3 ms·

I work at Microsoft 365, and yet my personal email is self-hosted Postfix and Dovecot. Why? Self-hosting email has been a part of my life since my high schoo

by neelc 5y ago

I *work* at Microsoft 365, and yet my personal email is self-hosted Postfix and Dovecot. Why? Self-hosting email has been a part of my life since my high school days, I have a sort of attachment to it. I know "you shouldn't run your own email", but to take that away from me after deeply wanting one is too much. In comparison, my job is just a job, I'm personally not too enthusiastic about it. I eventually plan to move to InfoSec or networking. While I *could* move my domain to M365, I simply won't for my personal email. I have ADHD, and don't want to make a mistake with two Outlook instances, one personal and one work. I'm a privacy nut, and want to separate my work and personal emails (Microsoft is better than Apple in this regard, but still). I also contribute to FOSS projects, and using Outlook is an impediment to projects whose mailing lists are based on inline posting, like the FreeBSD and Tor mailing lists. I hate Rainloop (which I switched to after nasty Roundcube attachment bugs), but at least I can inline post. (well, even at work I use Windows Mail instead of Outlook).

walrus01 5y ago
If I worked at Google or Microsoft (I don't, and am unlikely to ever do so) I absolutely would not use my own company's email services for my personal domains. Just for the general principle of keeping personal and work things compartmentalized.
- deleted 5y ago
  [deleted]
- neelc 5y ago
  I only joined Microsoft not because I wanted to, but because I really had to. I was a pretty die-hard *nix/self-hosting person for many years, and years of habits and conditioning can't be unwinded so easily. I use Git in a cmd even when doing code done in VS, since I'm used to doing it that way. The center of my digital world is a home server and not some cloud subscription service. For years I got angry when my dad wanted me not to use FreeBSD (or Linux) and just user Windows. We clashed with each other for this. I don't intend to stay with MSFT forever, nor do I want to. My parents pushed me towards staying, but I eventually want to work in a more *nix-environment. But then my dad is extremely change-averse when I'm not, well unless I am really in love with something (like FreeBSD or self-hosting) when I become more partial. I'm willing to use the less popular software for the sake of it in many cases (unless I literally can't) when my dad just sticks with the familiar. Heck, he can afford a uber high end Gaming PC with a Threadripper and RTX 3090 Ti, and he still uses an entry-level Core 2 Duo Dell desktop from 2009 which shipped with Vista (and was upgraded to W10 with an eBay key).
  - curt15 5y ago
    What beef did your dad have with FreeBSD or Linux?
u801e 5y ago
> I also contribute to FOSS projects, and using Outlook is an impediment to projects whose mailing lists are based on inline posting Based on my testing, that's not the only problem with using MS email clients on FOSS mailing lists. There's no concept of threading beyond the conversation view, and the client also mangles the email (wrapping or even sending base64 encoded test instead of the raw text. Even if your client sets the Message-ID header, MS servers will delete the header and replace it with their own.
- neelc 5y ago
  Yes, and that. I don't use Outlook/Exchange outside of work, frankly never did, but did read from time to time the issues with Outlook norms versus *nix email norms. I didn't need Outlook before I joined Microsoft, every student in my high school used their personal email (despite the school having an Exchange server), and my college used Google Workspace (I'm not that old TBH). I also lived entirely on FOSS software before joining MSFT, so to move every piece of personal self-hosted infrastructure to Microsoft's cloud services would be too painful and I have better things to do in my free time.
partiallypro 5y ago
Running your own email server isn't that complicated...running OTHER people's is. I worked for a company that had a few custom email servers running Postfix and Dovecot. Charged them very little for an inbox which make it incredible hard to offload them to others. The company that ran the datacenter for our email servers went out of business, migrating 10,000+ inboxes that haven't been cleaned in 15 years was an absolute nightmare. I don't wish it on anyone.
lnxg33k1 5y ago
The kind of people I love, those who can work for a company without joining the cult
binkHN 5y ago
> ...using Outlook is an impediment to projects whose mailing lists are based on inline posting... I never understood why, after all these years, this is still horribly broken. Yes, I understand commercial development tends to follow a monetary reasoning, but this has been broken for forever (~25 years?).
- jclulow 5y ago
  From their perspective, is it really _broken_? If you're Microsoft, especially Ballmer's Microsoft which accounts for most of those 25 years, who cares about a handful of hostile UNIX nerds on some mailing list -- they're not going to switch to using Outlook and we want to discredit and destroy their software anyway. From the perspective of market fit and success, there are countless less-technical business users who swear by Outlook. They are not familiar with anything other than the kind of endless thread top-posting in odd encodings that Outlook all but ensures users will do -- that's e-mail to them. Why stop selling it to them? To be clear, I loathe all of it and I haven't used client Windows for more than a decade. When I used to support small business IT customers back then, Outlook was by far my least favourite tyre on the raging intergalactic rubbish fire. But it's not hard to see why they don't care that Outlook is the way it is.
  - neelc 5y ago
    > From the perspective of market fit and success, there are countless less-technical business users who swear by Outlook. And I find Outlook painful enough that I use Windows Mail at work. That only because my team disabled EWS for using about anything else. > They are not familiar with anything other than the kind of endless thread top-posting in odd encodings that Outlook all but ensures users will do -- that's e-mail to them. Why stop selling it to them? Ahhh, the old "embrace, extend, extinguish" by breaking other email clients among other things. For Corporate America (as opposed to startups), Outlook is email. Well, Gmail, Yahoo, Thunderbird and Roundcube can view Outlook-composed email fine now since IE stagnated and Firefox/Chrome beat it. (assuming Outlook used IE for rendering, I don't work on the Outlook desktop client and joined after Edge went Chromium). And Outlook still can't inline post, because Microsoft borked the "standard" and built an email client for corporate users not Unix nerds.

