fix: slack bot authenticates via oauth

2026-06-05 18:52:26 +01:00
parent 4e8c26da0a
commit c59153439b
38 changed files with 8645 additions and 190 deletions
--- a/apps/leaf/README.md
+++ b/apps/leaf/README.md
@@ -15,12 +15,20 @@ bun run chat:tunnel
 2. Start Autumn with the same public URL:

 ```sh
-CHAT_URL=https://c.autumn.ngrok.app SLACK_BOT_URL=https://c.autumn.ngrok.app bun d
+NGROK_URL=https://c.autumn.ngrok.app bun d
 ```

+`bun d` derives `CHAT_URL`, `SLACK_BOT_URL`, and `SLACK_REDIRECT_URI` from
+`NGROK_URL`, so the Slack OAuth redirect becomes
+`https://c.autumn.ngrok.app/slack/oauth/callback`. This exact URL must be in
+the Slack app's OAuth redirect URLs.
+
 The chat SDK stores its own subscriptions, locks, and queues in Postgres. By
 default it uses the same `DATABASE_URL` host with the database name changed to
-`chat`; set `CHAT_STATE_DATABASE_URL` to override this.
+`chat`; set `CHAT_STATE_DATABASE_URL` to override this. `bun dev:services up`
+creates the local `chat` database. The `@chat-adapter/state-pg` package creates
+its state tables automatically on connect, so there is no separate migration
+command for the chat state database.

 3. Create a Slack app at https://api.slack.com/apps using `slack-manifest.example.json`.

--- a/apps/leaf/src/agent/agent.ts
+++ b/apps/leaf/src/agent/agent.ts
@@ -96,7 +96,7 @@ const readDocs = async (mcp: ReturnType<typeof createAutumnMcpClient>) => {
 };

 export const runChatAgent = async ({
-	apiKey,
+	token,
 	env,
 	logger = rootLogger,
 	message,
@@ -106,7 +106,7 @@ export const runChatAgent = async ({
 	provider,
 	recentMessages,
 }: {
-	apiKey: string;
+	token: string;
 	env: AppEnv;
 	logger?: AutumnLogger;
 	message: string;
@@ -116,7 +116,11 @@ export const runChatAgent = async ({
 	provider: string;
 	recentMessages?: ChatContextMessage[];
 }) => {
-	const mcp = createAutumnMcpClient(apiKey, { requireApproval: true });
+	const mcp = createAutumnMcpClient({
+		token,
+		appEnv: env,
+		options: { requireApproval: true },
+	});
 	let previewApproval:
 		| {
 				toolName: string;
@@ -138,12 +142,15 @@ export const runChatAgent = async ({
 		});
 		await onAction?.("Loading Autumn tools and guidance");
 		const [tools, docsText] = await Promise.all([
-			getAutumnMcpTools(mcp, {
-				applyApprovalPolicy: true,
-				logger,
-				onToolCall: onAction,
-				onPreview: (approval) => {
-					previewApproval = approval;
+			getAutumnMcpTools({
+				mcp,
+				options: {
+					applyApprovalPolicy: true,
+					logger,
+					onToolCall: onAction,
+					onPreview: (approval) => {
+						previewApproval = approval;
+					},
 				},
 			}),
 			readDocs(mcp),
--- a/apps/leaf/src/agent/mcp.ts
+++ b/apps/leaf/src/agent/mcp.ts
@@ -1,4 +1,6 @@
+import { isSecretKeyPrefix } from "@autumn/auth";
 import type { AutumnLogger } from "@autumn/logging";
+import type { AppEnv } from "@autumn/shared";
 import { MCPClient } from "@mastra/mcp";
 import { env } from "../lib/env.js";
 import { logger as rootLogger } from "../lib/logger.js";
@@ -26,29 +28,41 @@ type ToolOptions = {
 };

 const withAuthFetch =
-	(apiKey: string) => (input: RequestInfo | URL, init?: RequestInit) => {
+	({ appEnv, token }: { appEnv: AppEnv; token: string }) =>
+	(input: RequestInfo | URL, init?: RequestInit) => {
 		const headers = new Headers(init?.headers);
-		headers.set("Authorization", `Bearer ${apiKey}`);
-		headers.set("secret-key", apiKey);
+		headers.set("Authorization", `Bearer ${token}`);
+		headers.set("x-autumn-environment", appEnv);
+		if (isSecretKeyPrefix({ token })) {
+			headers.set("secret-key", token);
+		}
 		return fetch(input, { ...init, headers });
 	};

-export const createAutumnMcpClient = (
-	apiKey: string,
-	options: { requireApproval?: boolean } = {},
-) => {
-	const fetchWithAuth = withAuthFetch(apiKey);
+export const createAutumnMcpClient = ({
+	token,
+	appEnv,
+	options = {},
+}: {
+	token: string;
+	appEnv: AppEnv;
+	options?: { requireApproval?: boolean };
+}) => {
+	const fetchWithAuth = withAuthFetch({ appEnv, token });
+	const headers: Record<string, string> = {
+		Authorization: `Bearer ${token}`,
+		"x-autumn-environment": appEnv,
+	};
+	if (isSecretKeyPrefix({ token })) {
+		headers["secret-key"] = token;
+	}
+
 	return new MCPClient({
-		id: `autumn-${apiKey.slice(0, 14)}`,
+		id: `autumn-${token.slice(0, 14)}`,
 		servers: {
 			autumn: {
 				url: new URL("/mcp", env.MCP_SERVER_URL),
-				requestInit: {
-					headers: {
-						Authorization: `Bearer ${apiKey}`,
-						"secret-key": apiKey,
-					},
-				},
+				requestInit: { headers },
 				eventSourceInit: { fetch: fetchWithAuth },
 				fetch: fetchWithAuth,
 				requireToolApproval: options.requireApproval
@@ -59,7 +73,13 @@ export const createAutumnMcpClient = (
 	});
 };

-const formatToolAction = (toolName: string, args: Record<string, unknown>) => {
+const formatToolAction = ({
+	toolName,
+	args,
+}: {
+	toolName: string;
+	args: Record<string, unknown>;
+}) => {
 	const request =
 		args.request && typeof args.request === "object"
 			? (args.request as Record<string, unknown>)
@@ -76,10 +96,13 @@ const formatToolAction = (toolName: string, args: Record<string, unknown>) => {
 	return `${toolLabel(toolName)}${details.length ? ` (${details.join(", ")})` : ""}`;
 };

-export const getAutumnMcpTools = async (
-	mcp: MCPClient,
-	options: ToolOptions = {},
-) => {
+export const getAutumnMcpTools = async ({
+	mcp,
+	options = {},
+}: {
+	mcp: MCPClient;
+	options?: ToolOptions;
+}) => {
 	const logger = options.logger ?? rootLogger;
 	const { toolsets, errors } = await mcp.listToolsetsWithErrors();
 	if (Object.keys(errors).length) {
@@ -111,7 +134,7 @@ export const getAutumnMcpTools = async (
 					event: "leaf.mcp_tool_called",
 					tool: toolName,
 				});
-				await options.onToolCall?.(formatToolAction(toolName, args));
+				await options.onToolCall?.(formatToolAction({ toolName, args }));
 				const result = await execute(args, ...rest);
 				const writeTool = getWriteToolForPreview(toolName);
 				if (writeTool) {
@@ -136,17 +159,19 @@ export const getAutumnMcpTools = async (
 };

 export const executeAutumnMcpTool = async ({
-	apiKey,
+	env,
+	token,
 	toolName,
 	args,
 }: {
-	apiKey: string;
+	env: AppEnv;
+	token: string;
 	toolName: string;
 	args: Record<string, unknown>;
 }) => {
-	const mcp = createAutumnMcpClient(apiKey);
+	const mcp = createAutumnMcpClient({ token, appEnv: env });
 	try {
-		const tools = await getAutumnMcpTools(mcp);
+		const tools = await getAutumnMcpTools({ mcp });
 		const tool = tools[toolName.replace(/^autumn_/, "")];
 		if (!tool?.execute) throw new Error(`Unknown Autumn MCP tool: ${toolName}`);
 		return await tool.execute(args);
--- a/apps/leaf/src/agent/messages.ts
+++ b/apps/leaf/src/agent/messages.ts
@@ -1,5 +1,5 @@
+import { getInstallationOAuthAccessToken } from "../internal/installations/actions/getInstallationOAuthAccessToken.js";
 import { logger as rootLogger } from "../lib/logger.js";
-import { getInstallationKey } from "../providers/slack/installations.js";
 import { agentOutputSchema, type BotMessage } from "../types.js";
 import { runChatAgent, selectChatEnv } from "./agent.js";

