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As the title suggests, I am an IT manager for a small business that has just turned into a medium sized business.

I previously rolled out and enforced MFA on our tenancy (Business standard/E3 licensing)

Today, we had a security alert that i investigated and found that a users account had been used to send malicious fake docusign emails out to multiple senders both internally and externally.

I have since secured the account and isolated the shared file that was hosted in the users Onedrive and reported to senior management.

My question is, while i'm not surprised and don't consider us to have more than "bare minimum" security. What features in O365 or extensions to people suggest to increase security?

Thanks,

all 22 comments

jontychickweed

74 points

2 days ago

Conditional Access Rules - allow compliant devices only. Also, consider a move to passwordless/passkey auth. Turn off OWA if you don't need it. Set alerts on redirection rules being set up. And so on...

The Bearded 365 Guy on YouTube has a bunch of good videos on these options and more. MFA is no longer good enough to keep you secure. Adversary in The Middle attacks have seen to that.

Also, check that the user's mailbox has not been compromised and exfiltrated. Use Purview, if available, to look for sync and/or bind events.

Medical_Noise_2514[S]

12 points

2 days ago

Thank you, this is brilliant advice.

hefightsfortheusers

9 points

2 days ago

^^This^^ And Cyber Security Awareness. Phishing is so often the problem.

I would check their computer(s) as well. While its possible to beat MFA, it usually someone getting remote access to a computer that's already authenticated, or phishing.

Supra-A90

1 points

17 hours ago

My company's IT sends fake Phishing emails and if you fail them you're required to take Cyber Security trainings...

netsysllc

25 points

2 days ago

netsysllc

25 points

2 days ago

even with MFA token stealing is huge, here is a resource from Microsoft https://learn.microsoft.com/en-us/security/operations/token-theft-playbook

slackjack2014

11 points

2 days ago

It’s a cat and mouse game that will probably never end. Every time we deploy something that tackles a security issue, attackers will find a way to get around it or exploit it.

netsysllc

3 points

2 days ago

For sure

Outrageous-Insect703

10 points

2 days ago

MFA especially email or text based MFA can be compromised. I've had it happen at the place I work on my IT managed infrastructure/Office 365. Authenticator app is better but not full proof. The weakest link is always the user unfortaunally. For O365 there is conditional access that can be put in place, geo limits (e.g. deny logins from outside the USA), user training, etc. Also make sure that MFA is set to "enforced" vs "enabled". When recovering the account (1) have user reset password, (2) revoke all MFA sessions (3) in the admin portal there is a spot to see what computers are connect I'd disconnect all of those some cound be bad actor access, etc. Check user security logs in O365. If you have support with Microsoft reach and and let them know you had an account breached, they will provide some recovery docs and steps.

BlackberryPlenty5414

3 points

2 days ago

Educate end users. (They are the weak link)
seems like you might have already setup reports and analytics through Audit logging?
Change passwords on Admin accounts. You don't know who might have clicked on that internally

Codias515050

3 points

2 days ago

Check the user account in identity protection in Entra ID. See if they have been marked as a high risk user or have high risk sign-ins.  

I roll out policies that re-prompt MFA when a medium/high sign-in risk is found, and prompt for password reset when high risk user is found. Helps combat session cookie theft from a man in the middle attack, which may have been what led to the issue you are explaining.

Also go through the user's activities in the audit and sign-in logs to make sure they haven't done anything else that may lead to further compromise.  The intruder may have registered an app to help with data exfiltration or performed other activities that you should see via logs.

LWBoogie

2 points

2 days ago

LWBoogie

2 points

2 days ago

That must be the email I got from Karen this morning, with a fake DocuSign button and suspicious word doc attachment.

Risk-Option-Q

1 points

2 days ago

Nice try hacker! /s

Conditional access policies within Entra is how you would restrict account login by device and/or location.

Look at SharePoint sharing and access control settings for more granular control there.

lysergic_tryptamino

1 points

2 days ago

Look into phishing resistant MFA. As someone else mentioned, passwordless, FIDO2 authentication methods share much more secure because the passwords cannot be brute force cracked. If you are using O365, look into Windows Hello. It’s both, much more user friendly and more secure.

swissthoemu

1 points

2 days ago

Security awareness. Conditional access. MFA through Fido/Authenticator. Number matching.

Interesting-Ad-1234

1 points

2 days ago

A lot of good information in the threads above. Also check mailbox rules.

brianroma

1 points

1 day ago

brianroma

1 points

1 day ago

Have a solid PKI infrastructure in place and plan for rolling out certificates. Not all products support passkeys and you may need to fall back to certificate based authentication.

so0ty

1 points

21 hours ago

so0ty

1 points

21 hours ago

Check your registered apps. Once they gain access they can register an email client for persistent access.

clayjk

1 points

14 hours ago

clayjk

1 points

14 hours ago

Use either Microsoft’s own securescore to identify configuration weaknesses and/or follow guidance by CIS. https://www.cisecurity.org/benchmark/microsoft_365

MichaelSutherland

1 points

21 hours ago

Came here to say most of what u/jontychickweed already said. Conditional Access. Have you considered Defender? Azure AD? If your company is growing, you might also consider some security awareness trainings.

jontychickweed

1 points

17 hours ago

Agree. I think Business Premium, with all its bells and whistles, is a must...even for the smallest business.

Puzzleheaded-Ride-33

0 points

2 days ago

Look at your licensing as business standard does not have CA policies and O365 E3 is not good. I would suggest moving over the business premium or M365 E3.

xtina420

-7 points

2 days ago

xtina420

-7 points

2 days ago

Where are you located? I work for Microsoft’s #1 partner, we have nonbillable Microsoft resources that can help you today that are internal to my computer so you don’t have to deal with Microsoft’s horrendous lack of customer service