TagMicrosoft Office 365

It looks like OWA doesn’t support mailbox cleanup anymore. That means if you have a lot of email floating around from the last 10 or more years, you’re out of luck. You need to manually find and delete them. Retention policies are also a bear to get working.

Microsoft: Why are you making this hard?


I sometimes get to a point where I question a lot of what I do and what matters to me. Sometimes it’s because of simple things, like a broken tool, or a frustrating problem. Sometimes it’s more of a philosophy problem, where I question how I feel about something and if I should change my ideas or mannerisms behind some action.

Lately, it’s been a little of both. I use an iPhone, Apple Music, iCloud (storage, etc), Office 365, and probably other tools and services that would be considered “non-free” in the “libre” sense. This has lead to me thinking about what I actually want out of computing. It’s such a thorny question, because there are so many comfortable choices that I’m in, that upending them would probably throw my life (and my family’s) into temporary turmoil.

For instance: Office 365. I pay for just the Exchange Online component, because I don’t need the actual Office suite as we (my family) get it free from my school and other organizations that we’re associated with. Exchange Online has been fine from a end-user perspective. Very rarely do I have any real issues to speak of, other than paying for it. My real problem here is that it’s a very proprietary platform, and because of that, it’s moderately difficult to get out of and to connect to with free-software tools. The IMAP support is… functional, but the contacts and calendars are tied down.

Similarly, I have lots of Apple devices and services. Like Office 365, I don’t have any complaints, per se, it’s just that they’re extremely proprietary and that means getting out of the ecosystem is difficult, and like above, connecting using free-software tools is straight up impossible.

The reason I have these things in the first place is that my family, who don’t hold my free-software ideals, want/need access to reliable tools they can use from multiple places. This is not an unreasonable request, and is one that can be solved with enough time, free-software, capital and expertise. Unfortunately, I’m not willing or able to host all of that, or even administer it. I don’t have the time, and I certainly don’t have the specific expertise to do all of it. Hence the current implementation.

Balance between freedom, convenience and cost is a tricky one. While I’d personally like to model myself more in line with the FSF’s computing ideals. The problem is that I have family members that I have to support as well. I’d also like to move them toward more free-software systems. While I recognize their choice in platforms is their own, I also get to say what I will and will not support (kind of, family is so complicated).

I don’t have any kind of resolution for this, I’m still trying to figure out what kind of path I want to take. Is pragmatism the smarter choice? Idealism feels right, but is massively more difficult to implement. There is probably a good middle of the road, but I don’t know if I’m on it. Maybe it doesn’t matter?

What should I do?

Featured Image

“Ugh, a Mac”, by Joe Wilcox – License: CC BY-NC-SA 2.0

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