diff --git a/packages/db/src/migrations/0053_create_chat_files.sql b/packages/db/src/migrations/0053_create_chat_files.sql
new file mode 100644
index 00000000..1144920d
--- /dev/null
+++ b/packages/db/src/migrations/0053_create_chat_files.sql
@@ -0,0 +1,26 @@
+CREATE TABLE IF NOT EXISTS "chat_files" (
+  "id" uuid PRIMARY KEY DEFAULT gen_random_uuid() NOT NULL,
+  "company_id" uuid NOT NULL,
+  "conversation_id" uuid,
+  "message_id" uuid,
+  "filename" text NOT NULL,
+  "original_filename" text NOT NULL,
+  "mime_type" text NOT NULL,
+  "size_bytes" integer NOT NULL,
+  "object_key" text NOT NULL,
+  "sha256" text NOT NULL,
+  "source" text NOT NULL,
+  "category" text,
+  "project_id" uuid,
+  "created_at" timestamp with time zone DEFAULT now() NOT NULL,
+  "updated_at" timestamp with time zone DEFAULT now() NOT NULL,
+  CONSTRAINT "chat_files_company_id_companies_id_fk" FOREIGN KEY ("company_id") REFERENCES "companies"("id") ON DELETE NO ACTION ON UPDATE NO ACTION,
+  CONSTRAINT "chat_files_conversation_id_chat_conversations_id_fk" FOREIGN KEY ("conversation_id") REFERENCES "chat_conversations"("id") ON DELETE SET NULL ON UPDATE NO ACTION,
+  CONSTRAINT "chat_files_message_id_chat_messages_id_fk" FOREIGN KEY ("message_id") REFERENCES "chat_messages"("id") ON DELETE SET NULL ON UPDATE NO ACTION,
+  CONSTRAINT "chat_files_project_id_projects_id_fk" FOREIGN KEY ("project_id") REFERENCES "projects"("id") ON DELETE SET NULL ON UPDATE NO ACTION
+);
+
+CREATE INDEX IF NOT EXISTS "chat_files_conversation_idx" ON "chat_files" ("conversation_id");
+CREATE INDEX IF NOT EXISTS "chat_files_message_idx" ON "chat_files" ("message_id");
+CREATE INDEX IF NOT EXISTS "chat_files_company_created_idx" ON "chat_files" ("company_id", "created_at");
+CREATE INDEX IF NOT EXISTS "chat_files_project_idx" ON "chat_files" ("project_id");
diff --git a/packages/db/src/migrations/0054_create_chat_file_references.sql b/packages/db/src/migrations/0054_create_chat_file_references.sql
new file mode 100644
index 00000000..d1f5c66e
--- /dev/null
+++ b/packages/db/src/migrations/0054_create_chat_file_references.sql
@@ -0,0 +1,14 @@
+CREATE TABLE IF NOT EXISTS "chat_file_references" (
+  "id" uuid PRIMARY KEY DEFAULT gen_random_uuid() NOT NULL,
+  "file_id" uuid NOT NULL,
+  "conversation_id" uuid NOT NULL,
+  "message_id" uuid,
+  "created_at" timestamp with time zone DEFAULT now() NOT NULL,
+  CONSTRAINT "chat_file_references_file_id_chat_files_id_fk" FOREIGN KEY ("file_id") REFERENCES "chat_files"("id") ON DELETE CASCADE ON UPDATE NO ACTION,
+  CONSTRAINT "chat_file_references_conversation_id_chat_conversations_id_fk" FOREIGN KEY ("conversation_id") REFERENCES "chat_conversations"("id") ON DELETE CASCADE ON UPDATE NO ACTION,
+  CONSTRAINT "chat_file_references_message_id_chat_messages_id_fk" FOREIGN KEY ("message_id") REFERENCES "chat_messages"("id") ON DELETE SET NULL ON UPDATE NO ACTION
+);
+
+CREATE INDEX IF NOT EXISTS "chat_file_refs_file_idx" ON "chat_file_references" ("file_id");
+CREATE INDEX IF NOT EXISTS "chat_file_refs_conversation_idx" ON "chat_file_references" ("conversation_id");
+CREATE INDEX IF NOT EXISTS "chat_file_refs_message_idx" ON "chat_file_references" ("message_id");
diff --git a/packages/db/src/migrations/meta/_journal.json b/packages/db/src/migrations/meta/_journal.json
index 9e307a01..f330d22e 100644
--- a/packages/db/src/migrations/meta/_journal.json
+++ b/packages/db/src/migrations/meta/_journal.json
@@ -372,6 +372,20 @@
       "when": 1775200002000,
       "tag": "0052_create_chat_message_bookmarks",
       "breakpoints": true
+    },
+    {
+      "idx": 53,
+      "version": "7",
+      "when": 1775300000000,
+      "tag": "0053_create_chat_files",
+      "breakpoints": true
+    },
+    {
+      "idx": 54,
+      "version": "7",
+      "when": 1775300001000,
