Surface Pro 3 and Outlook – Disappointment

How the hell do Microsoft keep screwing this up?

It shouldn’t be hard, guys.


Microsoft and I have a pretty good relationship. I love Office, I love OneDrive, and the monthly/yearly fee for them is incredibly good value. is an exceptionally good email service for those who don’t want to use Gmail, and Skype is an excellent product too. But god damn do they screw some things up in a major way, and this is no more apparent than with the Surface Pro line of tablets. I’ve owned a Surface 2 Pro and now a Surface 3 Pro, and each one seems to display weird behaviour which I can’t pin down. Additionally, Windows 8.1 and its apps are still atrocious after all this time, and they can’t even reliably work with Microsoft’s own services.

Apple, by comparison, are doing some silly things with their cloud solutions (iCloud Drive is a mess as things stand, and no amount of OS integration will change that) but to be fair (and I can’t believe I’m saying this) they’re actually fairly reliable. Do they screw up? Yes. But they have yet to cause me the frustration that Windows 8.1, the Surface 3 Pro, and the Calendar app have caused me today.

It started innocently enough – I just wanted to input my roster projection from now until around February next year. I work a rotating roster of 2 day shifts followed by 2 night shifts and a variable number of days off, usually from 0700 until 1900 (and vice versa). Some days I’ll work 10 hours instead. This isn’t a difficult concept to understand, but putting this data into the Calendar app was a goddamn nightmare.

Firstly, there’s no copy and paste system, which leaves you with two options. The first is that you can set up repeating events, but this is an awful lot of extra work to set a start and end date (remember it’s 2 days, 2 nights, and days off are variable so there’s no easy pattern to work with) and takes more time. The second option is to just do everything manually, which is what I ended up doing because it was slightly quicker. Infuriatingly, and with no apparent option to disable it, each new event automatically gets an alert attached to it timed for 18 hours before it starts. If I was syncing my calendar with my iPhone, this would result in alerts to remind me that I’m working tomorrow (and I don’t need to know that). So it adds on a bit more extra work, just to be frustrating.

The UI for the calendar app is also a major pain in the arse. It’s still way too big, even for a touch screen, and options are pointlessly hidden by the “More Details” button (specifically that fucking alert setting). But whatever, I keep working away, and I put in a good 25 or so shifts, when I notice something out of the corner of my eye: the top right of the screen shows “[Account ID] is unavailable.” I hit the Sync button again – and get the same error. Anything I do (or don’t do) produces the exact same problem. I log onto the web portal for the calendar and see that it’s only successfully synced about 10 events, and the last 4 don’t have all the information put in. I’m pretty pissed off now.

I systematically start removing the various events from the Surface, trying to get it to sync. Nothing. I reboot it (and it installs a system update). Nope, still not syncing. I uninstall and reinstall the app. Nope. The next step would be to simply remove the account in its entirety and start again – but for fuck’s sake, why should I even have to do this? Why is it that the app or service can’t handle me putting in a bunch of appointments?

To add insult to injury, another bug from the past floated in and the Type Cover refused to work after the reboot. Actually that’s not entirely accurate – I could press the Backspace and Spacebar keys, but that’s it. The Windows Key soft-touch button also refused to work. Another reboot later and it started working again – only to promptly refuse to work after I tried rebooting again to get the calendar to sync. So for all of this screwing around, I still have a calendar that won’t sync properly. By this point I’ve given up – it’s taking me way too much time and effort to try to fix something that shouldn’t be such a drama. The worst part is that the Type Cover issue has been around since the very first iteration of the Surface devices, and it’s fucking ridiculous that it’s still such a big drama. Weird firmware issues, battery drainage, the pen calibration suddenly not working properly, and other input issues make the Surface Pro an all-round unreliable device for me. I just can’t trust it.


I also have a Macbook Retina Pro that I keep more as a curiosity these days than as a serious work machine – I sometimes use iWork for random projects, but predominately it’s used as an iCloud gateway and adjunct to my iOS devices. I still use OneDrive and Office on it (because they’re still some of the best around). How did I fare accomplishing the same task? Much better. For a start, I can copy and paste events, which drastically cut down on the workload. I had no sync issues at all. Everything just worked, and although that’s Apple’s motto that’s often derided as utter garbage, this time it actually did. You have failed if Apple’s apps and services are more reliable than yours. Apple’s iCloud solution isn’t known for its reliability. But this time it beat Microsoft’s solution, which gives me hope that one day iCloud Drive might not be as totally useless as it is right now (seriously, it’s hopeless – why can’t I select what I want to sync?).

The worst part? This is the second time I’ve had this problem. The first time was a week or so ago when I tried to do the exact same task, and it failed to sync after the first 8 or so entries. So I give up! Microsoft, start getting your shit together. I hope with Windows 10 you’ve completely overhauled these essential but thus far utterly useless apps, because if not, you’re starting to lose to Apple. Nobody should lose to Apple.


One thought on “Surface Pro 3 and Outlook – Disappointment

  1. This is a very well written article. People need to realize how much Microsoft is being terrible right now. They are trying to shove Windows 8 down everyone’s throats, and its obvious no one wants to use it. To be honest, I kind of always wondered about the whole idea of an x86 tablet, it seems kind of wonky and unstable at the moment. I wish they’d just do like Java and have “Windows Packages” that can run on any architecture. Then they coukr use ARM on mobile and x86 on desktop. But they never asked me so…

    If you could do me a favor and check out my tech blog, I would appreciate it. I am trying to grow my audience and i want to hear some comments about what I should post more of.


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