@@ -35,9 +35,13 @@ export const runMessage = async ({
 					provider: installation.provider,
 				},
 			});
+			const token = await getInstallationOAuthAccessToken({
+				installation,
+				env,
+			});
 			return agentOutputSchema.parse(
 				await runChatAgent({
-					apiKey: getInstallationKey(installation, env),
+					token,
 					env,
 					logger,
 					message: text,
--- a/apps/leaf/src/approvals/store.ts
+++ b/apps/leaf/src/approvals/store.ts
@@ -1,15 +1,15 @@
 import crypto from "node:crypto";
 import {
-	AppEnv,
+	type AppEnv,
 	type ChatProvider,
 	chatApprovals,
 	chatInstallations,
 } from "@autumn/shared";
 import { addMinutes, isPast } from "date-fns";
 import { and, eq, gt } from "drizzle-orm";
-import { decrypt } from "../lib/crypto.js";
-import { db } from "../lib/db.js";
 import { executeAutumnMcpTool } from "../agent/mcp.js";
+import { getInstallationOAuthAccessToken } from "../internal/installations/actions/getInstallationOAuthAccessToken.js";
+import { db } from "../lib/db.js";

 export const normalizeToolName = (toolName: string) =>
 	toolName.replace(/^autumn_/, "");
@@ -120,14 +120,14 @@ export const approveAndRun = async (id: string, providerUserId: string) => {
 		});
 		if (!installation) throw new Error("Chat installation not found");

-		const encryptedKey =
-			claimed.env === AppEnv.Live
-				? installation.live_api_key
-				: installation.sandbox_api_key;
-		if (!encryptedKey) throw new Error(`Missing ${claimed.env} API key`);
+		const token = await getInstallationOAuthAccessToken({
+			installation,
+			env: claimed.env,
+		});