I *work* at Microsoft 365, and yet my personal email is self-hosted Postfix and Dovecot. Why? Self-hosting email has been a part of my life since my high schoo

by neelc 5y ago

walrus01 5y ago

If I worked at Google or Microsoft (I don't, and am unlikely to ever do so) I absolutely would not use my own company's email services for my personal domains. Just for the general principle of keeping personal and work things compartmentalized.

deleted 5y ago
[deleted]
neelc 5y ago
I only joined Microsoft not because I wanted to, but because I really had to. I was a pretty die-hard *nix/self-hosting person for many years, and years of habits and conditioning can't be unwinded so easily. I use Git in a cmd even when doing code done in VS, since I'm used to doing it that way. The center of my digital world is a home server and not some cloud subscription service. For years I got angry when my dad wanted me not to use FreeBSD (or Linux) and just user Windows. We clashed with each other for this. I don't intend to stay with MSFT forever, nor do I want to. My parents pushed me towards staying, but I eventually want to work in a more *nix-environment. But then my dad is extremely change-averse when I'm not, well unless I am really in love with something (like FreeBSD or self-hosting) when I become more partial. I'm willing to use the less popular software for the sake of it in many cases (unless I literally can't) when my dad just sticks with the familiar. Heck, he can afford a uber high end Gaming PC with a Threadripper and RTX 3090 Ti, and he still uses an entry-level Core 2 Duo Dell desktop from 2009 which shipped with Vista (and was upgraded to W10 with an eBay key).
- curt15 5y ago
  What beef did your dad have with FreeBSD or Linux?

u801e 5y ago

> I also contribute to FOSS projects, and using Outlook is an impediment to projects whose mailing lists are based on inline posting Based on my testing, that's not the only problem with using MS email clients on FOSS mailing lists. There's no concept of threading beyond the conversation view, and the client also mangles the email (wrapping or even sending base64 encoded test instead of the raw text. Even if your client sets the Message-ID header, MS servers will delete the header and replace it with their own.

neelc 5y ago
Yes, and that. I don't use Outlook/Exchange outside of work, frankly never did, but did read from time to time the issues with Outlook norms versus *nix email norms. I didn't need Outlook before I joined Microsoft, every student in my high school used their personal email (despite the school having an Exchange server), and my college used Google Workspace (I'm not that old TBH). I also lived entirely on FOSS software before joining MSFT, so to move every piece of personal self-hosted infrastructure to Microsoft's cloud services would be too painful and I have better things to do in my free time.

partiallypro 5y ago

Running your own email server isn't that complicated...running OTHER people's is. I worked for a company that had a few custom email servers running Postfix and Dovecot. Charged them very little for an inbox which make it incredible hard to offload them to others. The company that ran the datacenter for our email servers went out of business, migrating 10,000+ inboxes that haven't been cleaned in 15 years was an absolute nightmare. I don't wish it on anyone.

lnxg33k1 5y ago

The kind of people I love, those who can work for a company without joining the cult

binkHN 5y ago

> ...using Outlook is an impediment to projects whose mailing lists are based on inline posting... I never understood why, after all these years, this is still horribly broken. Yes, I understand commercial development tends to follow a monetary reasoning, but this has been broken for forever (~25 years?).

jclulow 5y ago
From their perspective, is it really _broken_? If you're Microsoft, especially Ballmer's Microsoft which accounts for most of those 25 years, who cares about a handful of hostile UNIX nerds on some mailing list -- they're not going to switch to using Outlook and we want to discredit and destroy their software anyway. From the perspective of market fit and success, there are countless less-technical business users who swear by Outlook. They are not familiar with anything other than the kind of endless thread top-posting in odd encodings that Outlook all but ensures users will do -- that's e-mail to them. Why stop selling it to them? To be clear, I loathe all of it and I haven't used client Windows for more than a decade. When I used to support small business IT customers back then, Outlook was by far my least favourite tyre on the raging intergalactic rubbish fire. But it's not hard to see why they don't care that Outlook is the way it is.
- neelc 5y ago
  > From the perspective of market fit and success, there are countless less-technical business users who swear by Outlook. And I find Outlook painful enough that I use Windows Mail at work. That only because my team disabled EWS for using about anything else. > They are not familiar with anything other than the kind of endless thread top-posting in odd encodings that Outlook all but ensures users will do -- that's e-mail to them. Why stop selling it to them? Ahhh, the old "embrace, extend, extinguish" by breaking other email clients among other things. For Corporate America (as opposed to startups), Outlook is email. Well, Gmail, Yahoo, Thunderbird and Roundcube can view Outlook-composed email fine now since IE stagnated and Firefox/Chrome beat it. (assuming Outlook used IE for rendering, I don't work on the Outlook desktop client and joined after Edge went Chromium). And Outlook still can't inline post, because Microsoft borked the "standard" and built an email client for corporate users not Unix nerds.