diff --git a/server/api/oauth/callback/:issuer/index.ts b/server/api/oauth/callback/:issuer/index.ts
index 26421c01..f2dbd2fd 100644
--- a/server/api/oauth/callback/:issuer/index.ts
+++ b/server/api/oauth/callback/:issuer/index.ts
@@ -2,8 +2,9 @@ import { randomBytes } from "node:crypto";
 import { applyConfig, handleZodError } from "@api";
 import { oauthRedirectUri } from "@constants";
 import { zValidator } from "@hono/zod-validator";
-import { errorResponse, response } from "@response";
+import { errorResponse, jsonResponse, response } from "@response";
 import type { Hono } from "hono";
+import { SignJWT } from "jose";
 import {
     authorizationCodeGrantRequest,
     discoveryRequest,
@@ -19,10 +20,9 @@ import {
 import { z } from "zod";
 import { TokenType } from "~database/entities/Token";
 import { db } from "~drizzle/db";
-import { Tokens } from "~drizzle/schema";
+import { OpenIdAccounts, Tokens } from "~drizzle/schema";
 import { config } from "~packages/config-manager";
 import { User } from "~packages/database-interface/user";
-import { SignJWT } from "jose";
 
 export const meta = applyConfig({
     allowedMethods: ["GET"],
@@ -40,6 +40,11 @@ export const schemas = {
     query: z.object({
         clientId: z.string().optional(),
         flow: z.string(),
+        link: z
+            .string()
+            .transform((v) => ["true", "1", "on"].includes(v.toLowerCase()))
+            .optional(),
+        user_id: z.string().uuid().optional(),
     }),
     param: z.object({
         issuer: z.string(),
@@ -75,7 +80,7 @@ export default (app: Hono) =>
             // Remove state query parameter from URL
             currentUrl.searchParams.delete("state");
             const { issuer: issuerParam } = context.req.valid("param");
-            const { flow: flowId, clientId } = context.req.valid("query");
+            const { flow: flowId, user_id, link } = context.req.valid("query");
 
             const flow = await db.query.OpenIdLoginFlows.findFirst({
                 where: (flow, { eq }) => eq(flow.id, flowId),
@@ -193,6 +198,37 @@ export default (app: Hono) =>
                 ),
             );
 
+            if (link && user_id) {
+                // Check if userId is equal to application.clientId
+                if (!flow.application?.clientId.startsWith(user_id)) {
+                    return errorResponse("User ID does not match application");
+                }
+
+                // Check if account is already linked
+                const account = await db.query.OpenIdAccounts.findFirst({
+                    where: (account, { eq, and }) =>
+                        and(
+                            eq(account.serverId, sub),
+                            eq(account.issuerId, issuer.id),
+                        ),
+                });
+
+                if (account) {
+                    return errorResponse("Account already linked");
+                }
+
+                // Link the account
+                await db.insert(OpenIdAccounts).values({
+                    serverId: sub,
+                    issuerId: issuer.id,
+                    userId: user_id,
+                });
+
+                return response(null, 302, {
+                    Location: config.http.base_url,
+                });
+            }
+
             const userId = (
                 await db.query.OpenIdAccounts.findFirst({
                     where: (account, { eq, and }) =>
diff --git a/server/api/oauth/link/index.ts b/server/api/oauth/link/index.ts
new file mode 100644
index 00000000..d2d95a19
--- /dev/null
+++ b/server/api/oauth/link/index.ts
@@ -0,0 +1,111 @@
+import { randomBytes } from "node:crypto";
+import { applyConfig, auth, handleZodError } from "@api";
+import { oauthRedirectUri } from "@constants";
+import { zValidator } from "@hono/zod-validator";
+import { errorResponse, jsonResponse, redirect, response } from "@response";
+import type { Hono } from "hono";
+import {
+    calculatePKCECodeChallenge,
+    discoveryRequest,
+    generateRandomCodeVerifier,
+    processDiscoveryResponse,
+} from "oauth4webapi";
+import { z } from "zod";
+import { db } from "~drizzle/db";
+import { Applications, OpenIdLoginFlows } from "~drizzle/schema";
+import { config } from "~packages/config-manager";
+
+export const meta = applyConfig({
+    allowedMethods: ["GET"],
+    auth: {
+        required: true,
+    },
+    ratelimits: {
+        duration: 60,
+        max: 20,
+    },
+    route: "/oauth/link",
+});
+
+export const schemas = {
+    query: z.object({
+        issuer: z.string(),
+    }),
+};
+
+export default (app: Hono) =>
+    app.on(
+        meta.allowedMethods,
+        meta.route,
+        zValidator("query", schemas.query, handleZodError),
+        auth(meta.auth),
+        async (context) => {
+            const { issuer: issuerId } = context.req.valid("query");
+            const { user } = context.req.valid("header");
+
+            if (!user) {
+                return errorResponse("Unauthorized", 401);
+            }
+
+            const issuer = config.oidc.providers.find(
+                (provider) => provider.id === issuerId,
+            );
+
+            if (!issuer) {
+                return errorResponse(`Issuer ${issuerId} not found`, 404);
+            }
+
+            const issuerUrl = new URL(issuer.url);
+
+            const authServer = await discoveryRequest(issuerUrl, {
+                algorithm: "oidc",
+            }).then((res) => processDiscoveryResponse(issuerUrl, res));
+
+            const codeVerifier = generateRandomCodeVerifier();
+
+            const application = (
+                await db
+                    .insert(Applications)
+                    .values({
+                        clientId:
+                            user.id + randomBytes(32).toString("base64url"),
+                        name: "Lysand",
+                        redirectUri: `${oauthRedirectUri(issuerId)}`,
+                        scopes: "openid profile email",
+                        secret: "",
+                    })
+                    .returning()
+            )[0];
+
+            // Store into database
+            const newFlow = (
+                await db
+                    .insert(OpenIdLoginFlows)
+                    .values({
+                        codeVerifier,
+                        issuerId,
+                        applicationId: application.id,
+                    })
+                    .returning()
+            )[0];
+
+            const codeChallenge =
+                await calculatePKCECodeChallenge(codeVerifier);
+
+            return jsonResponse({
+                link: `${
+                    authServer.authorization_endpoint
+                }?${new URLSearchParams({
+                    client_id: issuer.client_id,
+                    redirect_uri: `${oauthRedirectUri(issuerId)}?flow=${
+                        newFlow.id
+                    }&link=true&user_id=${user.id}`,
+                    response_type: "code",
+                    scope: "openid profile email",
+                    // PKCE
+                    code_challenge_method: "S256",
+                    code_challenge: codeChallenge,
+                }).toString()}`,
+            });
+        },
+    );