 		const result = await executeAutumnMcpTool({
-			apiKey: decrypt(encryptedKey),
+			token,
+			env: claimed.env,
 			toolName: claimed.tool_name,
 			args: claimed.tool_args,
 		});
--- a/apps/leaf/src/internal/installations/actions/getInstallationOAuthAccessToken.ts
+++ b/apps/leaf/src/internal/installations/actions/getInstallationOAuthAccessToken.ts
@@ -0,0 +1,83 @@
+import type { AppEnv, ChatInstallation } from "@autumn/shared";
+import { decrypt, encrypt } from "../../../lib/crypto.js";
+import { db } from "../../../lib/db.js";
+import { env as leafEnv } from "../../../lib/env.js";
+import {
+	getChatOAuthCredentialByInstallationEnv,
+	updateChatOAuthCredentialTokens,
+} from "../repos/chatOAuthCredentialsRepo.js";
+import {
+	parseOAuthScopeString,
+	parseOAuthTokenResponse,
+} from "../utils/oauthTokenResponse.js";
+
+const TOKEN_EXPIRY_SKEW_MS = 60_000;
+
+const getTokenEndpoint = () =>
+	new URL("/api/auth/oauth2/token", leafEnv.BETTER_AUTH_URL).href;
+
+const getDefaultExpiresAt = () => Date.now() + 60 * 60 * 1000;
+
+export const getInstallationOAuthAccessToken = async ({
+	installation,
+	env,
+}: {
+	installation: ChatInstallation;
+	env: AppEnv;
+}) => {
+	const credential = await getChatOAuthCredentialByInstallationEnv({
+		db,
+		chatInstallationId: installation.id,
+		env,
+	});
+
+	if (!credential) {
+		throw new Error(
+			`Missing ${env} Autumn OAuth credentials for Slack install`,
+		);
+	}
+
+	if (credential.access_token_expires_at - TOKEN_EXPIRY_SKEW_MS > Date.now()) {
+		return decrypt(credential.access_token);
+	}
+
+	const refreshToken = decrypt(credential.refresh_token);
+	const body = new URLSearchParams({
+		grant_type: "refresh_token",
+		refresh_token: refreshToken,
+		client_id: credential.oauth_client_id,
+	});
+
+	const response = await fetch(getTokenEndpoint(), {
+		method: "POST",
+		headers: {
+			"Content-Type": "application/x-www-form-urlencoded",
+		},
+		body,
+	});
+
+	if (!response.ok) {
+		throw new Error(
+			`Could not refresh ${env} Autumn OAuth token for Slack install`,
+		);
+	}
+
+	const parsed = parseOAuthTokenResponse({ body: await response.json() });
+	const accessTokenExpiresAt = parsed.expires_in
+		? Date.now() + parsed.expires_in * 1000
+		: getDefaultExpiresAt();
+	const nextRefreshToken = parsed.refresh_token ?? refreshToken;
+	const scopes = parseOAuthScopeString({ scope: parsed.scope });
+
+	await updateChatOAuthCredentialTokens({
+		db,
+		id: credential.id,
+		accessToken: encrypt(parsed.access_token),
+		refreshToken: encrypt(nextRefreshToken),
+		accessTokenExpiresAt,
+		scopes: scopes.length > 0 ? scopes : credential.scopes,
+		updatedAt: Date.now(),
+	});
+
+	return parsed.access_token;
+};
--- a/apps/leaf/src/internal/installations/actions/replaceInstallationOAuthCredentials.ts
+++ b/apps/leaf/src/internal/installations/actions/replaceInstallationOAuthCredentials.ts
@@ -0,0 +1,218 @@
+import crypto from "node:crypto";
+import { prefixOAuthToken } from "@autumn/auth";
+import {
+	AppEnv,
+	type ChatInstallation,
+	chatOAuthCredentials,
+	oauthAccessToken,
+	oauthClient,
+	oauthConsent,
+	oauthRefreshToken,
+} from "@autumn/shared";
+import { ALL_SCOPES } from "@autumn/shared/utils/scopeDefinitions";
+import { and, eq } from "drizzle-orm";
+import { encrypt } from "../../../lib/crypto.js";
+import type { db } from "../../../lib/db.js";
+import { AUTUMN_SLACK_OAUTH_CLIENT_ID } from "./upsertInstallationOAuthCredential.js";
+
+type ChatTransaction = Parameters<Parameters<typeof db.transaction>[0]>[0];
+
+const ACCESS_TOKEN_TTL_MS = 60 * 60 * 1000;
+const REFRESH_TOKEN_TTL_MS = 365 * 24 * 60 * 60 * 1000;
+
+const tokenHash = ({ token }: { token: string }) => {
+	const hash = crypto.createHash("sha256").update(token).digest();
+	return hash
+		.toString("base64")
+		.replace(/\+/g, "-")
+		.replace(/\//g, "_")
+		.replace(/=/g, "");
+};
+
+const generateToken = () => crypto.randomBytes(48).toString("base64url");
+
+const ensureSlackMcpOAuthClient = async ({ tx }: { tx: ChatTransaction }) => {
+	const now = new Date();
+
+	await tx
+		.insert(oauthClient)
+		.values({
+			id: `oauth_client_${crypto.randomUUID().replace(/-/g, "")}`,
+			clientId: AUTUMN_SLACK_OAUTH_CLIENT_ID,
+			name: "Slack",
+			redirectUris: ["slack://autumn-chat"],
+			scopes: [...ALL_SCOPES],
+			tokenEndpointAuthMethod: "none",
+			grantTypes: ["authorization_code", "refresh_token"],
+			responseTypes: ["code"],
+			public: true,
+			type: "native",
+			metadata: {
+				kind: "mcp_client",
+				mcpClientType: "slack",
+			},
+			createdAt: now,
+			updatedAt: now,
+		})
+		.onConflictDoUpdate({
+			target: oauthClient.clientId,
+			set: {
+				name: "Slack",
+				scopes: [...ALL_SCOPES],
+				tokenEndpointAuthMethod: "none",
+				grantTypes: ["authorization_code", "refresh_token"],
+				responseTypes: ["code"],
+				public: true,
+				type: "native",
+				metadata: {
+					kind: "mcp_client",
+					mcpClientType: "slack",
+				},
+				updatedAt: now,
+			},
+		});
+};
+
+const upsertOAuthConsent = async ({
+	tx,
+	env,
+	orgId,
+	userId,
+}: {
+	tx: ChatTransaction;
+	env: AppEnv;
+	orgId: string;
+	userId: string;
+}) => {
+	const now = new Date();
+	const [existingConsent] = await tx
+		.select({ id: oauthConsent.id })
+		.from(oauthConsent)
+		.where(
+			and(
+				eq(oauthConsent.clientId, AUTUMN_SLACK_OAUTH_CLIENT_ID),
+				eq(oauthConsent.userId, userId),
+				eq(oauthConsent.referenceId, orgId),
+				eq(oauthConsent.env, env),
+			),
+		)
+		.limit(1);
+
+	if (existingConsent) {
+		await tx
+			.update(oauthConsent)
+			.set({
+				scopes: [...ALL_SCOPES],
+				updatedAt: now,
+			})
+			.where(eq(oauthConsent.id, existingConsent.id));
+		return existingConsent.id;
+	}
+
+	const consentId = `oauth_consent_${crypto.randomUUID().replace(/-/g, "")}`;
+	await tx.insert(oauthConsent).values({
+		id: consentId,
+		clientId: AUTUMN_SLACK_OAUTH_CLIENT_ID,
+		userId,
+		referenceId: orgId,
+		scopes: [...ALL_SCOPES],
+		env,
+		redirectUri: "slack://autumn-chat",
+		createdAt: now,
+		updatedAt: now,
+	});
+
+	return consentId;
+};
+
+const createCredentialForEnv = async ({
+	tx,
+	installation,
+	env,
+	userId,
+}: {
+	tx: ChatTransaction;
+	installation: ChatInstallation;
+	env: AppEnv;
+	userId: string;
+}) => {
+	const now = Date.now();
+	const nowDate = new Date(now);
+	const rawAccessToken = generateToken();
+	const rawRefreshToken = generateToken();
+	const accessTokenExpiresAt = now + ACCESS_TOKEN_TTL_MS;
+	const refreshTokenExpiresAt = now + REFRESH_TOKEN_TTL_MS;
+	const refreshTokenId = `oauth_refresh_${crypto.randomUUID().replace(/-/g, "")}`;
+	const accessTokenId = `oauth_access_${crypto.randomUUID().replace(/-/g, "")}`;
+	const consentId = await upsertOAuthConsent({
+		tx,
+		env,
+		orgId: installation.org_id,
+		userId,
+	});
+
+	await tx.insert(oauthRefreshToken).values({
+		id: refreshTokenId,
+		token: tokenHash({ token: rawRefreshToken }),
+		clientId: AUTUMN_SLACK_OAUTH_CLIENT_ID,
+		userId,
+		referenceId: installation.org_id,
+		expiresAt: new Date(refreshTokenExpiresAt),
+		createdAt: nowDate,
+		authTime: nowDate,
+		scopes: [...ALL_SCOPES],
+	});
+	await tx.insert(oauthAccessToken).values({
+		id: accessTokenId,
+		token: tokenHash({ token: rawAccessToken }),
+		clientId: AUTUMN_SLACK_OAUTH_CLIENT_ID,
+		userId,
+		referenceId: installation.org_id,
+		refreshId: refreshTokenId,
+		expiresAt: new Date(accessTokenExpiresAt),
+		createdAt: nowDate,
+		scopes: [...ALL_SCOPES],
+	});
+	await tx.insert(chatOAuthCredentials).values({
+		id: `chat_oauth_${crypto.randomUUID().replace(/-/g, "")}`,
+		chat_installation_id: installation.id,
+		org_id: installation.org_id,
+		env,
+		oauth_client_id: AUTUMN_SLACK_OAUTH_CLIENT_ID,
+		oauth_consent_id: consentId,
+		access_token: encrypt(prefixOAuthToken({ token: rawAccessToken })),
+		refresh_token: encrypt(rawRefreshToken),
+		access_token_expires_at: accessTokenExpiresAt,
+		scopes: [...ALL_SCOPES],
+		created_at: now,
+		updated_at: now,
+	});
+};
+
+export const replaceInstallationOAuthCredentials = async ({
+	tx,
+	installation,
+	userId,
+}: {
+	tx: ChatTransaction;
+	installation: ChatInstallation;
+	userId: string;
+}) => {
+	if (!userId) {
+		throw new Error("Missing user id for Slack MCP OAuth credentials");
+	}
+
+	await ensureSlackMcpOAuthClient({ tx });
+	await createCredentialForEnv({
+		tx,
+		installation,
+		env: AppEnv.Sandbox,
+		userId,
+	});
+	await createCredentialForEnv({
+		tx,
+		installation,
+		env: AppEnv.Live,
+		userId,
+	});
+};
--- a/apps/leaf/src/internal/installations/actions/upsertInstallationOAuthCredential.ts
+++ b/apps/leaf/src/internal/installations/actions/upsertInstallationOAuthCredential.ts
@@ -0,0 +1,47 @@
+import crypto from "node:crypto";
+import type { AppEnv, ChatInstallation } from "@autumn/shared";
+import { encrypt } from "../../../lib/crypto.js";
+import { db } from "../../../lib/db.js";
+import { upsertChatOAuthCredential } from "../repos/chatOAuthCredentialsRepo.js";
+
+export const AUTUMN_SLACK_OAUTH_CLIENT_ID = "autumn_mcp_slack";
+
+export const upsertInstallationOAuthCredential = async ({
+	installation,
+	env,
+	accessToken,
+	refreshToken,
+	accessTokenExpiresAt,
+	scopes,
+	oauthClientId = AUTUMN_SLACK_OAUTH_CLIENT_ID,
+	oauthConsentId,
+}: {
+	installation: ChatInstallation;
+	env: AppEnv;
+	accessToken: string;
+	refreshToken: string;
+	accessTokenExpiresAt: number;
+	scopes: string[];
+	oauthClientId?: string;
+	oauthConsentId?: string | null;
+}) => {
+	const now = Date.now();
+
+	return upsertChatOAuthCredential({
+		db,
+		credential: {
+			id: `chat_oauth_${crypto.randomUUID().replace(/-/g, "")}`,
+			chat_installation_id: installation.id,
+			org_id: installation.org_id,
+			env,
+			oauth_client_id: oauthClientId,
+			oauth_consent_id: oauthConsentId ?? null,
+			access_token: encrypt(accessToken),
+			refresh_token: encrypt(refreshToken),
+			access_token_expires_at: accessTokenExpiresAt,
+			scopes,
+			created_at: now,
+			updated_at: now,
+		},
+	});
+};
--- a/apps/leaf/src/internal/installations/repos/chatOAuthCredentialsRepo.ts
+++ b/apps/leaf/src/internal/installations/repos/chatOAuthCredentialsRepo.ts
@@ -0,0 +1,89 @@
+import {
+	type AppEnv,
+	type ChatOAuthCredential,
+	chatOAuthCredentials,
+} from "@autumn/shared";
+import { and, eq } from "drizzle-orm";
+import type { ChatDb } from "../../../lib/db.js";
+
+export type ChatOAuthCredentialInsert =
+	typeof chatOAuthCredentials.$inferInsert;
+
+export const getChatOAuthCredentialByInstallationEnv = async ({
+	db,
+	chatInstallationId,
+	env,
+}: {
+	db: ChatDb;
+	chatInstallationId: string;
+	env: AppEnv;
+}) =>
+	db.query.chatOAuthCredentials.findFirst({
+		where: and(
+			eq(chatOAuthCredentials.chat_installation_id, chatInstallationId),
+			eq(chatOAuthCredentials.env, env),
+		),
+	});
+
+export const upsertChatOAuthCredential = async ({
+	db,
+	credential,
+}: {
+	db: ChatDb;
+	credential: ChatOAuthCredentialInsert;
+}) => {
+	const [row] = await db
+		.insert(chatOAuthCredentials)
+		.values(credential)
+		.onConflictDoUpdate({
+			target: [
+				chatOAuthCredentials.chat_installation_id,
+				chatOAuthCredentials.env,
+			],
+			set: {
+				org_id: credential.org_id,
+				oauth_client_id: credential.oauth_client_id,
+				oauth_consent_id: credential.oauth_consent_id,
+				access_token: credential.access_token,
+				refresh_token: credential.refresh_token,
+				access_token_expires_at: credential.access_token_expires_at,
+				scopes: credential.scopes,
+				updated_at: credential.updated_at,
+			},
+		})
+		.returning();
+
+	return row as ChatOAuthCredential;
+};
+
+export const updateChatOAuthCredentialTokens = async ({
+	db,
+	id,
+	accessToken,
+	refreshToken,
+	accessTokenExpiresAt,
+	scopes,
+	updatedAt,
+}: {
+	db: ChatDb;
+	id: string;
+	accessToken: string;
+	refreshToken: string;
+	accessTokenExpiresAt: number;
+	scopes: string[];
+	updatedAt: number;
+}) => {
+	const [row] = await db
+		.update(chatOAuthCredentials)
+		.set({
+			access_token: accessToken,
+			refresh_token: refreshToken,
+			access_token_expires_at: accessTokenExpiresAt,
+			scopes,
+			updated_at: updatedAt,
+		})
+		.where(eq(chatOAuthCredentials.id, id))
+		.returning();
+
+	return row as ChatOAuthCredential | undefined;
+};
--- a/apps/leaf/src/internal/installations/utils/oauthTokenResponse.ts
+++ b/apps/leaf/src/internal/installations/utils/oauthTokenResponse.ts
@@ -0,0 +1,22 @@
+import { z } from "zod";
+
+const oauthTokenPayloadSchema = z.object({
+	access_token: z.string().min(1),
+	refresh_token: z.string().min(1).optional(),
+	expires_in: z.number().optional(),
+	scope: z.string().optional(),
+});
+
+const oauthTokenResponseSchema = z.preprocess((value) => {
+	if (value && typeof value === "object" && "response" in value) {
+		return (value as { response?: unknown }).response;
+	}
+
+	return value;
+}, oauthTokenPayloadSchema);
+
+export const parseOAuthTokenResponse = ({ body }: { body: unknown }) =>
+	oauthTokenResponseSchema.parse(body);
+
+export const parseOAuthScopeString = ({ scope }: { scope?: string }) =>
+	scope?.split(/\s+/).filter(Boolean) ?? [];
--- a/apps/leaf/src/mcp/auth/resolveRequestAuth.ts
+++ b/apps/leaf/src/mcp/auth/resolveRequestAuth.ts
@@ -1,14 +1,14 @@
 import { createHash } from "node:crypto";
-import { getBearerToken } from "@autumn/auth";
+import { getBearerToken, isOAuthToken, isSecretKeyPrefix } from "@autumn/auth";
 import {
 	getProtectedResourceMetadataUrl,
 	getWwwAuthenticateHeader,
 } from "@autumn/auth/oauth";
 import {
-	DEFAULT_API_VERSION,
-	MCP_OAUTH_SCOPES,
 	type AutumnMcpAuth,
+	DEFAULT_API_VERSION,
 	environmentSchema,
+	MCP_OAUTH_SCOPES,
 	type MCPServerFlags,
 	type OAuthEnvironment,
 } from "@autumn/mcp";
@@ -72,12 +72,21 @@ const getStaticApiKey = ({
 	flags: MCPOAuthFlags;
 }): string | undefined => {
 	const secretKey = headers.get("secret-key");
-	if (secretKey) return secretKey;
+	if (secretKey && isSecretKeyPrefix({ token: secretKey })) return secretKey;

 	const bearer = getBearerToken({ headers });
-	if (bearer?.startsWith("am_")) return bearer;
+	if (bearer && isSecretKeyPrefix({ token: bearer })) return bearer;

