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feat: telemetry and security hardening #52

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a3cbf47
docs(posthog): add comprehensive PostHog event plan and instrumentati…
leoisadev8 Oct 15, 2025
c30bc85
feat(analytics): refine and streamline PostHog event taxonomy and ins…
leoisadev8 Oct 15, 2025
c79243b
feat(analytics): enhance PostHog integration and event tracking
leoisadev8 Oct 15, 2025
3722fbd
fix: sanitize user id before bootstrapping client
leoisadev8 Oct 16, 2025
aca123e
fix: derive OpenRouter key with PBKDF2
leoisadev8 Oct 16, 2025
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7 changes: 5 additions & 2 deletions apps/server/src/lib/openrouter.ts
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Original file line number Diff line number Diff line change
@@ -1,5 +1,5 @@
import { Buffer } from "node:buffer";
import { createCipheriv, createDecipheriv, createHash, randomBytes } from "node:crypto";
import { createCipheriv, createDecipheriv, pbkdf2Sync, randomBytes } from "node:crypto";
import { eq } from "drizzle-orm";

import { db } from "../db";
Expand Down Expand Up @@ -67,7 +67,10 @@ function getEncryptionKey() {
if (!secret || secret.length < 16) {
throw new Error("Missing OPENROUTER_API_KEY_SECRET env for encrypting OpenRouter API keys");
}
return createHash("sha256").update(secret).digest();
const salt = "openrouter:key-derivation-salt";
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@greptile-apps greptile-apps bot Oct 16, 2025

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style: Using a fixed salt reduces security compared to random salts. Consider generating unique salts per user or per environment.

const iterations = 100_000;
const keyLength = 32; // AES-256-GCM expects 32-byte key
return pbkdf2Sync(secret, salt, iterations, keyLength, "sha256");
}

function base64UrlEncode(buffer: Buffer) {
Expand Down
48 changes: 41 additions & 7 deletions apps/server/src/lib/posthog.ts
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Original file line number Diff line number Diff line change
Expand Up @@ -3,6 +3,32 @@ import { withTracing } from "@posthog/ai";

let client: PostHog | null = null;

const APP_VERSION =
process.env.SERVER_APP_VERSION ??
process.env.APP_VERSION ??
process.env.NEXT_PUBLIC_APP_VERSION ??
process.env.VERCEL_GIT_COMMIT_SHA ??
"dev";

const DEPLOYMENT =
process.env.SERVER_DEPLOYMENT ??
process.env.DEPLOYMENT ??
process.env.POSTHOG_DEPLOYMENT ??
process.env.VERCEL_ENV ??
(process.env.NODE_ENV === "production" ? "prod" : "local");

const ENVIRONMENT = process.env.POSTHOG_ENVIRONMENT ?? process.env.NODE_ENV ?? "development";
const DEPLOYMENT_REGION =
process.env.POSTHOG_DEPLOYMENT_REGION ?? process.env.VERCEL_REGION ?? "local";

const BASE_SUPER_PROPERTIES = Object.freeze({
app: "openchat-server",
app_version: APP_VERSION,
deployment: DEPLOYMENT,
environment: ENVIRONMENT,
deployment_region: DEPLOYMENT_REGION,
});

function buildClient() {
const apiKey = process.env.POSTHOG_API_KEY;
if (!apiKey) return null;
Expand All @@ -13,6 +39,7 @@ function buildClient() {
flushAt: 1,
flushInterval: 5_000,
});
client.register(BASE_SUPER_PROPERTIES);
return client;
}

Expand All @@ -27,13 +54,20 @@ export function capturePosthogEvent(
) {
const instance = buildClient();
if (!instance || !distinctId) return;
instance.capture({
distinctId,
event,
properties,
}).catch((error: unknown) => {
console.error("[posthog] capture failed", error);
});
const sanitized: Record<string, unknown> = {};
for (const [key, value] of Object.entries(properties)) {
if (value === undefined) continue;
sanitized[key] = value;
}
instance
.capture({
distinctId,
event,
properties: sanitized,
})
.catch((error: unknown) => {
console.error("[posthog] capture failed", error);
});
}