+      "tag": "0054_create_chat_file_references",
+      "breakpoints": true
     }
   ]
 }
\ No newline at end of file
diff --git a/packages/db/src/schema/chat_file_references.ts b/packages/db/src/schema/chat_file_references.ts
new file mode 100644
index 00000000..aca50c20
--- /dev/null
+++ b/packages/db/src/schema/chat_file_references.ts
@@ -0,0 +1,20 @@
+import { pgTable, uuid, timestamp, index } from "drizzle-orm/pg-core";
+import { chatFiles } from "./chat_files.js";
+import { chatConversations } from "./chat_conversations.js";
+import { chatMessages } from "./chat_messages.js";
+
+export const chatFileReferences = pgTable(
+  "chat_file_references",
+  {
+    id: uuid("id").primaryKey().defaultRandom(),
+    fileId: uuid("file_id").notNull().references(() => chatFiles.id, { onDelete: "cascade" }),
+    conversationId: uuid("conversation_id").notNull().references(() => chatConversations.id, { onDelete: "cascade" }),
+    messageId: uuid("message_id").references(() => chatMessages.id, { onDelete: "set null" }),
+    createdAt: timestamp("created_at", { withTimezone: true }).notNull().defaultNow(),
+  },
+  (table) => ({
+    fileIdx: index("chat_file_refs_file_idx").on(table.fileId),
+    conversationIdx: index("chat_file_refs_conversation_idx").on(table.conversationId),
+    messageIdx: index("chat_file_refs_message_idx").on(table.messageId),
+  }),
+);
diff --git a/packages/db/src/schema/chat_files.ts b/packages/db/src/schema/chat_files.ts
new file mode 100644
index 00000000..7702a473
--- /dev/null
+++ b/packages/db/src/schema/chat_files.ts
@@ -0,0 +1,32 @@
+import { pgTable, uuid, text, integer, timestamp, index } from "drizzle-orm/pg-core";
+import { companies } from "./companies.js";
+import { chatConversations } from "./chat_conversations.js";
+import { chatMessages } from "./chat_messages.js";
+import { projects } from "./projects.js";
+
+export const chatFiles = pgTable(
+  "chat_files",
+  {
+    id: uuid("id").primaryKey().defaultRandom(),
+    companyId: uuid("company_id").notNull().references(() => companies.id),
+    conversationId: uuid("conversation_id").references(() => chatConversations.id, { onDelete: "set null" }),
+    messageId: uuid("message_id").references(() => chatMessages.id, { onDelete: "set null" }),
+    filename: text("filename").notNull(),
+    originalFilename: text("original_filename").notNull(),
+    mimeType: text("mime_type").notNull(),
+    sizeBytes: integer("size_bytes").notNull(),
+    objectKey: text("object_key").notNull(),
+    sha256: text("sha256").notNull(),
+    source: text("source").notNull(),
+    category: text("category"),
+    projectId: uuid("project_id").references(() => projects.id, { onDelete: "set null" }),
+    createdAt: timestamp("created_at", { withTimezone: true }).notNull().defaultNow(),
+    updatedAt: timestamp("updated_at", { withTimezone: true }).notNull().defaultNow(),
+  },
+  (table) => ({
+    conversationIdx: index("chat_files_conversation_idx").on(table.conversationId),
+    messageIdx: index("chat_files_message_idx").on(table.messageId),
+    companyCreatedIdx: index("chat_files_company_created_idx").on(table.companyId, table.createdAt),
+    projectIdx: index("chat_files_project_idx").on(table.projectId),
+  }),
+);
diff --git a/packages/db/src/schema/index.ts b/packages/db/src/schema/index.ts
index 465f97ba..e27ef5f7 100644
--- a/packages/db/src/schema/index.ts
+++ b/packages/db/src/schema/index.ts
@@ -59,3 +59,5 @@ export { pluginLogs } from "./plugin_logs.js";
 export { chatConversations } from "./chat_conversations.js";
 export { chatMessages } from "./chat_messages.js";
 export { chatMessageBookmarks } from "./chat_message_bookmarks.js";
+export { chatFiles } from "./chat_files.js";
+export { chatFileReferences } from "./chat_file_references.js";