-	return flags["oauth-enabled"] ? undefined : flags["secret-key"];
+	const fallbackSecretKey = flags["secret-key"];
+	if (
+		!flags["oauth-enabled"] &&
+		fallbackSecretKey &&
+		isSecretKeyPrefix({ token: fallbackSecretKey })
+	) {
+		return fallbackSecretKey;
+	}
+
+	return undefined;
 };

 const principalFromSecret = ({
@@ -134,7 +143,7 @@ export const buildAuthForRequest = async ({
 	}

 	const bearer = getBearerToken({ headers });
-	if (bearer) {
+	if (bearer && isOAuthToken({ token: bearer })) {
 		return {
 			apiKey: bearer,
 			authMethod: "oauth",
@@ -148,6 +157,14 @@ export const buildAuthForRequest = async ({
 		};
 	}

+	if (bearer) {
+		throw new OAuthHttpError(
+			401,
+			"Invalid OAuth token prefix",
+			"invalid_token",
+		);
+	}
+
 	if (flags["oauth-enabled"]) {
 		throw new OAuthHttpError(
 			401,
--- a/apps/leaf/src/providers/slack/installations.ts
+++ b/apps/leaf/src/providers/slack/installations.ts
@@ -5,29 +5,16 @@ import {
 	type ChatInstallation,
 	type ChatProvider,
 	chatInstallations,
-	Scopes,
 } from "@autumn/shared";
 import type { ChatInstallState } from "@autumn/shared/utils/chatState";
 import { and, eq, or } from "drizzle-orm";
+import { replaceInstallationOAuthCredentials } from "../../internal/installations/actions/replaceInstallationOAuthCredentials.js";
 import { decrypt, encrypt } from "../../lib/crypto.js";
 import { db } from "../../lib/db.js";
 import { env } from "../../lib/env.js";

 type ChatTransaction = Parameters<Parameters<typeof db.transaction>[0]>[0];

-const apiKeyScopes = [
-	Scopes.Customers.Read,
-	Scopes.Customers.Write,
-	Scopes.Plans.Read,
-	Scopes.Plans.Write,
-	Scopes.Billing.Read,
-	Scopes.Billing.Write,
-	Scopes.Balances.Write,
-];
-
-const apiKeyPrefix = (env: AppEnv) =>
-	env === AppEnv.Live ? "am_sk_live" : "am_sk_test";
-
 export const getStateSecret = () => env.CHAT_STATE_SECRET;

 export const findInstallation = (provider: ChatProvider, workspaceId: string) =>
@@ -50,33 +37,6 @@ export const getInstallationKey = (
 	return decrypt(key);
 };

-const buildApiKey = ({
-	orgId,
-	userId,
-	env,
-	provider,
-}: {
-	orgId: string;
-	userId: string;
-	env: AppEnv;
-	provider: ChatProvider;
-}) => {
-	const secret = `${apiKeyPrefix(env)}_${crypto.randomBytes(32).toString("base64url")}`;
-	const key = {
-		id: `key_${crypto.randomUUID().replace(/-/g, "")}`,
-		org_id: orgId,
-		user_id: userId,
-		name: `Chat MCP (${provider})`,
-		prefix: secret.substring(0, 14),
-		created_at: Date.now(),
-		env,
-		hashed_key: crypto.createHash("sha256").update(secret).digest("hex"),
-		meta: { created_via: "chat", provider },
-		scopes: apiKeyScopes,
-	};
-	return { key, secret };
-};
-
 const deleteInstallationApiKeys = async (
 	tx: ChatTransaction,
 	installation: ChatInstallation,
@@ -111,19 +71,6 @@ export const replaceInstallation = async ({
 	scopes: string[];
 	installedByProviderUserId?: string;
 }) => {
-	const sandbox = buildApiKey({
-		orgId: state.orgId,
-		userId: state.userId,
-		env: AppEnv.Sandbox,
-		provider,
-	});
-	const live = buildApiKey({
-		orgId: state.orgId,
-		userId: state.userId,
-		env: AppEnv.Live,
-		provider,
-	});
-
 	const sameOrg = and(
 		eq(chatInstallations.org_id, state.orgId),
 		eq(chatInstallations.provider, provider),
@@ -134,8 +81,6 @@ export const replaceInstallation = async ({
 	);

 	await db.transaction(async (tx) => {
-		await tx.insert(apiKeys).values([sandbox.key, live.key]);
-
 		const existingInstallations = await tx.query.chatInstallations.findMany({
 			where: or(sameOrg, sameWorkspace),
 		});
@@ -144,24 +89,29 @@ export const replaceInstallation = async ({
 		}

 		await tx.delete(chatInstallations).where(or(sameOrg, sameWorkspace));
-		await tx.insert(chatInstallations).values({
-			id: `chat_inst_${crypto.randomUUID().replace(/-/g, "")}`,
-			org_id: state.orgId,
-			provider,
-			workspace_id: workspaceId,
-			workspace_name: workspaceName,
-			bot_user_id: botUserId,
-			bot_access_token: encrypt(botAccessToken),
-			scopes,
-			default_env: state.env,
-			sandbox_api_key_id: sandbox.key.id,
-			sandbox_api_key: encrypt(sandbox.secret),
-			live_api_key_id: live.key.id,
-			live_api_key: encrypt(live.secret),
-			installed_by_user_id: state.userId,
-			installed_by_provider_user_id: installedByProviderUserId,
-			created_at: Date.now(),
-			updated_at: Date.now(),
+		const [installation] = await tx
+			.insert(chatInstallations)
+			.values({
+				id: `chat_inst_${crypto.randomUUID().replace(/-/g, "")}`,
+				org_id: state.orgId,
+				provider,
+				workspace_id: workspaceId,
+				workspace_name: workspaceName,
+				bot_user_id: botUserId,
+				bot_access_token: encrypt(botAccessToken),
+				scopes,
+				default_env: state.env,
+				installed_by_user_id: state.userId,
+				installed_by_provider_user_id: installedByProviderUserId,
+				created_at: Date.now(),
+				updated_at: Date.now(),
+			})
+			.returning();
+
+		await replaceInstallationOAuthCredentials({
+			tx,
+			installation,
+			userId: state.userId,
 		});
 	});
 };
--- a/packages/auth/src/utils/authTokenUtils.ts
+++ b/packages/auth/src/utils/authTokenUtils.ts
@@ -0,0 +1,23 @@
+const AUTUMN_SECRET_KEY_PREFIX = "am_sk";
+const AUTUMN_PUBLISHABLE_KEY_PREFIX = "am_pk";
+const AUTUMN_OAUTH_TOKEN_PREFIX = "am_oauth_";
+
+export const isSecretKeyPrefix = ({ token }: { token: string }) =>
+	token.startsWith(AUTUMN_SECRET_KEY_PREFIX);
+
+export const isPublishableKeyPrefix = ({ token }: { token: string }) =>
+	token.startsWith(AUTUMN_PUBLISHABLE_KEY_PREFIX);
+
+export const isAutumnApiKey = ({ token }: { token: string }) =>
+	isSecretKeyPrefix({ token }) || isPublishableKeyPrefix({ token });
+
+export const isOAuthToken = ({ token }: { token: string }) =>
+	token.startsWith(AUTUMN_OAUTH_TOKEN_PREFIX);
+
+export const prefixOAuthToken = ({ token }: { token: string }) =>
+	isOAuthToken({ token }) ? token : `${AUTUMN_OAUTH_TOKEN_PREFIX}${token}`;
+
+export const stripOAuthTokenPrefix = ({ token }: { token: string }) =>
+	isOAuthToken({ token })
+		? token.slice(AUTUMN_OAUTH_TOKEN_PREFIX.length)
+		: token;
--- a/packages/auth/src/utils/index.ts
+++ b/packages/auth/src/utils/index.ts
@@ -1 +1,2 @@
+export * from "./authTokenUtils.js";
 export * from "./getBearerToken.js";
--- a/packages/logging/src/streams/prettyLogStream.ts
+++ b/packages/logging/src/streams/prettyLogStream.ts
@@ -13,6 +13,7 @@ const FORMATTED_LOG_EXCLUDE_FIELDS = new Set([
 	"query",
 	"durationMs",
 	"duration_ms",
+	"event",
 	"context",
 	"workflow",
 	"trigger",
--- a/packages/mcp/src/server/auth/auth.ts
+++ b/packages/mcp/src/server/auth/auth.ts
@@ -74,6 +74,10 @@ export const createAutumnClient = (auth: AutumnMcpAuth) => ({
 		"Content-Type": "application/json",
 		Accept: "application/json",
 		"x-api-version": auth.xApiVersion ?? DEFAULT_API_VERSION,
+		"x-autumn-environment": auth.env,
+		...(auth.authMethod === "oauth"
+			? { "x-autumn-oauth-resource": auth.resource }
+			: {}),
 		...(auth.failOpen === undefined
 			? {}
 			: { "fail-open": String(auth.failOpen) }),
--- a/scripts/dev.ts
+++ b/scripts/dev.ts
@@ -24,6 +24,9 @@ const CHAT_PORT = process.env.CHAT_PORT
 const LOCAL_CLIENT_URL = `http://localhost:${VITE_PORT}`;
 const LOCAL_SERVER_URL = `http://localhost:${SERVER_PORT}`;
 const LOCAL_CHAT_URL = `http://localhost:${CHAT_PORT}`;
+const publicTunnelUrl = process.env.NGROK_URL?.replace(/\/$/, "");
+const CHAT_URL = process.env.CHAT_URL ?? publicTunnelUrl ?? LOCAL_CHAT_URL;
+const SLACK_BOT_URL = process.env.SLACK_BOT_URL ?? publicTunnelUrl ?? CHAT_URL;
 const skipWorkers = false;
 const isProductionMode = process.argv.includes("--production");

