Microsoft Office 365: Reasons for Caution

I came very close to calling this article “Why Office 365 Sucks.” I refrained from doing so because I think the cloud-based office collaboration suite CAN be a good fit for some small businesses.

However, as an IT consultant working with small and medium enterprises (SMEs), I will think very carefully before I let it near another one of my customer sites.

Here’s why:

Migration is horrible

Office 365 is great for start-ups who don’t already have a load of data. Everyone else will have gigabytes of file-level data (that probably hasn’t been cleared out in years), and thousands of historical emails.

There’s no way to make the process of moving this volume of data to the cloud anything other than slow, laborious and frustrating. It doesn’t help that Office 365 is very fussy about certain characters within filenames.

While these characters are likely to have been avoided by IT-types, familiar with them since the DOS days, you can’t expect the same from the less technical. Who’d have known that a migration could turn into a nightmare because a client uses lots of ampersands in filenames?

Office 365 is Not Perfect
Office 365 is Not Perfect

Desktop Integration is Flaky

If you want Office 365 to work well, you really need a fresh Windows install on each machine to start with. Try to migrate a PC that’s been previously connected to a domain or has used other Outlook profiles, and all kinds of weird stuff can happen.

While this clean-machine approach is good practice, it does add on migration time. When coupled with a slow data migration, a move to Office 365 can end up using more consultancy time than, for example, a move from Small Business Server 2003 to SBS 2011.

Key functionality is missing

Ask Microsoft how to implement a shard contact list and they’ll tell you several options, including using SharePoint or setting people up as “external contacts.”

However, if you want a shared contact list, available to everyone as an Outlook address book and editable by a whole team, it just cannot be done without clunky workarounds. This is functionality that all of my clients have had for years. It doesn’t go down well when you have to take it away.

Poor support

Support calls can take days to resolve satisfactorily, if they get resolved at all. You can also expect to have to re-explain the problem several times.

The support forums are hugely frustrating too. In the case of the shared contacts issue above, expect to see copy/paste answers that repeat the options that are available and fail to acknowledge the shortcomings that exist.

You have no control

When you reach the point of frustration, you eventually have to tell your customer that there is nothing more you can do – that the issue is in Microsoft’s hands. You can’t remote it and tweak the server any more. Those days are gone.


I’ll repeat what I said at the start: Office 365 CAN be a good fit for some businesses – especially start-ups who haven’t done things differently before. Others, especially those who have become used to the flexibility of something like Small Business Server, should tread very carefully – a migration to Office 365 could feel like a huge step backwards AND make your clients think you have become worse at your job!

  • Jorge Leitao

    I´m sorry but it looks to me that you simple didn´t do your homework and you´re looking for the easiest way out. So you blame the tool.
    It is like a guy who hits his own thumb and blames the hammer.
    Everything you said is at fault, but the lame support, is explained in the Office 365 Solution Guide and in Office 365 Deployment Guide –
    Have you simply gone thru either you´ll know that Public Folders aren´r there and without that you have no way to implement a shared contacts folder using only Exchange.
    I have personally installed the Office 365 client update in several PCs, most of them ´old installs and had only very limited issues, mostly with third party components or long non-updates machines. No issues with domain-joined machines or Outlook Profiles getting jammed. Again some fire-drill tests and planning could have got you safely thru.
    It doesn´t look like you did any planning at all. Is your company a Microsoft Partner? Case yes, Microsoft offers its Cloud Partners free training on planning and deploying Office 365.Have you taken any training on that before you decided to provide services to your customers?

    • David Andrews

      To the contrary, I have found the author’s article to actually be quite optimistic.

      Our office just “upgraded” 20 workstations to M365, and to call it a disaster is being nice.

      I could detail the problems at length, but then, I wouldn’t really be changing any minds. The Internet is where people go to announce their opinions, not change them.

      That said, I will note one particularly strange error of recurrence. After paying for a subscription (a year in advance for business use), the installations periodically lock the users out and declare the product “unlicensed”. In the year we’ve had the product, it’s done this 4 times now, leading to lost productivity, in one case over a month of a user not being able to use the product, even though we had paid for it.

      Unfortunately, Microsoft protects themselves first and foremost, at the expense of the customer in our case, and by locking paid users out of a paid product, most likely violates all kinds of consumer protection laws.

      The time spent to resolve these issues is not insignificant either, clocking in at nearly 4 hours for the last occurrence.

      Simply speaking, Microsoft 365 is a bug-riddled experiment that is not even close to being ready for prime time.

      At least not in our case. Every time I read reports like this, there’s always someone who says “that never happens to me!”, as if that makes it okay that other people are getting screwed, so long as they aren’t.

      Then, of course, there’s always the guy who blames the customer, as if Microsoft hasn’t been selling this product as a way to cut down on tech support. It’s never been identified that we did anything wrong, instead, support has always told us that the licensing bug was a known issue, and that they would fix it eventually.