export function withPosthogTracing<Model extends (...args: any[]) => any>(
Expand Down
95 changes: 68 additions & 27 deletions apps/server/src/routers/index.ts
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Original file line number Diff line number Diff line change
Expand Up @@ -113,45 +113,55 @@ export const appRouter = {
.optional(),
)
.handler(async ({ context, input }) => {
const userId = context.session!.user.id;
const id = input?.id ?? cuid();
const now = new Date();
const title = input?.title ?? "New Chat";
let storageBackend: "postgres" | "memory_fallback" = "postgres";
try {
await db.insert(chat).values({
id,
userId: context.session!.user.id,
userId,
title,
createdAt: now,
updatedAt: now,
lastMessageAt: now,
});
// emit sidebar add
publish(
`chats:index:${context.session!.user.id}`,
`chats:index:${userId}`,
"chats.index.add",
{ chatId: id, title, updatedAt: now, lastMessageAt: now },
);
} catch {
addFallbackChat(context.session!.user.id, {
storageBackend = "memory_fallback";
addFallbackChat(userId, {
id,
userId: context.session!.user.id,
userId,
title,
createdAt: now,
updatedAt: now,
lastMessageAt: now,
});
publish(
`chats:index:${context.session!.user.id}`,
`chats:index:${userId}`,
"chats.index.add",
{ chatId: id, title, updatedAt: now, lastMessageAt: now },
);
capturePosthogEvent("workspace.fallback_storage_used", userId, {
operation: "create",
chat_id: id,
fallback_size: (memChatsByUser.get(userId) ?? []).length,
workspace_id: userId,
});
}
capturePosthogEvent("chat_created", context.session!.user.id, {
chatId: id,
title,
recordedAt: now.toISOString(),
capturePosthogEvent("chat.created", userId, {
chat_id: id,
title_length: title.length,
storage_backend: storageBackend,
source: "server_router",
workspace_id: userId,
});
return { id };
return { id, storageBackend };
}),
// List chats for the current user (sorted by last activity)
list: protectedProcedure.handler(async ({ context }) => {
Expand All @@ -163,8 +173,15 @@ export const appRouter = {
.orderBy(desc(chat.lastMessageAt), desc(chat.updatedAt));
return rows;
} catch {
pruneUserChats(context.session!.user.id);
const list = memChatsByUser.get(context.session!.user.id) ?? [];
const userId = context.session!.user.id;
pruneUserChats(userId);
const list = memChatsByUser.get(userId) ?? [];
capturePosthogEvent("workspace.fallback_storage_used", userId, {
operation: "list",
chat_id: null,
fallback_size: list.length,
workspace_id: userId,
});
return list.map(({ id, title, lastMessageAt, updatedAt }) => ({ id, title, lastMessageAt, updatedAt }));
}
}),
Expand Down Expand Up @@ -231,13 +248,21 @@ export const appRouter = {
} else {
memMsgsByChat.delete(input.chatId);
}
const permissibleChats = pruneChatList(memChatsByUser.get(context.session!.user.id) ?? []);
const userId = context.session!.user.id;
const permissibleChats = pruneChatList(memChatsByUser.get(userId) ?? []);
if (permissibleChats.length > 0) {
memChatsByUser.set(context.session!.user.id, permissibleChats);
memChatsByUser.set(userId, permissibleChats);
}
const hasAccess = permissibleChats.some((c) => c.id === input.chatId);
if (!hasAccess) return [];
return (memMsgsByChat.get(input.chatId) ?? prunedMessages)
const fallbackMessages = memMsgsByChat.get(input.chatId) ?? prunedMessages;
capturePosthogEvent("workspace.fallback_storage_used", userId, {
operation: "list",
chat_id: input.chatId,
fallback_size: fallbackMessages.length,
workspace_id: userId,
});
return fallbackMessages
.map(({ id, role, content, createdAt }) => ({ id, role, content, createdAt }));
}
}),
Expand All @@ -261,6 +286,7 @@ export const appRouter = {
}),
)
.handler(async ({ context, input }) => {
const userId = context.session!.user.id;
const userCreatedAt = input.userMessage.createdAt ? new Date(input.userMessage.createdAt) : new Date();
const assistantProvided = input.assistantMessage != null;
const assistantCreatedAt = assistantProvided
Expand All @@ -275,7 +301,7 @@ export const appRouter = {
const owned = await db
.select({ id: chat.id })
.from(chat)
.where(and(eq(chat.id, input.chatId), eq(chat.userId, context.session!.user.id)));
.where(and(eq(chat.id, input.chatId), eq(chat.userId, userId)));
if (owned.length === 0) return { ok: false as const };

