Outlook | Web | Outlook on the web for business | Sign in
Accessing Outlook on the web for business using organizational credentials.
Signing in multiple times every day
![](data:image/svg+xml, %3Csvg xmlns='http://www.w3.org/2000/svg' height='64' class='font-weight-bold' style='font: 600 30.11764705882353px "SegoeUI", Arial' width='64'%3E%3Ccircle fill='hsl(278.4, 14.000000000000002%, 36%)' cx='32' cy='32' r='32' /%3E%3Ctext x='50%25' y='55%25' dominant-baseline='middle' text-anchor='middle' fill='%23FFF' %3EAM%3C/text%3E%3C/svg%3E)
Andrew McCandless
0
Reputation points
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?
Outlook | Web | Outlook on the web for business | Sign in
-
![](data:image/svg+xml, %3Csvg xmlns='http://www.w3.org/2000/svg' height='64' class='font-weight-bold' style='font: 600 30.11764705882353px "SegoeUI", Arial' width='64'%3E%3Ccircle fill='hsl(54.400000000000006, 68%, 15%)' cx='32' cy='32' r='32' /%3E%3Ctext x='50%25' y='55%25' dominant-baseline='middle' text-anchor='middle' fill='%23FFF' %3EH%3C/text%3E%3C/svg%3E)
Heimerdinger 1,635 Reputation points Independent Advisor2026-11-10T11:52:50.05+00:00 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?
Sign in to comment
Sign in to answer