ui ux enhancement

core/src/browser/extensions/index.ts

@@ -25,6 +25,6 @@ export { MCPExtension } from './mcp'
 export * from './engines'
 
 export { RAGExtension, RAG_INTERNAL_SERVER } from './rag'
-export type { AttachmentInput } from './rag'
+export type { AttachmentInput, IngestAttachmentsResult } from './rag'
 export { VectorDBExtension } from './vector-db'
-export type { SearchMode, VectorDBStatus, VectorChunkInput, VectorSearchResult, AttachmentFileInfo } from './vector-db'
+export type { SearchMode, VectorDBStatus, VectorChunkInput, VectorSearchResult, AttachmentFileInfo, VectorDBFileInput, VectorDBIngestOptions } from './vector-db'

core/src/browser/extensions/rag.ts

@@ -1,5 +1,6 @@
 import { BaseExtension, ExtensionTypeEnum } from '../extension'
 import type { MCPTool, MCPToolCallResult } from '../../types'
+import type { AttachmentFileInfo } from './vector-db'
 
 export interface AttachmentInput {
   path: string
@@ -8,6 +9,12 @@ export interface AttachmentInput {
   size?: number
 }
 
+export interface IngestAttachmentsResult {
+  filesProcessed: number
+  chunksInserted: number
+  files: AttachmentFileInfo[]
+}
+
 export const RAG_INTERNAL_SERVER = 'rag-internal'
 
 /**
@@ -25,8 +32,5 @@ export abstract class RAGExtension extends BaseExtension {
   abstract getToolNames(): Promise<string[]>
   abstract callTool(toolName: string, args: Record<string, unknown>): Promise<MCPToolCallResult>
 
-  abstract ingestAttachments(threadId: string, files: AttachmentInput[]): Promise<{
+  abstract ingestAttachments(threadId: string, files: AttachmentInput[]): Promise<IngestAttachmentsResult>
-    filesProcessed: number
-    chunksInserted: number
-  } | void>
 }

core/src/browser/extensions/vector-db.ts

@@ -7,10 +7,8 @@ export interface VectorDBStatus {
 }
 
 export interface VectorChunkInput {
-  id?: string
   text: string
   embedding: number[]
-  metadata?: Record<string, any>
 }
 
 export interface VectorSearchResult {
@@ -30,6 +28,19 @@ export interface AttachmentFileInfo {
   chunk_count: number
 }
 
+// High-level input types for file ingestion
+export interface VectorDBFileInput {
+  path: string
+  name?: string
+  type?: string
+  size?: number
+}
+
+export interface VectorDBIngestOptions {
+  chunkSize: number
+  chunkOverlap: number
+}
+
 /**
  * Vector DB extension base: abstraction over local vector storage and search.
  */
@@ -39,22 +50,31 @@ export abstract class VectorDBExtension extends BaseExtension {
   }
 
   abstract getStatus(): Promise<VectorDBStatus>
-  abstract createCollection(name: string, dimension: number): Promise<void>
+  abstract createCollection(threadId: string, dimension: number): Promise<void>
-  abstract insertChunks(collection: string, chunks: VectorChunkInput[]): Promise<void>
+  abstract insertChunks(
+    threadId: string,
+    fileId: string,
+    chunks: VectorChunkInput[]
+  ): Promise<void>
+  abstract ingestFile(
+    threadId: string,
+    file: VectorDBFileInput,
+    opts: VectorDBIngestOptions
+  ): Promise<AttachmentFileInfo>
   abstract searchCollection(
-    collection: string,
+    threadId: string,
     query_embedding: number[],
     limit: number,
     threshold: number,
     mode?: SearchMode,
     fileIds?: string[]
   ): Promise<VectorSearchResult[]>
-  abstract deleteChunks(collection: string, ids: string[]): Promise<void>
+  abstract deleteChunks(threadId: string, ids: string[]): Promise<void>
-  abstract deleteCollection(collection: string): Promise<void>
+  abstract deleteFile(threadId: string, fileId: string): Promise<void>
-  abstract chunkText(text: string, chunkSize: number, chunkOverlap: number): Promise<string[]>
+  abstract deleteCollection(threadId: string): Promise<void>
-  abstract listAttachments(collection: string, limit?: number): Promise<AttachmentFileInfo[]>
+  abstract listAttachments(threadId: string, limit?: number): Promise<AttachmentFileInfo[]>
   abstract getChunks(
-    collection: string,
+    threadId: string,
     fileId: string,
     startOrder: number,
     endOrder: number

extensions/rag-extension/src/index.ts

@@ -1,7 +1,5 @@
-import { RAGExtension, MCPTool, MCPToolCallResult, ExtensionTypeEnum, VectorDBExtension, type AttachmentInput, type SettingComponentProps, AIEngine } from '@janhq/core'
+import { RAGExtension, MCPTool, MCPToolCallResult, ExtensionTypeEnum, VectorDBExtension, type AttachmentInput, type SettingComponentProps, AIEngine, type AttachmentFileInfo } from '@janhq/core'
 import './env.d'
-import * as ragApi from '@janhq/tauri-plugin-rag-api'
-import * as vecdbApi from '@janhq/tauri-plugin-vector-db-api'
 import { getRAGTools, RETRIEVE, LIST_ATTACHMENTS, GET_CHUNKS } from './tools'
 
 export default class RagExtension extends RAGExtension {
@@ -75,11 +73,10 @@ export default class RagExtension extends RAGExtension {
     }
     try {
       const vec = window.core?.extensionManager.get(ExtensionTypeEnum.VectorDB) as unknown as VectorDBExtension
-      const collection = `attachments_${threadId}`
       if (!vec?.listAttachments) {
         return { error: 'Vector DB extension missing listAttachments', content: [{ type: 'text', text: 'Vector DB extension missing listAttachments' }] }
       }
-      const files = await vec.listAttachments(collection)
+      const files = await vec.listAttachments(threadId)
       return {
         error: '',
         content: [
@@ -143,9 +140,8 @@ export default class RagExtension extends RAGExtension {
         }
       }
 
-      const collection = `attachments_${threadId}`
       const results = await vec.searchCollection(
-        collection,
+        threadId,
         queryEmb,
         topK,
         threshold,
@@ -163,7 +159,6 @@ export default class RagExtension extends RAGExtension {
           file_id: r.file_id,
           chunk_file_order: r.chunk_file_order
         })) ?? [],
-        collection,
         mode,
       }
       return { error: '', content: [{ type: 'text', text: JSON.stringify(payload) }] }
@@ -203,8 +198,7 @@ export default class RagExtension extends RAGExtension {
         }
       }
 
-      const collection = `attachments_${threadId}`
+      const chunks = await vec.getChunks(threadId, fileId, startOrder, endOrder)
-      const chunks = await vec.getChunks(collection, fileId, startOrder, endOrder)
 
       const payload = {
         thread_id: threadId,
@@ -222,8 +216,15 @@ export default class RagExtension extends RAGExtension {
   async ingestAttachments(
     threadId: string,
     files: AttachmentInput[]
-  ): Promise<{ filesProcessed: number; chunksInserted: number } | void> {
+  ): Promise<{ filesProcessed: number; chunksInserted: number; files: AttachmentFileInfo[] }> {
-    if (!threadId || !Array.isArray(files) || files.length === 0) return
+    if (!threadId || !Array.isArray(files) || files.length === 0) {
+      return { filesProcessed: 0, chunksInserted: 0, files: [] }
+    }
+
+    // Respect feature flag: do nothing when disabled
+    if (this.config.enabled === false) {
+      return { filesProcessed: 0, chunksInserted: 0, files: [] }
+    }
 
     const vec = window.core?.extensionManager.get(ExtensionTypeEnum.VectorDB) as unknown as VectorDBExtension
     if (!vec?.createCollection || !vec?.insertChunks) {
@@ -237,41 +238,32 @@ export default class RagExtension extends RAGExtension {
     const chunkOverlap = s?.overlapTokens as number | undefined
 
     let totalChunks = 0
-    let processed = 0
+    const processedFiles: AttachmentFileInfo[] = []
-    const collection = `attachments_${threadId}`
-    let created = false
 
     for (const f of files) {
       if (!f?.path) continue
-      if (maxSize && f.size && f.size > maxSize * 1024 * 1024) continue
+      if (maxSize && f.size && f.size > maxSize * 1024 * 1024) {
+        throw new Error(`File '${f.name}' exceeds size limit (${f.size} bytes > ${maxSize} MB).`)
+      }
 
-      const type = f.type || 'application/octet-stream'
+      const fileName = f.name || f.path.split(/[\\/]/).pop()
-      const chunks = await this.parseAndEmbed(f.path, type, {
+      // Preferred/required path: let Vector DB extension handle full file ingestion
-        chunkSize: chunkSize ?? 512,
+      const canIngestFile = typeof (vec as any)?.ingestFile === 'function'
-        chunkOverlap: chunkOverlap ?? 64,
+      if (!canIngestFile) {
-        meta: { file: { name: f.name || f.path.split(/[\\/]/).pop(), path: f.path, type: f.type, size: f.size }, threadId },
+        console.error('[RAG] Vector DB extension missing ingestFile; cannot ingest document')
-      })
-
-      if (!chunks?.length) {
-        processed += 1
         continue
       }
-
+      const info = await (vec as VectorDBExtension).ingestFile(
-      // Ensure collection
+        threadId,
-      if (!created) {
+        { path: f.path, name: fileName, type: f.type, size: f.size },
-        await vec.createCollection(collection, chunks[0].embedding.length)
+        { chunkSize: chunkSize ?? 512, chunkOverlap: chunkOverlap ?? 64 }
-        created = true
-      }
-
-      await vec.insertChunks(
-        collection,
-        chunks.map((c) => ({ text: c.text, embedding: c.embedding, metadata: c.metadata }))
       )
-      totalChunks += chunks.length
+      totalChunks += Number(info?.chunk_count || 0)
-      processed += 1
+      processedFiles.push(info)
     }
 
-    return { filesProcessed: processed, chunksInserted: totalChunks }
+    // Return files we ingested with real IDs directly from ingestFile
+    return { filesProcessed: processedFiles.length, chunksInserted: totalChunks, files: processedFiles }
   }
 
   onSettingUpdate<T>(key: string, value: T): void {
@@ -310,19 +302,4 @@ export default class RagExtension extends RAGExtension {
     for (const item of data) out[item.index] = item.embedding
     return out
   }
-
-  private async parseAndEmbed(
-    filePath: string,
-    fileType: string,
-    opts: { chunkSize: number; chunkOverlap: number; meta?: Record<string, any> }
-  ): Promise<Array<{ text: string; embedding: number[]; metadata?: Record<string, any> }>> {
-    const text = await ragApi.parseDocument(filePath, fileType)
-    const chunks = await vecdbApi.chunkText(text, opts.chunkSize, opts.chunkOverlap)
-    const embeddings = await this.embedTexts(chunks)
-    return chunks.map((text, i) => ({
-      text,
-      embedding: embeddings[i],
-      metadata: opts.meta,
-    }))
-  }
 }

extensions/vector-db-extension/package.json

@@ -19,6 +19,7 @@
   },
   "dependencies": {
     "@janhq/core": "../../core/package.tgz",
+    "@janhq/tauri-plugin-rag-api": "link:../../src-tauri/plugins/tauri-plugin-rag",
     "@janhq/tauri-plugin-vector-db-api": "link:../../src-tauri/plugins/tauri-plugin-vector-db"
   },
   "files": [

extensions/vector-db-extension/src/index.ts

@@ -1,5 +1,6 @@
-import { VectorDBExtension, type SearchMode, type VectorDBStatus, type VectorChunkInput, type VectorSearchResult, type AttachmentFileInfo } from '@janhq/core'
+import { VectorDBExtension, type SearchMode, type VectorDBStatus, type VectorChunkInput, type VectorSearchResult, type AttachmentFileInfo, type VectorDBFileInput, type VectorDBIngestOptions, AIEngine } from '@janhq/core'
 import * as vecdb from '@janhq/tauri-plugin-vector-db-api'
+import * as ragApi from '@janhq/tauri-plugin-rag-api'
 
 export default class VectorDBExt extends VectorDBExtension {
   async onLoad(): Promise<void> {
@@ -12,47 +13,95 @@ export default class VectorDBExt extends VectorDBExtension {
     return await vecdb.getStatus() as VectorDBStatus
   }
 
