diff --git a/components/server/src/auth/api-subdomain-redirect.spec.ts b/components/server/src/auth/api-subdomain-redirect.spec.ts
new file mode 100644
index 00000000000000..26817f0a11680c
--- /dev/null
+++ b/components/server/src/auth/api-subdomain-redirect.spec.ts
@@ -0,0 +1,82 @@
+/**
+ * Copyright (c) 2024 Gitpod GmbH. All rights reserved.
+ * Licensed under the GNU Affero General Public License (AGPL).
+ * See License.AGPL.txt in the project root for license information.
+ */
+
+import { expect } from "chai";
+
+describe("API Subdomain Redirect Logic", () => {
+    // Test the core logic without complex dependency injection
+    function isApiSubdomainOfConfiguredHost(hostname: string, configuredHost: string): boolean {
+        return hostname === `api.${configuredHost}`;
+    }
+
+    describe("isApiSubdomainOfConfiguredHost", () => {
+        it("should detect api subdomain of configured host", () => {
+            const configuredHost = "gitpod.io";
+            const testCases = [
+                { hostname: "api.gitpod.io", expected: true },
+                { hostname: "api.preview.gitpod-dev.com", expected: false }, // Different configured host
+                { hostname: "gitpod.io", expected: false }, // Main domain
+                { hostname: "workspace-123.gitpod.io", expected: false }, // Other subdomain
+                { hostname: "api.evil.com", expected: false }, // Different domain
+            ];
+
+            testCases.forEach(({ hostname, expected }) => {
+                const result = isApiSubdomainOfConfiguredHost(hostname, configuredHost);
+                expect(result).to.equal(expected, `Failed for hostname: ${hostname}`);
+            });
+        });
+
+        it("should handle GitHub OAuth edge case correctly", () => {
+            // This is the specific case mentioned in the login completion handler
+            const configuredHost = "gitpod.io";
+            const apiSubdomain = `api.${configuredHost}`;
+
+            const result = isApiSubdomainOfConfiguredHost(apiSubdomain, configuredHost);
+            expect(result).to.be.true;
+        });
+
+        it("should handle preview environment correctly", () => {
+            const configuredHost = "preview.gitpod-dev.com";
+            const apiSubdomain = `api.${configuredHost}`;
+
+            const result = isApiSubdomainOfConfiguredHost(apiSubdomain, configuredHost);
+            expect(result).to.be.true;
+        });
+    });
+
+    describe("OAuth callback flow scenarios", () => {
+        it("should identify redirect scenarios correctly", () => {
+            const scenarios = [
+                {
+                    name: "GitHub OAuth Callback on API Subdomain",
+                    hostname: "api.gitpod.io",
+                    configuredHost: "gitpod.io",
+                    shouldRedirect: true,
+                },
+                {
+                    name: "Regular Login on Main Domain",
+                    hostname: "gitpod.io",
+                    configuredHost: "gitpod.io",
+                    shouldRedirect: false,
+                },
+                {
+                    name: "Workspace Port (Should Not Redirect)",
+                    hostname: "3000-gitpod.io",
+                    configuredHost: "gitpod.io",
+                    shouldRedirect: false,
+                },
+            ];
+
+            scenarios.forEach((scenario) => {
+                const result = isApiSubdomainOfConfiguredHost(scenario.hostname, scenario.configuredHost);
+                expect(result).to.equal(
+                    scenario.shouldRedirect,
+                    `${scenario.name}: Expected ${scenario.shouldRedirect} for ${scenario.hostname}`,
+                );
+            });
+        });
+    });
+});
diff --git a/components/server/src/auth/auth-provider.ts b/components/server/src/auth/auth-provider.ts
index 76259d6dc4562d..5d2929012e18cc 100644
--- a/components/server/src/auth/auth-provider.ts
+++ b/components/server/src/auth/auth-provider.ts
@@ -97,6 +97,7 @@ export interface AuthFlow {
     readonly host: string;
     readonly returnTo: string;
     readonly overrideScopes?: boolean;
+    readonly nonce?: string;
 }
 export namespace AuthFlow {
     export function is(obj: any): obj is AuthFlow {
diff --git a/components/server/src/auth/authenticator.ts b/components/server/src/auth/authenticator.ts
index eafd49e81af9f7..2467a4f26fcffa 100644
--- a/components/server/src/auth/authenticator.ts
+++ b/components/server/src/auth/authenticator.ts
@@ -18,6 +18,9 @@ import { UserService } from "../user/user-service";
 import { AuthFlow, AuthProvider } from "./auth-provider";
 import { HostContextProvider } from "./host-context-provider";
 import { SignInJWT } from "./jwt";
+import { NonceService } from "./nonce-service";
+import { getFeatureFlagEnableNonceValidation, getFeatureFlagEnableStrictAuthorizeReturnTo } from "../util/featureflags";
+import { validateLoginReturnToUrl, validateAuthorizeReturnToUrl, safeFragmentRedirect } from "../express-util";
 
 @injectable()
 export class Authenticator {
@@ -30,6 +33,7 @@ export class Authenticator {
     @inject(TokenProvider) protected readonly tokenProvider: TokenProvider;
     @inject(UserAuthentication) protected readonly userAuthentication: UserAuthentication;
     @inject(SignInJWT) protected readonly signInJWT: SignInJWT;
+    @inject(NonceService) protected readonly nonceService: NonceService;
 
     @postConstruct()
     protected setup() {
@@ -77,6 +81,42 @@ export class Authenticator {
                 if (!host) {
                     throw new Error("Auth flow state is missing 'host' attribute.");
                 }
+
+                // Handle GitHub OAuth edge case: redirect from api.* subdomain to base domain
+                // This allows nonce validation to work since cookies are accessible on base domain
+                if (this.isApiSubdomainOfConfiguredHost(req.hostname)) {
+                    log.info(`OAuth callback on api subdomain, redirecting to base domain for nonce validation`, {
+                        hostname: req.hostname,
+                        configuredHost: this.config.hostUrl.url.hostname,
+                    });
+                    const baseUrl = this.config.hostUrl.with({
+                        pathname: req.path,
+                        search: new URL(req.url, this.config.hostUrl.url).search,
+                    });
+                    safeFragmentRedirect(res, baseUrl.toString());
+                    return;
+                }
+
+                // Validate nonce for CSRF protection (if feature flag is enabled)
+                const isNonceValidationEnabled = await getFeatureFlagEnableNonceValidation();
+                if (isNonceValidationEnabled) {
+                    const stateNonce = flowState.nonce;
+                    const cookieNonce = this.nonceService.getNonceFromCookie(req);
+
+                    if (!this.nonceService.validateNonce(stateNonce, cookieNonce)) {
+                        log.error(`CSRF protection: Nonce validation failed`, {
+                            url: req.url,
+                            hasStateNonce: !!stateNonce,
+                            hasCookieNonce: !!cookieNonce,
+                        });
+                        res.status(403).send("Authentication failed");
+                        return;
+                    }
+                }
+
+                // Always clear the nonce cookie
+                this.nonceService.clearNonceCookie(res);
+
                 const hostContext = this.hostContextProvider.get(host);
                 if (!hostContext) {
                     throw new Error("No host context found.");
@@ -89,6 +129,8 @@ export class Authenticator {
                 await hostContext.authProvider.callback(req, res, next);
             } catch (error) {
                 log.error(`Failed to handle callback.`, error, { url: req.url });
+                // Always clear nonce cookie on error
+                this.nonceService.clearNonceCookie(res);
             }
         } else {
             // Otherwise proceed with other handlers
@@ -121,6 +163,15 @@ export class Authenticator {
         return state;
     }
 
