A constant recurring issue that I often encounter with many of the companies I work with is that their end users find it annoying that they often have to log in multiple times when they work in Office 365. This also applies to those who have just started using Microsoft Teams.
I want user adoption to work as smoothly as possible and I think one of the key success factors is that the end users should experience a seamlessness between Office 365 services / workloads. In order to accomplish this, it is important that you initially always begin to ensure that all end-users have the necessary Office 365 URLs and required Trusted sites rolled out on their clients.
Have any of you experienced the same challenge and, if so, how do you usually handle / solve this?
A step up from this is using Domain Hybrid Join, and or if possible just joining the machines to Azure AD. This allows true SSO from my testing and works really well and nearly no prompts. It even lets you use Windows Hello / TPM chip on your machine when two factor is enabled to not have to "respond" or provide codes when logging in to resources when you are on a Azure / Hyrid joined machine.