Working on Windows 10 — the switch back from macOS and Ubuntu

For the better part of the last 10 years, I’ve been using a Mac for work. Before that, I was using Ubuntu.

Recently I’ve been experimenting with moving to Windows as my platform for working, and not just gaming.

The “why” of this is a long discussion that isn’t really relevant to this topic, but in short: While macOS is fantastic, I am growing increasingly frustrated with some of the hardware decisions Apple has made over the past few years. I can’t upgrade elementary components like RAM in a MacBook Pro. The scissor-switch keyboard isn’t nice to type on.

But the main thing: by making a few fairly harmless trade-offs, I feel like I can get a much better machine for less than half the price of a new MacBook Pro.

To give an idea… Before the rand tanked, R16,000 could get you a 15" laptop with Windows 10 Pro, Intel i5-9300H, Nvidia GeForce GTX 1060 Ti, 8GB RAM (easily upgradeable), 128GB NVMe SSD (easily upgradeable), 1TB mechanical drive (easily upgradeable), and 1080p display with 144Hz refresh.

Yes the trackpad and built-in webcam will be rubbish, and 1080p isn’t quite Apple’s fancy-schmancy RETINA display, but I get some standard USB 3.0 ports (and one USB-C), HDMI and mini-DP outputs, and a great graphics card capable of gaming without much trouble at 1080p.

Anyway… now I’ve already written a whole bunch of explanation and that’s not what this topic is about.

Here are the major issues and surprises I’ve run into.

(Free) E-mail software sucks

I’ve tried Outlook, Thunderbird, eM Client, Spike and Mailspring, and I’ve investigated countless others. I’ve ended up sticking with Mailspring so far, despite its bugs and huge drain on my CPU when it checks for mail, because it handles my massive Gmail inbox the best so far.

Thunderbird would get in this infinite loop of downloading my whole multi-gigabyte inbox even after I left it overnight to download the whole thing.

I would’ve given Outlook more of a chance, but it requires that I enable a less secure authentication method for Gmail.

On Mac, I used Apple Mail / Mac Mail. I didn’t think it was great, but in hindsight it is actually amazing compared to what seems to be available on Windows.

MacOS’s Calendar, Mail, and Contacts apps play nice with Google’s services. I’ve not found an equivalent on Windows.

Does anyone have recommendations that I maybe haven’t looked at?

Markdown editors on Windows have got much better

Many years ago, I switched to doing most of my writing in proper Markdown editors rather than a full-on word processor.

Most people don’t realise this, but you almost never need a complete word processor for the basic writing you need to do for work on a day-to-day basis.

This was a revelation for someone like me who writes for a living. Almost all my stuff gets published online. What do I want with fonts, margins, headers, footers, or templates?

Anyway… for the longest time, Mac and Linux had the best Markdown editors. The ones available for Windows felt like they were mainly aimed at developers who needed Markdown for README files for Github or BitBucket.

Enter Typora. It’s great. It reminds me of Byword, which I paid money for on macOS many years ago.

No built-in dictionary or thesaurus

The one major issue with Windows compared to macOS, as a writer, is that Windows doesn’t have a built-in dictionary or thesaurus tool. On Mac, I could literally press on a word and immediately get a lookup of its meaning, synonyms, and antonyms.

To get this feature on Windows, I’ve installed WordWeb.

Windows Subsystem for Linux and Hyper-V

One of the main reasons I even considered switching back to Windows as my workhorse is Windows Subsystem for Linux.

The thought of having to do some of the commandline-related stuff I like to tinker with (e.g. Python) or use regularly (e.g. LaTeX) in Windows made me tired just to think about.

I am happy to report that my experience with with WSL has been pretty great. The fact that VS Code integrates so well with it, and that VS Code turned out to be excellent, certainly helped.

If I have one complaint it’s that I haven’t been able to get Zsh properly installed and working with Hyper.js the way I like.

In addition to needing a readily-available Unix-like environment for some of my tinkering and work, I also still maintain a mostly-disused PPA for Ubuntu called Gmate.

Since Docker doesn’t play nice with VirtualBox on Windows anymore, I had to find an alternative. Hyper-V, it turned out, is not completely terrible to use.

Those are my thoughts so far. If you have recommendations for e-mail clients I should be checking out, or other “How to use Windows for Work” tips, please let me have them.

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I gave up on mailing clients long time ago, now I do everything on google. I used to stress about Office licensing, no more.

I used to think that doing all my work online would lead to trouble but it has become such a standard in my working environment that the only thing I do locally is code in sublime text, run it through work staging/prod servers and be done with it. It all goes straight to gitlab and our CI so all, again, online.

On the odd occasion that my internet has broken, I can still do some work locally and then just test it when it is up again. As for documentation writing, I use google online until it isn’t then offline till it is. Enough said.

Last week I had such an issue with our support department, they could not figure out why their CSVs were not uploading properly on our system, turns out MS uses Windows 1252 encoding for exporting on spreadsheets. I did not have that problem, I use google, which exports in UTF-8 which works.

