diff --git a/packages/db/src/migrations/0050_add_branch_columns.sql b/packages/db/src/migrations/0050_add_branch_columns.sql
new file mode 100644
index 00000000..c4674b22
--- /dev/null
+++ b/packages/db/src/migrations/0050_add_branch_columns.sql
@@ -0,0 +1,4 @@
+ALTER TABLE "chat_conversations"
+  ADD COLUMN "parent_conversation_id" uuid REFERENCES "chat_conversations"("id") ON DELETE SET NULL,
+  ADD COLUMN "branch_from_message_id" uuid;
+CREATE INDEX "chat_conversations_parent_idx" ON "chat_conversations" ("parent_conversation_id");
diff --git a/packages/db/src/migrations/0051_add_message_search_vector.sql b/packages/db/src/migrations/0051_add_message_search_vector.sql
new file mode 100644
index 00000000..f5f2a84b
--- /dev/null
+++ b/packages/db/src/migrations/0051_add_message_search_vector.sql
@@ -0,0 +1,5 @@
+ALTER TABLE "chat_messages"
+  ADD COLUMN "content_search" tsvector
+  GENERATED ALWAYS AS (to_tsvector('english', "content")) STORED;
+CREATE INDEX "chat_messages_content_search_idx"
+  ON "chat_messages" USING GIN ("content_search");
diff --git a/packages/db/src/migrations/0052_create_chat_message_bookmarks.sql b/packages/db/src/migrations/0052_create_chat_message_bookmarks.sql
new file mode 100644
index 00000000..90376a80
--- /dev/null
+++ b/packages/db/src/migrations/0052_create_chat_message_bookmarks.sql
@@ -0,0 +1,9 @@
+CREATE TABLE "chat_message_bookmarks" (
+  "id" uuid PRIMARY KEY DEFAULT gen_random_uuid(),
+  "company_id" uuid NOT NULL REFERENCES "companies"("id"),
+  "message_id" uuid NOT NULL REFERENCES "chat_messages"("id") ON DELETE CASCADE,
+  "conversation_id" uuid NOT NULL REFERENCES "chat_conversations"("id") ON DELETE CASCADE,
+  "created_at" timestamp with time zone NOT NULL DEFAULT now()
+);
+CREATE INDEX "chat_bookmarks_company_message_idx" ON "chat_message_bookmarks" ("company_id", "message_id");
+CREATE INDEX "chat_bookmarks_company_conv_idx" ON "chat_message_bookmarks" ("company_id", "conversation_id");
diff --git a/packages/db/src/migrations/meta/_journal.json b/packages/db/src/migrations/meta/_journal.json
index ccc22bf1..80f73106 100644
--- a/packages/db/src/migrations/meta/_journal.json
+++ b/packages/db/src/migrations/meta/_journal.json
@@ -344,6 +344,27 @@
       "when": 1775145655557,
       "tag": "0048_flashy_marrow",
       "breakpoints": true
+    },
+    {
+      "idx": 50,
+      "version": "7",
+      "when": 1775200000000,
+      "tag": "0050_add_branch_columns",
+      "breakpoints": true
+    },
+    {
+      "idx": 51,
+      "version": "7",
+      "when": 1775200001000,
+      "tag": "0051_add_message_search_vector",
+      "breakpoints": true
+    },
+    {
+      "idx": 52,
+      "version": "7",
+      "when": 1775200002000,
+      "tag": "0052_create_chat_message_bookmarks",
+      "breakpoints": true
     }
   ]
 }
\ No newline at end of file
diff --git a/packages/db/src/schema/chat_conversations.ts b/packages/db/src/schema/chat_conversations.ts
index f1d781a9..cd6b8285 100644
--- a/packages/db/src/schema/chat_conversations.ts
+++ b/packages/db/src/schema/chat_conversations.ts
@@ -1,4 +1,4 @@
-import { pgTable, uuid, text, timestamp, index } from "drizzle-orm/pg-core";
+import { type AnyPgColumn, pgTable, uuid, text, timestamp, index } from "drizzle-orm/pg-core";
 import { companies } from "./companies.js";
 import { agents } from "./agents.js";
 
@@ -14,9 +14,12 @@ export const chatConversations = pgTable(
     deletedAt: timestamp("deleted_at", { withTimezone: true }),
     createdAt: timestamp("created_at", { withTimezone: true }).notNull().defaultNow(),
     updatedAt: timestamp("updated_at", { withTimezone: true }).notNull().defaultNow(),
+    parentConversationId: uuid("parent_conversation_id").references((): AnyPgColumn => chatConversations.id, { onDelete: "set null" }),
+    branchFromMessageId: uuid("branch_from_message_id"),
   },
   (table) => ({
     companyUpdatedIdx: index("chat_conversations_company_updated_idx").on(table.companyId, table.updatedAt),
     companyDeletedIdx: index("chat_conversations_company_deleted_idx").on(table.companyId, table.deletedAt),
+    parentIdx: index("chat_conversations_parent_idx").on(table.parentConversationId),
   }),
 );
diff --git a/packages/db/src/schema/chat_message_bookmarks.ts b/packages/db/src/schema/chat_message_bookmarks.ts
new file mode 100644
index 00000000..81c90d15
--- /dev/null
+++ b/packages/db/src/schema/chat_message_bookmarks.ts
@@ -0,0 +1,19 @@
+import { pgTable, uuid, timestamp, index } from "drizzle-orm/pg-core";
+import { companies } from "./companies.js";
+import { chatMessages } from "./chat_messages.js";
+import { chatConversations } from "./chat_conversations.js";
+
+export const chatMessageBookmarks = pgTable(
+  "chat_message_bookmarks",
+  {
+    id: uuid("id").primaryKey().defaultRandom(),
+    companyId: uuid("company_id").notNull().references(() => companies.id),
+    messageId: uuid("message_id").notNull().references(() => chatMessages.id, { onDelete: "cascade" }),
+    conversationId: uuid("conversation_id").notNull().references(() => chatConversations.id, { onDelete: "cascade" }),
+    createdAt: timestamp("created_at", { withTimezone: true }).notNull().defaultNow(),
+  },
+  (table) => ({
+    companyMessageIdx: index("chat_bookmarks_company_message_idx").on(table.companyId, table.messageId),
+    companyConvIdx: index("chat_bookmarks_company_conv_idx").on(table.companyId, table.conversationId),
+  }),
+);
diff --git a/packages/db/src/schema/chat_messages.ts b/packages/db/src/schema/chat_messages.ts
index e3c79daa..2fc1de96 100644
--- a/packages/db/src/schema/chat_messages.ts
+++ b/packages/db/src/schema/chat_messages.ts
@@ -13,6 +13,7 @@ export const chatMessages = pgTable(
     messageType: text("message_type"),
     createdAt: timestamp("created_at", { withTimezone: true }).notNull().defaultNow(),
     updatedAt: timestamp("updated_at", { withTimezone: true }).defaultNow(),
+    // content_search tsvector column exists in Postgres (generated stored) — queried via sql`` only
   },
   (table) => ({
     conversationCreatedIdx: index("chat_messages_conversation_created_idx").on(table.conversationId, table.createdAt),
diff --git a/packages/db/src/schema/index.ts b/packages/db/src/schema/index.ts
index 0c198b46..8a603bc1 100644
--- a/packages/db/src/schema/index.ts
+++ b/packages/db/src/schema/index.ts
@@ -60,3 +60,4 @@ export { pluginWebhookDeliveries } from "./plugin_webhooks.js";
 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";