+    /**
+     * Checks if the current hostname is api.{configured-domain}.
+     * This handles the GitHub OAuth edge case where callbacks may come to api.* subdomain.
+     */
+    private isApiSubdomainOfConfiguredHost(hostname: string): boolean {
+        const configuredHost = this.config.hostUrl.url.hostname;
+        return hostname === `api.${configuredHost}`;
+    }
+
     protected async getAuthProviderForHost(host: string): Promise<AuthProvider | undefined> {
         const hostContext = this.hostContextProvider.get(host);
         return hostContext && hostContext.authProvider;
@@ -131,18 +182,26 @@ export class Authenticator {
             log.info(`User is already authenticated. Continue.`, { "login-flow": true });
             return next();
         }
-        let returnTo: string | undefined = req.query.returnTo?.toString();
-        if (returnTo) {
-            log.info(`Stored returnTo URL: ${returnTo}`, { "login-flow": true });
+        let returnToParam: string | undefined = req.query.returnTo?.toString();
+        if (returnToParam) {
+            log.info(`Stored returnTo URL: ${returnToParam}`, { "login-flow": true });
+            // Validate returnTo URL against allowlist for login API
+            if (!validateLoginReturnToUrl(returnToParam, this.config.hostUrl)) {
+                log.warn(`Invalid returnTo URL rejected for login: ${returnToParam}`, { "login-flow": true });
+                safeFragmentRedirect(res, this.getSorryUrl(`Invalid return URL.`));
+                return;
+            }
         }
         // returnTo defaults to workspaces url
         const workspaceUrl = this.config.hostUrl.asDashboard().toString();
-        returnTo = returnTo || workspaceUrl;
+        returnToParam = returnToParam || workspaceUrl;
+        const returnTo = returnToParam;
+
         const host: string = req.query.host?.toString() || "";
         const authProvider = host && (await this.getAuthProviderForHost(host));
         if (!host || !authProvider) {
             log.info(`Bad request: missing parameters.`, { "login-flow": true });
-            res.redirect(this.getSorryUrl(`Bad request: missing parameters.`));
+            safeFragmentRedirect(res, this.getSorryUrl(`Bad request: missing parameters.`));
             return;
         }
         // Logins with organizational Git Auth is not permitted
@@ -151,12 +210,12 @@ export class Authenticator {
                 "authorize-flow": true,
                 ap: authProvider.info,
             });
-            res.redirect(this.getSorryUrl(`Login with "${host}" is not permitted.`));
+            safeFragmentRedirect(res, this.getSorryUrl(`Login with "${host}" is not permitted.`));
             return;
         }
         if (this.config.disableDynamicAuthProviderLogin && !authProvider.params.builtin) {
             log.info(`Auth Provider is not allowed.`, { ap: authProvider.info });
-            res.redirect(this.getSorryUrl(`Login with ${authProvider.params.host} is not allowed.`));
+            safeFragmentRedirect(res, this.getSorryUrl(`Login with ${authProvider.params.host} is not allowed.`));
             return;
         }
 
@@ -166,13 +225,18 @@ export class Authenticator {
                 "login-flow": true,
                 ap: authProvider.info,
             });
-            res.redirect(this.getSorryUrl(`Login with "${host}" is not permitted.`));
+            safeFragmentRedirect(res, this.getSorryUrl(`Login with "${host}" is not permitted.`));
             return;
         }
 
+        // Always generate nonce for CSRF protection (validation controlled by feature flag)
+        const nonce = this.nonceService.generateNonce();
+        this.nonceService.setNonceCookie(res, nonce);
+
         const state = await this.signInJWT.sign({
             host,
             returnTo,
+            nonce,
         });
 
         // authenticate user
@@ -183,7 +247,7 @@ export class Authenticator {
         const user = req.user;
         if (!req.isAuthenticated() || !User.is(user)) {
             log.info(`User is not authenticated.`);
-            res.redirect(this.getSorryUrl(`Not authenticated. Please login.`));
+            safeFragmentRedirect(res, this.getSorryUrl(`Not authenticated. Please login.`));
             return;
         }
         const returnTo: string = req.query.returnTo?.toString() || this.config.hostUrl.asDashboard().toString();
@@ -193,20 +257,21 @@ export class Authenticator {
 
         if (!host || !authProvider) {
             log.warn(`Bad request: missing parameters.`);
-            res.redirect(this.getSorryUrl(`Bad request: missing parameters.`));
+            safeFragmentRedirect(res, this.getSorryUrl(`Bad request: missing parameters.`));
             return;
         }
 
         try {
             await this.userAuthentication.deauthorize(user, authProvider.authProviderId);
-            res.redirect(returnTo);
+            safeFragmentRedirect(res, returnTo);
         } catch (error) {
             next(error);
             log.error(`Failed to disconnect a provider.`, error, {
                 host,
                 userId: user.id,
             });
-            res.redirect(
+            safeFragmentRedirect(
+                res,
                 this.getSorryUrl(
                     `Failed to disconnect a provider: ${error && error.message ? error.message : "unknown reason"}`,
                 ),
@@ -218,27 +283,45 @@ export class Authenticator {
         const user = req.user;
         if (!req.isAuthenticated() || !User.is(user)) {
             log.info(`User is not authenticated.`, { "authorize-flow": true });
-            res.redirect(this.getSorryUrl(`Not authenticated. Please login.`));
+            safeFragmentRedirect(res, this.getSorryUrl(`Not authenticated. Please login.`));
             return;
         }
         if (user.id === BUILTIN_INSTLLATION_ADMIN_USER_ID) {
             log.info(`Authorization is not permitted for admin user.`);
-            res.redirect(
+            safeFragmentRedirect(
+                res,
                 this.getSorryUrl(`Authorization is not permitted for admin user. Please login with a user account.`),
             );
             return;
         }
-        const returnTo: string | undefined = req.query.returnTo?.toString();
+        const returnToParam: string | undefined = req.query.returnTo?.toString();
         const host: string | undefined = req.query.host?.toString();
         const scopes: string = req.query.scopes?.toString() || "";
         const override = req.query.override === "true";
         const authProvider = host && (await this.getAuthProviderForHost(host));
-        if (!returnTo || !host || !authProvider) {
+
+        if (!returnToParam || !host || !authProvider) {
             log.info(`Bad request: missing parameters.`, { "authorize-flow": true });
-            res.redirect(this.getSorryUrl(`Bad request: missing parameters.`));
+            safeFragmentRedirect(res, this.getSorryUrl(`Bad request: missing parameters.`));
             return;
         }
 
+        // Validate returnTo URL against allowlist for authorize API
+        const isStrictAuthorizeValidationEnabled = await getFeatureFlagEnableStrictAuthorizeReturnTo();
+        if (isStrictAuthorizeValidationEnabled) {
+            const isValidReturnTo = validateAuthorizeReturnToUrl(returnToParam, this.config.hostUrl);
+            if (!isValidReturnTo) {
+                log.warn(`Invalid returnTo URL rejected for authorize`, {
+                    "authorize-flow": true,
+                    returnToParam,
+                });
+                safeFragmentRedirect(res, this.getSorryUrl(`Invalid return URL.`));
+                return;
+            }
+        }
+
+        const returnTo = returnToParam;
+
         // For non-verified org auth provider, ensure user is an owner of the org
         if (!authProvider.info.verified && authProvider.info.organizationId) {
             const member = await this.teamDb.findTeamMembership(user.id, authProvider.info.organizationId);
@@ -247,7 +330,7 @@ export class Authenticator {
                     "authorize-flow": true,
                     ap: authProvider.info,
                 });
-                res.redirect(this.getSorryUrl(`Authorization with "${host}" is not permitted.`));
+                safeFragmentRedirect(res, this.getSorryUrl(`Authorization with "${host}" is not permitted.`));
                 return;
             }
         }
@@ -258,7 +341,7 @@ export class Authenticator {
                 "authorize-flow": true,
                 ap: authProvider.info,
             });
-            res.redirect(this.getSorryUrl(`Authorization with "${host}" is not permitted.`));
+            safeFragmentRedirect(res, this.getSorryUrl(`Authorization with "${host}" is not permitted.`));
             return;
         }
 
