel.ts
@@ -182,7 +182,7 @@ const pluginBase = createChannelPluginBase({
       '- Kilo Chat uses the shared `message` tool. Prefer `target` for explicit conversation destinations; omit it to act in the current conversation when supported.',
       '- `send`: pass `message` plus `target`; `conversationId` and `groupId` are accepted compatibility aliases. To send any attachment, pass base64 `buffer`, `filename`, and `contentType`, or pass a local workspace path with `filePath`/`media` and a caption in `message`.',
       '- For generated text files or arbitrary local file types, prefer `send` with `filePath`/`media`, or `upload-file` with base64 `buffer`. Do not use `upload-file` with a local `filePath` for plain text or unknown file types.',
-      '- `upload-file`: use for direct file uploads when you already have base64 `buffer`, `filename`, and `contentType`; local `media`/`path`/`filePath` is best for images, audio, video, PDF, and Office documents.',
+      '- `upload-file`: use for direct file uploads when you already have base64 `buffer`, `filename`, and `contentType`; local `media`/`path`/`filePath` is best for images, audio, video, PDF, and Office documents. Prefer absolute file paths (e.g. `/root/clawd/report.md`).',
       '- Kilo Chat actions: `channel-list` lists conversations with optional `limit`; `channel-create` creates a conversation with optional `name`.',
       '- `read`: omit `target` for the current conversation, or pass `target`/`conversationId`; use `limit` and `before` for pagination.',
       '- `react`: pass `messageId` and the actual emoji in `emoji`; set `remove=true` to remove that emoji. If `messageId` is omitted, the current inbound message is used when available.',
diff --git a/services/kiloclaw/plugins/kilo-chat/src/media-delivery.test.ts b/services/kiloclaw/plugins/kilo-chat/src/media-delivery.test.ts
index 263ebd8808..286d19816c 100644
--- a/services/kiloclaw/plugins/kilo-chat/src/media-delivery.test.ts
+++ b/services/kiloclaw/plugins/kilo-chat/src/media-delivery.test.ts
@@ -27,6 +27,83 @@ describe('loadOutboundMedia', () => {
     }
   });
 
+  it('resolves relative paths against the agent working dir, not the OpenClaw workspace', async () => {
+    const agentDir = await mkdtemp(join(tmpdir(), 'kilo-chat-agent-'));
+    const openclawWorkspace = await mkdtemp(join(tmpdir(), 'kilo-chat-ws-'));
+    const previousCwd = process.cwd();
+    try {
+      await writeFile(join(agentDir, 'report.md'), '# Weekly Report');
+      process.chdir(agentDir);
+
+      const media = await loadOutboundMedia('report.md', {
+        mediaAccess: {
+          localRoots: [openclawWorkspace],
+          workspaceDir: openclawWorkspace,
+          readFile: async path => Buffer.from(await readFile(path)),
+        },
+      });
+
+      expect(media.buffer.toString('utf8')).toBe('# Weekly Report');
+      expect(media.fileName).toBe('report.md');
+    } finally {
+      process.chdir(previousCwd);
+      await rm(agentDir, { recursive: true, force: true });
+      await rm(openclawWorkspace, { recursive: true, force: true });
+    }
+  });
+
+  it('resolves relative filenames containing colons against the agent working dir', async () => {
+    const agentDir = await mkdtemp(join(tmpdir(), 'kilo-chat-agent-'));
+    const openclawWorkspace = await mkdtemp(join(tmpdir(), 'kilo-chat-ws-'));
+    const previousCwd = process.cwd();
+    try {
+      await writeFile(join(agentDir, 'report:2026-07-03.md'), '# Weekly Report');
+      process.chdir(agentDir);
+
+      const media = await loadOutboundMedia('report:2026-07-03.md', {
+        mediaAccess: {
+          localRoots: [openclawWorkspace],
+          workspaceDir: openclawWorkspace,
+          readFile: async path => Buffer.from(await readFile(path)),
+        },
+      });
+
+      expect(media.buffer.toString('utf8')).toBe('# Weekly Report');
+      expect(media.fileName).toBe('report:2026-07-03.md');
+    } finally {
+      process.chdir(previousCwd);
+      await rm(agentDir, { recursive: true, force: true });
+      await rm(openclawWorkspace, { recursive: true, force: true });
+    }
+  });
+
+  it('allows files under the agent working dir even when it is outside the configured local roots', async () => {
+    const agentDir = await mkdtemp(join(tmpdir(), 'kilo-chat-agent-'));
+    const openclawWorkspace = await mkdtemp(join(tmpdir(), 'kilo-chat-ws-'));
+    const previousCwd = process.cwd();
+    try {
+      const filePath = join(agentDir, 'report.md');
+      await writeFile(filePath, '# Weekly Report');
+      process.chdir(agentDir);
+
+      // No readFile → exercises the real OpenClaw loader and its local-roots gating.
+      const media = await loadOutboundMedia(filePath, {
+        mediaAccess: {
+          localRoots: [openclawWorkspace],
+          workspaceDir: openclawWorkspace,
+        },
+      });
+
+      expect(media.buffer.toString('utf8')).toBe('# Weekly Report');
+      expect(media.contentType).toBe('text/markdown');
+      expect(media.fileName).toBe('report.md');
+    } finally {
+      process.chdir(previousCwd);
+      await rm(agentDir, { recursive: true, force: true });
+      await rm(openclawWorkspace, { recursive: true, force: true });
+    }
+  });
+
   it('passes custom mediaReadFile through to the OpenClaw media loader', async () => {
     const media = await loadOutboundMedia('/virtual/generated.txt', {
       mediaLocalRoots: 'any',
diff --git a/services/kiloclaw/plugins/kilo-chat/src/media-delivery.ts b/services/kiloclaw/plugins/kilo-chat/src/media-delivery.ts
index f2d261090f..ba979f4694 100644
--- a/services/kiloclaw/plugins/kilo-chat/src/media-delivery.ts
+++ b/services/kiloclaw/plugins/kilo-chat/src/media-delivery.ts
@@ -2,6 +2,7 @@ import {
   loadOutboundMediaFromUrl,
   type OutboundMediaLoadOptions,
 } from 'openclaw/plugin-sdk/outbound-media';
+import { existsSync } from 'node:fs';
 import { basename, isAbsolute, resolve } from 'node:path';
 import type { ContentBlock, KiloChatClient } from './client.js';
 import { ATTACHMENT_MAX_BYTES } from './synced/schemas.js';
@@ -90,10 +91,31 @@ function resolveFilename(contentType: string | undefined, suggested: string | un
   return 'file.bin';
 }
 
