diff --git a/packages/server/src/enterprise/middleware/passport/index.ts b/packages/server/src/enterprise/middleware/passport/index.ts
index e5cd8cb79..3055b7885 100644
--- a/packages/server/src/enterprise/middleware/passport/index.ts
+++ b/packages/server/src/enterprise/middleware/passport/index.ts
@@ -259,11 +259,18 @@ export const initializeJwtCookieMiddleware = async (app: express.Application, id
                 if (identityManager.isEnterprise() && !identityManager.isLicenseValid()) {
                     return res.status(401).json({ redirectUrl: '/license-expired' })
                 }
-                req.login(user, { session: true }, async (error) => {
-                    if (error) {
-                        return next ? next(error) : res.status(401).json(error)
+
+                req.session.regenerate((regenerateErr) => {
+                    if (regenerateErr) {
+                        return next ? next(regenerateErr) : res.status(500).json({ message: 'Session regeneration failed' })
                     }
-                    return setTokenOrCookies(res, user, true, req)
+
+                    req.login(user, { session: true }, async (error) => {
+                        if (error) {
+                            return next ? next(error) : res.status(401).json(error)
+                        }
+                        return setTokenOrCookies(res, user, true, req)
+                    })
                 })
             } catch (error: any) {
                 return next ? next(error) : res.status(401).json(error)
diff --git a/packages/server/src/enterprise/sso/Auth0SSO.ts b/packages/server/src/enterprise/sso/Auth0SSO.ts
index d338feede..07a551f06 100644
--- a/packages/server/src/enterprise/sso/Auth0SSO.ts
+++ b/packages/server/src/enterprise/sso/Auth0SSO.ts
@@ -92,9 +92,16 @@ class Auth0SSO extends SSOBase {
                         }
                         return next ? next(err) : res.status(401).json(err)
                     }
-                    req.login(user, { session: true }, async (error) => {
-                        if (error) return next ? next(error) : res.status(401).json(error)
-                        return setTokenOrCookies(res, user, true, req, true, true)
+
+                    req.session.regenerate((regenerateErr) => {
+                        if (regenerateErr) {
+                            return next ? next(regenerateErr) : res.status(500).json({ message: 'Session regeneration failed' })
+                        }
+
+                        req.login(user, { session: true }, async (error) => {
+                            if (error) return next ? next(error) : res.status(401).json(error)
+                            return setTokenOrCookies(res, user, true, req, true, true)
+                        })
                     })
                 } catch (error) {
                     return next ? next(error) : res.status(401).json(error)
diff --git a/packages/server/src/enterprise/sso/AzureSSO.ts b/packages/server/src/enterprise/sso/AzureSSO.ts
index 4e5781f50..35c6d744f 100644
--- a/packages/server/src/enterprise/sso/AzureSSO.ts
+++ b/packages/server/src/enterprise/sso/AzureSSO.ts
@@ -48,9 +48,16 @@ class AzureSSO extends SSOBase {
                         }
                         return next ? next(err) : res.status(401).json(err)
                     }
-                    req.login(user, { session: true }, async (error) => {
-                        if (error) return next ? next(error) : res.status(401).json(error)
-                        return setTokenOrCookies(res, user, true, req, true, true)
+
+                    req.session.regenerate((regenerateErr) => {
+                        if (regenerateErr) {
+                            return next ? next(regenerateErr) : res.status(500).json({ message: 'Session regeneration failed' })
+                        }
+
+                        req.login(user, { session: true }, async (error) => {
+                            if (error) return next ? next(error) : res.status(401).json(error)
+                            return setTokenOrCookies(res, user, true, req, true, true)
+                        })
                     })
                 } catch (error) {
                     return next ? next(error) : res.status(401).json(error)
diff --git a/packages/server/src/enterprise/sso/GithubSSO.ts b/packages/server/src/enterprise/sso/GithubSSO.ts
index 11f5ad234..f52745ab0 100644
--- a/packages/server/src/enterprise/sso/GithubSSO.ts
+++ b/packages/server/src/enterprise/sso/GithubSSO.ts
@@ -81,9 +81,16 @@ class GithubSSO extends SSOBase {
                         }
                         return next ? next(err) : res.status(401).json(err)
                     }
-                    req.login(user, { session: true }, async (error) => {
-                        if (error) return next ? next(error) : res.status(401).json(error)
-                        return setTokenOrCookies(res, user, true, req, true, true)
+
+                    req.session.regenerate((regenerateErr) => {
+                        if (regenerateErr) {
+                            return next ? next(regenerateErr) : res.status(500).json({ message: 'Session regeneration failed' })
+                        }
+
+                        req.login(user, { session: true }, async (error) => {
+                            if (error) return next ? next(error) : res.status(401).json(error)
+                            return setTokenOrCookies(res, user, true, req, true, true)
+                        })
                     })
                 } catch (error) {
                     return next ? next(error) : res.status(401).json(error)
diff --git a/packages/server/src/enterprise/sso/GoogleSSO.ts b/packages/server/src/enterprise/sso/GoogleSSO.ts
index 8dd97cf09..a4e3ae8ab 100644
--- a/packages/server/src/enterprise/sso/GoogleSSO.ts
+++ b/packages/server/src/enterprise/sso/GoogleSSO.ts
@@ -97,9 +97,16 @@ class GoogleSSO extends SSOBase {
                         }
                         return next ? next(err) : res.status(401).json(err)
                     }
-                    req.login(user, { session: true }, async (error) => {
-                        if (error) return next ? next(error) : res.status(401).json(error)
-                        return setTokenOrCookies(res, user, true, req, true, true)
+
+                    req.session.regenerate((regenerateErr) => {
+                        if (regenerateErr) {
+                            return next ? next(regenerateErr) : res.status(500).json({ message: 'Session regeneration failed' })
+                        }
+
+                        req.login(user, { session: true }, async (error) => {
+                            if (error) return next ? next(error) : res.status(401).json(error)
+                            return setTokenOrCookies(res, user, true, req, true, true)
+                        })
                     })
                 } catch (error) {
                     return next ? next(error) : res.status(401).json(error)