@@ -36,6 +39,12 @@ const viteAppEnv = envFile.includes(".env.prod")
 const useLocalAuthUrls = viteAppEnv === "dev" && !isProductionMode;
 const localUrl = (value: string | undefined, fallback: string) =>
 	value && !value.includes(".useautumn.com") ? value : fallback;
+const SLACK_REDIRECT_URI = useLocalAuthUrls
+	? localUrl(
+			process.env.SLACK_REDIRECT_URI,
+			`${SLACK_BOT_URL}/slack/oauth/callback`,
+		)
+	: (process.env.SLACK_REDIRECT_URI ?? `${SLACK_BOT_URL}/slack/oauth/callback`);

 /**
 * Read environment variable from .env file
@@ -266,8 +275,9 @@ async function startDev() {
 				MCP_RESOURCE_URLS:
 					process.env.MCP_RESOURCE_URLS ?? `http://localhost:${CHAT_PORT}/mcp`,
 				AUTUMN_API_URL: process.env.AUTUMN_API_URL ?? LOCAL_SERVER_URL,
-				CHAT_URL: process.env.CHAT_URL ?? LOCAL_CHAT_URL,
-				SLACK_BOT_URL: process.env.SLACK_BOT_URL ?? LOCAL_CHAT_URL,
+				CHAT_URL,
+				SLACK_BOT_URL,
+				SLACK_REDIRECT_URI,
 				DISCORD_BOT_URL: process.env.DISCORD_BOT_URL ?? LOCAL_CHAT_URL,
 				VITE_APP_ENV: viteAppEnv,
 				...(useLocalAuthUrls && {
--- a/scripts/devServices/index.ts
+++ b/scripts/devServices/index.ts
@@ -11,6 +11,7 @@ const localConfig = {
 	redisStackPort: 6379,
 	dragonflyPort: 6380,
 	databaseUrl: "postgresql://postgres:postgres@localhost:5432/autumn",
+	chatStateDatabaseUrl: "postgresql://postgres:postgres@localhost:5432/chat",
 	cacheUrl: "redis://localhost:6379",
 	dragonflyUrl: "redis://localhost:6380",
 };
@@ -166,6 +167,32 @@ const doctor = async () => {
 	if (results.some((result) => !result)) process.exit(1);
 };

+const psql = ({ args, quiet = false }: { args: string[]; quiet?: boolean }) =>
+	dockerCompose({
+		args: ["exec", "-T", "postgres", "psql", "-U", "postgres", ...args],
+		quiet,
+	});
+
+const ensureChatDatabase = () => {
+	const result = psql({
+		args: [
+			"-d",
+			"postgres",
+			"-tAc",
+			"SELECT 1 FROM pg_database WHERE datname = 'chat'",
+		],
+		quiet: true,
+	});
+	const exists = new TextDecoder().decode(result.stdout).trim() === "1";
+	if (exists) {
+		log("chat database already exists");
+		return;
+	}
+
+	log("creating chat database");
+	psql({ args: ["-d", "postgres", "-c", "CREATE DATABASE chat"] });
+};
+
 const up = async () => {
 	log("starting Docker services");
 	dockerCompose({ args: ["up", "-d", "--remove-orphans"] });
@@ -176,6 +203,7 @@ const up = async () => {
 		waitForTcp({ port: localConfig.dragonflyPort, label: "Dragonfly" }),
 	]);

+	ensureChatDatabase();
 	await doctor();
 };

@@ -219,6 +247,7 @@ Commands:

 Local service values:
  DATABASE_URL=${localConfig.databaseUrl}
+  CHAT_STATE_DATABASE_URL=${localConfig.chatStateDatabaseUrl}
  CACHE_URL=${localConfig.cacheUrl}
  CACHE_URL_US_EAST=${localConfig.cacheUrl}
  CACHE_V2_DRAGONFLY_URL=${localConfig.dragonflyUrl}
--- a/server/src/db/pgPoolMonitor.ts
+++ b/server/src/db/pgPoolMonitor.ts
@@ -49,23 +49,23 @@ export const attachPoolErrorHandlers = ({
 };

 const emitSnapshot = (): void => {
-	const role = getRole();
-	for (const { pool, name, max } of registry.values()) {
-		const totalCount = pool.totalCount;
-		const idleCount = pool.idleCount;
-		const waitingCount = pool.waitingCount;
-		logger.debug("pg_pool_stats", {
-			type: "pg_pool_stats",
-			pool: name,
-			pid: process.pid,
-			role,
-			totalCount,
-			idleCount,
-			waitingCount,
-			max,
-			utilization: max > 0 ? totalCount / max : 0,
-		});
-	}
+	// const role = getRole();
+	// for (const { pool, name, max } of registry.values()) {
+	// 	const totalCount = pool.totalCount;
+	// 	const idleCount = pool.idleCount;
+	// 	const waitingCount = pool.waitingCount;
+	// 	logger.debug("pg_pool_stats", {
+	// 		type: "pg_pool_stats",
+	// 		pool: name,
+	// 		pid: process.pid,
+	// 		role,
+	// 		totalCount,
+	// 		idleCount,
+	// 		waitingCount,
+	// 		max,
+	// 		utilization: max > 0 ? totalCount / max : 0,
+	// 	});
+	// }
 };

 export const startPgPoolMonitor = (intervalMs = 30_000): void => {
--- a/server/src/honoMiddlewares/authMiddlewares/handleOAuthMiddleware.ts
+++ b/server/src/honoMiddlewares/authMiddlewares/handleOAuthMiddleware.ts
@@ -0,0 +1,79 @@
+import {
+	AppEnv,
+	AuthType,
+	ErrCode,
+	RecaseError,
+	sortFeatures,
+} from "@autumn/shared";
+import type { Context, Next } from "hono";
+import type { HonoEnv } from "@/honoUtils/HonoEnv.js";
+import { getOAuthAccessTokenRecord } from "@/internal/auth/oauth/oauthAccessTokenApiKey.js";
+import { oauthConsentRepo } from "@/internal/auth/repos/index.js";
+import { OrgService } from "@/internal/orgs/OrgService.js";
+
+const getOAuthEnvironment = ({ c }: { c: Context<HonoEnv> }) => {
+	const env = c.req.header("x-autumn-environment") ?? AppEnv.Sandbox;
+	if (env === AppEnv.Live || env === AppEnv.Sandbox) return env;
+
+	throw new RecaseError({
+		message: "Invalid x-autumn-environment",
+		code: ErrCode.InvalidRequest,
+		statusCode: 400,
+	});
+};
+
+export const handleOAuthMiddleware = async ({
+	c,
+	token,
+	next,
+}: {
+	c: Context<HonoEnv>;
+	token: string;
+	next: Next;
+}) => {
+	const ctx = c.get("ctx");
+	const env = getOAuthEnvironment({ c });
+	const tokenRecord = await getOAuthAccessTokenRecord({
+		db: ctx.db,
+		accessToken: token,
+		resource: c.req.header("x-autumn-oauth-resource") ?? null,
+		requestedScopes: null,
+	});
+	const consent = await oauthConsentRepo.getForClientUserOrg({
+		db: ctx.db,
+		clientId: tokenRecord.clientId,
+		userId: tokenRecord.userId,
+		referenceId: tokenRecord.referenceId,
+		env,
+	});
+
+	if (!consent) {
+		throw new RecaseError({
+			message: "OAuth consent not found for environment",
+			code: ErrCode.InvalidRequest,
+			statusCode: 401,
+		});
+	}
+
+	const data = await OrgService.getWithFeatures({
+		db: ctx.db,
+		orgId: tokenRecord.referenceId,
+		env,
+	});
+	if (!data) {
+		throw new RecaseError({
+			message: "Org not found",
+			code: ErrCode.OrgNotFound,
+			statusCode: 404,
+		});
+	}
+
+	ctx.org = data.org;
+	ctx.features = sortFeatures({ features: data.features }) ?? [];
+	ctx.env = env;
+	ctx.userId = tokenRecord.userId;
+	ctx.authType = AuthType.SecretKey;
+	ctx.scopes = tokenRecord.scopes;
+
+	await next();
+};
--- a/server/src/honoMiddlewares/secretKeyMiddleware.ts
+++ b/server/src/honoMiddlewares/secretKeyMiddleware.ts
@@ -1,8 +1,14 @@
-import { getBearerToken } from "@autumn/auth";
-import { AuthType, ErrCode, type Feature, RecaseError } from "@autumn/shared";
+import {
+	getBearerToken,
+	isOAuthToken,
+	isPublishableKeyPrefix,
+	isSecretKeyPrefix,
+} from "@autumn/auth";
+import { AuthType, ErrCode, RecaseError, sortFeatures } from "@autumn/shared";
 import type { Context, Next } from "hono";
 import type { HonoEnv } from "@/honoUtils/HonoEnv.js";
 import { verifyKey } from "@/internal/dev/api-keys/apiKeyUtils.js";
+import { handleOAuthMiddleware } from "./authMiddlewares/handleOAuthMiddleware.js";
 import { betterAuthMiddleware } from "./betterAuthMiddleware.js";
 import { publicKeyMiddleware } from "./publicKeyMiddleware.js";