@@ -270,7 +353,7 @@ export class Authenticator {
                     "authorize-flow": true,
                     ap: authProvider.info,
                 });
-                res.redirect(this.getSorryUrl(`Authorization with "${host}" is not permitted.`));
+                safeFragmentRedirect(res, this.getSorryUrl(`Authorization with "${host}" is not permitted.`));
                 return;
             }
         }
@@ -297,7 +380,12 @@ export class Authenticator {
         }
         // authorize Gitpod
         log.info(`(doAuthorize) wanted scopes (${override ? "overriding" : "merging"}): ${wantedScopes.join(",")}`);
-        const state = await this.signInJWT.sign({ host, returnTo, overrideScopes: override });
+
+        // Always generate nonce for CSRF protection (validation controlled by feature flag)
+        const nonce = this.nonceService.generateNonce();
+        this.nonceService.setNonceCookie(res, nonce);
+
+        const state = await this.signInJWT.sign({ host, returnTo, overrideScopes: override, nonce });
         authProvider.authorize(req, res, next, this.deriveAuthState(state), wantedScopes);
     }
     private mergeScopes(a: string[], b: string[]) {
diff --git a/components/server/src/auth/fragment-protection.spec.ts b/components/server/src/auth/fragment-protection.spec.ts
new file mode 100644
index 00000000000000..3f22f5172914be
--- /dev/null
+++ b/components/server/src/auth/fragment-protection.spec.ts
@@ -0,0 +1,52 @@
+/**
+ * Copyright (c) 2024 Gitpod GmbH. All rights reserved.
+ * Licensed under the GNU Affero General Public License (AGPL).
+ * See License.AGPL.txt in the project root for license information.
+ */
+
+import { expect } from "chai";
+import { ensureUrlHasFragment } from "./fragment-utils";
+
+describe("Fragment Protection", () => {
+    describe("ensureUrlHasFragment", () => {
+        it("should add empty fragment to URL without fragment", () => {
+            const url = "https://gitpod.io/workspaces";
+            const result = ensureUrlHasFragment(url);
+
+            expect(result).to.equal("https://gitpod.io/workspaces#");
+        });
+
+        it("should preserve existing fragment", () => {
+            const url = "https://gitpod.io/workspaces#existing";
+            const result = ensureUrlHasFragment(url);
+
+            expect(result).to.equal(url);
+        });
+
+        it("should handle URLs with query parameters", () => {
+            const url = "https://gitpod.io/workspaces?tab=recent";
+            const result = ensureUrlHasFragment(url);
+
+            expect(result).to.equal("https://gitpod.io/workspaces?tab=recent#");
+        });
+
+        it("should handle invalid URLs gracefully", () => {
+            const url = "not-a-valid-url";
+            const result = ensureUrlHasFragment(url);
+
+            expect(result).to.equal("not-a-valid-url#");
+        });
+
+        it("should prevent OAuth token inheritance attack", () => {
+            // Scenario: OAuth provider redirects with token in fragment
+            // If returnTo URL has no fragment, browser inherits the token fragment
+            const returnToWithoutFragment = "https://gitpod.io/workspaces";
+            const protectedUrl = ensureUrlHasFragment(returnToWithoutFragment);
+
+            // Now when OAuth provider redirects to: protectedUrl + token fragment
+            // The existing fragment prevents inheritance
+            expect(protectedUrl).to.include("#");
+            expect(protectedUrl).to.not.equal(returnToWithoutFragment);
+        });
+    });
+});
diff --git a/components/server/src/auth/fragment-utils.ts b/components/server/src/auth/fragment-utils.ts
new file mode 100644
index 00000000000000..16c538c0403a11
--- /dev/null
+++ b/components/server/src/auth/fragment-utils.ts
@@ -0,0 +1,32 @@
+/**
+ * Copyright (c) 2024 Gitpod GmbH. All rights reserved.
+ * Licensed under the GNU Affero General Public License (AGPL).
+ * See License.AGPL.txt in the project root for license information.
+ */
+
+/**
+ * Ensures a returnTo URL has a fragment to prevent OAuth token inheritance attacks.
+ *
+ * When OAuth providers use response_type=token, they redirect with access tokens
+ * in URL fragments. If the returnTo URL doesn't have a fragment, browsers inherit
+ * the current page's fragment, potentially exposing tokens to malicious sites.
+ *
+ * Uses an empty fragment (#) to prevent inheritance without interfering with
+ * Gitpod's context provider resolution.
+ */
+export function ensureUrlHasFragment(url: string): string {
+    try {
+        const parsedUrl = new URL(url);
+        // If URL already has a fragment, return as-is
+        if (parsedUrl.hash) {
+            return url;
+        }
+        // Add empty fragment to prevent inheritance
+        // Using just "#" to avoid interfering with context provider resolution that
+        // treats fragments as git URLs
+        return url + "#";
+    } catch (error) {
+        // If URL is invalid, add fragment anyway
+        return url + "#";
+    }
+}
diff --git a/components/server/src/auth/generic-auth-provider.ts b/components/server/src/auth/generic-auth-provider.ts
index 1295f3d96030b4..22cf40dd013108 100644
--- a/components/server/src/auth/generic-auth-provider.ts
+++ b/components/server/src/auth/generic-auth-provider.ts
@@ -23,7 +23,7 @@ import {
     UnconfirmedUserException,
 } from "../auth/errors";
 import { Config } from "../config";
-import { getRequestingClientInfo } from "../express-util";
+import { getRequestingClientInfo, safeFragmentRedirect } from "../express-util";
 import { TokenProvider } from "../user/token-provider";
 import { UserAuthentication } from "../user/user-authentication";
 import { AuthProviderService } from "./auth-provider-service";
@@ -287,7 +287,8 @@ export abstract class GenericAuthProvider implements AuthProvider {
         const state = request.query.state;
         if (!state) {
             log.error(cxt, `(${strategyName}) No state present on callback request.`, { clientInfo });
-            response.redirect(
+            safeFragmentRedirect(
+                response,
                 this.getSorryUrl(`No state was present on the authentication callback. Please try again.`),
             );
             return;
@@ -298,15 +299,7 @@ export abstract class GenericAuthProvider implements AuthProvider {
             log.error(`(${strategyName}) Auth flow state is missing.`);
 
             reportLoginCompleted("failed", "git");
-            response.redirect(this.getSorryUrl(`Auth flow state is missing.`));
-            return;
-        }
-
-        if (!this.loginCompletionHandler.isBaseDomain(request)) {
-            // For auth requests that are not targetting the base domain, we redirect to the base domain, so they come with our cookie.
-            log.info(`(${strategyName}) Auth request on subdomain, redirecting to base domain`, { clientInfo });
-            const target = new URL(request.url, this.config.hostUrl.url.toString()).toString();
-            response.redirect(target);
+            safeFragmentRedirect(response, this.getSorryUrl(`Auth flow state is missing.`));
             return;
         }
 
@@ -317,7 +310,7 @@ export abstract class GenericAuthProvider implements AuthProvider {
                     `(${strategyName}) User is already logged in. No auth info provided. Redirecting to dashboard.`,
                     { clientInfo },
                 );
-                response.redirect(this.config.hostUrl.asDashboard().toString());
+                safeFragmentRedirect(response, this.config.hostUrl.asDashboard().toString());
                 return;
             }
         }
@@ -328,7 +321,10 @@ export abstract class GenericAuthProvider implements AuthProvider {
             reportLoginCompleted("failed_client", "git");
 
             log.error(cxt, `(${strategyName}) No session found during auth callback.`, { clientInfo });
-            response.redirect(this.getSorryUrl(`Please allow Cookies in your browser and try to log in again.`));
+            safeFragmentRedirect(
+                response,
+                this.getSorryUrl(`Please allow Cookies in your browser and try to log in again.`),
+            );
             return;
         }
 
@@ -336,7 +332,7 @@ export abstract class GenericAuthProvider implements AuthProvider {
             reportLoginCompleted("failed", "git");
 
             log.error(cxt, `(${strategyName}) Host does not match.`, { clientInfo });
-            response.redirect(this.getSorryUrl(`Host does not match.`));
+            safeFragmentRedirect(response, this.getSorryUrl(`Host does not match.`));
             return;
         }
 
@@ -367,7 +363,7 @@ export abstract class GenericAuthProvider implements AuthProvider {
                 authenticate(request, response, next);
             });
         } catch (error) {
-            response.redirect(this.getSorryUrl(`OAuth2 error. (${error})`));
+            safeFragmentRedirect(response, this.getSorryUrl(`OAuth2 error. (${error})`));
             return;
         }
         const [err, userOrIdentity, flowContext] = result;
@@ -479,7 +475,7 @@ export abstract class GenericAuthProvider implements AuthProvider {
                     );
 
                     const { returnTo } = authFlow;
-                    response.redirect(returnTo);
+                    safeFragmentRedirect(response, returnTo);
                     return;
                 } else {
                     // Complete login into an existing account
@@ -544,7 +540,7 @@ export abstract class GenericAuthProvider implements AuthProvider {
                 search: "message=error:" + Buffer.from(JSON.stringify(error), "utf-8").toString("base64"),
             })
             .toString();
-        response.redirect(url);
+        safeFragmentRedirect(response, url);
     }
 
     /**
diff --git a/components/server/src/auth/login-completion-handler.ts b/components/server/src/auth/login-completion-handler.ts
index 3345100df9783c..d4978b74ac7980 100644
--- a/components/server/src/auth/login-completion-handler.ts
+++ b/components/server/src/auth/login-completion-handler.ts
@@ -6,7 +6,6 @@
 
 import { inject, injectable } from "inversify";
 import express from "express";
-import * as crypto from "crypto";
 import { User } from "@gitpod/gitpod-protocol";
 import { log, LogContext } from "@gitpod/gitpod-protocol/lib/util/logging";
 import { Config } from "../config";
@@ -17,7 +16,7 @@ import { IAnalyticsWriter } from "@gitpod/gitpod-protocol/lib/analytics";
 import { trackLogin } from "../analytics";
 import { SessionHandler } from "../session-handler";
 import { AuthJWT } from "./jwt";
-import { OneTimeSecretServer } from "../one-time-secret-server";
+import { safeFragmentRedirect } from "../express-util";
 
 /**
  * The login completion handler pulls the strings between the OAuth2 flow, the ToS flow, and the session management.
@@ -30,7 +29,6 @@ export class LoginCompletionHandler {
     @inject(AuthProviderService) protected readonly authProviderService: AuthProviderService;
     @inject(AuthJWT) protected readonly authJWT: AuthJWT;
     @inject(SessionHandler) protected readonly session: SessionHandler;
-    @inject(OneTimeSecretServer) private readonly otsServer: OneTimeSecretServer;
 
     async complete(
         request: express.Request,
@@ -52,12 +50,17 @@ export class LoginCompletionHandler {
         } catch (err) {
             reportLoginCompleted("failed", "git");
             log.error(logContext, `Failed to login user. Redirecting to /sorry on login.`, err);
-            response.redirect(this.config.hostUrl.asSorry("Oops! Something went wrong during login.").toString());
+            safeFragmentRedirect(
+                response,
+                this.config.hostUrl.asSorry("Oops! Something went wrong during login.").toString(),
+            );
             return;
         }
 