      So, take it for what it is. One businesses experience with Microsoft 365. Hopefully others will have better luck, but the author is in no way out of line in my experience.

    • FistedSister

      The brave defender of Microsoft. Good serf. Good for you.

  • Lilian

    I started using Office 365 2 months ago and I find Sharepoint very frustrating. I have never used Sharepoint before and am not a technical person. I found it difficult to learn how to manage it and Sharepoint integration with desktop has many more steps. I found that I couldn’t create a new document in Sharepoint, and then setting up this step is ridiculously tedious. You have to do it for each and every document type e.g. powerpoint, word, excel and you must do it for every folder you want to allow document to be created , so if you have 20 folders, you have to manage the settings of that 20 folders. You must use Internet Explorer to optimise your use of Sharepoint, so it means that I have to think twice before using Microsoft Office 365 on a Linux machine. My office package comes with a support package and I have found it very helpful although I shouldn’t have to call them to find out how to set up Sharepoint to be able to create a new document in Sharepoint.

  • Kevin Fream

    Ben – My firm migrates about 2,000 subscribers per year to Office 365. In order:

    1) E-mail migration works well even for large mailboxes, but many customers have not purchased a commercial SSL certificate or configured Outlook Anywhere which are required for the online migration. SharePoint online now fully supports folders, so data migration is truly as easy as mapping a drive and drag and drop.

    2) It’s a well-kept secret, but you almost have to run the Office 365 Desktop Update to get the few files necessary to work smoothly on workstations.

    3) Public folders died a quiet death several years ago. If customers don’t like the resource mailbox approach they can have a full mailbox shared for everyone with virtually the same functionality as public folders.

    4) I’m not a forum fan either – of anything, but unless it’s an extremely complex issue Microsoft support is actually pretty good. However, nothing beats using a Partner that is American, speaks English, and has done it before.

    5) The whole idea is for you and the customer to escape the hassle. We’ve had the experience of migrating to Office 365 and have obviously learned some tricks just like on-premise migrations. We’ve moved many established organizations with no problems and really feel it is the small businesses at risk who may unknowingly pick the Office 365 P1 plan which Microsoft will likely discontinue next year.

    If you have any customers in pain, then we can definitely help.

    • frozenjim

      Kevin, I think you are talking like you have something to sell. It is disingenuous to state “data migration is as easy as mapping a drive and drag and drop” because, as you must be aware, it takes DAYS to move a medium amount of data and there is no way to move data from SharePoint into Onedrive for Business without downloading from one and then uploading to the other.

      You also fail to mention that the 1TB of “free storage” is a bit of a scam as well; it applies only to OneDrive for Business (which as I have pointed out cannot be easily moved back and forth to SharePoint) which, if you SYNC a GB it stores a GB on your drive AND it stores ANOTHER GB on your c: drive in the cache. So since most laptops today come with 256GB SSD drives, and Windows uses 50 of those, you REALLY have only 100 GB available on OneDrive for business. Oh, and to make this even more painful, you cannot sync PART of your OneDrive – you must sync ALL of it – or nothing. So in truth, users must pay for their storage by upping the SharePoint storage fees and then syncing only the libraries that they require synchronized.

      You also fail to mention that the admin panel is so sluggish that it is virtually unusable if you need to maintain your users or do any actual work.

      As the original poster points out, when you have a support issue (and these DO happen a lot more than they would if you owned your own servers) then your hands are tied. You call one level 1 technician in India who will spend an hour or two getting a handle on EVERYTHING from your dog’s last name to the color of your chair. With THAT accomplished, they then escalate to level 2 who does exactly the same thing – only a day or two later. Finally, if you are patient, and if you are lucky, they will find you an answer at level 3 after another day of waiting. On approximately 50% of my client’s support calls, someone from India support phones them at the appointed time and the voice connection is so bad that it just drops – so the tech sends an email asking the client to ask the tech to schedule another support session. It makes the clients furious.

      Unless you have hardware hosted Active Directory, your users will need one set of credentials to log onto their PC and ANOTHER set of Microsoft credentials to log into Outlook/o365 because Microsoft has not implemented any form of SSO. THIS is a support nightmare if you support unsophisticated users.

      I agree with the original poster that o365 must be approached from a position of understanding these limitations and with much caution. I still use it for a few micro clients, but I then am forced to charge them my hourly rate as the middle-man with Microsoft Support. And it makes me feel a bit dirty.

      Very disappointed. MS had a chance to really make something great here and they just chose not to.

  • Jenny Gershwin

    More trash from Microsoft. Took their 30 day trial and after 3 days I cancelled and uninstalled. Too many issues, loading, too long, etc. Back to my Office 2003 where I will stay for as long as I can.

