Hi Kris, Pleased to meet you, thank you for contacting Okta Support, my name is Alex, I'm happy to answer your question.

If you are planning to have for example, 4 Gmail accounts, you'd need to have 4 Gmail separate accounts in Okta, as the article below states in order for SSO to work, it must be a 1:1 authentication. Creating multiple accounts for a single user would complicate the intended functionality of single sign-on. Unfortunately, that means storing multiple usernames and passwords is not possible.

Your option however would be to create SWA, you do have the option of creating multiple integrations and assigning the user to each app under a different username. They would then click a different chiclet for each authentication.

Please see Okta's documentation below:

https://support.okta.com/help/s/article/Is-it-possible-to-have-multiple-usernames-associated-to-one-Okta-account-for-a-SAML-app?language=en_US

Thank you very much.