         // Update session info
-        let returnTo = returnToUrl || this.config.hostUrl.asDashboard().toString();
+        const returnToParam = returnToUrl || this.config.hostUrl.asDashboard().toString();
+        let returnTo = returnToParam;
+
         if (elevateScopes) {
             const elevateScopesUrl = this.config.hostUrl
                 .withApi({
@@ -81,25 +84,6 @@ export class LoginCompletionHandler {
             );
         }
 
-        if (!this.isBaseDomain(request)) {
-            // (GitHub edge case) If we got redirected here onto a sub-domain (e.g. api.gitpod.io), we need to redirect to the base domain in order to Set-Cookie properly.
-            const secret = crypto
-                .createHash("sha256")
-                .update(user.id + this.config.session.secret)
-                .digest("hex");
-            const expirationDate = new Date(Date.now() + 1000 * 60); // 1 minutes
-            const token = await this.otsServer.serveToken({}, secret, expirationDate);
-
-            reportLoginCompleted("succeeded_via_ots", "git");
-            log.info(
-                logContext,
-                `User will be logged in via OTS on the base domain. (Indirect) redirect to: ${returnTo}`,
-            );
-            const baseDomainRedirect = this.config.hostUrl.asLoginWithOTS(user.id, token.token, returnTo).toString();
-            response.redirect(baseDomainRedirect);
-            return;
-        }
-
         // (default case) If we got redirected here onto the base domain of the Gitpod installation, we can just issue the cookie right away.
         const cookie = await this.session.createJWTSessionCookie(user.id);
         response.cookie(cookie.name, cookie.value, cookie.opts);
@@ -108,11 +92,7 @@ export class LoginCompletionHandler {
 
         log.info(logContext, `User is logged in successfully. Redirect to: ${returnTo}`);
         reportLoginCompleted("succeeded", "git");
-        response.redirect(returnTo);
-    }
-
-    public isBaseDomain(req: express.Request): boolean {
-        return req.hostname === this.config.hostUrl.url.hostname;
+        safeFragmentRedirect(response, returnTo);
     }
 
