Cyberattacks against Microsoft 365 accounts have increased dramatically over the last few years, and attackers are now far more focused on exploiting stolen session tokens than guessing passwords. Because of this shift, one of the simplest and most effective steps organizations can take to strengthen their security posture is to implement a daily sign-in frequency policy through Conditional Access.

This policy requires users to reauthenticate once every 24 hours. It may seem like a small change, but its security impact is significant.

Executive Summary

Strengthening identity security has become one of the most effective ways to reduce cyber risk for Microsoft 365 tenants. A daily sign‑in requirement gives your organization a major security boost by limiting how long stolen tokens can be used and forcing Microsoft to re‑verify users every 24 hours. For employees, the impact is minimal — usually just a quick daily sign‑in or approval — but the protection gained is substantial. This policy is simple to deploy, provided it’s implemented carefully with proper safeguards such as a break‑glass admin account. It’s one of the highest‑value, lowest‑effort steps any company can take toward a stronger, more resilient security posture.

Why Daily Sign-In Improves Your Security Posture

1. It Limits the Damage from Stolen Tokens

Most modern attacks don’t rely on guessing passwords — they rely on stealing session cookies, refresh tokens, or OAuth tokens. Without a sign‑in frequency policy, these tokens can remain valid for weeks or even months.

A daily sign-in breaks that window down to just 24 hours.

Even if an attacker gets a token, the token will become useless the next day.

2. It Forces Azure AD to Re-Evaluate Risk Every Day

Each sign-in renewal triggers a complete Conditional Access evaluation:

• Device compliance
• User risk
• Location risk
• Sign-in behavior
• MFA requirements

This means compromised accounts, risky sign-ins, or suspicious locations are caught far earlier.

3. It Encourages Adoption of Passwordless Security

On properly configured Windows 10/11 or Windows 365 devices, Windows Hello for Business silently handles daily sign-ins.

Users unlock their PC with a PIN or biometrics, and the system handles the rest.

This is a strong push toward passwordless authentication — one of Microsoft’s most recommended security baselines.

The Real-World Downsides (And They’re Minor)

There are only two practical impacts on users:

1. Once-a-day sign‑in or approval on each device.
2. More frequent MFA approvals if users work from changing locations or devices.

Windows users with Windows Hello barely notice the change.

Mac and mobile users usually only tap “Approve” in the Authenticator app.

For most organizations, the inconvenience is measured in seconds — far outweighed by the security benefits.

Deployment Is Easy — But Must Be Done Carefully

Technically, implementing this policy is simple:

• One Conditional Access policy
• One setting: “Sign-in frequency = 1 day”

It can be rolled out globally in minutes.

Although conditional access can be deployed easily, many choose to leave it to an expert because if done incorrectly, Conditional Access can lock you out of your own tenant.

This is one area where caution is critical.

Always Follow These Safety Rules

• Create and test with a pilot group first
• Exclude emergency Break‑Glass accounts
• Ensure MFA methods and Conditional Access baselines are in place
• Document the fallback procedure before enforcement

A Break‑Glass account is a permanently excluded high‑priority admin account with strong passwords and strict protections. Without one, you run the risk of accidentally blocking global admin access — a mistake many companies only make once.

Real-World Impact and Statistics

According to Microsoft’s most recent identity security reports:

• More than 70% of account break-ins were achieved through a token replay attack  
• Accounts protected with daily reauthentication experience 80–95% fewer successful persistent attacks
• Most organizations see no measurable drop in productivity after the first week of rollout
• Windows Hello-enabled environments report fewer than 1 visible prompt per day per user

These Statistics show that implementing conditional access can greatly reduce your company’s risk of being compromised.

Other Conditional Access Policies to Consider

The daily sign-in policy is just one piece of a modern Zero Trust strategy.

Companies should also evaluate:

• MFA enforcement for all users
• Blocking legacy authentication
• Device-based access control
• Location-based restrictions
• App-specific access policies
• Token protection (Continuous Access Evaluation)
• Session controls for risky sign-ins

We’ll be publishing more deep-dive articles on these topics — keep an eye on our blog for details.

How Byte Solutions Can Help

Byte Solutions has been securing Microsoft 365 environments since the early days of BPOS and Office 365.

We specialize in:

• Designing safe and effective Conditional Access policies
• Implementing secure MFA and passwordless authentication
• Protecting against token theft and identity-based attacks
• Hardening tenants without disrupting users
• Responding to breach activity and securing compromised accounts

Whether you need a full security review or just want help implementing this policy safely, we’re here for you.

Contact Byte Solutions:

Phone: 561- 556-2000

Website: https://bytesolutions.com

Email: [email protected]

Let’s secure your Microsoft 365 environment — the right way.

Conditional Access – Q and A

Microsoft Entra Conditional Access: Zero Trust Policy Engine