@@ -30,11 +36,11 @@ export const secretKeyMiddleware = async (c: Context<HonoEnv>, next: Next) => {
 		return betterAuthMiddleware(c, next);
 	}

-	const apiKey = getBearerToken({ headers: c.req.raw.headers });
+	const bearerToken = getBearerToken({ headers: c.req.raw.headers });

 	// Step 1 & 2: Check if Authorization header exists
 	// If from dashboard and no Bearer token, use Better Auth session instead
-	if (!apiKey) {
+	if (!bearerToken) {
 		throw new RecaseError({
 			message: "Secret key not found in Authorization header",
 			code: ErrCode.NoSecretKey,
@@ -42,27 +48,31 @@ export const secretKeyMiddleware = async (c: Context<HonoEnv>, next: Next) => {
 		});
 	}

-	if (!apiKey.startsWith("am_")) {
-		throw new RecaseError({
-			message: `Invalid secret key: ${maskApiKey(apiKey)}`,
-			code: ErrCode.InvalidSecretKey,
-			statusCode: 401,
-		});
+	if (isOAuthToken({ token: bearerToken })) {
+		return handleOAuthMiddleware({ c, token: bearerToken, next });
 	}

 	// Step 3: Handle publishable key verification
-	if (apiKey.startsWith("am_pk")) {
-		return publicKeyMiddleware(c, apiKey, next);
+	if (isPublishableKeyPrefix({ token: bearerToken })) {
+		return publicKeyMiddleware(c, bearerToken, next);
+	}
+
+	if (!isSecretKeyPrefix({ token: bearerToken })) {
+		throw new RecaseError({
+			message: "Invalid authorization token prefix",
+			code: ErrCode.InvalidRequest,
+			statusCode: 401,
+		});
 	}

 	// Step 4: Verify the API key
 	const { valid, data } = await verifyKey({
 		db: ctx.db,
-		key: apiKey,
+		key: bearerToken,
 	});

 	if (!valid || !data) {
-		const maskedKey = maskApiKey(apiKey);
+		const maskedKey = maskApiKey(bearerToken);
 		throw new RecaseError({
 			message: `Invalid secret key: ${maskedKey}`,
 			code: ErrCode.InvalidSecretKey,
@@ -74,13 +84,7 @@ export const secretKeyMiddleware = async (c: Context<HonoEnv>, next: Next) => {
 	const { org, features, env, userId } = data;
 	const scopes = (data as { scopes?: string[] | null }).scopes ?? [];

-	if (features) {
-		features.sort((a: Feature, b: Feature) => {
-			if (a.archived && !b.archived) return 1;
-			if (!a.archived && b.archived) return -1;
-			return 0;
-		});
-	}
+	sortFeatures({ features });

 	ctx.org = org;
 	ctx.features = features;
--- a/server/src/internal/admin/adminRouter.ts
+++ b/server/src/internal/admin/adminRouter.ts
@@ -45,6 +45,7 @@ import { handleUpsertAdminRateLimitRedisAllowlistConfig } from "./handleUpsertAd
 import { handleUpsertAdminRedisV2CacheConfig } from "./handleUpsertAdminRedisV2CacheConfig";
 import { handleUpsertAdminRequestBlockConfig } from "./handleUpsertAdminRequestBlockConfig";
 import { handleUpsertAdminStripeSyncConfig } from "./handleUpsertAdminStripeSyncConfig";
+import { handleUpsertSlackMcpOAuthClient } from "./handleUpsertSlackMcpOAuthClient";
 import { handleDeleteRollout } from "./rollouts/handleDeleteRollout";
 import { handleDeleteRolloutOrg } from "./rollouts/handleDeleteRolloutOrg";
 import { handleGetRollouts } from "./rollouts/handleGetRollouts";
@@ -160,6 +161,10 @@ honoAdminRouter.delete("/cache-v2-ramp", ...handleDeleteAdminCacheV2Ramp);
 honoAdminRouter.get("/org-member", ...handleGetOrgMember);
 honoAdminRouter.get("/master-stripe-account", ...handleGetMasterStripeAccount);
 honoAdminRouter.get("/oauth-clients", ...handleListOAuthClients);
+honoAdminRouter.post(
+	"/oauth-clients/slack-mcp",
+	...handleUpsertSlackMcpOAuthClient,
+);
 honoAdminRouter.post("/invoice-line-items", ...handleGetInvoiceLineItems);
 honoAdminRouter.post(
 	"/customer-products/:customer_product_id/send-updated-webhook",
--- a/server/src/internal/admin/handleUpsertSlackMcpOAuthClient.ts
+++ b/server/src/internal/admin/handleUpsertSlackMcpOAuthClient.ts
@@ -0,0 +1,37 @@
+import { ErrCode, RecaseError, Scopes } from "@autumn/shared";
+import { registerMcpOAuthClient } from "@/internal/auth/actions/index.js";
+import { createRoute } from "../../honoMiddlewares/routeHandler";
+
+const getClientUrl = () =>
+	(process.env.CLIENT_URL || "http://localhost:3000").replace(/\/+$/, "");
+
+const getSlackMcpRedirectUris = () => {
+	const clientUrl = getClientUrl();
+	return [
+		`${clientUrl}/admin/oauth/slack-mcp/callback`,
+		`${clientUrl}/sandbox/admin/oauth/slack-mcp/callback`,
+	];
+};
+
+export const handleUpsertSlackMcpOAuthClient = createRoute({
+	scopes: [Scopes.Superuser],
+	handler: async (c) => {
+		const { db } = c.get("ctx");
+		const result = await registerMcpOAuthClient({
+			db,
+			clientName: "Slack MCP",
+			redirectUris: getSlackMcpRedirectUris(),
+			scope: undefined,
+		});
+
+		if ("error" in result) {
+			throw new RecaseError({
+				message: result.error,
+				code: ErrCode.InvalidRequest,
+				statusCode: result.status,
+			});
+		}
+
+		return c.json(result.body, result.status);
+	},
+});
--- a/server/src/internal/auth/actions/registerMcpOAuthClient.ts
+++ b/server/src/internal/auth/actions/registerMcpOAuthClient.ts
@@ -4,6 +4,7 @@ import { generateId } from "@/utils/genUtils.js";
 import { type OAuthClientRecord, oauthClientRepo } from "../repos/index.js";

 const MCP_CLIENT_KIND = "mcp_client";
+export const SLACK_MCP_OAUTH_CLIENT_ID = "autumn_mcp_slack";
 const REGISTER_CACHE_TTL_MS = 5 * 60 * 1000;
 const DANGEROUS_REDIRECT_SCHEMES = new Set([
 	"javascript:",
@@ -107,7 +108,11 @@ const classifyMcpClient = ({
 		return { type: "codex", name: "Codex", clientId: "autumn_mcp_codex" };
 	}
 	if (haystack.includes("slack")) {
-		return { type: "slack", name: "Slack", clientId: "autumn_mcp_slack" };
+		return {
+			type: "slack",
+			name: "Slack",
+			clientId: SLACK_MCP_OAUTH_CLIENT_ID,
+		};
 	}

 	return null;
--- a/server/src/internal/auth/oauth/handleOAuthTokenWithApiKey.ts
+++ b/server/src/internal/auth/oauth/handleOAuthTokenWithApiKey.ts
@@ -1,7 +1,9 @@
+import { prefixOAuthToken } from "@autumn/auth";
 import { RecaseError } from "@autumn/shared";
 import type { Context } from "hono";
 import { db } from "@/db/initDrizzle.js";
 import { auth } from "@/utils/auth.js";
+import { SLACK_MCP_OAUTH_CLIENT_ID } from "../actions/registerMcpOAuthClient.js";
 import {
 	getExternalOAuthApiKeyForToken,
 	getOAuthAccessTokenRecord,
@@ -48,6 +50,30 @@ const rewriteTokenBody = ({
 	};
 };