     public async updateAuthProviderAsVerified(hostname: string, user: User) {
diff --git a/components/server/src/auth/nonce-service.spec.ts b/components/server/src/auth/nonce-service.spec.ts
new file mode 100644
index 00000000000000..fd60e975a0e4fe
--- /dev/null
+++ b/components/server/src/auth/nonce-service.spec.ts
@@ -0,0 +1,67 @@
+/**
+ * Copyright (c) 2024 Gitpod GmbH. All rights reserved.
+ * Licensed under the GNU Affero General Public License (AGPL).
+ * See License.AGPL.txt in the project root for license information.
+ */
+
+import { expect } from "chai";
+import { Container } from "inversify";
+import { Config } from "../config";
+import { NonceService } from "./nonce-service";
+
+describe("NonceService", () => {
+    let container: Container;
+    let nonceService: NonceService;
+
+    beforeEach(() => {
+        container = new Container();
+        container.bind(Config).toConstantValue({
+            hostUrl: {
+                url: new URL("https://gitpod.io"),
+            },
+            auth: {
+                session: {
+                    cookie: {
+                        secure: true,
+                    },
+                },
+            },
+        } as any);
+        container.bind(NonceService).toSelf();
+        nonceService = container.get(NonceService);
+    });
+
+    describe("generateNonce", () => {
+        it("should generate unique nonces", () => {
+            const nonce1 = nonceService.generateNonce();
+            const nonce2 = nonceService.generateNonce();
+
+            expect(nonce1).to.be.a("string");
+            expect(nonce2).to.be.a("string");
+            expect(nonce1).to.not.equal(nonce2);
+            expect(nonce1.length).to.be.greaterThan(40); // base64url encoded 32 bytes
+        });
+    });
+
+    describe("validateNonce", () => {
+        it("should validate matching nonces", () => {
+            const nonce = nonceService.generateNonce();
+            const isValid = nonceService.validateNonce(nonce, nonce);
+            expect(isValid).to.be.true;
+        });
+
+        it("should reject different nonces", () => {
+            const nonce1 = nonceService.generateNonce();
+            const nonce2 = nonceService.generateNonce();
+            const isValid = nonceService.validateNonce(nonce1, nonce2);
+            expect(isValid).to.be.false;
+        });
+
+        it("should reject undefined nonces", () => {
+            const nonce = nonceService.generateNonce();
+            expect(nonceService.validateNonce(nonce, undefined)).to.be.false;
+            expect(nonceService.validateNonce(undefined, nonce)).to.be.false;
+            expect(nonceService.validateNonce(undefined, undefined)).to.be.false;
+        });
+    });
+});
diff --git a/components/server/src/auth/nonce-service.ts b/components/server/src/auth/nonce-service.ts
new file mode 100644
index 00000000000000..b4ac005c3f9c29
--- /dev/null
+++ b/components/server/src/auth/nonce-service.ts
@@ -0,0 +1,80 @@
+/**
+ * Copyright (c) 2024 Gitpod GmbH. All rights reserved.
+ * Licensed under the GNU Affero General Public License (AGPL).
+ * See License.AGPL.txt in the project root for license information.
+ */
+
+import { injectable, inject } from "inversify";
+import express from "express";
+import * as crypto from "crypto";
+import { Config } from "../config";
+
+const NONCE_COOKIE_NAME = "__Host-_gitpod_oauth_nonce_";
+const NONCE_LENGTH = 32; // 32 bytes = 256 bits
+
+@injectable()
+export class NonceService {
+    @inject(Config) protected readonly config: Config;
+
+    /**
+     * Generates a cryptographically secure random nonce
+     */
+    generateNonce(): string {
+        return crypto.randomBytes(NONCE_LENGTH).toString("base64url");
+    }
+
+    /**
+     * Sets the nonce cookie in the response
+     */
+    setNonceCookie(res: express.Response, nonce: string): void {
+        res.cookie(NONCE_COOKIE_NAME, nonce, {
+            httpOnly: true,
+            secure: this.config.auth.session.cookie.secure,
+            sameSite: "lax",
+            maxAge: 5 * 60 * 1000, // 5 minutes (same as JWT state expiry)
+            path: "/",
+        });
+    }
+
+    /**
+     * Gets the nonce from the request cookies
+     */
+    getNonceFromCookie(req: express.Request): string | undefined {
+        return req.cookies?.[NONCE_COOKIE_NAME];
+    }
+
+    /**
+     * Clears the nonce cookie
+     */
+    clearNonceCookie(res: express.Response): void {
+        res.clearCookie(NONCE_COOKIE_NAME, {
+            httpOnly: true,
+            secure: this.config.auth.session.cookie.secure,
+            sameSite: "lax",
+            path: "/",
+        });
+    }
+
+    /**
+     * Validates that the nonce from the state matches the nonce from the cookie
+     */
+    validateNonce(stateNonce: string | undefined, cookieNonce: string | undefined): boolean {
+        if (!stateNonce || !cookieNonce) {
+            return false;
+        }
+
+        // Use crypto.timingSafeEqual to prevent timing attacks
+        if (stateNonce.length !== cookieNonce.length) {
+            return false;
+        }
+
+        const stateBuffer = Buffer.from(stateNonce, "base64url");
+        const cookieBuffer = Buffer.from(cookieNonce, "base64url");
+
+        if (stateBuffer.length !== cookieBuffer.length) {
+            return false;
+        }
+
+        return crypto.timingSafeEqual(stateBuffer, cookieBuffer);
+    }
+}
diff --git a/components/server/src/auth/return-to-validation.spec.ts b/components/server/src/auth/return-to-validation.spec.ts
new file mode 100644
index 00000000000000..e1eea9555f5532
--- /dev/null
+++ b/components/server/src/auth/return-to-validation.spec.ts
@@ -0,0 +1,307 @@
+/**
+ * Copyright (c) 2024 Gitpod GmbH. All rights reserved.
+ * Licensed under the GNU Affero General Public License (AGPL).
+ * See License.AGPL.txt in the project root for license information.
+ */
+
+import { expect } from "chai";
+import { GitpodHostUrl } from "@gitpod/gitpod-protocol/lib/util/gitpod-host-url";
+import { validateLoginReturnToUrl, validateAuthorizeReturnToUrl } from "../express-util";
+
+describe("ReturnTo URL Validation", () => {
+    const hostUrl = new GitpodHostUrl("https://gitpod.io");
+
+    describe("validateLoginReturnToUrl", () => {
+        it("should accept any valid path after domain validation", () => {
+            const validUrls = [
+                "https://gitpod.io/",
+                "https://gitpod.io/workspaces",
+                "https://gitpod.io/workspaces/123",
+                "https://gitpod.io/settings",
+                "https://gitpod.io/settings/integrations",
+                "https://gitpod.io/user-settings",
+                "https://gitpod.io/user-settings/account",
+                "https://gitpod.io/integrations",
+                "https://gitpod.io/integrations/github",
+                "https://gitpod.io/repositories",
+                "https://gitpod.io/repositories/123",
+                "https://gitpod.io/prebuilds",
+                "https://gitpod.io/prebuilds/456",
+                "https://gitpod.io/members",
+                "https://gitpod.io/billing",
+                "https://gitpod.io/usage",
+                "https://gitpod.io/insights",
+                "https://gitpod.io/new",
+                "https://gitpod.io/login",
+                "https://gitpod.io/login/org-slug",
+                "https://gitpod.io/quickstart",
+                "https://gitpod.io/admin", // Now allowed since login doesn't restrict paths
+                "https://gitpod.io/api/workspace", // Now allowed
+                "https://gitpod.io/any-path", // Any path is allowed
+            ];
+
+            validUrls.forEach((url) => {
+                const result = validateLoginReturnToUrl(url, hostUrl);
+                expect(result).to.equal(true, `Should accept valid login URL: ${url}`);
+            });
+        });
+
+        it("should accept complete-auth with ONLY message parameter", () => {
+            const validCompleteAuthUrls = [
+                "https://gitpod.io/complete-auth?message=success:123",
+                "https://gitpod.io/complete-auth?message=success",
+            ];
+
+            validCompleteAuthUrls.forEach((url) => {
+                const result = validateLoginReturnToUrl(url, hostUrl);
+                expect(result).to.equal(true, `Should accept complete-auth with only message: ${url}`);
+            });
+        });
+
+        it("should reject complete-auth with additional parameters", () => {
+            const invalidCompleteAuthUrls = [
+                "https://gitpod.io/complete-auth?message=success&other=param",
+                "https://gitpod.io/complete-auth?other=param&message=success",
+                "https://gitpod.io/complete-auth",
+                "https://gitpod.io/complete-auth?other=param",
+                "https://gitpod.io/complete-auth?msg=success", // Wrong parameter name
+            ];
+
+            invalidCompleteAuthUrls.forEach((url) => {
+                const result = validateLoginReturnToUrl(url, hostUrl);
+                expect(result).to.equal(false, `Should reject complete-auth with extra params: ${url}`);
+            });
+        });
+
+        it("should accept www.gitpod.io root only", () => {
+            const result = validateLoginReturnToUrl("https://www.gitpod.io/", hostUrl);
+            expect(result).to.equal(true, "Should accept www.gitpod.io root");
+
+            const invalidWwwUrls = [
+                "https://www.gitpod.io/workspaces",
+                "https://www.gitpod.io/login",
+                "http://www.gitpod.io/", // Wrong protocol
+            ];
+
+            invalidWwwUrls.forEach((url) => {
+                const result = validateLoginReturnToUrl(url, hostUrl);
+                expect(result).to.equal(false, `Should reject www.gitpod.io non-root: ${url}`);
+            });
+        });
+
+        describe("Feature Flag Integration", () => {
+            it("should document nonce validation feature flag behavior", () => {
+                // Feature flag: enable_nonce_validation (default: false)
+                // When enabled: Full CSRF protection with nonce validation
+                // When disabled: Nonce is generated but not validated (for future compatibility)
+
+                // This test documents the expected behavior:
+                // 1. Nonce is always generated and stored in cookie
+                // 2. Nonce is always included in JWT state
+                // 3. Nonce validation only occurs when feature flag is enabled
+                // 4. Cookie is always cleared after callback processing
+
+                expect(true).to.equal(true); // Documentation test
+            });
+
+            it("should document strict authorize returnTo validation feature flag behavior", () => {
+                // Feature flag: enable_strict_authorize_return_to (default: false)
+                // When enabled: Uses validateAuthorizeReturnToUrl (strict patterns)
+                // When disabled: Falls back to validateLoginReturnToUrl (broader patterns)
+
+                // This test documents the expected behavior:
+                // 1. /api/authorize endpoint checks the feature flag
+                // 2. If enabled: Only allows complete-auth, root, /new, /quickstart
+                // 3. If disabled: Falls back to login validation (broader patterns)
+                // 4. /api/login endpoint always uses login validation
+
+                expect(true).to.equal(true); // Documentation test
+            });
+
+            it("should show difference between strict and fallback validation", () => {
+                const testUrls = [
+                    { url: "https://gitpod.io/workspaces", strictAllowed: false, fallbackAllowed: true },
+                    { url: "https://gitpod.io/settings", strictAllowed: false, fallbackAllowed: true },
+                    { url: "https://gitpod.io/new", strictAllowed: true, fallbackAllowed: true },
+                    { url: "https://gitpod.io/quickstart", strictAllowed: true, fallbackAllowed: true },
+                    {
+                        url: "https://gitpod.io/complete-auth?message=success",
+                        strictAllowed: true,
+                        fallbackAllowed: true,
+                    },
+                ];
+
+                testUrls.forEach(({ url, strictAllowed, fallbackAllowed }) => {
+                    const strictResult = validateAuthorizeReturnToUrl(url, hostUrl);
+                    const fallbackResult = validateLoginReturnToUrl(url, hostUrl);
+
+                    expect(strictResult).to.equal(strictAllowed, `Strict validation failed for: ${url}`);
+                    expect(fallbackResult).to.equal(fallbackAllowed, `Fallback validation failed for: ${url}`);
+                });
+            });
+        });
+    });
+
+    describe("validateAuthorizeReturnToUrl", () => {
+        it("should accept only specific allowlisted paths", () => {
+            const validUrls = [
+                "https://gitpod.io/", // Root
+                "https://gitpod.io/new", // Create workspace page
+                "https://gitpod.io/quickstart", // Quickstart page
+            ];
+
+            validUrls.forEach((url) => {
+                const result = validateAuthorizeReturnToUrl(url, hostUrl);
+                expect(result).to.equal(true, `Should accept valid authorize URL: ${url}`);
+            });
+        });
+
+        it("should accept complete-auth with ONLY message parameter", () => {
+            const validCompleteAuthUrls = [
+                "https://gitpod.io/complete-auth?message=success:123",
+                "https://gitpod.io/complete-auth?message=success",
+            ];
+
+            validCompleteAuthUrls.forEach((url) => {
+                const result = validateAuthorizeReturnToUrl(url, hostUrl);
+                expect(result).to.equal(true, `Should accept complete-auth with only message: ${url}`);
+            });
+        });
+
+        it("should reject paths not in authorize allowlist", () => {
+            const rejectedUrls = [
+                "https://gitpod.io/workspaces",
+                "https://gitpod.io/workspaces/123",
+                "https://gitpod.io/user-settings",
+                "https://gitpod.io/integrations",
+                "https://gitpod.io/prebuilds",
+                "https://gitpod.io/members",
+                "https://gitpod.io/billing",
+                "https://gitpod.io/usage",
+                "https://gitpod.io/insights",
+                "https://gitpod.io/login",
+                "https://gitpod.io/settings",
+                "https://gitpod.io/repositories",
+                "https://gitpod.io/admin",
+                "https://gitpod.io/api/workspace",
+            ];
+
+            rejectedUrls.forEach((url) => {
+                const result = validateAuthorizeReturnToUrl(url, hostUrl);
+                expect(result).to.equal(false, `Should reject authorize URL: ${url}`);
+            });
+        });
+
+        it("should accept www.gitpod.io root only", () => {
+            const result = validateAuthorizeReturnToUrl("https://www.gitpod.io/", hostUrl);
+            expect(result).to.equal(true, "Should accept www.gitpod.io root");
+        });
+    });
+
+    describe("Common validation tests", () => {
+        it("should reject different origins", () => {
+            const invalidOriginUrls = [
+                "https://evil.com/workspaces",
+                "http://gitpod.io/workspaces", // Different protocol
+                "https://gitpod.io:8080/workspaces", // Different port
+                "https://subdomain.gitpod.io/workspaces", // Different subdomain
+            ];
+
+            invalidOriginUrls.forEach((url) => {
+                expect(validateLoginReturnToUrl(url, hostUrl)).to.equal(false, `Login should reject: ${url}`);
+                expect(validateAuthorizeReturnToUrl(url, hostUrl)).to.equal(false, `Authorize should reject: ${url}`);
+            });
+        });
+
+        it("should have different path restrictions for login vs authorize", () => {
+            const pathsAllowedInLoginOnly = [
+                "https://gitpod.io/admin",
+                "https://gitpod.io/workspace-123",
+                "https://gitpod.io/api/workspace",
+                "https://gitpod.io/workspaces",
+                "https://gitpod.io/settings",
+                "https://gitpod.io/any-arbitrary-path",
+            ];
+
+            pathsAllowedInLoginOnly.forEach((url) => {
+                expect(validateLoginReturnToUrl(url, hostUrl)).to.equal(true, `Login should allow: ${url}`);
+                expect(validateAuthorizeReturnToUrl(url, hostUrl)).to.equal(false, `Authorize should reject: ${url}`);
+            });
+        });
+
+        it("should reject invalid URLs", () => {
+            const invalidUrls = [
+                "not-a-url",
+                "javascript:alert('xss')",
+                "data:text/html,<script>alert('xss')</script>",
+                "",
+                "//evil.com/workspaces",
+                "ftp://gitpod.io/workspaces",
+            ];
+
+            invalidUrls.forEach((url) => {
+                expect(validateLoginReturnToUrl(url, hostUrl)).to.equal(false, `Login should reject: ${url}`);
+                expect(validateAuthorizeReturnToUrl(url, hostUrl)).to.equal(false, `Authorize should reject: ${url}`);
+            });
+        });
+
+        it("should work with different host configurations", () => {
+            const previewHostUrl = new GitpodHostUrl("https://preview.gitpod-dev.com");
+
+            // Login should accept any path on same origin
+            const validLoginUrls = [
+                "https://preview.gitpod-dev.com/workspaces",
+                "https://preview.gitpod-dev.com/complete-auth?message=success",
+                "https://preview.gitpod-dev.com/any-path",
+            ];
+
+            validLoginUrls.forEach((url) => {
+                expect(validateLoginReturnToUrl(url, previewHostUrl)).to.equal(true, `Login should accept: ${url}`);
+            });
+
+            // Authorize should only accept allowlisted paths
+            const validAuthorizeUrls = [
+                "https://preview.gitpod-dev.com/", // Root
+                "https://preview.gitpod-dev.com/new", // Create workspace page
+                "https://preview.gitpod-dev.com/quickstart", // Quickstart page
+                "https://preview.gitpod-dev.com/complete-auth?message=success",
+            ];
+
+            validAuthorizeUrls.forEach((url) => {
+                expect(validateAuthorizeReturnToUrl(url, previewHostUrl)).to.equal(
+                    true,
+                    `Authorize should accept: ${url}`,
+                );
+            });
+
+            // Should reject /workspaces for authorize since it's not in allowlist
+            expect(validateAuthorizeReturnToUrl("https://preview.gitpod-dev.com/workspaces", previewHostUrl)).to.equal(
+                false,
+            );
+
+            // Should reject URLs for different hosts
+            expect(validateLoginReturnToUrl("https://gitpod.io/workspaces", previewHostUrl)).to.equal(false);
+            expect(validateAuthorizeReturnToUrl("https://gitpod.io/workspaces", previewHostUrl)).to.equal(false);
+        });
+
+        it("should validate www.gitpod.io specifically", () => {
+            // Test with production gitpod.io
+            const prodHostUrl = new GitpodHostUrl("https://gitpod.io");
+            expect(validateLoginReturnToUrl("https://www.gitpod.io/", prodHostUrl)).to.equal(true);
+            expect(validateAuthorizeReturnToUrl("https://www.gitpod.io/", prodHostUrl)).to.equal(true);
+
+            // Test with different deployment - www.gitpod.io should still work as it's hardcoded
+            const customHostUrl = new GitpodHostUrl("https://gitpod.example.com");
+            expect(validateLoginReturnToUrl("https://www.gitpod.io/", customHostUrl)).to.equal(true);
+            expect(validateAuthorizeReturnToUrl("https://www.gitpod.io/", customHostUrl)).to.equal(true);
+
+            // Test that other www subdomains don't work
+            expect(validateLoginReturnToUrl("https://www.gitpod.example.com/", prodHostUrl)).to.equal(false);
+            expect(validateAuthorizeReturnToUrl("https://www.gitpod.example.com/", prodHostUrl)).to.equal(false);
+
+            // Test domain injection prevention
+            expect(validateLoginReturnToUrl("https://www.gitpod.io.evil.com/", prodHostUrl)).to.equal(false);
+            expect(validateAuthorizeReturnToUrl("https://www.gitpod.io.evil.com/", prodHostUrl)).to.equal(false);
+        });
+    });
+});
diff --git a/components/server/src/container-module.ts b/components/server/src/container-module.ts
index 5164b779a1529c..40a1a05be788a1 100644
--- a/components/server/src/container-module.ts
+++ b/components/server/src/container-module.ts
@@ -45,6 +45,7 @@ import { HostContainerMapping } from "./auth/host-container-mapping";
 import { HostContextProvider, HostContextProviderFactory } from "./auth/host-context-provider";
 import { HostContextProviderImpl } from "./auth/host-context-provider-impl";
 import { AuthJWT, SignInJWT } from "./auth/jwt";
+import { NonceService } from "./auth/nonce-service";
 import { LoginCompletionHandler } from "./auth/login-completion-handler";
 import { VerificationService } from "./auth/verification-service";
 import { InstallationService } from "./auth/installation-service";
@@ -366,6 +367,7 @@ export const productionContainerModule = new ContainerModule(
 