-  async createCollection(name: string, dimension: number): Promise<void> {
+  private collectionForThread(threadId: string): string {
-    return await vecdb.createCollection(name, dimension)
+    return `attachments_${threadId}`
   }
 
-  async insertChunks(collection: string, chunks: VectorChunkInput[]): Promise<void> {
+  async createCollection(threadId: string, dimension: number): Promise<void> {
-    return await vecdb.insertChunks(collection, chunks)
+    return await vecdb.createCollection(this.collectionForThread(threadId), dimension)
+  }
+
+  async insertChunks(threadId: string, fileId: string, chunks: VectorChunkInput[]): Promise<void> {
+    return await vecdb.insertChunks(this.collectionForThread(threadId), fileId, chunks)
   }
 
   async searchCollection(
-    collection: string,
+    threadId: string,
     query_embedding: number[],
     limit: number,
     threshold: number,
     mode?: SearchMode,
     fileIds?: string[]
   ): Promise<VectorSearchResult[]> {
-    return await vecdb.searchCollection(collection, query_embedding, limit, threshold, mode, fileIds) as VectorSearchResult[]
+    return await vecdb.searchCollection(this.collectionForThread(threadId), query_embedding, limit, threshold, mode, fileIds) as VectorSearchResult[]
   }
 
-  async deleteChunks(collection: string, ids: string[]): Promise<void> {
+  async deleteChunks(threadId: string, ids: string[]): Promise<void> {
-    return await vecdb.deleteChunks(collection, ids)
+    return await vecdb.deleteChunks(this.collectionForThread(threadId), ids)
   }
 
-  async deleteCollection(collection: string): Promise<void> {
+  async deleteCollection(threadId: string): Promise<void> {
-    return await vecdb.deleteCollection(collection)
+    return await vecdb.deleteCollection(this.collectionForThread(threadId))
   }
 
-  async chunkText(text: string, chunkSize: number, chunkOverlap: number): Promise<string[]> {
+  // Optional helper for chunking
+  private async chunkText(text: string, chunkSize: number, chunkOverlap: number): Promise<string[]> {
     return await vecdb.chunkText(text, chunkSize, chunkOverlap)
   }
 
-  async listAttachments(collection: string, limit?: number): Promise<AttachmentFileInfo[]> {
+  private async embedTexts(texts: string[]): Promise<number[][]> {
-    return await vecdb.listAttachments(collection, limit) as AttachmentFileInfo[]
+    const llm = window.core?.extensionManager.getByName('@janhq/llamacpp-extension') as AIEngine & { embed?: (texts: string[]) => Promise<{ data: Array<{ embedding: number[]; index: number }> }> }
+    if (!llm?.embed) throw new Error('llamacpp extension not available')
+    const res = await llm.embed(texts)
+    const data: Array<{ embedding: number[]; index: number }> = res?.data || []
+    const out: number[][] = new Array(texts.length)
+    for (const item of data) out[item.index] = item.embedding
+    return out
+  }
+
+  async ingestFile(threadId: string, file: VectorDBFileInput, opts: VectorDBIngestOptions): Promise<AttachmentFileInfo> {
+    // Check for duplicate file (same name + path)
+    const existingFiles = await vecdb.listAttachments(this.collectionForThread(threadId)).catch(() => [])
+    const duplicate = existingFiles.find((f: any) => f.name === file.name && f.path === file.path)
+    if (duplicate) {
+      throw new Error(`File '${file.name}' has already been attached to this thread`)
+    }
+
+    const text = await ragApi.parseDocument(file.path, file.type || 'application/octet-stream')
+    const chunks = await this.chunkText(text, opts.chunkSize, opts.chunkOverlap)
+    if (!chunks.length) {
+      const fi = await vecdb.createFile(this.collectionForThread(threadId), file)
+      return fi
+    }
+    const embeddings = await this.embedTexts(chunks)
+    const dimension = embeddings[0]?.length || 0
+    if (dimension <= 0) throw new Error('Embedding dimension not available')
+    await this.createCollection(threadId, dimension)
+    const fi = await vecdb.createFile(this.collectionForThread(threadId), file)
+    await vecdb.insertChunks(
+      this.collectionForThread(threadId),
+      fi.id,
+      chunks.map((t, i) => ({ text: t, embedding: embeddings[i] }))
+    )
+    const infos = await vecdb.listAttachments(this.collectionForThread(threadId))
+    const updated = infos.find((e) => e.id === fi.id)
+    return updated || { ...fi, chunk_count: chunks.length }
+  }
+
+  async listAttachments(threadId: string, limit?: number): Promise<AttachmentFileInfo[]> {
+    return await vecdb.listAttachments(this.collectionForThread(threadId), limit) as AttachmentFileInfo[]
   }
 
   async getChunks(
-    collection: string,
+    threadId: string,
     fileId: string,
     startOrder: number,
     endOrder: number
   ): Promise<VectorSearchResult[]> {
-    return await vecdb.getChunks(collection, fileId, startOrder, endOrder) as VectorSearchResult[]
+    return await vecdb.getChunks(this.collectionForThread(threadId), fileId, startOrder, endOrder) as VectorSearchResult[]
+  }
+
+  async deleteFile(threadId: string, fileId: string): Promise<void> {
+    return await vecdb.deleteFile(this.collectionForThread(threadId), fileId)
   }
 }

src-tauri/Cargo.toml

@@ -63,7 +63,9 @@ log = "0.4"
 rmcp = { version = "0.6.0", features = [
     "client",
     "transport-sse-client",
+    "transport-sse-client-reqwest",
     "transport-streamable-http-client",
+    "transport-streamable-http-client-reqwest",
     "transport-child-process",
     "tower",
     "reqwest",

src-tauri/plugins/tauri-plugin-rag/src/parser.rs

@@ -13,8 +13,24 @@ use std::borrow::Cow;
 
 pub fn parse_pdf(file_path: &str) -> Result<String, RagError> {
     let bytes = fs::read(file_path)?;
-    pdf_extract::extract_text_from_mem(&bytes)
+    let text = pdf_extract::extract_text_from_mem(&bytes)
-        .map_err(|e| RagError::ParseError(format!("PDF parse error: {}", e)))
+        .map_err(|e| RagError::ParseError(format!("PDF parse error: {}", e)))?;
+
+    // Validate that the PDF has extractable text (not image-based/scanned)
+    // Count meaningful characters (excluding whitespace)
+    let meaningful_chars = text.chars()
+        .filter(|c| !c.is_whitespace())
+        .count();
+
+    // Require at least 50 non-whitespace characters to consider it a text PDF
+    // This threshold filters out PDFs that are purely images or scanned documents
+    if meaningful_chars < 50 {
+        return Err(RagError::ParseError(
+            "PDF appears to be image-based or scanned. OCR is not supported yet. Please use a text-based PDF.".to_string()
+        ));
+    }
+
+    Ok(text)
 }
 
 pub fn parse_text(file_path: &str) -> Result<String, RagError> {

src-tauri/plugins/tauri-plugin-vector-db/build.rs

@@ -1,12 +1,16 @@
 fn main() {
     tauri_plugin::Builder::new(&[
         "create_collection",
+        "create_file",
         "insert_chunks",
         "search_collection",
         "delete_chunks",
+        "delete_file",
         "delete_collection",
         "chunk_text",
         "get_status",
+        "list_attachments",
+        "get_chunks",
     ])
     .build();
 }

src-tauri/plugins/tauri-plugin-vector-db/guest-js/index.ts

@@ -2,13 +2,6 @@ import { invoke } from '@tauri-apps/api/core'
 
 export type SearchMode = 'auto' | 'ann' | 'linear'
 
-export interface ChunkInput {
-  id?: string
-  text: string
-  embedding: number[]
-  metadata?: Record<string, any>
-}
-
 export interface SearchResult {
   id: string
   text: string
@@ -42,11 +35,26 @@ export async function createCollection(name: string, dimension: number): Promise
   return await invoke('plugin:vector-db|create_collection', { name, dimension })
 }
 
+export async function createFile(
+  collection: string,
+  file: { path: string; name?: string; type?: string; size?: number }
+): Promise<AttachmentFileInfo> {
+  return await invoke('plugin:vector-db|create_file', { collection, file })
+}
+
 export async function insertChunks(
   collection: string,
-  chunks: ChunkInput[]
+  fileId: string,
+  chunks: Array<{ text: string; embedding: number[] }>
 ): Promise<void> {
-  return await invoke('plugin:vector-db|insert_chunks', { collection, chunks })
+  return await invoke('plugin:vector-db|insert_chunks', { collection, fileId, chunks })
+}
+
+export async function deleteFile(
+  collection: string,
+  fileId: string
+): Promise<void> {
+  return await invoke('plugin:vector-db|delete_file', { collection, fileId })
 }
 
 export async function searchCollection(

src-tauri/plugins/tauri-plugin-vector-db/permissions/autogenerated/commands/create_file.toml

@@ -0,0 +1,13 @@
+# Automatically generated - DO NOT EDIT!
+
+"$schema" = "../../schemas/schema.json"
+
+[[permission]]
+identifier = "allow-create-file"
+description = "Enables the create_file command without any pre-configured scope."
+commands.allow = ["create_file"]
+
+[[permission]]
+identifier = "deny-create-file"
+description = "Denies the create_file command without any pre-configured scope."
+commands.deny = ["create_file"]

src-tauri/plugins/tauri-plugin-vector-db/permissions/autogenerated/commands/delete_file.toml

@@ -0,0 +1,13 @@
+# Automatically generated - DO NOT EDIT!
+
+"$schema" = "../../schemas/schema.json"
+
+[[permission]]
+identifier = "allow-delete-file"
+description = "Enables the delete_file command without any pre-configured scope."
+commands.allow = ["delete_file"]
+
+[[permission]]
+identifier = "deny-delete-file"
+description = "Denies the delete_file command without any pre-configured scope."
+commands.deny = ["delete_file"]

src-tauri/plugins/tauri-plugin-vector-db/permissions/autogenerated/commands/list_attachments.toml

@@ -11,4 +11,3 @@ commands.allow = ["list_attachments"]
 identifier = "deny-list-attachments"
 description = "Denies the list_attachments command without any pre-configured scope."
 commands.deny = ["list_attachments"]
-

src-tauri/plugins/tauri-plugin-vector-db/permissions/autogenerated/reference.md

@@ -7,8 +7,10 @@ Default permissions for the vector-db plugin
 - `allow-get-status`
 - `allow-create-collection`
 - `allow-insert-chunks`
+- `allow-create-file`
 - `allow-search-collection`
 - `allow-delete-chunks`
+- `allow-delete-file`
 - `allow-delete-collection`
 - `allow-chunk-text`
 - `allow-list-attachments`
@@ -78,6 +80,32 @@ Denies the create_collection command without any pre-configured scope.
 <tr>
 <td>
 
