Basic Auth and Exchange Online – February 2020 Update

Greg Taylor - EXCHANGE— your time is precious so I'll be as succinct and terse as I can—apologies if the tone is too critical. Though I've worked with Exchange since v4 on NT, I do not think you have thought this communication, and especially your today's (28 Feb 2020) mass mailing titled "Basic Authentication Retirement - Updated Info" from the perspective of small and medium business users who subscribe to O365 but are disinterested in the inner workings of your service and its relationship to Azure AD. Your email has clearly been targeted at enterprises and you missed several key points:

• The report for checking authentication type mentioned at the start does not work for regular O365 Exchange users who only have a bundled free Azure AD—I am being told I need to purchase an enterprise Azure AD plan just to see which few of my colleagues may not be using OAuth. Won't happen.
• The steps to filter and find out what is modern auth and what is not in that report are much too complex—you need to make it super-clear who is running what and offer that report for free, if that matters to you. Better, forget about pushing this onto the customer, and sort it out on your end with a clear, customer-specific, targeted email showing who has what issue. A bit like AWS does when important change is imminent (RDS certs and auth come to mind in the last couple of months).
• Our organisation, like many of our business partners, *only* uses iOS devices with no Windows (Phones, tablets or PCs) in sight. I am afraid you have made a veiled comment that the native Apple iPhone and iPad app will stop working and you suggest people must switch to Microsoft Outlook, and anyway it is "better" as per the quoted Forrester paid-for marketing bit.
• Let me be clear: Microsoft Outlook is an inferior mail client on iOS devices in comparison to Apple's for many reasons: lack of both broad and deep integration into the rest of the iPhone and its apps (VIPs, notifications, reminders, Watch, data scanners in other apps, flagging, sync with desktop, iMessage, browsers to name just a few), poor iOS Calendar and Contacts integration causing duplication of data, unexpected loss of data/emails in its offline behaviour, too much reliance on constant connectivity, poor recovery from networking issues, poor authentication experience for customers who have both an organisational and a personal identity. Further, I, and many others, place much trust in the Apple ecosystem, preferring its apps to Microsoft's, notably because of Microsoft's privacy policy that does not, by default, stop its behavioural data collection/telemetry. In my industry, that is not acceptable.
• If by virtue of this authentication change you are trying to make people abandon the Apple mail client in iOS or on macOS desktop you will find us, and I am sure many other "long tail" customers switching to another email provider. That would also mean a loss to Teams and other O365 departments.

Perhaps you are doing everything fine and there is nothing for iOS users to be worried about and it was all just a poor piece of communication. I really hope that is the case! If so, please make that clear. Please send much less technical mail missives explaining that. Even better, segment your mailings by the type of the user: if they have a paid Azure AD which they use extensively, go ahead with the above, but for the rest of us, just give us a good, worry-free service. That'll buy you another 10 years of great many O365 subscriptions. Thank you.