         bind(AuthJWT).toSelf().inSingletonScope();
         bind(SignInJWT).toSelf().inSingletonScope();
+        bind(NonceService).toSelf().inSingletonScope();
 
         bind(PrebuildManager).toSelf().inSingletonScope();
         bind(LazyPrebuildManager).toFactory((ctx) => {
diff --git a/components/server/src/express-util.ts b/components/server/src/express-util.ts
index 8cdd6eb5343ade..f3f96984cc513b 100644
--- a/components/server/src/express-util.ts
+++ b/components/server/src/express-util.ts
@@ -8,6 +8,10 @@ import { URL } from "url";
 import express from "express";
 import * as crypto from "crypto";
 import { IncomingHttpHeaders } from "http";
+import { GitpodHostUrl } from "@gitpod/gitpod-protocol/lib/util/gitpod-host-url";
+import { ensureUrlHasFragment } from "./auth/fragment-utils";
+import { log } from "@gitpod/gitpod-protocol/lib/util/logging";
+import { TrustedValue } from "@gitpod/gitpod-protocol/lib/util/scrubbing";
 
 export const query = (...tuples: [string, string][]) => {
     if (tuples.length === 0) {
@@ -159,3 +163,117 @@ export function toClientHeaderFields(expressReq: express.Request): ClientHeaderF
         clientRegion: takeFirst(expressReq.headers["x-glb-client-region"]),
     };
 }
+
+/**
+ * Common validation logic for returnTo URLs.
+ * @param returnTo The URL to validate
+ * @param hostUrl The host URL configuration
+ * @param allowedPatterns Array of regex patterns that are allowed for the pathname
+ * @returns true if the URL is valid, false otherwise
+ */
+function validateReturnToUrlWithPatterns(
+    returnTo: string,
+    allowedBaseUrl: GitpodHostUrl,
+    allowedPatterns?: RegExp[],
+): boolean {
+    try {
+        const url = new URL(returnTo);
+        const baseUrl = allowedBaseUrl.url;
+
+        // Must be same origin OR www.gitpod.io exception
+        const isSameOrigin = url.origin === baseUrl.origin;
+        const isGitpodWebsite = url.protocol === "https:" && url.hostname === "www.gitpod.io";
+
+        if (!isSameOrigin && !isGitpodWebsite) {
+            return false;
+        }
+
+        // For www.gitpod.io, only allow root path
+        if (isGitpodWebsite) {
+            return url.pathname === "/";
+        }
+
+        if (allowedPatterns !== undefined) {
+            // Check if pathname matches any allowed pattern
+            const isAllowedPath = allowedPatterns.some((pattern) => pattern.test(url.pathname));
+            if (!isAllowedPath) {
+                return false;
+            }
+        }
+
+        // For complete-auth, require ONLY message parameter (used by OAuth flows)
+        if (url.pathname === "/complete-auth") {
+            const searchParams = new URLSearchParams(url.search);
+            const paramKeys = Array.from(searchParams.keys());
+            return paramKeys.length === 1 && paramKeys[0] === "message" && searchParams.has("message");
+        }
+
+        return true;
+    } catch (error) {
+        // Invalid URL
+        return false;
+    }
+}
+
+/**
+ * Validates returnTo URLs for login API endpoints.
+ * Login API allows broader navigation after authentication.
+ */
+export function validateLoginReturnToUrl(returnTo: string, hostUrl: GitpodHostUrl): boolean {
+    // We just verify the domain
+    return validateReturnToUrlWithPatterns(returnTo, hostUrl, undefined);
+}
+
+/**
+ * Validates returnTo URLs for authorize API endpoints.
+ * Authorize API allows complete-auth callbacks and dashboard pages for scope elevation.
+ */
+export function validateAuthorizeReturnToUrl(returnTo: string, hostUrl: GitpodHostUrl): boolean {
+    const allowedPatterns = [
+        // 1. complete-auth callback for OAuth popup windows
+        /^\/complete-auth$/,
+
+        // 2. Dashboard pages (for scope elevation flows)
+        /^\/$/, // Root
+        /^\/new\/?$/, // Create workspace page
+        /^\/quickstart\/?$/, // Quickstart page
+    ];
+
+    return validateReturnToUrlWithPatterns(returnTo, hostUrl, allowedPatterns);
+}
+
+export function getSafeReturnToParam(req: express.Request, validator?: (url: string) => boolean): string | undefined {
+    // @ts-ignore Type 'ParsedQs' is not assignable
+    const returnToURL: string | undefined = req.query.redirect || req.query.returnTo;
+    if (!returnToURL) {
+        return;
+    }
+
+    if (validator && !validator(returnToURL)) {
+        log.debug("The redirect URL does not match allowed patterns", { query: new TrustedValue(req.query).value });
+        return;
+    }
+
+    return returnToURL;
+}
+
+/**
+ * Safe redirect wrapper that automatically ensures URLs have fragments to prevent
+ * OAuth token inheritance attacks.
+ *
+ * When OAuth providers redirect with tokens in URL fragments, browsers inherit
+ * fragments from the current page if the target URL doesn't have one. This wrapper
+ * automatically applies fragment protection to all redirects.
+ *
+ * @param res Express response object
+ * @param url URL to redirect to
+ * @param status Optional HTTP status code (default: 302)
+ */
+export function safeFragmentRedirect(res: express.Response, url: string, status?: number): void {
+    const protectedUrl = ensureUrlHasFragment(url);
+    if (status) {
+        res.redirect(status, protectedUrl);
+    } else {
+        res.redirect(protectedUrl);
+    }
+}
diff --git a/components/server/src/oauth-server/oauth-controller.ts b/components/server/src/oauth-server/oauth-controller.ts
index 408ed570254674..33bb32f8fc0309 100644
--- a/components/server/src/oauth-server/oauth-controller.ts
+++ b/components/server/src/oauth-server/oauth-controller.ts
@@ -14,6 +14,7 @@ import express from "express";
 import { inject, injectable } from "inversify";
 import { URL } from "url";
 import { Config } from "../config";
+import { safeFragmentRedirect } from "../express-util";
 import { clientRepository, createAuthorizationServer } from "./oauth-authorization-server";
 import { inMemoryDatabase, toolboxClient } from "./db";
 import { getFeatureFlagEnableExperimentalJBTB } from "../util/featureflags";
@@ -28,7 +29,7 @@ export class OAuthController {
         if (!req.isAuthenticated() || !User.is(req.user)) {
             const returnToPath = encodeURIComponent(`/api${req.originalUrl}`);
             const redirectTo = `${this.config.hostUrl}login?returnToPath=${returnToPath}`;
-            res.redirect(redirectTo);
+            safeFragmentRedirect(res, redirectTo);
             return null;
         }
         const user = req.user as User;
@@ -88,7 +89,7 @@ export class OAuthController {
 