+`vector-db:allow-create-file`
+
+</td>
+<td>
+
+Enables the create_file command without any pre-configured scope.
+
+</td>
+</tr>
+
+<tr>
+<td>
+
+`vector-db:deny-create-file`
+
+</td>
+<td>
+
+Denies the create_file command without any pre-configured scope.
+
+</td>
+</tr>
+
+<tr>
+<td>
+
 `vector-db:allow-delete-chunks`
 
 </td>
@@ -130,6 +158,32 @@ Denies the delete_collection command without any pre-configured scope.
 <tr>
 <td>
 
+`vector-db:allow-delete-file`
+
+</td>
+<td>
+
+Enables the delete_file command without any pre-configured scope.
+
+</td>
+</tr>
+
+<tr>
+<td>
+
+`vector-db:deny-delete-file`
+
+</td>
+<td>
+
+Denies the delete_file command without any pre-configured scope.
+
+</td>
+</tr>
+
+<tr>
+<td>
+
 `vector-db:allow-get-chunks`
 
 </td>

src-tauri/plugins/tauri-plugin-vector-db/permissions/default.toml

@@ -4,8 +4,10 @@ permissions = [
   "allow-get-status",
   "allow-create-collection",
   "allow-insert-chunks",
+  "allow-create-file",
   "allow-search-collection",
   "allow-delete-chunks",
+  "allow-delete-file",
   "allow-delete-collection",
   "allow-chunk-text",
   "allow-list-attachments",

src-tauri/plugins/tauri-plugin-vector-db/permissions/schemas/schema.json

@@ -318,6 +318,18 @@
           "const": "deny-create-collection",
           "markdownDescription": "Denies the create_collection command without any pre-configured scope."
         },
+        {
+          "description": "Enables the create_file command without any pre-configured scope.",
+          "type": "string",
+          "const": "allow-create-file",
+          "markdownDescription": "Enables the create_file command without any pre-configured scope."
+        },
+        {
+          "description": "Denies the create_file command without any pre-configured scope.",
+          "type": "string",
+          "const": "deny-create-file",
+          "markdownDescription": "Denies the create_file command without any pre-configured scope."
+        },
         {
           "description": "Enables the delete_chunks command without any pre-configured scope.",
           "type": "string",
@@ -342,6 +354,18 @@
           "const": "deny-delete-collection",
           "markdownDescription": "Denies the delete_collection command without any pre-configured scope."
         },
+        {
+          "description": "Enables the delete_file command without any pre-configured scope.",
+          "type": "string",
+          "const": "allow-delete-file",
+          "markdownDescription": "Enables the delete_file command without any pre-configured scope."
+        },
+        {
+          "description": "Denies the delete_file command without any pre-configured scope.",
+          "type": "string",
+          "const": "deny-delete-file",
+          "markdownDescription": "Denies the delete_file command without any pre-configured scope."
+        },
         {
           "description": "Enables the get_chunks command without any pre-configured scope.",
           "type": "string",
@@ -403,10 +427,10 @@
           "markdownDescription": "Denies the search_collection command without any pre-configured scope."
         },
         {
-          "description": "Default permissions for the vector-db plugin\n#### This default permission set includes:\n\n- `allow-get-status`\n- `allow-create-collection`\n- `allow-insert-chunks`\n- `allow-search-collection`\n- `allow-delete-chunks`\n- `allow-delete-collection`\n- `allow-chunk-text`\n- `allow-list-attachments`\n- `allow-get-chunks`",
+          "description": "Default permissions for the vector-db plugin\n#### This default permission set includes:\n\n- `allow-get-status`\n- `allow-create-collection`\n- `allow-insert-chunks`\n- `allow-create-file`\n- `allow-search-collection`\n- `allow-delete-chunks`\n- `allow-delete-file`\n- `allow-delete-collection`\n- `allow-chunk-text`\n- `allow-list-attachments`\n- `allow-get-chunks`",
           "type": "string",
           "const": "default",
-          "markdownDescription": "Default permissions for the vector-db plugin\n#### This default permission set includes:\n\n- `allow-get-status`\n- `allow-create-collection`\n- `allow-insert-chunks`\n- `allow-search-collection`\n- `allow-delete-chunks`\n- `allow-delete-collection`\n- `allow-chunk-text`\n- `allow-list-attachments`\n- `allow-get-chunks`"
+          "markdownDescription": "Default permissions for the vector-db plugin\n#### This default permission set includes:\n\n- `allow-get-status`\n- `allow-create-collection`\n- `allow-insert-chunks`\n- `allow-create-file`\n- `allow-search-collection`\n- `allow-delete-chunks`\n- `allow-delete-file`\n- `allow-delete-collection`\n- `allow-chunk-text`\n- `allow-list-attachments`\n- `allow-get-chunks`"
         }
       ]
     }

src-tauri/plugins/tauri-plugin-vector-db/src/commands.rs

@@ -1,6 +1,6 @@
 use crate::{VectorDBError, VectorDBState};
 use crate::db::{
-    self, AttachmentFileInfo, ChunkInput, SearchResult,
+    self, AttachmentFileInfo, SearchResult, MinimalChunkInput,
 };
 use serde::{Deserialize, Serialize};
 use tauri::State;
@@ -10,6 +10,15 @@ pub struct Status {
     pub ann_available: bool,
 }
 
+#[derive(Debug, Serialize, Deserialize)]
+pub struct FileInput {
+    pub path: String,
+    pub name: Option<String>,
+    #[serde(rename = "type")]
+    pub file_type: Option<String>,
+    pub size: Option<i64>,
+}
+
 // ============================================================================
 // Tauri Command Handlers
 // ============================================================================
@@ -74,18 +83,48 @@ pub async fn create_collection<R: tauri::Runtime>(
     Ok(())
 }
 
+#[tauri::command]
+pub async fn create_file<R: tauri::Runtime>(
+    _app: tauri::AppHandle<R>,
+    state: State<'_, VectorDBState>,
+    collection: String,
+    file: FileInput,
+) -> Result<AttachmentFileInfo, VectorDBError> {
+    let path = db::collection_path(&state.base_dir, &collection);
+    let conn = db::open_or_init_conn(&path)?;
+    db::create_file(
+        &conn,
+        &file.path,
+        file.name.as_deref(),
+        file.file_type.as_deref(),
+        file.size,
+    )
+}
+
 #[tauri::command]
 pub async fn insert_chunks<R: tauri::Runtime>(
     _app: tauri::AppHandle<R>,
     state: State<'_, VectorDBState>,
     collection: String,
-    chunks: Vec<ChunkInput>,
+    file_id: String,
+    chunks: Vec<MinimalChunkInput>,
 ) -> Result<(), VectorDBError> {
     let path = db::collection_path(&state.base_dir, &collection);
     let conn = db::open_or_init_conn(&path)?;
     let vec_loaded = db::try_load_sqlite_vec(&conn);
-    db::insert_chunks(&conn, chunks, vec_loaded)?;
+    db::insert_chunks(&conn, &file_id, chunks, vec_loaded)
-    Ok(())
+}
+
+#[tauri::command]
+pub async fn delete_file<R: tauri::Runtime>(
+    _app: tauri::AppHandle<R>,
+    state: State<'_, VectorDBState>,
+    collection: String,
+    file_id: String,
+) -> Result<(), VectorDBError> {
+    let path = db::collection_path(&state.base_dir, &collection);
+    let conn = db::open_or_init_conn(&path)?;
+    db::delete_file(&conn, &file_id)
 }
 
 #[tauri::command]

src-tauri/plugins/tauri-plugin-vector-db/src/db.rs

@@ -2,7 +2,6 @@ use crate::VectorDBError;
 use crate::utils::{cosine_similarity, from_le_bytes_vec, to_le_bytes_vec};
 use rusqlite::{params, Connection, OptionalExtension};
 use serde::{Deserialize, Serialize};
-use std::collections::HashMap;
 use std::fs;
 use std::path::PathBuf;
 use uuid::Uuid;
@@ -16,18 +15,6 @@ pub struct FileMetadata {
     pub size: Option<i64>,
 }
 
-#[derive(Debug, Serialize, Deserialize, Clone)]
-pub struct ChunkMetadata {
-    pub file: FileMetadata,
-}
-
-#[derive(Debug, Serialize, Deserialize)]
-pub struct ChunkInput {
-    pub id: Option<String>,
-    pub text: String,
-    pub embedding: Vec<f32>,
-    pub metadata: Option<ChunkMetadata>,
-}
 
 #[derive(Debug, Serialize, Deserialize)]
 pub struct SearchResult {
@@ -49,6 +36,13 @@ pub struct AttachmentFileInfo {
     pub chunk_count: i64,
 }
 
+// New minimal chunk input (no id/metadata) for file-scoped insertion
+#[derive(Debug, Serialize, Deserialize, Clone)]
+pub struct MinimalChunkInput {
+    pub text: String,
+    pub embedding: Vec<f32>,
+}
+
 // ============================================================================
 // Connection & Path Management
 // ============================================================================
@@ -190,14 +184,84 @@ pub fn create_schema(conn: &Connection, dimension: usize) -> Result<bool, Vector
 // Insert Operations
 // ============================================================================
 
+pub fn create_file(
+    conn: &Connection,
+    path: &str,
+    name: Option<&str>,
+    file_type: Option<&str>,
+    size: Option<i64>,
+) -> Result<AttachmentFileInfo, VectorDBError> {
+    let tx = conn.unchecked_transaction()?;
+
+    // Try get existing by path
+    if let Ok(Some(id)) = tx
+        .prepare("SELECT id FROM files WHERE path = ?1")
+        .and_then(|mut s| s.query_row(params![path], |r| r.get::<_, String>(0)).optional())
+    {
+        let row: AttachmentFileInfo = {
+            let mut stmt = tx.prepare(
+                "SELECT id, path, name, type, size, chunk_count FROM files WHERE id = ?1",
+            )?;
+            stmt.query_row(params![id.as_str()], |r| {
+                Ok(AttachmentFileInfo {
+                    id: r.get(0)?,
+                    path: r.get(1)?,
+                    name: r.get(2)?,
+                    file_type: r.get(3)?,
+                    size: r.get(4)?,
+                    chunk_count: r.get(5)?,
+                })
+            })?
+        };
+        tx.commit()?;
+        return Ok(row);
+    }
+
+    let new_id = Uuid::new_v4().to_string();
+    // Determine file size if not provided
+    let computed_size: Option<i64> = match size {
+        Some(s) if s > 0 => Some(s),
+        _ => {
+            match std::fs::metadata(path) {
+                Ok(meta) => Some(meta.len() as i64),
+                Err(_) => None,
+            }
+        }
+    };
+    tx.execute(
+        "INSERT INTO files (id, path, name, type, size, chunk_count) VALUES (?1, ?2, ?3, ?4, ?5, 0)",
+        params![new_id, path, name, file_type, computed_size],
+    )?;
+
+    let row: AttachmentFileInfo = {
+        let mut stmt = tx.prepare(
+            "SELECT id, path, name, type, size, chunk_count FROM files WHERE path = ?1",
+        )?;
+        stmt.query_row(params![path], |r| {
+            Ok(AttachmentFileInfo {
+                id: r.get(0)?,
+                path: r.get(1)?,
+                name: r.get(2)?,
+                file_type: r.get(3)?,
+                size: r.get(4)?,
+                chunk_count: r.get(5)?,
+            })
+        })?
+    };
+
+    tx.commit()?;
+    Ok(row)
+}
+
 pub fn insert_chunks(
     conn: &Connection,
-    chunks: Vec<ChunkInput>,
+    file_id: &str,
+    chunks: Vec<MinimalChunkInput>,
     vec_loaded: bool,
 ) -> Result<(), VectorDBError> {
     let tx = conn.unchecked_transaction()?;
 