+const rewriteOAuthAccessTokenBody = ({
+	accessToken,
+	body,
+}: {
+	accessToken: string;
+	body: Record<string, unknown>;
+}) => {
+	const response = body.response;
+	if (isRecord(response)) {
+		return {
+			...body,
+			response: {
+				...response,
+				access_token: accessToken,
+			},
+		};
+	}
+
+	return {
+		...body,
+		access_token: accessToken,
+	};
+};
+
 const tokenResponseHeaders = (response?: Response) => {
 	const headers = new Headers(response?.headers);
 	headers.set("Content-Type", "application/json");
@@ -116,6 +142,16 @@ export const handleOAuthTokenWithApiKey = async (c: Context) => {
 			resource,
 			requestedScopes,
 		});
+		if (tokenRecord.clientId === SLACK_MCP_OAUTH_CLIENT_ID) {
+			return jsonTokenResponse({
+				body: rewriteOAuthAccessTokenBody({
+					accessToken: prefixOAuthToken({ token: accessToken }),
+					body,
+				}),
+				response,
+				status: response.status,
+			});
+		}
 		apiKeyResult = await getExternalOAuthApiKeyForToken({
 			db,
 			tokenRecord,
--- a/server/src/internal/auth/oauth/oauthAccessTokenApiKey.ts
+++ b/server/src/internal/auth/oauth/oauthAccessTokenApiKey.ts
@@ -1,3 +1,4 @@
+import { stripOAuthTokenPrefix } from "@autumn/auth";
 import {
 	AppEnv,
 	checkScopes,
@@ -59,12 +60,13 @@ export const getOAuthAccessTokenRecord = async ({
 	resource: string | null;
 	requestedScopes: ScopeString[] | null;
 }) => {
-	const hashedToken = await hashOAuthToken(accessToken);
-	const tokenValues = [...new Set([hashedToken, accessToken])];
+	const rawAccessToken = stripOAuthTokenPrefix({ token: accessToken });
+	const hashedToken = await hashOAuthToken(rawAccessToken);
+	const tokenValues = [...new Set([hashedToken, rawAccessToken])];
 	const tokenRecord =
 		(await oauthAccessTokenRepo.getValidByTokenValues({ db, tokenValues })) ??
 		(await verifyResourceAccessToken({
-			accessToken,
+			accessToken: rawAccessToken,
 			resource,
 			requestedScopes,
 		}));
--- a/server/src/internal/auth/repos/oauthConsentRepo.ts
+++ b/server/src/internal/auth/repos/oauthConsentRepo.ts
@@ -80,11 +80,13 @@ export const getOAuthConsentForClientUserOrg = async ({
 	clientId,
 	userId,
 	referenceId,
+	env,
 }: {
 	db: DrizzleCli;
 	clientId: string;
 	userId: string;
 	referenceId: string;
+	env?: AppEnv;
 }) => {
 	const [consent] = await db
 		.select({
@@ -99,6 +101,7 @@ export const getOAuthConsentForClientUserOrg = async ({
 				eq(oauthConsent.clientId, clientId),
 				eq(oauthConsent.userId, userId),
 				eq(oauthConsent.referenceId, referenceId),
+				...(env ? [eq(oauthConsent.env, env)] : []),
 			),
 		)
 		.limit(1);
--- a/shared/db/schema.ts
+++ b/shared/db/schema.ts
@@ -5,6 +5,7 @@ import { actions } from "../models/analyticsModels/actionTable.js";
 import {
 	chatApprovals,
 	chatInstallations,
+	chatOAuthCredentials,
 } from "../models/chatModels/chatTable.js";
 import { chatResults } from "../models/chatResultModels/chatResultTable.js";
 import { checkoutsRelations } from "../models/checkouts/checkoutRelations.js";
@@ -107,6 +108,7 @@ export {
 	autoTopupLimitStates as autoTopupLimits,
 	chatApprovals,
 	chatInstallations,
+	chatOAuthCredentials,
 	chatResults,
 	checkouts,
 	checkoutsRelations,
--- a/shared/drizzle/0001_concerned_ravenous.sql
+++ b/shared/drizzle/0001_concerned_ravenous.sql
@@ -16,10 +16,10 @@ CREATE TABLE "passkey" (
 ALTER TABLE "passkey" ENABLE ROW LEVEL SECURITY;--> statement-breakpoint
 ALTER TABLE "migration_runs" ADD COLUMN "target_limit" numeric;--> statement-breakpoint
 ALTER TABLE "passkey" ADD CONSTRAINT "passkey_user_id_user_id_fk" FOREIGN KEY ("user_id") REFERENCES "public"."user"("id") ON DELETE cascade ON UPDATE no action;--> statement-breakpoint
-CREATE INDEX "passkey_userId_idx" ON "passkey" USING btree ("user_id");--> statement-breakpoint
-CREATE INDEX "passkey_credentialId_idx" ON "passkey" USING btree ("credential_id");--> statement-breakpoint
-CREATE INDEX "idx_customer_products_revenuecat_processor" ON "customer_products" USING btree ("internal_customer_id") WHERE ("customer_products"."processor" ->> 'type') = 'revenuecat';--> statement-breakpoint
-CREATE INDEX "idx_customers_cursor" ON "customers" USING btree ("org_id","env","created_at" DESC,"id" DESC);--> statement-breakpoint
-CREATE INDEX "idx_entities_cursor" ON "entities" USING btree ("org_id","env","created_at" DESC,"id" DESC);--> statement-breakpoint
-CREATE INDEX "idx_entitlements_internal_reward_id_c_partial" ON "entitlements" USING btree ("internal_reward_id" COLLATE "C") WHERE "entitlements"."internal_reward_id" IS NOT NULL;--> statement-breakpoint
-CREATE UNIQUE INDEX "vercel_resources_installation_name_unique_idx" ON "vercel_resources" USING btree ("org_id","env","installation_id","name") WHERE status <> 'uninstalled';
+CREATE INDEX CONCURRENTLY "passkey_userId_idx" ON "passkey" USING btree ("user_id");--> statement-breakpoint
+CREATE INDEX CONCURRENTLY "passkey_credentialId_idx" ON "passkey" USING btree ("credential_id");--> statement-breakpoint
+CREATE INDEX CONCURRENTLY "idx_customer_products_revenuecat_processor" ON "customer_products" USING btree ("internal_customer_id") WHERE ("customer_products"."processor" ->> 'type') = 'revenuecat';--> statement-breakpoint
+CREATE INDEX CONCURRENTLY "idx_customers_cursor" ON "customers" USING btree ("org_id","env","created_at" DESC,"id" DESC);--> statement-breakpoint
+CREATE INDEX CONCURRENTLY "idx_entities_cursor" ON "entities" USING btree ("org_id","env","created_at" DESC,"id" DESC);--> statement-breakpoint
+CREATE INDEX CONCURRENTLY "idx_entitlements_internal_reward_id_c_partial" ON "entitlements" USING btree ("internal_reward_id" COLLATE "C") WHERE "entitlements"."internal_reward_id" IS NOT NULL;--> statement-breakpoint
+CREATE UNIQUE INDEX CONCURRENTLY "vercel_resources_installation_name_unique_idx" ON "vercel_resources" USING btree ("org_id","env","installation_id","name") WHERE status <> 'uninstalled';
--- a/shared/drizzle/0007_cute_ikaris.sql
+++ b/shared/drizzle/0007_cute_ikaris.sql
@@ -1 +1 @@
-CREATE INDEX "idx_invoice_line_items_customer_product_ids" ON "invoice_line_items" USING gin ("customer_product_ids");
+CREATE INDEX CONCURRENTLY "idx_invoice_line_items_customer_product_ids" ON "invoice_line_items" USING gin ("customer_product_ids");
--- a/shared/drizzle/0008_premium_pet_avengers.sql
+++ b/shared/drizzle/0008_premium_pet_avengers.sql
@@ -0,0 +1,18 @@
+CREATE TABLE "chat_oauth_credentials" (
+	"id" text PRIMARY KEY NOT NULL,
+	"chat_installation_id" text NOT NULL,
+	"org_id" text NOT NULL,
+	"env" text NOT NULL,
+	"oauth_client_id" text NOT NULL,
+	"oauth_consent_id" text,
+	"access_token" text NOT NULL,
+	"refresh_token" text NOT NULL,
+	"access_token_expires_at" numeric NOT NULL,
+	"scopes" jsonb NOT NULL,
+	"created_at" numeric DEFAULT ROUND(date_part('epoch', NOW()) * 1000)::BIGINT NOT NULL,
+	"updated_at" numeric DEFAULT ROUND(date_part('epoch', NOW()) * 1000)::BIGINT NOT NULL,
+	CONSTRAINT "chat_oauth_credentials_installation_env_key" UNIQUE("chat_installation_id","env")
+);
+--> statement-breakpoint
+ALTER TABLE "chat_oauth_credentials" ADD CONSTRAINT "chat_oauth_credentials_installation_id_fkey" FOREIGN KEY ("chat_installation_id") REFERENCES "public"."chat_installations"("id") ON DELETE cascade ON UPDATE no action;--> statement-breakpoint
+ALTER TABLE "chat_oauth_credentials" ADD CONSTRAINT "chat_oauth_credentials_org_id_fkey" FOREIGN KEY ("org_id") REFERENCES "public"."organizations"("id") ON DELETE cascade ON UPDATE no action;
--- a/shared/drizzle/meta/0008_snapshot.json
+++ b/shared/drizzle/meta/0008_snapshot.json
@@ -1,5 +1,5 @@
 {
-  "id": "b9eaa778-a288-48ca-8e0f-42b17e0dc873",
+  "id": "40c5361a-8cff-473f-93c1-4dfbc06b00d7",
  "prevId": "9e1bb4b2-1869-4ca9-ba67-8fbcea263c37",
  "version": "7",
  "dialect": "postgresql",
@@ -840,6 +840,129 @@
      "checkConstraints": {},
      "isRLSEnabled": false
    },
+    "public.chat_oauth_credentials": {
+      "name": "chat_oauth_credentials",
+      "schema": "",
+      "columns": {
+        "id": {
+          "name": "id",
+          "type": "text",
+          "primaryKey": true,
+          "notNull": true
+        },
+        "chat_installation_id": {
+          "name": "chat_installation_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "org_id": {
+          "name": "org_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "env": {
+          "name": "env",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "oauth_client_id": {
+          "name": "oauth_client_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "oauth_consent_id": {
+          "name": "oauth_consent_id",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": false
+        },
+        "access_token": {
+          "name": "access_token",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "refresh_token": {
+          "name": "refresh_token",
+          "type": "text",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "access_token_expires_at": {
+          "name": "access_token_expires_at",
+          "type": "numeric",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "scopes": {
+          "name": "scopes",
+          "type": "jsonb",
+          "primaryKey": false,
+          "notNull": true
+        },
+        "created_at": {
+          "name": "created_at",
+          "type": "numeric",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "ROUND(date_part('epoch', NOW()) * 1000)::BIGINT"
+        },
+        "updated_at": {
+          "name": "updated_at",
+          "type": "numeric",
+          "primaryKey": false,
+          "notNull": true,
+          "default": "ROUND(date_part('epoch', NOW()) * 1000)::BIGINT"
+        }
+      },
+      "indexes": {},
+      "foreignKeys": {
+        "chat_oauth_credentials_installation_id_fkey": {
+          "name": "chat_oauth_credentials_installation_id_fkey",
+          "tableFrom": "chat_oauth_credentials",
+          "tableTo": "chat_installations",
+          "columnsFrom": [
+            "chat_installation_id"
+          ],
+          "columnsTo": [
+            "id"
+          ],
+          "onDelete": "cascade",
+          "onUpdate": "no action"
+        },
+        "chat_oauth_credentials_org_id_fkey": {
+          "name": "chat_oauth_credentials_org_id_fkey",
+          "tableFrom": "chat_oauth_credentials",
+          "tableTo": "organizations",
+          "columnsFrom": [
+            "org_id"
+          ],
+          "columnsTo": [
+            "id"
+          ],
+          "onDelete": "cascade",
+          "onUpdate": "no action"
+        }
+      },
+      "compositePrimaryKeys": {},
+      "uniqueConstraints": {
+        "chat_oauth_credentials_installation_env_key": {
+          "name": "chat_oauth_credentials_installation_env_key",
+          "nullsNotDistinct": false,
+          "columns": [
+            "chat_installation_id",
+            "env"
+          ]
+        }
+      },
+      "policies": {},
+      "checkConstraints": {},
+      "isRLSEnabled": false
+    },
    "public.chat_results": {
      "name": "chat_results",
      "schema": "",
@@ -4524,13 +4647,6 @@
          "notNull": true,
          "default": false
        },
-        "archived": {
-          "name": "archived",
-          "type": "boolean",
-          "primaryKey": false,
-          "notNull": true,
-          "default": false
-        },
        "created_at": {
          "name": "created_at",
          "type": "numeric",
@@ -7397,4 +7513,4 @@
    "schemas": {},
    "tables": {}
  }
-}
+}
--- a/shared/drizzle/meta/0009_snapshot.json
+++ b/shared/drizzle/meta/0009_snapshot.json
--- a/shared/drizzle/meta/_journal.json
+++ b/shared/drizzle/meta/_journal.json
@@ -61,6 +61,13 @@
    {
      "idx": 8,
      "version": "7",
+      "when": 1780679328640,
+      "tag": "0008_premium_pet_avengers",
+      "breakpoints": true
+    },
+    {
+      "idx": 9,
+      "version": "7",
      "when": 1780665982843,
      "tag": "0008_slippery_william_stryker",
      "breakpoints": true
--- a/shared/models/chatModels/chatTable.ts
+++ b/shared/models/chatModels/chatTable.ts
@@ -81,5 +81,42 @@ export const chatApprovals = pgTable(
 	],
 );