             const redirectUri = new URL(req.query.redirect_uri);
             redirectUri.searchParams.append("approved", "no");
-            res.redirect(redirectUri.toString());
+            safeFragmentRedirect(res, redirectUri.toString());
             return false;
         } else if (wasApproved == "yes") {
             const additionalData = (user.additionalData = user.additionalData || {});
@@ -104,7 +105,7 @@ export class OAuthController {
                 if (client) {
                     const returnToPath = encodeURIComponent(`/api${req.originalUrl}`);
                     const redirectTo = `${this.config.hostUrl}oauth-approval?clientID=${client.id}&clientName=${client.name}&returnToPath=${returnToPath}`;
-                    res.redirect(redirectTo);
+                    safeFragmentRedirect(res, redirectTo);
                     return false;
                 } else {
                     log.error(`/oauth/authorize unknown client id: "${clientID}"`);
diff --git a/components/server/src/prebuilds/github-app.ts b/components/server/src/prebuilds/github-app.ts
index 6ca30d52feb5e5..60d7b7edf9b90c 100644
--- a/components/server/src/prebuilds/github-app.ts
+++ b/components/server/src/prebuilds/github-app.ts
@@ -21,6 +21,7 @@ import {
 } from "@gitpod/gitpod-db/lib";
 import express from "express";
 import { log, LogContext, LogrusLogLevel } from "@gitpod/gitpod-protocol/lib/util/logging";
+import { safeFragmentRedirect } from "../express-util";
 import {
     WorkspaceConfig,
     User,
@@ -111,7 +112,7 @@ export class GithubApp {
             options
                 .getRouter("/pbs")
                 .get("/*", (req: express.Request, res: express.Response, next: express.NextFunction) => {
-                    res.redirect(301, this.getBadgeImageURL());
+                    safeFragmentRedirect(res, this.getBadgeImageURL(), 301);
                 });
 
         app.on("installation.created", (ctx: Context<"installation.created">) => {
@@ -190,7 +191,7 @@ export class GithubApp {
                         const slug = data.data.slug;
 
                         const state = req.query.state;
-                        res.redirect(`https://github.com/apps/${slug}/installations/new?state=${state}`);
+                        safeFragmentRedirect(res, `https://github.com/apps/${slug}/installations/new?state=${state}`);
                     } catch (error) {
                         console.error(error, { error });
                         res.status(500).send("GitHub App is not configured.");
@@ -213,12 +214,12 @@ export class GithubApp {
                                 "message=payload:" + Buffer.from(JSON.stringify(payload), "utf-8").toString("base64"),
                         })
                         .toString();
-                    res.redirect(url);
+                    safeFragmentRedirect(res, url);
                 } else {
                     const url = this.config.hostUrl
                         .with({ pathname: "install-github-app", search: `installation_id=${installationId}` })
                         .toString();
-                    res.redirect(url);
+                    safeFragmentRedirect(res, url);
                 }
             });
     }
diff --git a/components/server/src/user/newsletter-subscription-controller.ts b/components/server/src/user/newsletter-subscription-controller.ts
index 4eaeae7792c453..9cb1adad808858 100644
--- a/components/server/src/user/newsletter-subscription-controller.ts
+++ b/components/server/src/user/newsletter-subscription-controller.ts
@@ -8,6 +8,7 @@ import express from "express";
 import { inject, injectable } from "inversify";
 import { UserDB } from "@gitpod/gitpod-db/lib";
 import { IAnalyticsWriter } from "@gitpod/gitpod-protocol/lib/analytics";
+import { safeFragmentRedirect } from "../express-util";
 
 @injectable()
 export class NewsletterSubscriptionController {
@@ -72,7 +73,7 @@ export class NewsletterSubscriptionController {
                             [newsletterProperties[newsletterType].property]: true,
                         },
                     });
-                    res.redirect(successPageUrl);
+                    safeFragmentRedirect(res, successPageUrl);
                 } else {
                     this.analytics.identify({
                         userId: email,
@@ -80,7 +81,7 @@ export class NewsletterSubscriptionController {
                             [newsletterProperties[newsletterType].property]: true,
                         },
                     });
-                    res.redirect(successPageUrl);
+                    safeFragmentRedirect(res, successPageUrl);
                 }
             } catch (error) {
                 res.send({
diff --git a/components/server/src/user/user-controller.ts b/components/server/src/user/user-controller.ts
index 558c9c86c87365..8ded6409126ee1 100644
--- a/components/server/src/user/user-controller.ts
+++ b/components/server/src/user/user-controller.ts
@@ -17,7 +17,13 @@ import { Permission } from "@gitpod/gitpod-protocol/lib/permission";
 import { parseWorkspaceIdFromHostname } from "@gitpod/gitpod-protocol/lib/util/parse-workspace-id";
 import { SessionHandler } from "../session-handler";
 import { URL } from "url";
-import { getRequestingClientInfo } from "../express-util";
+import {
+    getRequestingClientInfo,
+    validateAuthorizeReturnToUrl,
+    validateLoginReturnToUrl,
+    safeFragmentRedirect,
+    getSafeReturnToParam,
+} from "../express-util";
 import { GitpodToken, GitpodTokenType, User } from "@gitpod/gitpod-protocol";
 import { HostContextProvider } from "../auth/host-context-provider";
 import { reportJWTCookieIssued } from "../prometheus-metrics";
@@ -37,7 +43,7 @@ import { UserService } from "./user-service";
 import { WorkspaceService } from "../workspace/workspace-service";
 import { runWithSubjectId } from "../util/request-context";
 import { SubjectId } from "../auth/subject-id";
-import { TrustedValue } from "@gitpod/gitpod-protocol/lib/util/scrubbing";
+import { getFeatureFlagEnableStrictAuthorizeReturnTo } from "../util/featureflags";
 
 export const ServerFactory = Symbol("ServerFactory");
 export type ServerFactory = () => GitpodServerImpl;
@@ -65,8 +71,8 @@ export class UserController {
             if (req.isAuthenticated()) {
                 log.info("(Auth) User is already authenticated.", { "login-flow": true });
                 // redirect immediately
-                const redirectTo = this.getSafeReturnToParam(req) || this.config.hostUrl.asDashboard().toString();
-                res.redirect(redirectTo);
+                const redirectTo = this.ensureSafeReturnToParam(req) || this.config.hostUrl.asDashboard().toString();
+                safeFragmentRedirect(res, redirectTo);
                 return;
             }
             const clientInfo = getRequestingClientInfo(req);
@@ -81,11 +87,11 @@ export class UserController {
             // If there is no known auth host, we need to ask the user
             const redirectToLoginPage = !req.query.host;
             if (redirectToLoginPage) {
-                const returnTo = this.getSafeReturnToParam(req);
+                const returnTo = this.ensureSafeReturnToParam(req);
                 const search = returnTo ? `returnTo=${returnTo}` : "";
                 const loginPageUrl = this.config.hostUrl.asLogin().with({ search }).toString();
                 log.info(`Redirecting to login ${loginPageUrl}`);
-                res.redirect(loginPageUrl);
+                safeFragmentRedirect(res, loginPageUrl);
                 return;
             }
 