-    // Check if vec virtual table exists
+    // Check if vec table exists
     let has_vec = if vec_loaded {
         conn
             .prepare("SELECT name FROM sqlite_master WHERE type='table' AND name='chunks_vec'")
@@ -209,69 +273,22 @@ pub fn insert_chunks(
         false
     };
 
-    let mut file_id_cache: HashMap<String, String> = HashMap::new();
+    // Determine current max order
-    let mut file_chunk_counters: HashMap<String, i64> = HashMap::new();
+    let mut current_order: i64 = tx
+        .query_row(
+            "SELECT COALESCE(MAX(chunk_file_order), -1) FROM chunks WHERE file_id = ?1",
+            params![file_id],
+            |row| row.get::<_, i64>(0),
+        )
+        .unwrap_or(-1);
 
     for ch in chunks.into_iter() {
+        current_order += 1;
         let emb = to_le_bytes_vec(&ch.embedding);
-
+        let chunk_id = Uuid::new_v4().to_string();
-        // Extract file info from metadata and get/create file_id
-        let mut file_id: Option<String> = None;
-        if let Some(ref meta) = ch.metadata {
-            let file_path = &meta.file.path;
-
-            // Check cache first
-            if let Some(cached_id) = file_id_cache.get(file_path) {
-                file_id = Some(cached_id.clone());
-            } else {
-                // Generate UUID for new file
-                let uuid = Uuid::new_v4().to_string();
-
-                // Insert or ignore if path already exists
-                tx.execute(
-                    "INSERT OR IGNORE INTO files (id, path, name, type, size) VALUES (?1, ?2, ?3, ?4, ?5)",
-                    params![
-                        &uuid,
-                        &meta.file.path,
-                        &meta.file.name,
-                        &meta.file.file_type,
-                        meta.file.size
-                    ],
-                )?;
-
-                // Get the actual id (either the one we just inserted or existing one)
-                let id: String = tx.query_row(
-                    "SELECT id FROM files WHERE path = ?1",
-                    params![file_path],
-                    |row| row.get(0),
-                )?;
-                file_id = Some(id.clone());
-                file_id_cache.insert(file_path.clone(), id);
-            }
-        }
-
-        // Get or initialize chunk order for this file
-        let chunk_order = if let Some(ref fid) = file_id {
-            let counter = file_chunk_counters.entry(fid.clone()).or_insert_with(|| {
-                // Get max existing order for this file
-                tx.query_row(
-                    "SELECT COALESCE(MAX(chunk_file_order), -1) FROM chunks WHERE file_id = ?1",
-                    params![fid],
-                    |row| row.get::<_, i64>(0),
-                ).unwrap_or(-1)
-            });
-            *counter += 1;
-            *counter
-        } else {
-            0
-        };
-
-        // Generate UUID for chunk if not provided
-        let chunk_id = ch.id.unwrap_or_else(|| Uuid::new_v4().to_string());
-
         tx.execute(
             "INSERT OR REPLACE INTO chunks (id, text, embedding, file_id, chunk_file_order) VALUES (?1, ?2, ?3, ?4, ?5)",
-            params![chunk_id, ch.text, emb, file_id, chunk_order],
+            params![chunk_id, ch.text, emb, file_id, current_order],
         )?;
 
         if has_vec {
@@ -279,35 +296,36 @@ pub fn insert_chunks(
                 .prepare("SELECT rowid FROM chunks WHERE id=?1")?
                 .query_row(params![chunk_id], |r| r.get(0))?;
             let json_vec = serde_json::to_string(&ch.embedding).unwrap_or("[]".to_string());
-            match tx.execute(
+            let _ = tx.execute(
                 "INSERT OR REPLACE INTO chunks_vec(rowid, embedding) VALUES (?1, ?2)",
                 params![rowid, json_vec],
-            ) {
+            );
-                Ok(_) => {}
-                Err(e) => {
-                    println!("[VectorDB] ✗ Failed to insert into chunks_vec: {}", e);
-                }
-            }
         }
     }
 
-    // Update chunk_count for all affected files
+    // Update chunk_count
-    for file_id in file_id_cache.values() {
+    let count: i64 = tx.query_row(
-        let count: i64 = tx.query_row(
+        "SELECT COUNT(*) FROM chunks WHERE file_id = ?1",
-            "SELECT COUNT(*) FROM chunks WHERE file_id = ?1",
+        params![file_id],
-            params![file_id],
+        |row| row.get(0),
-            |row| row.get(0),
+    )?;
-        )?;
+    tx.execute(
-        tx.execute(
+        "UPDATE files SET chunk_count = ?1 WHERE id = ?2",
-            "UPDATE files SET chunk_count = ?1 WHERE id = ?2",
+        params![count, file_id],
-            params![count, file_id],
+    )?;
-        )?;
-    }
 
     tx.commit()?;
     Ok(())
 }
 
+pub fn delete_file(conn: &Connection, file_id: &str) -> Result<(), VectorDBError> {
+    let tx = conn.unchecked_transaction()?;
+    tx.execute("DELETE FROM chunks WHERE file_id = ?1", params![file_id])?;
+    tx.execute("DELETE FROM files WHERE id = ?1", params![file_id])?;
+    tx.commit()?;
+    Ok(())
+}
+
 // ============================================================================
 // Search Operations
 // ============================================================================

src-tauri/plugins/tauri-plugin-vector-db/src/lib.rs

@@ -18,8 +18,10 @@ pub fn init<R: Runtime>() -> TauriPlugin<R> {
         .invoke_handler(tauri::generate_handler![
             commands::create_collection,
             commands::insert_chunks,
+            commands::create_file,
             commands::search_collection,
             commands::delete_chunks,
+            commands::delete_file,
             commands::delete_collection,
             commands::chunk_text,
             commands::get_status,

src-tauri/src/core/mcp/helpers.rs

@@ -496,6 +496,9 @@ async fn schedule_mcp_start_task<R: Runtime>(
             client_info: Implementation {
                 name: "Jan Streamable Client".to_string(),
                 version: "0.0.1".to_string(),
+                title: None,
+                website_url: None,
+                icons: None,
             },
         };
         let client = client_info.serve(transport).await.inspect_err(|e| {
@@ -567,6 +570,9 @@ async fn schedule_mcp_start_task<R: Runtime>(
             client_info: Implementation {
                 name: "Jan SSE Client".to_string(),
                 version: "0.0.1".to_string(),
+                title: None,
+                website_url: None,
+                icons: None,
             },
         };
         let client = client_info.serve(transport).await.map_err(|e| {

web-app/src/containers/ChatInput.tsx

@@ -23,6 +23,7 @@ import {
   IconX,
   IconPaperclip,
   IconLoader2,
+  IconCheck,
 } from '@tabler/icons-react'
 import { useTranslation } from '@/i18n/react-i18next-compat'
 import { useGeneralSetting } from '@/hooks/useGeneralSetting'
@@ -40,7 +41,7 @@ import { TokenCounter } from '@/components/TokenCounter'
 import { useMessages } from '@/hooks/useMessages'
 import { useShallow } from 'zustand/react/shallow'
 import { McpExtensionToolLoader } from './McpExtensionToolLoader'
-import { ExtensionTypeEnum, MCPExtension, RAGExtension } from '@janhq/core'
+import { ExtensionTypeEnum, MCPExtension, fs, RAGExtension } from '@janhq/core'
 import { ExtensionManager } from '@/lib/extension'
 import { useAttachments } from '@/hooks/useAttachments'
 import { open } from '@tauri-apps/plugin-dialog'
@@ -49,6 +50,7 @@ import { PlatformFeatures } from '@/lib/platform/const'
 import { PlatformFeature } from '@/lib/platform/types'
 import { useAnalytic } from '@/hooks/useAnalytic'
 import posthog from 'posthog-js'
+import { Attachment, createImageAttachment, createDocumentAttachment } from '@/types/attachment'
 
 type ChatInputProps = {
   className?: string
@@ -101,33 +103,20 @@ const ChatInput = ({
   const [message, setMessage] = useState('')
   const [dropdownToolsAvailable, setDropdownToolsAvailable] = useState(false)
   const [tooltipToolsAvailable, setTooltipToolsAvailable] = useState(false)
-  const [uploadedFiles, setUploadedFiles] = useState<
+  const [attachments, setAttachments] = useState<Attachment[]>([])
-    Array<{
-      name: string
-      type: string
-      size: number
-      base64: string
-      dataUrl: string
-    }>
-  >([])
-  // Document attachments (desktop RAG ingestion). We only index on send.
-  const [docFiles, setDocFiles] = useState<
-    Array<{
-      name: string
-      path: string
-      size?: number
-      type?: string
-    }>
-  >([])
   const [connectedServers, setConnectedServers] = useState<string[]>([])
   const [isDragOver, setIsDragOver] = useState(false)
   const [hasMmproj, setHasMmproj] = useState(false)
   const [hasActiveModels, setHasActiveModels] = useState(false)
   const attachmentsEnabled = useAttachments((s) => s.enabled)
-  const [ingestingDocs, setIngestingDocs] = useState(false)
   // Determine whether to show the Attach documents button (simple gating)
   const showAttachmentButton =
     attachmentsEnabled && PlatformFeatures[PlatformFeature.ATTACHMENTS]
+  // Derived: any document currently processing (ingestion in progress)
+  const ingestingDocs = attachments.some(
+    (a) => a.type === 'document' && a.processing
+  )
+  const ingestingAny = attachments.some((a) => a.processing)
 
   // Check for connected MCP servers
   useEffect(() => {
@@ -208,36 +197,10 @@ const ChatInput = ({
       setMessage('Please select a model to start chatting.')
       return
     }
-    if (!prompt.trim() && uploadedFiles.length === 0 && docFiles.length === 0) {
+    if (!prompt.trim()) {
       return
     }
-    // If we have pending doc files, index them first
+
-    if (docFiles.length > 0) {
-      try {
-        setIngestingDocs(true)
-        const rag = extensionManager.get<RAGExtension>(ExtensionTypeEnum.RAG)
-        if (!rag?.ingestAttachments) throw new Error('Retrieval extension not available')
-        for (const f of docFiles) {
-          const id = (toast as any).loading
-            ? (toast as any).loading(`Indexing ${f.name || f.path}…`)
-            : undefined
-          try {
-            await rag.ingestAttachments(currentThreadId!, [{ path: f.path, name: f.name }])
-            if (id) toast.success(`Indexed ${f.name || f.path}`, { id })
-          } catch (err) {
-            if (id) toast.error(`Failed to index ${f.name || f.path}`, { id })
-            throw err
-          }
-        }
-        setDocFiles([])
-      } catch (err) {
-        const desc = err instanceof Error ? err.message : String(err)
-        toast.error('Failed to index attachments', { description: desc })
-        setIngestingDocs(false)
-        return
-      }
-      setIngestingDocs(false)
-    }
     setMessage('')
 
     // Track message send event with PostHog (only if product analytics is enabled)
@@ -252,13 +215,39 @@ const ChatInput = ({
       }
     }
 
