Viss, (edited )
@Viss@mastodon.social avatar

how badly does azure have to mess up before people go back to self-hosting exchange?

how bad does outlook have to get before people move off of exchange for mail/calendaring?

Asymmetricblue,
@Asymmetricblue@mastodon.social avatar

@Viss And when you say “Outlook”, do you mean the web based version (i.e. Hotmail, not owa), the Windows version, the mobile version, etc? All distinctly different things with the same name.

I’m not sure where people would go though. The competition all seems it’s own kind of horrible.

ocdtrekkie,
@ocdtrekkie@mastodon.social avatar

@Viss On one hand, I consider moving back on-prem inevitable and mostly laugh at people who do expensive cloud migration projects anywhere on-prem remains an option.

On the other hand, I've spent enough time on Exchange migration to understand why people do.

#exchange

Viss,
@Viss@mastodon.social avatar

@ocdtrekkie ive had to manage exchange, although not in quite some time, but given the options today, its entirely possible to completely insulate exchange from the internet and still have it able to talk to outlook and relay mail.

its work, sure, and that seems to be the crux of it - nobody feels like doing the work

ocdtrekkie,
@ocdtrekkie@mastodon.social avatar

@Viss I feel like most Exchange (and Windows Server, for that matter) problems can be boiled down to "Microsoft would make this suck less but they want you to go to 365/Azure and moved all the engineers there".

Viss,
@Viss@mastodon.social avatar

@ocdtrekkie you dont even have to feel it - theyve flat out said as much.

they are intentionally making life miserable for exchange admins in an effort to make them go to azure, only then to skimp on their own security and promises.

they're even trying to make windows itself as an os 'a subscription paid monthly'.

ocdtrekkie,
@ocdtrekkie@mastodon.social avatar

@Viss Monthly pricing for enterprise software doesn't bother me nearly as much as taking it off-site does. Arguably if they are going to ship monthly updates to it, the subscription is more than just rent-seeking.

But making my network vulnerable to an additional several thousand Microsoft employees being engineered in addition to my own is a big nonstarter.

Viss,
@Viss@mastodon.social avatar
ocdtrekkie,
@ocdtrekkie@mastodon.social avatar

@Viss Yeah I'm aware, the issue there for me is "in the cloud". The on-prem Exchange version coming in 2025 is supposed to be on-prem software but sold as a subscription. (A model I would not be shocked to see Windows Server also pick up at some point.)

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