+// The kiloclaw agent works in the process cwd (/root/clawd), but OpenClaw's
+// media workspace defaults to ~/.openclaw/workspace — a directory the agent
+// never writes to. Resolve agent-relative paths against cwd first and include
+// cwd in the allowed local roots, so files the agent generates are attachable.
+function agentWorkingDir(): string {
+  return process.cwd();
+}
+
+function hasUriScheme(raw: string): boolean {
+  return /^[a-z][a-z0-9+.-]*:\/\//i.test(raw.trim());
+}
+
+function withAgentDirRoot(
+  roots: OutboundMediaLoadOptions['mediaLocalRoots']
+): readonly string[] | 'any' {
+  if (roots === 'any') return roots;
+  return [...(roots ?? []), agentWorkingDir()];
+}
+
 function resolveLocalMediaPath(mediaUrl: string, context: OutboundMediaLoadContext): string {
+  if (isAbsolute(mediaUrl) || hasUriScheme(mediaUrl)) return mediaUrl;
+  const cwdPath = resolve(agentWorkingDir(), mediaUrl);
+  if (existsSync(cwdPath)) return cwdPath;
   const workspaceDir = context.mediaAccess?.workspaceDir;
-  if (workspaceDir && !isAbsolute(mediaUrl)) return resolve(workspaceDir, mediaUrl);
-  return mediaUrl;
+  return workspaceDir ? resolve(workspaceDir, mediaUrl) : cwdPath;
 }
 
 function inferMimeFromFilename(fileName: string | undefined): string | undefined {
@@ -118,10 +140,14 @@ export async function loadOutboundMedia(
   }
 
   const channelMediaAccess = mediaAccessForChannelRead(context.mediaAccess);
-  const loaded = await loadOutboundMediaFromUrl(mediaUrl, {
+  const localRoots = withAgentDirRoot(context.mediaLocalRoots ?? channelMediaAccess?.localRoots);
+  const loaded = await loadOutboundMediaFromUrl(resolveLocalMediaPath(mediaUrl, context), {
     maxBytes: ATTACHMENT_MAX_BYTES,
-    mediaAccess: channelMediaAccess,
-    mediaLocalRoots: context.mediaLocalRoots ?? channelMediaAccess?.localRoots,
+    mediaAccess: channelMediaAccess && {
+      ...channelMediaAccess,
+      ...(localRoots === 'any' ? {} : { localRoots: [...localRoots] }),
+    },
+    mediaLocalRoots: localRoots,
   });
   return {
     buffer: Buffer.isBuffer(loaded.buffer) ? loaded.buffer : Buffer.from(loaded.buffer),