Trick Dog Technology
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6-month staff aug engagement with an IAM SME who has experience in Okta to Entra ID migrations.

Project Overview

·         Current State: Okta SSO with approximately 80-95 applications

·         Timeline:

o    Okta contract expires March 2026 (hard deadline for migration completion)

o    Plan to button up project by late August 2025

o    Migration window: March to August 2025 (6 months)

 

Key Migration Components

1.    Applications: 80-95 apps to migrate from Okta to Microsoft Entra ID

2.    Groups: 100-120 groups to be converted to Entra dynamic groups

3.    SSO Functionality: Maintain all current SSO capabilities

 

Technical Considerations

·         Current Architecture:

o    On-prem AD serves as the source of truth for both Okta & O365

o    Entra ID Connect sync keeps on-prem AD and Entra in sync

o    Multiple Okta instances in use

o    Okta configured with custom rules for dynamic group management

o    API integrations currently in use

 

·         Challenges:

o    Some dynamic group functionality in Okta may not have direct equivalents in Entra ID

o    Previous integration issues between Okta & Azure AD required on-prem AD as intermediary

o    Some fields available in Okta may not be available in Entra ID

o    Significant tribal knowledge exists in current environment

 

Resource Requirements

·         Staff augmentation needed for:

o    Discovery with internal stakeholders

o    Pre-work and planning

o    Migration execution

o    Documentation development

·         Recommended: Full-time 6-month engagement (timeline already tight)

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