diff --git a/app/server/lib/Authorizer.ts b/app/server/lib/Authorizer.ts
index 13c29cdd..3637d17c 100644
--- a/app/server/lib/Authorizer.ts
+++ b/app/server/lib/Authorizer.ts
@@ -6,7 +6,7 @@ import {canEdit, canView, getWeakestRole, Role} from 'app/common/roles';
 import {Document} from 'app/gen-server/entity/Document';
 import {User} from 'app/gen-server/entity/User';
 import {DocAuthKey, DocAuthResult, HomeDBManager} from 'app/gen-server/lib/HomeDBManager';
-import {getSessionProfiles, getSessionUser, getSignInStatus, linkOrgWithEmail, SessionObj,
+import {forceSessionChange, getSessionProfiles, getSessionUser, getSignInStatus, linkOrgWithEmail, SessionObj,
         SessionUserObj, SignInStatus} from 'app/server/lib/BrowserSession';
 import {RequestWithOrg} from 'app/server/lib/extractOrg';
 import {COOKIE_MAX_AGE, getAllowedOrgForSessionID, getCookieDomain,
@@ -188,6 +188,7 @@ export async function addRequestUser(dbManager: HomeDBManager, permitStore: IPer
     // If we haven't set a maxAge yet, set it now.
     if (session && session.cookie && !session.cookie.maxAge) {
       session.cookie.maxAge = COOKIE_MAX_AGE;
+      forceSessionChange(session);
     }
 
     // See if we have a profile linked with the active organization already.
@@ -262,7 +263,7 @@ export function redirectToLoginUnconditionally(
   return async (req: Request, resp: Response, next: NextFunction) => {
     const mreq = req as RequestWithLogin;
     // Tell express-session to set our cookie: session handling post-login relies on it.
-    mreq.session.alive = true;
+    forceSessionChange(mreq.session);
 
     // Redirect to sign up if it doesn't look like the user has ever logged in (on
     // this browser)  After logging in, `users` will be set in the session.  Even after
@@ -294,8 +295,9 @@ export function redirectToLogin(
                                                                  getSignUpRedirectUrl);
   return async (req: Request, resp: Response, next: NextFunction) => {
     const mreq = req as RequestWithLogin;
-    mreq.session.alive = true;  // This will ensure that express-session will set our cookie
-                                // if it hasn't already - we'll need it if we redirect.
+    // This will ensure that express-session will set our cookie if it hasn't already -
+    // we'll need it if we redirect.
+    forceSessionChange(mreq.session);
     if (mreq.userIsAuthorized) { return next(); }
 
     try {
diff --git a/app/server/lib/BrowserSession.ts b/app/server/lib/BrowserSession.ts
index 50926325..68df1bb6 100644
--- a/app/server/lib/BrowserSession.ts
+++ b/app/server/lib/BrowserSession.ts
@@ -45,8 +45,13 @@ export interface SessionObj {
   // This is optional since the session may already exist.
   orgToUser?: {[org: string]: number};
 
-  // This gets set to encourage express-session to set a cookie.
-  alive?: boolean;
+  // This gets set to encourage express-session to set a cookie. Was a boolean in the past.
+  alive?: number;
+}
+
+// Make an artificial change to a session to encourage express-session to set a cookie.
+export function forceSessionChange(session: SessionObj) {
+  session.alive = Number(session.alive || 0) + 1;
 }
 
 // We expose a sign-in status in a cookie accessible to all subdomains, to assist in auto-signin.
diff --git a/app/server/lib/FlexServer.ts b/app/server/lib/FlexServer.ts
index d35fc509..310b6b58 100644
--- a/app/server/lib/FlexServer.ts
+++ b/app/server/lib/FlexServer.ts
@@ -21,6 +21,7 @@ import {attachAppEndpoint} from 'app/server/lib/AppEndpoint';
 import {addRequestUser, getUser, getUserId, isSingleUserMode,
         redirectToLoginUnconditionally} from 'app/server/lib/Authorizer';
 import {redirectToLogin, RequestWithLogin, signInStatusMiddleware} from 'app/server/lib/Authorizer';
+import {forceSessionChange} from 'app/server/lib/BrowserSession';
 import * as Comm from 'app/server/lib/Comm';
 import {create} from 'app/server/lib/create';
 import {addDiscourseConnectEndpoints} from 'app/server/lib/DiscourseConnect';
@@ -593,7 +594,8 @@ export class FlexServer implements GristServer {
 
     // Create an endpoint for making cookies during testing.
     this.app.get('/test/session', async (req, res) => {
-      (req as any).session.alive = true;
+      const mreq = req as RequestWithLogin;
+      forceSessionChange(mreq.session);
       res.status(200).send(`Grist ${this.name} is alive and is interested in you.`);
     });
 
@@ -800,9 +802,9 @@ export class FlexServer implements GristServer {
       this: FlexServer, signUp: boolean|null, req: express.Request, resp: express.Response,
     ) {
       const mreq = req as RequestWithLogin;
-      mreq.session.alive = true;  // This will ensure that express-session will set our cookie
-                                  // if it hasn't already - we'll need it when we come back
-                                  // from Cognito.
+      // This will ensure that express-session will set our cookie if it hasn't already -
+      // we'll need it when we come back from Cognito.
+      forceSessionChange(mreq.session);
       // Redirect to "/" on our requested hostname (in test env, this will redirect further)
       const next = req.protocol + '://' + req.get('host') + '/';
       if (signUp === null) {