Signing in multiple times every day

Question

Signing in multiple times every day

Andrew McCandless 0

Each day I have to sign in to my laptop using my office365 account, then to Outlook with the same account, then to my web browser with the same account, now to Onedrive with the same office365 account. The I use my phone and have to sign in to Outlook on it. This is clearly far, far too much.

I believe One single sign in should be enough and it then covers every application on that device.

Managing multiple client M365 accounts compounds this into dozens of 2FA requests every single day. The current authentication flow creates massive friction and severe MFA fatigue.

Surely if you sign in to the device once a day, that's enough?

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Answer 1

Heimerdinger 1,635 Independent Advisor

Hello @Andrew McCandless,

To help narrow down why your sign-in sessions are not being retained, could you please confirm the following?

Is your laptop Windows 10 or Windows 11, and is it managed by your organization?
Under Settings > Accounts > Access work or school, is your Microsoft 365 work account connected?
Does this happen every time you restart the device, or are you also signed out of Outlook, OneDrive, and your browser during the day?
Do other users in your organization experience the same repeated sign-in and MFA prompts?
Is your organization using Microsoft Entra Conditional Access, particularly any policies that configure sign-in frequency or session controls?
When you receive the MFA prompts, are they always for the same Microsoft 365 account, or mainly when switching between the different client Microsoft 365 accounts?

These details should help determine whether the repeated authentication is related to the device/account configuration, a Conditional Access policy, or the way the multiple Microsoft 365 accounts are being used.

Thank you again for your time and understanding. I really appreciate your patience, and I’m here to help. Looking forward to your response.        

Andrew McCandless 0 Reputation points

2026-11-10T12:14:33.5066667+00:00

Hi Heimerdinger,

Thank you for your interest. I sign into my laptop using my Microsoft 365 account, but then I still have to sign into Outlook, OneDrive, and Edge/Chrome separately using the exact same account and approve 2FA for every single one.

The thing is I have to do MFA well over a dozen times a day.

Is there a setting I can change locally or in the admin center to streamline this?
Heimerdinger 1,635 Reputation points Independent Advisor

2026-11-11T14:54:35.8133333+00:00
Hello @Andrew McCandless,

Thank you for clarifying. Since you are receiving MFA prompts more than a dozen times per day for the same account across Outlook, OneDrive, and your browser, I would recommend reviewing the authentication/session policies in the Microsoft Entra admin center.

If you are an administrator, go to:

Sign in to the Microsoft Entra admin center.

Go to Entra ID > Conditional Access > Policies.

Review policies applying to your account and Microsoft 365 applications.

Open the Conditional Access policies that apply to your account and check Session, particularly Sign-in frequency and Persistent browser session. A short sign-in frequency can cause users to be required to authenticate again more frequently.

I would not recommend disabling MFA. Instead, the goal would be to ensure that Single Sign-On (SSO) and session persistence are configured appropriately while keeping MFA enabled.

You can refer to this Microsoft documentation for the detailed configuration steps:

Configure adaptive session lifetime policies - Microsoft Entra ID | Microsoft Learn

I would also recommend checking Settings > Accounts > Access work or school on the laptop and confirming that your Microsoft 365 work account is properly connected. If the device is correctly registered or managed, Windows can use SSO to reduce unnecessary authentication prompts across Microsoft applications.

Thank you again for your time and understanding.