@@ -185,12 +191,12 @@ export class UserController {
                 // Redirect the admin-user to the Org Settings page.
                 // The dashboard is expected to render the Onboading flow instead of the regular view,
                 // but if the browser is reloaded after completion of the flow, it should be fine to see the settings.
-                res.redirect("/settings", 307);
+                safeFragmentRedirect(res, "/settings", 307);
             } catch (e) {
                 log.error("Failed to sign-in as admin with OTS Token", e);
 
                 // Always redirect to an expired token page if there's an error
-                res.redirect("/error/expired-ots", 307);
+                safeFragmentRedirect(res, "/error/expired-ots", 307);
                 return;
             }
         });
@@ -215,10 +221,10 @@ export class UserController {
                 reportJWTCookieIssued();
 
                 // If returnTo was passed and it's safe, redirect to it
-                const returnTo = this.getSafeReturnToParam(req);
+                const returnTo = this.ensureSafeReturnToParam(req);
                 if (returnTo) {
                     log.info(`Redirecting after OTS login ${returnTo}`);
-                    res.redirect(returnTo);
+                    safeFragmentRedirect(res, returnTo);
                     return;
                 }
 
@@ -236,7 +242,15 @@ export class UserController {
                 return;
             }
             this.ensureSafeReturnToParam(req);
-            this.authenticator.authorize(req, res, next).catch((err) => log.error("authenticator.authorize", err));
+            this.ensureSafeReturnToParamForAuthorize(req)
+                .then(() => {
+                    this.authenticator
+                        .authorize(req, res, next)
+                        .catch((err) => log.error("authenticator.authorize", err));
+                })
+                .catch((err) => {
+                    log.error("authenticator.authorize", err);
+                });
         });
         router.get("/deauthorize", (req: express.Request, res: express.Response, next: express.NextFunction) => {
             if (!User.is(req.user)) {
@@ -248,7 +262,15 @@ export class UserController {
                 return;
             }
             this.ensureSafeReturnToParam(req);
-            this.authenticator.deauthorize(req, res, next).catch((err) => log.error("authenticator.deauthorize", err));
+            this.ensureSafeReturnToParamForAuthorize(req)
+                .then(() => {
+                    this.authenticator
+                        .deauthorize(req, res, next)
+                        .catch((err) => log.error("authenticator.deauthorize", err));
+                })
+                .catch((err) => {
+                    log.error("authenticator.deauthorize", err);
+                });
         });
         router.get("/logout", async (req: express.Request, res: express.Response, next: express.NextFunction) => {
             const logContext = LogContext.from({ user: req.user, request: req });
@@ -271,7 +293,7 @@ export class UserController {
                 });
             }
 
-            const redirectToUrl = this.getSafeReturnToParam(req) || this.config.hostUrl.toString();
+            const redirectToUrl = this.ensureSafeReturnToParam(req) || this.config.hostUrl.toString();
 
             if (req.isAuthenticated()) {
                 req.logout();
@@ -282,7 +304,7 @@ export class UserController {
 
             // then redirect
             log.info(logContext, "(Logout) Redirecting...", { redirectToUrl, ...logPayload });
-            res.redirect(redirectToUrl);
+            safeFragmentRedirect(res, redirectToUrl);
         });
 
         router.get("/auth/jwt-cookie", this.sessionHandler.jwtSessionConvertor());
@@ -504,7 +526,7 @@ export class UserController {
                     otsExpirationTime.setMinutes(otsExpirationTime.getMinutes() + 2);
                     const ots = await this.otsServer.serve({}, token, otsExpirationTime);
 
-                    res.redirect(`http://${rt}/?ots=${encodeURI(ots.url)}`);
+                    safeFragmentRedirect(res, `http://${rt}/?ots=${encodeURI(ots.url)}`);
                 },
             );
         }
@@ -561,7 +583,7 @@ export class UserController {
     }
 
     protected async augmentLoginRequest(req: express.Request) {
-        const returnToURL = this.getSafeReturnToParam(req);
+        const returnToURL = this.ensureSafeReturnToParam(req);
         if (req.query.host) {
             // This login request points already to an auth host
             return;
@@ -603,32 +625,28 @@ export class UserController {
         }
     }
 
-    protected ensureSafeReturnToParam(req: express.Request) {
-        req.query.returnTo = this.getSafeReturnToParam(req);
-    }
-
-    protected urlStartsWith(url: string, prefixUrl: string): boolean {
-        prefixUrl += prefixUrl.endsWith("/") ? "" : "/";
-        return url.toLowerCase().startsWith(prefixUrl.toLowerCase());
+    protected ensureSafeReturnToParam(req: express.Request): string | undefined {
+        const returnTo = getSafeReturnToParam(req, (url) => validateLoginReturnToUrl(url, this.config.hostUrl));
+        req.query.returnTo = returnTo;
+        return returnTo;
     }
 
-    protected getSafeReturnToParam(req: express.Request) {
-        // @ts-ignore Type 'ParsedQs' is not assignable
-        const returnToURL: string | undefined = req.query.redirect || req.query.returnTo;
-        if (!returnToURL) {
-            log.debug("Empty redirect URL");
-            return;
-        }
-
-        if (
-            this.urlStartsWith(returnToURL, this.config.hostUrl.toString()) ||
-            this.urlStartsWith(returnToURL, "https://www.gitpod.io")
-        ) {
-            return returnToURL;
+    // TODO(gpl): Once we drop the feature flag, turn into the same form as above method.
+    protected async ensureSafeReturnToParamForAuthorize(req: express.Request): Promise<string | undefined> {
+        let returnTo = getSafeReturnToParam(req);
+        if (returnTo) {
+            const isStrictAuthorizeValidationEnabled = await getFeatureFlagEnableStrictAuthorizeReturnTo();
+            if (isStrictAuthorizeValidationEnabled) {
+                // Validate returnTo URL against allowlist for authorize API
+                if (!validateAuthorizeReturnToUrl(returnTo, this.config.hostUrl)) {
+                    log.warn(`Invalid returnTo URL rejected for authorize: ${returnTo}`, { "login-flow": true });
+                    returnTo = undefined;
+                }
+            }
         }
 
-        log.debug("The redirect URL does not match", { query: new TrustedValue(req.query).value });
-        return;
+        req.query.returnTo = returnTo;
+        return returnTo;
     }
 
     private createGitpodServer(user: User, resourceGuard: ResourceAccessGuard) {
diff --git a/components/server/src/util/featureflags.ts b/components/server/src/util/featureflags.ts
index aeec45cfe39339..d1264c7115a0c1 100644
--- a/components/server/src/util/featureflags.ts
+++ b/components/server/src/util/featureflags.ts
@@ -17,3 +17,19 @@ export async function getFeatureFlagEnableContextEnvVarValidation(userId: string
         user: { id: userId },
     });
 }
+
+/**
+ * Feature flag for enabling nonce validation in OAuth flows.
+ * Default: false (disabled)
+ */
+export async function getFeatureFlagEnableNonceValidation(): Promise<boolean> {
+    return getExperimentsClientForBackend().getValueAsync("enable_nonce_validation", false, {});
+}
+
+/**
+ * Feature flag for enabling strict returnTo validation for /api/authorize endpoint.
+ * Default: false (disabled, falls back to login validation)
+ */
+export async function getFeatureFlagEnableStrictAuthorizeReturnTo(): Promise<boolean> {
+    return getExperimentsClientForBackend().getValueAsync("enable_strict_authorize_return_to", false, {});
+}
diff --git a/components/server/src/workspace/headless-log-controller.ts b/components/server/src/workspace/headless-log-controller.ts
index b6aab3455caa98..a02a3f9e18e52a 100644
--- a/components/server/src/workspace/headless-log-controller.ts
+++ b/components/server/src/workspace/headless-log-controller.ts
@@ -15,6 +15,7 @@ import {
     WorkspaceInstance,
 } from "@gitpod/gitpod-protocol";
 import { log, LogContext } from "@gitpod/gitpod-protocol/lib/util/logging";
+import { safeFragmentRedirect } from "../express-util";
 import {
     CompositeResourceAccessGuard,
     OwnerResourceGuard,
@@ -252,7 +253,7 @@ export class HeadlessLogController {
                             );
                         });
                         if (redirect) {
-                            res.redirect(302, redirect.taskUrl);
+                            safeFragmentRedirect(res, redirect.taskUrl, 302);
                             return;
                         }
 
diff --git a/memory-bank/components/server.md b/memory-bank/components/server.md
index 24fdc5cb548b47..e154aa145ddf19 100644
--- a/memory-bank/components/server.md
+++ b/memory-bank/components/server.md
@@ -117,6 +117,7 @@ The Server integrates with:
 - Implements proper error handling and logging
 - Uses HTTPS for secure communication
 - Manages sensitive data securely
+- Uses `safeFragmentRedirect()` for all HTTP redirects to prevent OAuth token inheritance attacks
 
 ## Common Usage Patterns