So my advise is: make the transition to your new interwebs overlord Google, you will never look back (your life will be erased, nothing to look back to ;-P)


I am guessing you are talking about this option:

There is a setting in gmail that you can use to assign an application a specific password, which will allow it to connect without having to enable this option, it becomes available after setting up 2-factor verification. I have used this on 2 client PCs so far and they have had no problems.

I have used thunderbird forever now and have never had a problem, which I know doesn’t really help you but it is still strange that you had problems with the mailbox

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I’ve given up trying to use Windows for anything other than games and browsing the web.

On the mail client side…meh, It’s pretty much Outlook as far as features go. Thunderbird if you don’t want to pay for something.

I like using extensible text editors and it becomes very personal. I personally like Atom purely because I can bend it to do what I like and it has a rich (8000+) collection of extensions for most use cases.

I’ve used Sublime and it’s got some very nice features which some people find useful.

There’s also Brackets which also has a few neat features


My on topic 2 cents: Apple does email and integration right. Gnome deskop (ie. any major linux distro) is somewhat of the way there with online accounts, but it’s not perfect.

And Gmail is amazing and trash at the same time. I hate them for all that comes with google and it’s insidious privacy flaunting bs, but it’s spam filters are next level. They literally put the world’s alternative of email services/clients to shame.

Lastly, the combo of slow open source dev, and shitty integration support, has resulted in many email clients integrating with a subpar experience, feeling sluggish, not handling monstrous email inboxes/archives, and just generally, not using the extra services well, that make gmail good ie. jumping to contacts, calendar, gdrive, notes seamlessly.

Side question, and no I am not suggesting you switch. Have you tried Ubuntu since you left it? Seeing as you were using it at one point.

WSL v2 is coming. v1 is just a glorified userspace only shell, with no syscalls, so anything that uses systemd, is pretty much hosed. You can just use LyX instead of cli LaTeX. I mean really, it’s 2020. Use a UI. This guy seems to have gotten zsh with hyperjs working.

Frankly, I use windows like a console device. And Ubuntu on a laptop for work. I would love email in a client, but frankly gmail is best used in a chrome-based browser. Meh.

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I’ve never used any Apple products. I’m firmly in the Microsoft camp. I’m a C# programmer and play on XBox etc. Eh, even when I was a C/C++ programmer I used to work with DirectX and Pocket PC and such.

Email wise I use Outlook at work and my browser at home. Outlook does support two factor authentication with Gmail. What’s your problem there? Maybe I can help.

@PsychoFish mentioned it and yes I use Sublime Text. I prefer it over Atom. Tried Atom for a short bit and then went back to Sublime. Just love the look and feel of it.


So I just tried it again, and this time Outlook went through the standard Google OAuth prompt and everything seems to work. Very weird.

Not sure why this didn’t work before. Maybe my laptop shipped with a slightly older version of Outlook which didn’t yet have OAuth.

Thanks, @Solitude! I’ll give Outlook a try and report back. Mailspring has pretty amazing features and works very well with Gmail, but it has this way of bugging out the formatting of some e-mail replies that is incredibly frustrating.

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Awesome. I’m glad you came right.

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Something put me off Sublime, and I’ve just stuck to using Atom. My main thing is that I choose tools that work on Mac (my main development/productivity platform), Linux (Which I use for almost everything else) and Windows ('cause sometimes I’m in front of my gaming PC and need to do work)

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Status update: Outlook has been stuck on this “33 minutes remaining” for at least the last hour :rofl:


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Oh be prepared that could easily take all day


Microsoft time is very strange.


Update: The ETA has just gone up :rofl:



initial sync?

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Yep. Outlook downloads the whole inbox for offline access by default.


Too late to mention this now, but you can change that behaviour


Update the third: The ETA briefly went up to 4 hours, and suddenly the task ended for no reason.

One problem: My inbox was not completely up-to-date. For one, none of the messages that came in since about 13:30 this afternoon were listed.

So I’ve clicked Send/Receive, and now its running again.

I’ll give Mailspring this: its initial set-up experience is much nicer than Outlook so far. It’s a crying shame about its showstopper bugs in replies when switching signatures or aliases, and its high CPU usage when checking e-mail.

Yeah… I just don’t know what a good setting for that would be. I’ll see how much space my mailbox takes up in the end and decide from there.


While Mailspring is buggy, Outlook is finicky.

I left it to run overnight and it hit the error (paraphrasing): Can’t show you any e-mails because you’ve hit the file size limit for your Outlook database file.

Went into my Outlook folder. Apparently the file size limit is 50GB. So I changed the setting that @PsychoFish was referring to earlier so I can see the last 3 months’ e-mails instead of everything. Now my database file is 2GB.

This is another area where Mailspring’s integration with Gmail is just streets ahead of Outlook… I can see/search my entire Gmail inbox with Mailspring and it intelligently caches and downloads e-mails as I click on them.

Oh well. My earlier point stands… E-mail clients suck. They all just suck differently.

At least Outlook lets me switch between e-mail aliases and signatures without breaking spectacularly. Getting that set up was a bit of a pain, though.

Won’t bore y’all with that, but let’s just say that involved setting up a separate IMAP account that I don’t need to download e-mails for, and then setting up a rule to move all sent mail to my Gmail account. Like so:

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