We moved from Okta to Entra ID six months ago, about 5,000 users. Overall, it's been a net positive, especially on cost and the Microsoft-integrated side. But it wasn't a simple swap.
The good first: The Azure AD Sync (now Entra Connect) setup was straightforward for our on-prem AD. The conditional access policies are powerful and, for our Microsoft-heavy stack (M365, Azure), everything just clicks. The cost savings were significant.
The rough parts were around non-Microsoft apps. The SAML/SSO configuration feels clunkier than Okta's polished dashboard. We also had to rebuild a lot of our lifecycle automation using PowerShell and the Graph API, which is more verbose. Some user provisioning workflows needed rethinking.
If your world is already Microsoft, it's a compelling move. Just budget more time for the tooling shift and API work than you think. The integration depth is worth it, but you lose some of Okta's app-store simplicity.