+export const chatOAuthCredentials = pgTable(
+	"chat_oauth_credentials",
+	{
+		id: text().primaryKey().notNull(),
+		chat_installation_id: text("chat_installation_id").notNull(),
+		org_id: text("org_id").notNull(),
+		env: text("env").$type<AppEnv>().notNull(),
+		oauth_client_id: text("oauth_client_id").notNull(),
+		oauth_consent_id: text("oauth_consent_id"),
+		access_token: text("access_token").notNull(),
+		refresh_token: text("refresh_token").notNull(),
+		access_token_expires_at: numeric("access_token_expires_at", {
+			mode: "number",
+		}).notNull(),
+		scopes: jsonb().$type<string[]>().notNull(),
+		created_at: numeric({ mode: "number" }).notNull().default(sqlNow),
+		updated_at: numeric({ mode: "number" }).notNull().default(sqlNow),
+	},
+	(table) => [
+		foreignKey({
+			columns: [table.chat_installation_id],
+			foreignColumns: [chatInstallations.id],
+			name: "chat_oauth_credentials_installation_id_fkey",
+		}).onDelete("cascade"),
+		foreignKey({
+			columns: [table.org_id],
+			foreignColumns: [organizations.id],
+			name: "chat_oauth_credentials_org_id_fkey",
+		}).onDelete("cascade"),
+		unique("chat_oauth_credentials_installation_env_key").on(
+			table.chat_installation_id,
+			table.env,
+		),
+	],
+);
+
 export type ChatInstallation = typeof chatInstallations.$inferSelect;
 export type ChatApproval = typeof chatApprovals.$inferSelect;
+export type ChatOAuthCredential = typeof chatOAuthCredentials.$inferSelect;
--- a/shared/utils/featureUtils/index.ts
+++ b/shared/utils/featureUtils/index.ts
@@ -7,6 +7,7 @@ export * from "./apiFeatureToDbFeature";
 export * from "./convertFeatureUtils";
 export * from "./creditSystemUtils";
 export * from "./findFeatureUtils";
+export * from "./sortFeatures";

 export const featureUtils = {
 	isConsumable: isConsumableFeature,
--- a/shared/utils/featureUtils/sortFeatures.ts
+++ b/shared/utils/featureUtils/sortFeatures.ts
@@ -0,0 +1,13 @@
+import type { Feature } from "../../models/featureModels/featureModels.js";
+
+export const sortFeatures = ({ features }: { features?: Feature[] }) => {
+	if (!features) return features;
+
+	features.sort((a, b) => {
+		if (a.archived && !b.archived) return 1;
+		if (!a.archived && b.archived) return -1;
+		return 0;
+	});
+
+	return features;
+};
--- a/vite/src/views/admin/oauth/OAuthClientsView.tsx
+++ b/vite/src/views/admin/oauth/OAuthClientsView.tsx
@@ -1,9 +1,10 @@
 import { AppEnv } from "@autumn/shared";
-import { useQuery } from "@tanstack/react-query";
+import { useMutation, useQuery } from "@tanstack/react-query";
 import {
 	ArrowLeft,
 	Globe,
 	Key,
+	MessageSquare,
 	Pencil,
 	Plus,
 	RefreshCw,
@@ -62,6 +63,25 @@ export const OAuthClientsView = () => {
 	});

 	const clients: OAuthClient[] = data?.clients || [];
+	const upsertSlackMcpMutation = useMutation({
+		mutationFn: async () => {
+			const { data } = await axiosInstance.post(
+				"/admin/oauth-clients/slack-mcp",
+			);
+			return data;
+		},
+		onSuccess: (client) => {
+			toast.success(
+				`Slack MCP OAuth client ready: ${client.client_id ?? "autumn_mcp_slack"}`,
+			);
+			refetch();
+		},
+		onError: (error) => {
+			toast.error(
+				getBackendErr(error, "Failed to create Slack MCP OAuth client"),
+			);
+		},
+	});

 	const handleDeleteClient = async (client_id: string) => {
 		if (!confirm("Are you sure you want to delete this OAuth client?")) {
@@ -157,6 +177,15 @@ export const OAuthClientsView = () => {
 					>
 						Refresh
 					</IconButton>
+					<IconButton
+						variant="secondary"
+						size="sm"
+						icon={<MessageSquare className="w-4 h-4" />}
+						onClick={() => upsertSlackMcpMutation.mutate()}
+						disabled={upsertSlackMcpMutation.isPending}
+					>
+						Add Slack MCP
+					</IconButton>
 					<IconButton
 						variant="primary"
 						size="sm"