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Add “Reauthentication After Risk Events” section and cross-links in Authentication, Session Management, and MFA cheat sheets #1709

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@pankajtaneja5 pankajtaneja5 commented Jun 20, 2025

Summary

This PR introduces a new Reauthentication After Risk Events section in the Authentication Cheat Sheet and adds cross-links to it from two related documents:

  1. Session_Management_Cheat_Sheet.md

    • Under Session ID Life Cycle, adds a link pointing to the new reauthentication guidance.
  2. Multifactor_Authentication_Cheat_Sheet.md

    • In the Adaptive or Risk-Based Authentication section, adds a link to the same reauthentication guidance.
  3. Authentication_Cheat_Sheet.md

    • Adds the full Reauthentication After Risk Events section, detailing when and how to trigger reauthentication after high-risk activities (e.g., password resets, suspicious logins, account recovery).

Motivation

Developers often need to know when to require users to reauthenticate following critical security events. By:

  • Centralizing best practices in the Authentication Cheat Sheet, and
  • Surface-linking that section directly from session-management and MFA contexts,

we make it easy to discover and implement consistent reauthentication flows across applications.

Changes

  • Authentication_Cheat_Sheet.md

    • Add new Reauthentication After Risk Events section with guidance on triggers, mechanisms, and implementation recommendations.
  • Session_Management_Cheat_Sheet.md

    • Insert cross-link under Session ID Life Cycle to the new reauthentication section.
  • Multifactor_Authentication_Cheat_Sheet.md

    • Insert cross-link in Adaptive or Risk-Based Authentication section to the same reauthentication section.

Next Steps

  • Once merged, readers will be able to jump from session- and MFA-focused guidance straight to the detailed reauthentication best practices.
  • Feedback welcome on link placement, section content, or further integrations!

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This PR fixes issue #1694 .

Thank you again for your contribution 😃

@pankajtaneja5 pankajtaneja5 force-pushed the reauthentication-risk-events branch from f2caa95 to 3117b65 Compare June 20, 2025 22:23
@pankajtaneja5 pankajtaneja5 force-pushed the reauthentication-risk-events branch from 3117b65 to 48c7647 Compare June 20, 2025 22:25
@pankajtaneja5 pankajtaneja5 marked this pull request as ready for review June 20, 2025 22:26
@kwwall
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kwwall commented Jun 21, 2025

Just ran into this and thought it would be worth mentioning here as a cautionary tale: https://tailscale.com/blog/frequent-reauth-security?lid=5wso20mx4knj

szh
szh previously approved these changes Jun 24, 2025
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Love this work, amazing job. LGTM!

@szh szh linked an issue Jun 24, 2025 that may be closed by this pull request
@pankajtaneja5
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Thanks for the suggestion, @kwwall! I’ve added the Tailscale post under Additional Resources. Could you please take another look when you get a chance?

@szh can you please review again!

Also tagging @mackowski and @jmanico for review. Thanks!

jmanico
jmanico previously approved these changes Jun 25, 2025
@pankajtaneja5 pankajtaneja5 requested a review from mackowski June 26, 2025 13:33
@pankajtaneja5
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Hi @mackowski, thanks again for your review! I’ve removed the legacy V1 contributor entry and fixed the cross-sheet link—could you please take another look and re-approve when you have a moment?

Also, since @kwwall is on hiatus until the end of June, could someone with admin rights please dismiss the pending review request from @kwwall so we can merge as soon as we have two active approvals? Thanks everyone! 🙏

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New CS proposal: Reauthentication After Risk Events
6 participants