diff --git a/server/src/__tests__/secrets-routes.test.ts b/server/src/__tests__/secrets-routes.test.ts
index cd7152e3b0e..86d4b7cb1ed 100644
--- a/server/src/__tests__/secrets-routes.test.ts
+++ b/server/src/__tests__/secrets-routes.test.ts
@@ -18,6 +18,7 @@ const mockSecretService = vi.hoisted(() => ({
   getById: vi.fn(),
   create: vi.fn(),
   update: vi.fn(),
+  remove: vi.fn(),
   previewRemoteImport: vi.fn(),
   importRemoteSecrets: vi.fn(),
 }));
@@ -418,4 +419,36 @@ describe("secret routes", () => {
     expect(mockLogActivity).not.toHaveBeenCalled();
     expect(JSON.stringify(mockLogActivity.mock.calls)).not.toContain("shared/repointed");
   });
+
+  it("allows DELETE to retry cleanup for already soft-deleted secrets", async () => {
+    const secret = {
+      id: "33333333-3333-4333-8333-333333333333",
+      companyId: "company-1",
+      name: "OpenAI API Key__deleted__33333333-3333-4333-8333-333333333333",
+      key: "openai-api-key__deleted__33333333-3333-4333-8333-333333333333",
+      provider: "aws_secrets_manager",
+      managedMode: "paperclip_managed",
+      status: "deleted",
+    };
+    mockSecretService.getById.mockResolvedValue(secret);
+    mockSecretService.remove.mockResolvedValue(secret);
+
+    const res = await request(createApp()).delete(
+      "/api/secrets/33333333-3333-4333-8333-333333333333",
+    );
+
+    expect(res.status).toBe(200);
+    expect(res.body).toEqual({ ok: true });
+    expect(mockSecretService.remove).toHaveBeenCalledWith(
+      "33333333-3333-4333-8333-333333333333",
+    );
+    expect(mockLogActivity).toHaveBeenCalledWith(
+      expect.anything(),
+      expect.objectContaining({
+        action: "secret.deleted",
+        companyId: "company-1",
+        entityId: secret.id,
+      }),
+    );
+  });
 });
diff --git a/server/src/routes/secrets.ts b/server/src/routes/secrets.ts
index a7f28c78914..be9d503f3de 100644
--- a/server/src/routes/secrets.ts
+++ b/server/src/routes/secrets.ts
@@ -454,10 +454,6 @@ 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) {
diff --git a/server/src/services/secrets.ts b/server/src/services/secrets.ts
index 398316300f0..8bbfe892af6 100644
--- a/server/src/services/secrets.ts
+++ b/server/src/services/secrets.ts
@@ -1944,16 +1944,18 @@ export function secretService(db: Db) {
       const versionRow = await getSecretVersion(secret.id, secret.latestVersion);
       const providerId = secret.provider as SecretProvider;
       const provider = getSecretProvider(providerId);
-      await db
-        .update(companySecrets)
-        .set({
-          key: `${secret.key}__deleted__${secret.id}`,
-          name: `${secret.name}__deleted__${secret.id}`,
-          status: "deleted",
-          deletedAt: secret.deletedAt ?? new Date(),
-          updatedAt: new Date(),
-        })
-        .where(eq(companySecrets.id, secretId));
+      if (secret.status !== "deleted") {
+        await db
+          .update(companySecrets)
+          .set({
+            key: `${secret.key}__deleted__${secret.id}`,
+            name: `${secret.name}__deleted__${secret.id}`,
+            status: "deleted",
+            deletedAt: secret.deletedAt ?? new Date(),
+            updatedAt: new Date(),
+          })
+          .where(eq(companySecrets.id, secretId));
+      }
       const providerConfig = secret.providerConfigId
         ? await getProviderConfigById(secret.providerConfigId)
         : null;