+    // Callback to update attachment processing state
+    const updateAttachmentProcessing = (
+      fileName: string,
+      status: 'processing' | 'done' | 'error' | 'clear_docs' | 'clear_all'
+    ) => {
+      if (status === 'clear_docs') {
+        setAttachments((prev) => prev.filter((a) => a.type !== 'document'))
+        return
+      }
+      if (status === 'clear_all') {
+        setAttachments([])
+        return
+      }
+      setAttachments((prev) =>
+        prev.map((att) =>
+          att.name === fileName
+            ? {
+                ...att,
+                processing: status === 'processing',
+                processed: status === 'done' ? true : att.processed,
+              }
+            : att
+        )
+      )
+    }
+
     sendMessage(
       prompt,
       true,
-      uploadedFiles.length > 0 ? uploadedFiles : undefined,
+      attachments.length > 0 ? attachments : undefined,
-      projectId
+      projectId,
+      updateAttachmentProcessing
     )
-    setUploadedFiles([])
   }
 
   useEffect(() => {
@@ -333,10 +322,6 @@ const ChatInput = ({
         toast.info('Attachments are disabled in Settings')
         return
       }
-      if (!currentThreadId) {
-        toast.info('Please start a thread first to attach documents.')
-        return
-      }
       const selection = await open({
         multiple: true,
         filters: [
@@ -349,24 +334,128 @@ const ChatInput = ({
       if (!selection) return
       const paths = Array.isArray(selection) ? selection : [selection]
       if (!paths.length) return
-      setDocFiles((prev) => [
+
-        ...prev,
+      // Check for duplicates and fetch file sizes
-        ...paths.map((p) => ({
+      const existingPaths = new Set(
-          path: p,
+        attachments
-          name: p.split(/[\\/]/).pop() || p,
+          .filter((a) => a.type === 'document' && a.path)
-        })),
+          .map((a) => a.path)
-      ])
+      )
+
+      const duplicates: string[] = []
+      const newDocAttachments: Attachment[] = []
+
+      for (const p of paths) {
+        if (existingPaths.has(p)) {
+          duplicates.push(p.split(/[\\/]/).pop() || p)
+          continue
+        }
+
+        const name = p.split(/[\\/]/).pop() || p
+        const fileType = name.split('.').pop()?.toLowerCase()
+        let size: number | undefined = undefined
+        try {
+          const stat = await fs.fileStat(p)
+          size = stat?.size ? Number(stat.size) : undefined
+        } catch (e) {
+          console.warn('Failed to read file size for', p, e)
+        }
+        newDocAttachments.push(
+          createDocumentAttachment({
+            name,
+            path: p,
+            fileType,
+            size,
+          })
+        )
+      }
+
+      if (duplicates.length > 0) {
+        toast.warning('Files already attached', {
+          description: `${duplicates.join(', ')} ${duplicates.length === 1 ? 'is' : 'are'} already in the list`,
+        })
+      }
+
+      if (newDocAttachments.length > 0) {
+        // Add to state first with processing flag
+        setAttachments((prev) => [...prev, ...newDocAttachments])
+
+        // If thread exists, ingest immediately
+        if (currentThreadId) {
+          const ragExtension = ExtensionManager.getInstance().get(
+            ExtensionTypeEnum.RAG
+          ) as RAGExtension | undefined
+          if (!ragExtension) {
+            toast.error('RAG extension not available')
+            return
+          }
+
+          // Ingest each document
+          for (const doc of newDocAttachments) {
+            try {
+              // Mark as processing
+              setAttachments((prev) =>
+                prev.map((a) =>
+                  a.path === doc.path && a.type === 'document'
+                    ? { ...a, processing: true }
+                    : a
+                )
+              )
+
+              const result = await ragExtension.ingestAttachments(
+                currentThreadId,
+                [
+                  {
+                    path: doc.path!,
+                    name: doc.name,
+                    type: doc.fileType,
+                    size: doc.size,
+                  },
+                ]
+              )
+
+              const fileInfo = result.files?.[0]
+              if (fileInfo?.id) {
+                // Mark as processed with ID
+                setAttachments((prev) =>
+                  prev.map((a) =>
+                    a.path === doc.path && a.type === 'document'
+                      ? {
+                          ...a,
+                          processing: false,
+                          processed: true,
+                          id: fileInfo.id,
+                          chunkCount: fileInfo.chunk_count,
+                        }
+                      : a
+                  )
+                )
+              } else {
+                throw new Error('No file ID returned from ingestion')
+              }
+            } catch (error) {
+              console.error('Failed to ingest document:', error)
+              // Remove failed document
+              setAttachments((prev) =>
+                prev.filter((a) => !(a.path === doc.path && a.type === 'document'))
+              )
+              toast.error(`Failed to ingest ${doc.name}`, {
+                description:
+                  error instanceof Error ? error.message : String(error),
+              })
+            }
+          }
+        }
+      }
     } catch (e) {
-      console.error('Failed to ingest attachments:', e)
+      console.error('Failed to attach documents:', e)
       const desc = e instanceof Error ? e.message : String(e)
       toast.error('Failed to attach documents', { description: desc })
     }
   }
 
-  const handleRemoveFile = (indexToRemove: number) => {
+  const handleRemoveAttachment = (indexToRemove: number) => {
-    setUploadedFiles((prev) =>
+    setAttachments((prev) => prev.filter((_, index) => index !== indexToRemove))
-      prev.filter((_, index) => index !== indexToRemove)
-    )
   }
 
   const getFileTypeFromExtension = (fileName: string): string => {
@@ -382,20 +471,39 @@ const ChatInput = ({
     }
   }
 
+  const formatBytes = (bytes?: number): string => {
+    if (!bytes || bytes <= 0) return ''
+    const units = ['B', 'KB', 'MB', 'GB']
+    let i = 0
+    let val = bytes
+    while (val >= 1024 && i < units.length - 1) {
+      val /= 1024
+      i++
+    }
+    return `${val.toFixed(i === 0 ? 0 : 1)} ${units[i]}`
+  }
+
   const handleFileChange = (e: React.ChangeEvent<HTMLInputElement>) => {
     const files = e.target.files
 
     if (files && files.length > 0) {
       const maxSize = 10 * 1024 * 1024 // 10MB in bytes
-      const newFiles: Array<{
+      const newFiles: Attachment[] = []
-        name: string
+      const duplicates: string[] = []
-        type: string
+      const existingImageNames = new Set(
-        size: number
+        attachments
-        base64: string
+          .filter((a) => a.type === 'image')
-        dataUrl: string
+          .map((a) => a.name)
-      }> = []
+      )
 
       Array.from(files).forEach((file) => {
+        // Check for duplicate image names
+        if (existingImageNames.has(file.name)) {
+          duplicates.push(file.name)
+          return
+        }
+
+
         // Check file size
         if (file.size > maxSize) {
           setMessage(`File is too large. Maximum size is 10MB.`)
@@ -429,26 +537,92 @@ const ChatInput = ({
           const result = reader.result
           if (typeof result === 'string') {
             const base64String = result.split(',')[1]
-            const fileData = {
+            const att = createImageAttachment({
               name: file.name,
               size: file.size,
-              type: actualType,
+              mimeType: actualType,
               base64: base64String,
               dataUrl: result,
-            }
+            })
-            newFiles.push(fileData)
+            newFiles.push(att)
             // Update state
             if (
               newFiles.length ===
               Array.from(files).filter((f) => {
                 const fType = getFileTypeFromExtension(f.name) || f.type
-                return f.size <= maxSize && allowedTypes.includes(fType)
+                return (
+                  f.size <= maxSize &&
+                  allowedTypes.includes(fType) &&
+                  !existingImageNames.has(f.name)
+                )
               }).length
             ) {
-              setUploadedFiles((prev) => {
+              if (newFiles.length > 0) {
-                const updated = [...prev, ...newFiles]
+                setAttachments((prev) => {
-                return updated
+                  const updated = [...prev, ...newFiles]
-              })
+                  return updated
+                })
+
+                // If thread exists, ingest images immediately
+                if (currentThreadId) {
+                  ;(async () => {
+                    for (const img of newFiles) {
+                      try {
+                        // Mark as processing
+                        setAttachments((prev) =>
+                          prev.map((a) =>
+                            a.name === img.name && a.type === 'image'
+                              ? { ...a, processing: true }
+                              : a
+                          )
+                        )
+
+                        const result = await serviceHub.uploads().ingestImage(
+                          currentThreadId,
+                          img
+                        )
+
+                        if (result?.id) {
+                          // Mark as processed with ID
+                          setAttachments((prev) =>
+                            prev.map((a) =>
+                              a.name === img.name && a.type === 'image'
+                                ? {
+                                    ...a,
+                                    processing: false,
+                                    processed: true,
+                                    id: result.id,
+                                  }
+                                : a
+                            )
+                          )
+                        } else {
+                          throw new Error('No ID returned from image ingestion')
+                        }
+                      } catch (error) {
+                        console.error('Failed to ingest image:', error)
+                        // Remove failed image
+                        setAttachments((prev) =>
+                          prev.filter(
+                            (a) => !(a.name === img.name && a.type === 'image')
+                          )
+                        )
+                        toast.error(`Failed to ingest ${img.name}`, {
+                          description:
+                            error instanceof Error ? error.message : String(error),
+                        })
+                      }
+                    }
+                  })()
+                }
+              }
+
+              if (duplicates.length > 0) {
+                toast.warning('Some images already attached', {
+                  description: `${duplicates.join(', ')} ${duplicates.length === 1 ? 'is' : 'are'} already in the list`,
+                })
+              }
+
               // Reset the file input value to allow re-uploading the same file
               if (fileInputRef.current) {
                 fileInputRef.current.value = ''
@@ -662,54 +836,90 @@ const ChatInput = ({
             onDragOver={hasMmproj ? handleDragOver : undefined}
             onDrop={hasMmproj ? handleDrop : undefined}
           >
-            {(uploadedFiles.length > 0 || docFiles.length > 0) && (
+            {attachments.length > 0 && (
               <div className="flex gap-3 items-center p-2 pb-0">
-                {uploadedFiles.map((file, index) => {
+                {attachments
-                  return (
+                  .map((att, idx) => ({ att, idx }))
-                    <div
+                  .map(({ att, idx }) => {
-                      key={index}
+                    const isImage = att.type === 'image'
-                      className={cn(
+                    const ext = att.fileType || att.mimeType?.split('/')[1]
-                        'relative border border-main-view-fg/5 rounded-lg',
+                    return (
-                        file.type.startsWith('image/') ? 'size-14' : 'h-14 '
+                      <div key={`${att.type}-${idx}-${att.name}`} className="relative">
-                      )}
+                        <TooltipProvider>
-                    >
+                          <Tooltip>
-                      {file.type.startsWith('image/') && (
+                            <TooltipTrigger asChild>
-                        <img
+                              <div
-                          className="object-cover w-full h-full rounded-lg"
+                                className={cn(
-                          src={file.dataUrl}
+                                  'relative border border-main-view-fg/5 rounded-lg size-14 overflow-hidden bg-main-view/40',
-                          alt={`${file.name} - ${index}`}
+                                  'flex items-center justify-center'
-                        />
+                                )}
-                      )}
+                              >
-                      <div
+                                {/* Inner content by state */}
-                        className="absolute -top-1 -right-2.5 bg-destructive size-5 flex rounded-full items-center justify-center cursor-pointer"
+                                {isImage && att.dataUrl ? (
-                        onClick={() => handleRemoveFile(index)}
+                                  <img
-                      >
+                                    className="object-cover w-full h-full"
-                        <IconX className="text-destructive-fg" size={16} />
+                                    src={att.dataUrl}
+                                    alt={`${att.name}`}
+                                  />
+                                ) : (
+                                  <div className="flex flex-col items-center justify-center text-main-view-fg/70">
+                                    <IconPaperclip size={18} />
+                                    {ext && (
+                                      <span className="text-[10px] leading-none mt-0.5 uppercase opacity-70">
+                                        .{ext}
+                                      </span>
+                                    )}
+                                  </div>
+                                )}
+
+                                {/* Overlay spinner when processing */}
+                                {att.processing && (
+                                  <div className="absolute inset-0 flex items-center justify-center bg-black/10">
+                                    <IconLoader2
+                                      size={18}
+                                      className="text-main-view-fg/80 animate-spin"
+                                    />
+                                  </div>
+                                )}
+
+                                {/* Overlay success check when processed */}
+                                {att.processed && !att.processing && (
+                                  <div className="absolute inset-0 flex items-center justify-center bg-black/5">
+                                    <div className="bg-green-600/90 rounded-full p-1">
+                                      <IconCheck size={14} className="text-white" />
+                                    </div>
+                                  </div>
+                                )}
+                              </div>
+                            </TooltipTrigger>
+                            <TooltipContent>
+                              <div className="text-xs">
+                                <div className="font-medium truncate max-w-52" title={att.name}>
+                                  {att.name}
+                                </div>
+                                <div className="opacity-70">
+                                  {isImage
+                                    ? (att.mimeType || 'image')
+                                    : (ext ? `.${ext}` : 'document')}
+                                  {att.size ? ` · ${formatBytes(att.size)}` : ''}
+                                </div>
+                              </div>
+                            </TooltipContent>
+                          </Tooltip>
+                        </TooltipProvider>
+
+                        {/* Remove button disabled while processing - outside overflow-hidden container */}
+                        {!att.processing && (
+                          <div
+                            className="absolute -top-1 -right-2.5 bg-destructive size-5 flex rounded-full items-center justify-center cursor-pointer"
+                            onClick={() => handleRemoveAttachment(idx)}
+                          >
+                            <IconX className="text-destructive-fg" size={16} />
+                          </div>
+                        )}
                       </div>
-                    </div>
+                    )
-                  )
+                  })}
-                })}
-                {docFiles.map((file, index) => (
-                  <div
-                    key={`doc-${index}`}
-                    className="relative border border-main-view-fg/5 rounded-lg px-2 py-1 text-xs flex items-center gap-2 bg-main-view/40"
-                  >
-                    <IconPaperclip size={14} className="text-main-view-fg/50" />
-                    <span className="max-w-48 truncate" title={file.name}>
-                      {file.name}
-                    </span>
-                    <div
-                      className="absolute -top-1 -right-2.5 bg-destructive size-5 flex rounded-full items-center justify-center cursor-pointer"
-                      onClick={() =>
-                        setDocFiles((prev) =>
-                          prev.filter((_, i) => i !== index)
-                        )
-                      }
-                    >
-                      <IconX className="text-destructive-fg" size={16} />
-                    </div>
-                  </div>
-                ))}
               </div>
             )}
             <TextareaAutosize
@@ -975,7 +1185,15 @@ const ChatInput = ({
                     <TokenCounter
                       messages={threadMessages || []}
                       compact={true}
-                      uploadedFiles={uploadedFiles}
+                      uploadedFiles={attachments
+                        .filter((a) => a.type === 'image' && a.dataUrl)
+                        .map((a) => ({
+                          name: a.name,
+                          type: a.mimeType || getFileTypeFromExtension(a.name),
+                          size: a.size || 0,
+                          base64: a.base64 || '',
+                          dataUrl: a.dataUrl!,
+                        }))}
                     />
                   </div>
                 )}
@@ -992,24 +1210,13 @@ const ChatInput = ({
                 </Button>
               ) : (
                 <Button
-                  variant={
+                  variant={!prompt.trim() ? null : 'default'}
-                    !prompt.trim() &&
-                    uploadedFiles.length === 0 &&
-                    docFiles.length === 0
-                      ? null
-                      : 'default'
-                  }
                   size="icon"
-                  disabled={
+                  disabled={!prompt.trim() || ingestingAny}
-                    (!prompt.trim() &&
-                      uploadedFiles.length === 0 &&
-                      docFiles.length === 0) ||
-                    ingestingDocs
-                  }
                   data-test-id="send-message-button"
                   onClick={() => handleSendMessage(prompt)}
                 >
-                  {streamingContent || ingestingDocs ? (
+                  {streamingContent || ingestingAny ? (
                     <span className="animate-spin h-4 w-4 border-2 border-current border-t-transparent rounded-full" />
                   ) : (
                     <ArrowRight className="text-primary-fg" />
@@ -1048,7 +1255,15 @@ const ChatInput = ({
             <TokenCounter
               messages={threadMessages || []}
               compact={false}
-              uploadedFiles={uploadedFiles}
+              uploadedFiles={attachments
+                .filter((a) => a.type === 'image' && a.dataUrl)
+                .map((a) => ({
+                  name: a.name,
+                  type: a.mimeType || getFileTypeFromExtension(a.name),
+                  size: a.size || 0,
+                  base64: a.base64 || '',
+                  dataUrl: a.dataUrl!,
+                }))}
             />
           </div>
         )}

