Scope env binding sync deletes

server/src/__tests__/secrets-service.test.ts

@@ -205,6 +205,47 @@ describeEmbeddedPostgres("secretService", () => {
     expect(JSON.stringify(events)).not.toContain("runtime-secret");
   });
 
+  it("scopes env binding sync deletes to the env path prefix", async () => {
+    const companyId = await seedCompany();
+    const svc = secretService(db);
+    const runtimeSecret = await svc.create(companyId, {
+      name: `runtime-ref-${randomUUID()}`,
+      provider: "local_encrypted",
+      value: "runtime-secret",
+    });
+    const envSecret = await svc.create(companyId, {
+      name: `env-ref-${randomUUID()}`,
+      provider: "local_encrypted",
+      value: "env-secret",
+    });
+
+    await svc.createBinding({
+      companyId,
+      secretId: runtimeSecret.id,
+      targetType: "agent",
+      targetId: "agent-1",
+      configPath: "runtime.token",
+    });
+    await svc.syncEnvBindingsForTarget(
+      companyId,
+      { targetType: "agent", targetId: "agent-1" },
+      {
+        API_KEY: { type: "secret_ref", secretId: envSecret.id, version: "latest" },
+      },
+    );
+    await svc.syncEnvBindingsForTarget(
+      companyId,
+      { targetType: "agent", targetId: "agent-1" },
+      {},
+    );
+
+    const bindings = await db
+      .select()
+      .from(companySecretBindings)
+      .where(eq(companySecretBindings.targetId, "agent-1"));
+    expect(bindings.map((binding) => binding.configPath)).toEqual(["runtime.token"]);
+  });
+
   it("returns resolved secrets even when success metadata writes fail", async () => {
     const companyId = await seedCompany();
     const svc = secretService(db);

server/src/routes/secrets.ts

@@ -454,6 +454,10 @@ export function secretRoutes(db: Db) {
       return;
     }
     assertCompanyAccess(req, existing.companyId);
+    if (existing.status === "deleted") {
+      res.status(404).json({ error: "Secret not found" });
+      return;
+    }
 
     const removed = await svc.remove(id);
     if (!removed) {

server/src/services/secrets.ts

@@ -1,4 +1,4 @@
-import { and, desc, eq, inArray, ne, notInArray, sql } from "drizzle-orm";
+import { and, desc, eq, inArray, like, ne, notInArray, sql } from "drizzle-orm";
 import type { Db } from "@paperclipai/db";
 import {
   agents,
@@ -1902,6 +1902,7 @@ export function secretService(db: Db) {
               eq(companySecretBindings.companyId, companyId),
               eq(companySecretBindings.targetType, target.targetType),
               eq(companySecretBindings.targetId, target.targetId),
+              like(companySecretBindings.configPath, `${pathPrefix}.%`),
             ),
           );
         if (refs.length === 0) return;