await db
Expand Down Expand Up @@ -333,14 +359,14 @@ export const appRouter = {
.set({ updatedAt: lastActivity, lastMessageAt: lastActivity })
.where(eq(chat.id, input.chatId));
publish(
`chats:index:${context.session!.user.id}`,
`chats:index:${userId}`,
"chats.index.update",
{ chatId: input.chatId, updatedAt: lastActivity, lastMessageAt: lastActivity },
);
return { ok: true as const, userMessageId: userMsgId, assistantMessageId: assistantMsgId };
} catch {
pruneUserChats(context.session!.user.id);
const userChats = memChatsByUser.get(context.session!.user.id) ?? [];
pruneUserChats(userId);
const userChats = memChatsByUser.get(userId) ?? [];
if (!userChats.some((c) => c.id === input.chatId)) return { ok: false as const };
addFallbackMessage(input.chatId, {
id: userMsgId,
Expand Down Expand Up @@ -377,12 +403,19 @@ export const appRouter = {
record.updatedAt = latest;
record.lastMessageAt = latest;
}
memChatsByUser.set(context.session!.user.id, pruneChatList(owned));
memChatsByUser.set(userId, pruneChatList(owned));
publish(
`chats:index:${context.session!.user.id}`,
`chats:index:${userId}`,
"chats.index.update",
{ chatId: input.chatId, updatedAt: assistantCreatedAt ?? userCreatedAt, lastMessageAt: assistantCreatedAt ?? userCreatedAt },
);
const fallbackMessages = memMsgsByChat.get(input.chatId) ?? [];
capturePosthogEvent("workspace.fallback_storage_used", userId, {
operation: "send",
chat_id: input.chatId,
fallback_size: fallbackMessages.length,
workspace_id: userId,
});
return { ok: true as const, userMessageId: userMsgId, assistantMessageId: assistantMsgId };
}
}),
Expand All @@ -398,6 +431,7 @@ export const appRouter = {
}),
)
.handler(async ({ context, input }) => {
const userId = context.session!.user.id;
const createdAt = input.createdAt ? new Date(input.createdAt) : new Date();
const now = new Date();
const content = input.content ?? '';
Expand All @@ -408,7 +442,7 @@ export const appRouter = {
const owned = await db
.select({ id: chat.id })
.from(chat)
.where(and(eq(chat.id, input.chatId), eq(chat.userId, context.session!.user.id)));
.where(and(eq(chat.id, input.chatId), eq(chat.userId, userId)));
if (owned.length === 0) return { ok: false as const };

let inserted = false;
Expand Down Expand Up @@ -456,7 +490,7 @@ export const appRouter = {
}

publish(
`chats:index:${context.session!.user.id}`,
`chats:index:${userId}`,
'chats.index.update',
sidebarPayload,
);
Expand All @@ -477,8 +511,8 @@ export const appRouter = {

return { ok: true as const };
} catch {
pruneUserChats(context.session!.user.id);
const userChats = memChatsByUser.get(context.session!.user.id) ?? [];
pruneUserChats(userId);
const userChats = memChatsByUser.get(userId) ?? [];
if (!userChats.some((c) => c.id === input.chatId)) return { ok: false as const };

const existingMessages = memMsgsByChat.get(input.chatId) ?? [];
Expand Down Expand Up @@ -514,7 +548,7 @@ export const appRouter = {
record.lastMessageAt = createdAt;
}
}
memChatsByUser.set(context.session!.user.id, pruneChatList(userChats));
memChatsByUser.set(userId, pruneChatList(userChats));

publish(
`chat:${input.chatId}`,
Expand All @@ -529,6 +563,13 @@ export const appRouter = {
updatedAt: now,
},
);
const fallbackMessages = memMsgsByChat.get(input.chatId) ?? [];
capturePosthogEvent("workspace.fallback_storage_used", userId, {
operation: "streamUpsert",
chat_id: input.chatId,
fallback_size: fallbackMessages.length,
workspace_id: userId,
});
return { ok: true as const };
}
}),
Expand Down
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