web-app/src/containers/ThreadContent.tsx

@@ -26,6 +26,8 @@ import TokenSpeedIndicator from '@/containers/TokenSpeedIndicator'
 
 import { useTranslation } from '@/i18n/react-i18next-compat'
 import { useModelProvider } from '@/hooks/useModelProvider'
+import { extractFilesFromPrompt } from '@/lib/fileMetadata'
+import { createImageAttachment } from '@/types/attachment'
 
 const CopyButton = ({ text }: { text: string }) => {
   const [copied, setCopied] = useState(false)
@@ -102,6 +104,14 @@ export const ThreadContent = memo(
       [item.content]
     )
 
+    // Extract file metadata from user message text
+    const { files: attachedFiles, cleanPrompt } = useMemo(() => {
+      if (item.role === 'user') {
+        return extractFilesFromPrompt(text)
+      }
+      return { files: [], cleanPrompt: text }
+    }, [text, item.role])
+
     const { reasoningSegment, textSegment } = useMemo(() => {
       // Check for thinking formats
       const hasThinkTag = text.includes('<think>') && !text.includes('</think>')
@@ -153,9 +163,9 @@ export const ThreadContent = memo(
       if (toSendMessage) {
         deleteMessage(toSendMessage.thread_id, toSendMessage.id ?? '')
         // Extract text content and any attachments
-        const textContent =
+        const rawText =
-          toSendMessage.content?.find((c) => c.type === 'text')?.text?.value ||
+          toSendMessage.content?.find((c) => c.type === 'text')?.text?.value || ''
-          ''
+        const { cleanPrompt: textContent } = extractFilesFromPrompt(rawText)
         const attachments = toSendMessage.content
           ?.filter((c) => (c.type === 'image_url' && c.image_url?.url) || false)
           .map((c) => {
@@ -164,24 +174,19 @@ export const ThreadContent = memo(
               const [mimeType, base64] = url
                 .replace('data:', '')
                 .split(';base64,')
-              return {
+              return createImageAttachment({
-                name: 'image', // We don't have the original filename
+                name: 'image', // Original filename unavailable
-                type: mimeType,
+                mimeType,
-                size: 0, // We don't have the original size
+                size: 0,
                 base64: base64,
                 dataUrl: url,
-              }
+              })
             }
             return null
           })
-          .filter(Boolean) as Array<{
+          .filter(Boolean)
-          name: string
+        // Keep embedded document metadata in the message for regenerate
-          type: string
+        sendMessage(rawText, true, attachments)
-          size: number
-          base64: string
-          dataUrl: string
-        }>
-        sendMessage(textContent, true, attachments)
       }
     }, [deleteMessage, getMessages, item, sendMessage])
 
@@ -225,7 +230,56 @@ export const ThreadContent = memo(
       <Fragment>
         {item.role === 'user' && (
           <div className="w-full">
-            {/* Render attachments above the message bubble */}
+            {/* Render text content in the message bubble */}
+            {cleanPrompt && (
+              <div className="flex justify-end w-full h-full text-start break-words whitespace-normal">
+                <div className="bg-main-view-fg/4 relative text-main-view-fg p-2 rounded-md inline-block max-w-[80%] ">
+                  <div className="select-text">
+                    <RenderMarkdown
+                      content={cleanPrompt}
+                      components={linkComponents}
+                      isUser
+                    />
+                  </div>
+                </div>
+              </div>
+            )}
+
+            {/* Render document file attachments (extracted from message text) - below text */}
+            {attachedFiles.length > 0 && (
+              <div className="flex justify-end w-full mt-2 mb-2">
+                <div className="flex flex-wrap gap-2 max-w-[80%] justify-end">
+                  {attachedFiles.map((file, index) => (
+                    <div
+                      key={file.id || index}
+                      className="flex items-center gap-2 px-3 py-2 bg-main-view-fg/5 rounded-md border border-main-view-fg/10 text-xs"
+                    >
+                      <svg
+                        className="w-4 h-4 text-main-view-fg/50"
+                        fill="none"
+                        viewBox="0 0 24 24"
+                        stroke="currentColor"
+                      >
+                        <path
+                          strokeLinecap="round"
+                          strokeLinejoin="round"
+                          strokeWidth={2}
+                          d="M9 12h6m-6 4h6m2 5H7a2 2 0 01-2-2V5a2 2 0 012-2h5.586a1 1 0 01.707.293l5.414 5.414a1 1 0 01.293.707V19a2 2 0 01-2 2z"
+                        />
+                      </svg>
+                      <span className="text-main-view-fg">{file.name}</span>
+                      {file.type && (
+                        <span className="text-main-view-fg/40 text-[10px]">
+                          .{file.type}
+                        </span>
+                      )}
+                    </div>
+                  ))}
+                </div>
+              </div>
+            )}
+
+            {/* Render image attachments - below files */}
             {item.content?.some(
               (c) => (c.type === 'image_url' && c.image_url?.url) || false
             ) && (
@@ -258,33 +312,9 @@ export const ThreadContent = memo(
               </div>
             )}
 