    If this is the “future” I dont want any part of it…..Microsoft after Win 8 and then this, in my opinion is waning, and on the way to ruin.

  • Geta LifeLoser

    Benny Taylor, do yourself a favor, and leave the IT work for people that knows what they are doing. We all understand that End-User collect useless email…etc. But its the IT/Exchange administrator job to manage that mess!
    I do Partner work for Microsoft/Office 365, and every time I think about migrating a Mail Server to other service, I do my Maintenance work first.
    See, Microsoft Cloud Services has been around for at least 4 years now, and everyday I get people complaining Microsoft this, and Microsoft that, but the whole time, the client/user answer was sitting on, guess why?
    The fact that you sat here, and wrote a blog about Microsoft Office 365 services, only tells me that you are terrible IT administrator, or have to much time on your hand, which should being used to be a better IT Administrator. Maybe you should leave the dos days behind!!!

  • freak

    office 365 SUCKS!!! and microsoft 2 !!! finally i saw the light..never again !!!
    unix systems only ; linux , mac , even ANDROID is better correctly configed…
    payed more for the time talkin to the support instead of staying healthy…. stress, anxiety…repeating evertime my email address over the phone.. big god , WHY ??
    please let it rain, clouds please save me from this

    Help your self , don`t use microsoft. we all will die cause of wasting time with this software.

    I bet the Tepco used the office suite to organize the fukushima reactor. =O

    YES it is always the software, cause humans are not made for using them. I don`t want to be a slave to software, it makes no sense to know more about how to survive in the deepths of any program then about having fun enjoying this life (if live is not a holographic program ;-/ ) Good that microsoft helped creating so many useless companys to figure out their mistakes and still using the same poison roots to cool the moment if payed with enough pieces of your soul… (dang i`m good :-)
    try to cut that rope from your neck Jorge, Kevin and all you lazzy bs programing noobs .

    ..and now I`ll repeat, will the real Slim Shadys please stand up? please stand up?

  • FistedSister

    Ever since my company forced a switch to 365 I feel like I am back in the stone age. Sooooooooo ridiculously slow!! This is 2014 and it is fricking EMAIL!!!!! This should not be so hard!

  • digitalbeachbum

    Office 365 does suck. There is no common sense to it when you are trying to migrate over to the “cloud”. Microsoft just screwed the pooch on this one. After our subscription is over in one year we are dropping them and switching to Open Office.

  • didodido

    I am providing support for individual users. Office 365 is just ridiculous with their activation. There are very few people who have a Microsoft account. Once they have activated Office 365, they will forget their Microsoft account details. If a client need to reinstall Office 365, but cannot remember their account details including the e-mail address they have signed up with, the only way to go is to purchase Office 365 again. It is extremely frustrating for my clients and it can be difficult to explain this.

  • eric299

    I haven’t tried it and I won’t. This concept is based around Microsoft’s dreams of subscription income first and foremost, not any value proposition for the user.

    Three things come to mind: 1) I suppose “The Cloud” is OK for vacation pictures. But you’d have to be crazy to store any sensitive documents on machines you don’t control. 2) Even if you have a fast machine and connection the Internet can be a nuisance. I don’t mind if bombs and I have to reload it. But when I’m trying to get work done? Forget it. 3) I have posted selected spreadsheets for online collaboration from time to time. I used Google Docs (free) and it worked fine. Why in God’s name would I pay?

    I hope Microsoft doesn’t stop selling local installs of Office. If they do I’ll have to find something else. I’ve played with Open Office a little and I think Corel still sells a package of office software as well.

  • BulletPeople

    Some notes on the November 2014 video portal rollout, what they have called their NextGen Portal for video:
    – No progress bar or percentage counter shows while you upload files.
    – No progress bar or percentage counter shows while the files are being processed, and apparently because they do not support auto-refresh you are presented with the advice “To check processing status, refresh the page.”
    – There is no “share” option on the viewing page. If you copy the URL at the top of the page to send the link to colleagues it is more than 250 characters long.
    – If you inspect the source of the viewing page you can copy the path to the video file, run it through a plain vanilla URL decoder to convert the escaped character codes, paste it into Google Chrome to play it, right click on the video pane while it is playing and choose the “Save video as” option to save the converted file stored on Azure.
    – The file you download with the process above is identical to the file you uploaded, so the “processing” step is probably a step to create a smaller bandwidth version of the file for playback on mobile devices.
    – An mp4 file you download with the process above is not optimized for streaming (i.e. the moov atom has not been moved to the beginning of the file). This is a different approach than YouTube, which re-encodes all .mp4s for streaming. That’s not a problem for modern browsers but browsers that do not support HTML 5 such as IE 8 or earlier–basically any IE on a Windows XP machine–will require buffering the entire file before playback begins. In testing, playback failed altogether on IE 8, which NETMARKETSHARE currently lists as having 19% of the browser market share.