diff --git a/AgentCompany-New/src/main/services/compliance-service.ts b/AgentCompany-New/src/main/services/compliance-service.ts
index 23a62f7c..b857bbf6 100644
--- a/AgentCompany-New/src/main/services/compliance-service.ts
+++ b/AgentCompany-New/src/main/services/compliance-service.ts
@@ -186,14 +186,80 @@ export class ComplianceService {
     const legalHold = this.db.prepare(`
       select id from legal_holds
       where org_id = ? and active = 1
-        and ((entity_type = ? and entity_id = ?) or (entity_type = 'organization' and entity_id = ?))
+        and (
+          (entity_type = ? and entity_id = ?)
+          or (entity_type = 'organization' and entity_id = ?)
+          or (
+            entity_type = 'chat_thread'
+            and exists (
+              select 1 from chat_messages
+              where org_id = ?
+                and thread_id = legal_holds.entity_id
+                and sender_type = ?
+                and sender_id = ?
+            )
+          )
+          or (
+            entity_type = 'file_object'
+            and exists (
+              select 1 from file_objects
+              where org_id = ?
+                and id = legal_holds.entity_id
+                and owner_type = ?
+                and owner_id = ?
+            )
+          )
+        )
       limit 1
-    `).get(input.orgId, input.subjectType, input.subjectId, input.orgId);
+    `).get(
+      input.orgId,
+      input.subjectType,
+      input.subjectId,
+      input.orgId,
+      input.orgId,
+      input.subjectType,
+      input.subjectId,
+      input.orgId,
+      input.subjectType,
+      input.subjectId,
+    );
     const retentionFreeze = this.db.prepare(`
       select id from retention_freezes
-      where org_id = ? and active = 1 and scope_type = 'organization' and scope_id = ?
+      where org_id = ? and active = 1
+        and (
+          (scope_type = 'organization' and scope_id = ?)
+          or (
+            scope_type = 'chat_space'
+            and exists (
+              select 1 from chat_messages
+              where org_id = ?
+                and space_id = retention_freezes.scope_id
+                and sender_type = ?
+                and sender_id = ?
+            )
+          )
+          or (
+            scope_type = 'file_object'
+            and exists (
+              select 1 from file_objects
+              where org_id = ?
+                and id = retention_freezes.scope_id
+                and owner_type = ?
+                and owner_id = ?
+            )
+          )
+        )
       limit 1
-    `).get(input.orgId, input.orgId);
+    `).get(
+      input.orgId,
+      input.orgId,
+      input.orgId,
+      input.subjectType,
+      input.subjectId,
+      input.orgId,
+      input.subjectType,
+      input.subjectId,
+    );
     if (legalHold || retentionFreeze) throw new Error("Active compliance hold prevents GDPR delete.");
   }
 
diff --git a/AgentCompany-New/tests/unit/compliance-service.test.ts b/AgentCompany-New/tests/unit/compliance-service.test.ts
index 4aa9d774..6fd871ef 100644
--- a/AgentCompany-New/tests/unit/compliance-service.test.ts
+++ b/AgentCompany-New/tests/unit/compliance-service.test.ts
@@ -162,4 +162,88 @@ describe("compliance service", () => {
     }))).toThrow("Active compliance hold prevents GDPR delete.");
     connection.close();
   });
+
+  test("blocks GDPR delete under related chat and file holds", () => {
+    const connection = createConnection();
+    const organization = new OrganizationService(connection.db);
+    const chat = new ChatService(connection.db);
+    const compliance = new ComplianceService(connection.db);
+    let orgId = "";
+    let employeeId = "";
+    let spaceId = "";
+    let threadId = "";
+    let fileId = "";
+    let holdId = "";
+    let freezeId = "";
+
+    connection.transaction(() => {
+      orgId = organization.createOrganization({
+        organizationName: "Acme Operations",
+        employeeName: "Dana Lee",
+        mission: "Coordinate agents with auditable approvals.",
+        goal: "Ship a verified control plane.",
+      });
+      employeeId = (connection.db.prepare("select id from employees where org_id = ?").get(orgId) as { id: string }).id;
+      spaceId = chat.createSpace({ orgId, spaceType: "project", name: "release", topic: "Release coordination", visibility: "workspace" });
+      chat.sendMessage({ orgId, spaceId, threadId: null, senderType: "employee", senderId: employeeId, bodyMd: "Held chat", attachmentFileIds: [] });
+      threadId = (connection.db.prepare("select thread_id from chat_messages where org_id = ?").get(orgId) as { thread_id: string }).thread_id;
+      fileId = "file-held";
+      connection.db.prepare(`
+        insert into file_objects(id, org_id, name, kind, size_bytes, sha256, storage_path, owner_type, owner_id, created_at)
+        values (?, ?, ?, ?, ?, ?, ?, ?, ?, ?)
+      `).run(fileId, orgId, "held.txt", "text/plain", 4, "a".repeat(64), "artifacts/held.txt", "employee", employeeId, new Date().toISOString());
+      holdId = compliance.createLegalHold({
+        orgId,
+        entityType: "chat_thread",
+        entityId: threadId,
+        reason: "Thread discovery",
+        createdByEmployeeId: employeeId,
+      });
+    });
+
+    expect(() => connection.transaction(() => compliance.createExport({
+      orgId,
+      subjectType: "employee",
+      subjectId: employeeId,
+      exportType: "gdpr_delete",
+      requestedByEmployeeId: employeeId,
+    }))).toThrow("Active compliance hold prevents GDPR delete.");
+
+    connection.transaction(() => {
+      compliance.setLegalHoldState({ orgId, legalHoldId: holdId, active: false, employeeId });
+      freezeId = compliance.createRetentionFreeze({
+        orgId,
+        scopeType: "chat_space",
+        scopeId: spaceId,
+        reason: "Space retention",
+        createdByEmployeeId: employeeId,
+      });
+    });
+    expect(() => connection.transaction(() => compliance.createExport({
+      orgId,
+      subjectType: "employee",
+      subjectId: employeeId,
+      exportType: "gdpr_delete",
+      requestedByEmployeeId: employeeId,
+    }))).toThrow("Active compliance hold prevents GDPR delete.");
+
+    connection.transaction(() => {
+      compliance.setRetentionFreezeState({ orgId, retentionFreezeId: freezeId, active: false, employeeId });
+      compliance.createLegalHold({
+        orgId,
+        entityType: "file_object",
+        entityId: fileId,
+        reason: "File discovery",
+        createdByEmployeeId: employeeId,
+      });
+    });
+    expect(() => connection.transaction(() => compliance.createExport({
+      orgId,
+      subjectType: "employee",
+      subjectId: employeeId,
+      exportType: "gdpr_delete",
+      requestedByEmployeeId: employeeId,
+    }))).toThrow("Active compliance hold prevents GDPR delete.");
+    connection.close();
+  });
 });