-            {/* Render text content in the message bubble */}
-            {item.content?.some((c) => c.type === 'text' && c.text?.value) && (
-              <div className="flex justify-end w-full h-full text-start break-words whitespace-normal">
-                <div className="bg-main-view-fg/4 relative text-main-view-fg p-2 rounded-md inline-block max-w-[80%] ">
-                  <div className="select-text">
-                    {item.content
-                      ?.filter((c) => c.type === 'text' && c.text?.value)
-                      .map((contentPart, index) => (
-                        <div key={index}>
-                          <RenderMarkdown
-                            content={contentPart.text!.value}
-                            components={linkComponents}
-                            isUser
-                          />
-                        </div>
-                      ))}
-                  </div>
-                </div>
-              </div>
-            )}
-
             <div className="flex items-center justify-end gap-2 text-main-view-fg/60 text-xs mt-2">
               <EditMessageDialog
-                message={
+                message={cleanPrompt || ''}
-                  item.content?.find((c) => c.type === 'text')?.text?.value ||
-                  ''
-                }
                 imageUrls={
                   item.content
                     ?.filter((c) => c.type === 'image_url' && c.image_url?.url)

web-app/src/hooks/useChat.ts

@@ -37,6 +37,8 @@ import {
 import { useAssistant } from './useAssistant'
 import { useShallow } from 'zustand/shallow'
 import { TEMPORARY_CHAT_QUERY_ID, TEMPORARY_CHAT_ID } from '@/constants/chat'
+import { toast } from 'sonner'
+import { Attachment } from '@/types/attachment'
 
 export const useChat = () => {
   const [
@@ -257,14 +259,12 @@ export const useChat = () => {
     async (
       message: string,
       troubleshooting = true,
-      attachments?: Array<{
+      attachments?: Attachment[],
-        name: string
+      projectId?: string,
-        type: string
+      updateAttachmentProcessing?: (
-        size: number
+        fileName: string,
-        base64: string
+        status: 'processing' | 'done' | 'error' | 'clear_docs' | 'clear_all'
-        dataUrl: string
+      ) => void
-      }>,
-      projectId?: string
     ) => {
       const activeThread = await getCurrentThread(projectId)
       const selectedProvider = useModelProvider.getState().selectedProvider
@@ -272,14 +272,124 @@ export const useChat = () => {
 
       resetTokenSpeed()
       if (!activeThread || !activeProvider) return
+
+      // Separate images and documents
+      const images = attachments?.filter((a) => a.type === 'image') || []
+      const documents = attachments?.filter((a) => a.type === 'document') || []
+
+      // Process attachments BEFORE sending
+      const processedAttachments: Attachment[] = []
+
+      // 1) Images ingestion (placeholder/no-op for now)
+      // Track attachment ingestion; all must succeed before sending
+
+      if (images.length > 0) {
+        for (const img of images) {
+          try {
+            // Skip if already processed (ingested in ChatInput when thread existed)
+            if (img.processed && img.id) {
+              processedAttachments.push(img)
+              continue
+            }
+
+            if (updateAttachmentProcessing) {
+              updateAttachmentProcessing(img.name, 'processing')
+            }
+            // Upload image, get id/URL
+            const res = await serviceHub.uploads().ingestImage(activeThread.id, img)
+            processedAttachments.push({
+              ...img,
+              id: res.id,
+              processed: true,
+              processing: false,
+            })
+            if (updateAttachmentProcessing) {
+              updateAttachmentProcessing(img.name, 'done')
+            }
+          } catch (err) {
+            console.error(`Failed to ingest image ${img.name}:`, err)
+            if (updateAttachmentProcessing) {
+              updateAttachmentProcessing(img.name, 'error')
+            }
+            const desc = err instanceof Error ? err.message : String(err)
+            toast.error('Failed to ingest image attachment', { description: desc })
+            return
+          }
+        }
+      }
+
+      if (documents.length > 0) {
+        try {
+          for (const doc of documents) {
+            // Skip if already processed (ingested in ChatInput when thread existed)
+            if (doc.processed && doc.id) {
+              processedAttachments.push(doc)
+              continue
+            }
+
+            // Update UI to show spinner on this file
+            if (updateAttachmentProcessing) {
+              updateAttachmentProcessing(doc.name, 'processing')
+            }
+
+            try {
+              const res = await serviceHub
+                .uploads()
+                .ingestFileAttachment(activeThread.id, doc)
+
+              // Add processed document with ID
+              processedAttachments.push({
+                ...doc,
+                id: res.id,
+                size: res.size ?? doc.size,
+                chunkCount: res.chunkCount ?? doc.chunkCount,
+                processing: false,
+                processed: true,
+              })
+
+              // Update UI to show done state
+              if (updateAttachmentProcessing) {
+                updateAttachmentProcessing(doc.name, 'done')
+              }
+            } catch (err) {
+              console.error(`Failed to ingest ${doc.name}:`, err)
+              if (updateAttachmentProcessing) {
+                updateAttachmentProcessing(doc.name, 'error')
+              }
+              throw err // Re-throw to handle in outer catch
+            }
+          }
+        } catch (err) {
+          console.error('Failed to ingest documents:', err)
+          const desc = err instanceof Error ? err.message : String(err)
+          toast.error('Failed to index attachments', { description: desc })
+          // Don't continue with message send if ingestion failed
+          return
+        }
+      }
+
+      // All attachments prepared successfully
+
       const messages = getMessages(activeThread.id)
       const abortController = new AbortController()
       setAbortController(activeThread.id, abortController)
       updateStreamingContent(emptyThreadContent)
       updatePromptProgress(undefined)
       // Do not add new message on retry
-      if (troubleshooting)
+      // All attachments (images + docs) ingested successfully.
-        addMessage(newUserThreadContent(activeThread.id, message, attachments))
+      // Build the user content once; use it for both the outbound request
+      // and persisting to the store so both are identical.
+      if (updateAttachmentProcessing) {
+        updateAttachmentProcessing('__CLEAR_ALL__' as any, 'clear_all')
+      }
+      const userContent = newUserThreadContent(
+        activeThread.id,
+        message,
+        processedAttachments
+      )
+      if (troubleshooting) {
+        addMessage(userContent)
+      }
       updateThreadTimestamp(activeThread.id)
       usePrompt.getState().setPrompt('')
       const selectedModel = useModelProvider.getState().selectedModel
@@ -296,7 +406,8 @@ export const useChat = () => {
             ? renderInstructions(currentAssistant.instructions)
             : undefined
         )
-        if (troubleshooting) builder.addUserMessage(message, attachments)
+        // Using addUserMessage to respect legacy code. Should be using the userContent above.
+        if (troubleshooting) builder.addUserMessage(userContent)
 
         let isCompleted = false
 

web-app/src/lib/__tests__/messages.test.ts

@@ -137,7 +137,9 @@ describe('CompletionMessagesBuilder', () => {
     it('should add user message to messages array', () => {
       const builder = new CompletionMessagesBuilder([])
 
-      builder.addUserMessage('Hello, how are you?')
+      builder.addUserMessage(
+        createMockThreadMessage('user', 'Hello, how are you?')
+      )
 
       const result = builder.getMessages()
       expect(result).toHaveLength(1)
@@ -150,8 +152,8 @@ describe('CompletionMessagesBuilder', () => {
     it('should not add consecutive user messages', () => {
       const builder = new CompletionMessagesBuilder([])
 
-      builder.addUserMessage('First message')
+      builder.addUserMessage(createMockThreadMessage('user', 'First message'))
-      builder.addUserMessage('Second message')
+      builder.addUserMessage(createMockThreadMessage('user', 'Second message'))
 
       const result = builder.getMessages()
       expect(result).toHaveLength(1)
@@ -161,7 +163,7 @@ describe('CompletionMessagesBuilder', () => {
     it('should handle empty user message', () => {
       const builder = new CompletionMessagesBuilder([])
 
-      builder.addUserMessage('')
+      builder.addUserMessage(createMockThreadMessage('user', ''))
 
       const result = builder.getMessages()
       expect(result).toHaveLength(1)
@@ -338,7 +340,7 @@ describe('CompletionMessagesBuilder', () => {
         'You are helpful'
       )
 
-      builder.addUserMessage('How are you?')
+      builder.addUserMessage(createMockThreadMessage('user', 'How are you?'))
       builder.addAssistantMessage('I am well, thank you!')
       builder.addToolMessage('Tool response', 'call_123')
 
@@ -353,7 +355,7 @@ describe('CompletionMessagesBuilder', () => {
     it('should return the same array reference (not immutable)', () => {
       const builder = new CompletionMessagesBuilder([])
 
-      builder.addUserMessage('Test message')
+      builder.addUserMessage(createMockThreadMessage('user', 'Test message'))
       const result1 = builder.getMessages()
 
       builder.addAssistantMessage('Response')

web-app/src/lib/completion.ts

@@ -36,6 +36,8 @@ import { CompletionMessagesBuilder } from './messages'
 import { ChatCompletionMessageToolCall } from 'openai/resources'
 import { ExtensionManager } from './extension'
 import { useAppState } from '@/hooks/useAppState'
+import { injectFilesIntoPrompt } from './fileMetadata'
+import { Attachment } from '@/types/attachment'
 
 export type ChatCompletionResponse =
   | chatCompletion
@@ -54,38 +56,48 @@ export type ChatCompletionResponse =
 export const newUserThreadContent = (
   threadId: string,
   content: string,
-  attachments?: Array<{
+  attachments?: Attachment[]
-    name: string
-    type: string
-    size: number
-    base64: string
-    dataUrl: string
-  }>
 ): ThreadMessage => {
+  // Separate images and documents
+  const images = attachments?.filter((a) => a.type === 'image') || []
+  const documents = attachments?.filter((a) => a.type === 'document') || []
+
+  // Inject document metadata into the text content (id, name, fileType only - no path)
+  const docMetadata = documents
+    .filter((doc) => doc.id) // Only include processed documents
+    .map((doc) => ({
+      id: doc.id!,
+      name: doc.name,
+      type: doc.fileType,
+      size: typeof doc.size === 'number' ? doc.size : undefined,
+      chunkCount: typeof doc.chunkCount === 'number' ? doc.chunkCount : undefined,
+    }))
+
+  const textWithFiles =
+    docMetadata.length > 0 ? injectFilesIntoPrompt(content, docMetadata) : content
+
   const contentParts = [
     {
       type: ContentType.Text,
       text: {
-        value: content,
+        value: textWithFiles,
         annotations: [],
       },
     },
   ]
 
-  // Add attachments to content array
+  // Add image attachments to content array
-  if (attachments) {
+  images.forEach((img) => {
-    attachments.forEach((attachment) => {
+    if (img.base64 && img.mimeType) {
-      if (attachment.type.startsWith('image/')) {
+      contentParts.push({
-        contentParts.push({
+        type: ContentType.Image,
-          type: ContentType.Image,
+        image_url: {
-          image_url: {
+          url: `data:${img.mimeType};base64,${img.base64}`,
-            url: `data:${attachment.type};base64,${attachment.base64}`,
+          detail: 'auto',
-            detail: 'auto',
+        },
-          },
+      } as any)
-        } as any)
+    }
-      }
+  })
-    })
-  }
 
   return {
     type: 'text',

web-app/src/lib/fileMetadata.ts

@@ -0,0 +1,96 @@
+/**
+ * Utility functions for embedding and extracting file metadata from user prompts
+ */
+
+export interface FileMetadata {
+  id: string
+  name: string
+  type?: string
+  size?: number
+  chunkCount?: number
+}
+
+const FILE_METADATA_START = '[ATTACHED_FILES]'
+const FILE_METADATA_END = '[/ATTACHED_FILES]'
+
+/**
+ * Inject file metadata into user prompt at the end
+ * @param prompt - The user's message
+ * @param files - Array of file metadata
+ * @returns Prompt with embedded file metadata
+ */
+export function injectFilesIntoPrompt(
+  prompt: string,
+  files: FileMetadata[]
+): string {
+  if (!files || files.length === 0) return prompt
+
+  const fileLines = files
+    .map((file) => {
+      const parts = [`file_id: ${file.id}`, `name: ${file.name}`]
+      if (file.type) parts.push(`type: ${file.type}`)
+      if (typeof file.size === 'number') parts.push(`size: ${file.size}`)
+      if (typeof file.chunkCount === 'number') parts.push(`chunks: ${file.chunkCount}`)
+      return `- ${parts.join(', ')}`
+    })
+    .join('\n')
+
+  const fileBlock = `\n\n${FILE_METADATA_START}\n${fileLines}\n${FILE_METADATA_END}`
+
+  return prompt + fileBlock
+}
+
+/**
+ * Extract file metadata from user prompt
+ * @param prompt - The prompt potentially containing file metadata
+ * @returns Object containing extracted files and clean prompt
+ */
+export function extractFilesFromPrompt(prompt: string): {
+  files: FileMetadata[]
+  cleanPrompt: string
+} {
+  if (!prompt.includes(FILE_METADATA_START)) {
+    return { files: [], cleanPrompt: prompt }
+  }
+
+  const startIndex = prompt.indexOf(FILE_METADATA_START)
+  const endIndex = prompt.indexOf(FILE_METADATA_END)
+
+  if (startIndex === -1 || endIndex === -1 || endIndex <= startIndex) {
+    return { files: [], cleanPrompt: prompt }
+  }
+
+  // Extract the file metadata block
+  const fileBlock = prompt.substring(
+    startIndex + FILE_METADATA_START.length,
+    endIndex
+  )
+
+  // Parse file metadata (flexible key:value parser)
+  const files: FileMetadata[] = []
+  const lines = fileBlock.trim().split('\n')
+  for (const line of lines) {
+    const trimmed = line.replace(/^\s*-\s*/, '').trim()
+    const parts = trimmed.split(',')
+    const map: Record<string, string> = {}
+    for (const part of parts) {
+      const [k, ...rest] = part.split(':')
+      if (!k || rest.length === 0) continue
+      map[k.trim()] = rest.join(':').trim()
+    }
+    const id = map['file_id']
+    const name = map['name']
+    if (!id || !name) continue
+    const type = map['type']
+    const size = map['size'] ? Number(map['size']) : undefined
+    const chunkCount = map['chunks'] ? Number(map['chunks']) : undefined
+    files.push({ id, name, ...(type && { type }), ...(typeof size === 'number' && !Number.isNaN(size) ? { size } : {}), ...(typeof chunkCount === 'number' && !Number.isNaN(chunkCount) ? { chunkCount } : {}) })
+  }
+
+  // Extract clean prompt (everything before [ATTACHED_FILES])
+  const cleanPrompt = prompt
+    .substring(0, startIndex)
+    .trim()
+
+  return { files, cleanPrompt }
+}

