Keith Weaver
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keithmweaver.com
Keith Weaver
@keithmweaver.com
Christian, husband, & father. Passionate about security. #Microsoft365 #MicrosoftTeams
Reposted by Keith Weaver
Oof, the sycophancy problem in LLM's + triggering on any irrelevant details you feed them, recently led a P2 problem call down the wrong pathing for hours.

The chatbot is never going to TELL you to step back and ask if this entire inquiry is irrelevant to larger goal.

This is your moat. It's mine.
August 29, 2025 at 2:59 AM
Reposted by Keith Weaver
Someone smarter than me described customer data as toxic waste. Whatever you can't destroy must be buried deep, with heavy security.
July 26, 2025 at 1:02 AM
Reposted by Keith Weaver
Part of the job as a cybersecurity professional is in fact arguing to purge and not log information about your customers.

Data is not oil. It's risk.
July 26, 2025 at 12:56 AM
Having an issue with Windows 365/AVD Entra SSO to session hosts and web sign-in for RDP. All users receive this error when trying to connect.
Sign-in error code: 500032
Failure reason: Cannot find signing certificate/private key to issue a certificate.
March 4, 2025 at 3:08 AM
Reposted by Keith Weaver
If you want to work in security, just know up front it's a thankless job most of the time.

1. People do not understand why it's necessary
2. People will complain about it all the time
3. People will not see the value in your job, unless you get popped, then they will blame you anyway
February 27, 2025 at 5:47 AM