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You can try and create a rule in Office 365 that explicitly allows the welcome email. You can resend the welcome email.
User pools are a good way for a few users to test the AppStream 2.0 environment. As a best practice, we recommend that customers use SAML 2.0. We have documentation on using Azure AD and many others. If you don't already have a SSO provider, consider using AWS Single Sign-On.
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If you have your own identity provider (for example, you are a software vendor) that isn't SAML2.0 compliant, you can use AppStream 2.0's APIs to integrate with your web portal. AppStream 2.0 has a workshop that outlines this workflow: https://aws.amazon.com/appstream2/getting-started/isv-workshops/. Specifically "Create an online software trial with AppStream 2.0" - you'll just want to gate it by your auth instead of the open access the workshop has.