web-app/src/lib/messages.ts

@@ -3,6 +3,7 @@ import { ChatCompletionMessageParam } from 'token.js'
 import { ChatCompletionMessageToolCall } from 'openai/resources'
 import { ThreadMessage } from '@janhq/core'
 import { removeReasoningContent } from '@/utils/reasoning'
+// Attachments are now handled upstream in newUserThreadContent
 
 /**
  * @fileoverview Helper functions for creating chat completion request.
@@ -21,106 +22,62 @@ export class CompletionMessagesBuilder {
     this.messages.push(
       ...messages
         .filter((e) => !e.metadata?.error)
-        .map<ChatCompletionMessageParam>((msg) => {
+        .map<ChatCompletionMessageParam>((msg) => this.toCompletionParamFromThread(msg))
-          if (msg.role === 'assistant') {
-            return {
-              role: msg.role,
-              content: removeReasoningContent(
-                msg.content[0]?.text?.value || '.'
-              ),
-            } as ChatCompletionMessageParam
-          } else {
-            // For user messages, handle multimodal content
-            if (msg.content.length > 1) {
-              // Multiple content parts (text + images + files)
-
-              const content = msg.content.map((contentPart) => {
-                if (contentPart.type === 'text') {
-                  return {
-                    type: 'text',
-                    text: contentPart.text?.value || '',
-                  }
-                } else if (contentPart.type === 'image_url') {
-                  return {
-                    type: 'image_url',
-                    image_url: {
-                      url: contentPart.image_url?.url || '',
-                      detail: contentPart.image_url?.detail || 'auto',
-                    },
-                  }
-                } else {
-                  return contentPart
-                }
-              })
-              return {
-                role: msg.role,
-                content,
-              } as ChatCompletionMessageParam
-            } else {
-              // Single text content
-              return {
-                role: msg.role,
-                content: msg.content[0]?.text?.value || '.',
-              } as ChatCompletionMessageParam
-            }
-          }
-        })
     )
   }
 
+  // Normalize a ThreadMessage into a ChatCompletionMessageParam for Token.js
+  private toCompletionParamFromThread(msg: ThreadMessage): ChatCompletionMessageParam {
+    if (msg.role === 'assistant') {
+      return {
+        role: 'assistant',
+        content: removeReasoningContent(msg.content?.[0]?.text?.value || '.'),
+      } as ChatCompletionMessageParam
+    }
+
+    // System messages are uncommon here; normalize to plain text
+    if (msg.role === 'system') {
+      return {
+        role: 'system',
+        content: msg.content?.[0]?.text?.value || '.',
+      } as ChatCompletionMessageParam
+    }
+
+    // User messages: handle multimodal content
+    if (Array.isArray(msg.content) && msg.content.length > 1) {
+      const content = msg.content.map((part: any) => {
+        if (part.type === 'text') {
+          return { type: 'text', text: part.text?.value ?? '' }
+        }
+        if (part.type === 'image_url') {
+          return {
+            type: 'image_url',
+            image_url: { url: part.image_url?.url || '', detail: part.image_url?.detail || 'auto' },
+          }
+        }
+        return part
+      })
+      return { role: 'user', content } as any
+    }
+    // Single text part
+    const text = msg?.content?.[0]?.text?.value ?? '.'
+    return { role: 'user', content: text }
+  }
+
   /**
-   * Add a user message to the messages array.
+   * Add a user message to the messages array from a parsed ThreadMessage.
-   * @param content - The content of the user message.
+   * Upstream code should construct the message via newUserThreadContent
-   * @param attachments - Optional attachments for the message.
+   * and pass it here to avoid duplicated logic.
    */
-  addUserMessage(
+  addUserMessage(message: ThreadMessage) {
-    content: string,
+    if (message.role !== 'user') {
-    attachments?: Array<{
+      throw new Error('addUserMessage expects a user ThreadMessage')
-      name: string
+    }
-      type: string
-      size: number
-      base64: string
-      dataUrl: string
-    }>
-  ) {
     // Ensure no consecutive user messages
     if (this.messages[this.messages.length - 1]?.role === 'user') {
       this.messages.pop()
     }
-
+    this.messages.push(this.toCompletionParamFromThread(message))
-    // Handle multimodal content with attachments
-    if (attachments && attachments.length > 0) {
-      const messageContent: any[] = [
-        {
-          type: 'text',
-          text: content,
-        },
-      ]
-
-      // Add attachments (images and PDFs)
-      attachments.forEach((attachment) => {
-        if (attachment.type.startsWith('image/')) {
-          messageContent.push({
-            type: 'image_url',
-            image_url: {
-              url: `data:${attachment.type};base64,${attachment.base64}`,
-              detail: 'auto',
-            },
-          })
-        }
-      })
-
-      this.messages.push({
-        role: 'user',
-        content: messageContent,
-      } as any)
-    } else {
-      // Text-only message
-      this.messages.push({
-        role: 'user',
-        content: content,
-      })
-    }
   }
 
   /**

web-app/src/services/index.ts

@@ -29,6 +29,8 @@ import { DefaultDeepLinkService } from './deeplink/default'
 import { DefaultProjectsService } from './projects/default'
 import { DefaultRAGService } from './rag/default'
 import type { RAGService } from './rag/types'
+import { DefaultUploadsService } from './uploads/default'
+import type { UploadsService } from './uploads/types'
 
 // Import service types
 import type { ThemeService } from './theme/types'
@@ -73,6 +75,7 @@ export interface ServiceHub {
   deeplink(): DeepLinkService
   projects(): ProjectsService
   rag(): RAGService
+  uploads(): UploadsService
 }
 
 class PlatformServiceHub implements ServiceHub {
@@ -96,6 +99,7 @@ class PlatformServiceHub implements ServiceHub {
   private deepLinkService: DeepLinkService = new DefaultDeepLinkService()
   private projectsService: ProjectsService = new DefaultProjectsService()
   private ragService: RAGService = new DefaultRAGService()
+  private uploadsService: UploadsService = new DefaultUploadsService()
   private initialized = false
 
   /**
@@ -352,6 +356,11 @@ class PlatformServiceHub implements ServiceHub {
     this.ensureInitialized()
     return this.ragService
   }
+
+  uploads(): UploadsService {
+    this.ensureInitialized()
+    return this.uploadsService
+  }
 }
 
 export async function initializeServiceHub(): Promise<ServiceHub> {

web-app/src/services/uploads/default.ts

@@ -0,0 +1,32 @@
+import type { UploadsService, UploadResult } from './types'
+import type { Attachment, } from '@/types/attachment'
+import { ulid } from 'ulidx'
+import { ExtensionManager } from '@/lib/extension'
+import { ExtensionTypeEnum, type RAGExtension, type IngestAttachmentsResult } from '@janhq/core'
+
+export class DefaultUploadsService implements UploadsService {
+  async ingestImage(_threadId: string, attachment: Attachment): Promise<UploadResult> {
+    if (attachment.type !== 'image') throw new Error('ingestImage: attachment is not image')
+    // Placeholder upload flow; swap for real API call when backend is ready
+    await new Promise((r) => setTimeout(r, 100))
+    return { id: ulid() }
+  }
+
+  async ingestFileAttachment(threadId: string, attachment: Attachment): Promise<UploadResult> {
+    if (attachment.type !== 'document') throw new Error('ingestFileAttachment: attachment is not document')
+    const ext = ExtensionManager.getInstance().get<RAGExtension>(ExtensionTypeEnum.RAG)
+    if (!ext?.ingestAttachments) throw new Error('RAG extension not available')
+    const res: IngestAttachmentsResult = await ext.ingestAttachments(threadId, [
+      { path: attachment.path!, name: attachment.name, type: attachment.fileType, size: attachment.size },
+    ])
+    const files = res.files
+    if (Array.isArray(files) && files[0]?.id) {
+      return {
+        id: files[0].id,
+        size: typeof files[0].size === 'number' ? Number(files[0].size) : undefined,
+        chunkCount: typeof files[0].chunk_count === 'number' ? Number(files[0].chunk_count) : undefined,
+      }
+    }
+    throw new Error('Failed to resolve ingested attachment id')
+  }
+}

web-app/src/services/uploads/types.ts

@@ -0,0 +1,16 @@
+import type { Attachment } from '@/types/attachment'
+
+export type UploadResult = {
+  id: string
+  url?: string
+  size?: number
+  chunkCount?: number
+}
+
+export interface UploadsService {
+  // Ingest an image attachment (placeholder upload)
+  ingestImage(threadId: string, attachment: Attachment): Promise<UploadResult>
+
+  // Ingest a document attachment in the context of a thread
+  ingestFileAttachment(threadId: string, attachment: Attachment): Promise<UploadResult>
+}

web-app/src/types/attachment.ts

@@ -0,0 +1,57 @@
+/**
+ * Unified attachment type for both images and documents
+ */
+export type Attachment = {
+  name: string
+  type: 'image' | 'document'
+
+  // Common fields
+  size?: number
+  chunkCount?: number
+  processing?: boolean
+  processed?: boolean
+  error?: string
+
+  // For images (before upload)
+  base64?: string
+  dataUrl?: string
+  mimeType?: string
+
+  // For documents (local files)
+  path?: string
+  fileType?: string // e.g., 'pdf', 'docx'
+
+  // After processing (images uploaded, documents ingested)
+  id?: string
+}
+
+/**
+ * Helper to create image attachment
+ */
+export function createImageAttachment(data: {
+  name: string
+  base64: string
+  dataUrl: string
+  mimeType: string
+  size: number
+}): Attachment {
+  return {
+    ...data,
+    type: 'image',
+  }
+}
+
+/**
+ * Helper to create document attachment
+ */
+export function createDocumentAttachment(data: {
+  name: string
+  path: string
+  fileType?: string
+  size?: number
+}): Attachment {
+  return {
+    ...data,
+    type: 'document',
+  }
+}