diff --git a/server/api/account/discord-unlink.post.ts b/server/api/account/discord-unlink.post.ts
index d6783a6..03e40df 100644
--- a/server/api/account/discord-unlink.post.ts
+++ b/server/api/account/discord-unlink.post.ts
@@ -1,3 +1,5 @@
+import { removeDiscordMemberSupporterRole, removeDiscordMemberTesterRole } from "~~/server/utils/discord";
+
 export default defineEventHandler(async (event): Promise<void> => {
 	const auth = enforceLoggedIn(event);
 	const discord = useDiscord(event);
@@ -7,9 +9,26 @@ export default defineEventHandler(async (event): Promise<void> => {
 	})
 
 	const grpc = useApiGrpcWithToken(event, auth.token);
+	const oldUserData = await grpc.getUserData({});
+	const oldDiscordId = oldUserData.connections?.discord?.id;
 	await grpc.setDiscordConnectionData({
 		id: '',
 	});
 
-	// TODO set roles based on stripe info
+	const priceId = oldUserData.connections?.stripe?.priceId;
+	const stripe = useStripe(event);
+	if (stripe) {
+		if (priceId && oldDiscordId) {
+			const price = await stripe.prices.retrieve(priceId);
+			const product = await stripe.products.retrieve(price.product as string);
+			const discordRoleId = product.metadata.discord_role_id;
+
+			if (discordRoleId) {
+				await removeDiscordMemberSupporterRole(discord, oldDiscordId, discordRoleId);
+			}
+			if (product.metadata.beta === 'true') {
+				await removeDiscordMemberTesterRole(discord, oldDiscordId);
+			}
+		}
+	}
 });
diff --git a/server/middleware/auth.ts b/server/middleware/auth.ts
index a45e5a5..e5ca46c 100644
--- a/server/middleware/auth.ts
+++ b/server/middleware/auth.ts
@@ -17,6 +17,8 @@ export default defineEventHandler(async (event) => {
 				pid: userData.pid,
 				username: userData.username,
 				token: token,
+				accessLevel: userData.accessLevel,
+				email: userData.emailAddress,
 			})
 		} catch (err) {
 			console.error('Failed to request user data: ', err);
diff --git a/server/routes/account/connect/discord.get.ts b/server/routes/account/connect/discord.get.ts
index 5003bfe..af36ffc 100644
--- a/server/routes/account/connect/discord.get.ts
+++ b/server/routes/account/connect/discord.get.ts
@@ -1,3 +1,5 @@
+import { assignDiscordMemberSupporterRole, assignDiscordMemberTesterRole } from "~~/server/utils/discord";
+
 type DiscordTokenResponse = {
 	"access_token": string,
 	"token_type": string,
@@ -15,6 +17,10 @@ type DiscordUserResponse = {
 // Discord oauth callback
 export default defineEventHandler(async (event) => {
 	const discord = useDiscord(event);
+	if (!discord) {
+		return sendRedirect(event, '/');
+	}
+
 	const discordFetch = $fetch.create({
 		baseURL: discord.baseUrl,
 	});
@@ -42,12 +48,29 @@ export default defineEventHandler(async (event) => {
 		return sendRedirect(event, '/'); // No identify scope
 	}
 
+	const discordId = authInfo.user.id;
 	const grpc = useApiGrpcWithToken(event, accessTokenCookie ?? '');
 	await grpc.setDiscordConnectionData({
-		id: authInfo.user.id
+		id: discordId
 	});
 
-	// TODO set roles based on stripe info
+	const userData = await grpc.getUserData({});
+	const priceId = userData.connections?.stripe?.priceId;
+	const stripe = useStripe(event);
+	if (stripe && priceId) {
+		if (priceId) {
+			const price = await stripe.prices.retrieve(priceId);
+			const product = await stripe.products.retrieve(price.product as string);
+			const discordRoleId = product.metadata.discord_role_id;
+
+			if (discordRoleId) {
+				await assignDiscordMemberSupporterRole(discord, discordId, discordRoleId);
+			}
+			if (product.metadata.beta === 'true') {
+				await assignDiscordMemberTesterRole(discord, discordId);
+			}
+		}
+	}
 
 	return sendRedirect(event, '/account');
 });
diff --git a/server/utils/enforceAuth.ts b/server/utils/enforceAuth.ts
index 0337c1b..3e69dcd 100644
--- a/server/utils/enforceAuth.ts
+++ b/server/utils/enforceAuth.ts
@@ -4,6 +4,8 @@ export type AuthContext = {
 	pid: number;
 	username: string;
 	token: string;
+	email: string;
+	accessLevel: number;
 };
 
 export function setAuthContext(event: H3Event, context: AuthContext | null): void {
diff --git a/shared/api-types.ts b/shared/api-types.ts
index ac1b167..1a3544e 100644
--- a/shared/api-types.ts
+++ b/shared/api-types.ts
@@ -64,3 +64,8 @@ export const ForgotPasswordSchema = z.object({
 	emailOrPassword: z.string(),
 });
 export type ApiAuthForgotPasswordRequest = z.infer<typeof ForgotPasswordSchema>;
+
+export const CheckoutSchema = z.object({
+	priceId: z.string(),
+});
+export type ApiAccountCheckoutRequest = z.infer<typeof CheckoutSchema>;