Office 365 Troubleshooter: a start, but not as accurate as you need

On November 8, Microsoft announced “Support Made Simple” on the Office 365 technical blog. By this Microsoft means that they’ve provided a Do-It-Yourself (DIY) troubleshooting tool to help Office 365 administrators and users determine the likely cause of problems that they experience. The tool is free to all to try out and being that I am both an Office 365 administrator and user, I thought that I’d give it a whirl. Mind you, as my wife keeps on reminding me, my DIY skills are not in the artisan category so I didn’t have high hopes of what I might achieve.

The blog says:

The Troubleshooter pinpoints key technical support issues and provides immediate solutions without the need to post questions to the community or submit a support request ticket. The tool’s cool and modern interface conveniently displays hundreds of possible help and support assets (i.e. Help topics, KB articles, videos, wikis, blog posts) from within the Office 365 suite. As you move through a list of troubleshooting options, the tool dynamically displays funneled-down content to lead you towards the answers you need.

The tool is so simple, documentation is overkill. All the information you need is condensed into 5 interactive panels. ;-)”

How nice. All available knowledge about Office 365 condensed into five interactive panels. Why would anyone ever need to phone a support technician or log a support ticket again? Full of confidence, I headed over to the Office 365 Troubleshooting site and began to navigate through the aforementioned five panels.

First, I declared whether I was an administrator or user and whether I used Office 365 for professionals and small businesses (Plan P) or Office 365 for enterprises (Plan E). I chose to be a Plan P administrator.

Panel 1 offers four options to help focus in on the service that’s causing the problem. These are Exchange Online, Lync Online, SharePoint Online, and the catch-all Office 365. Panel 2 takes you to the major areas of functionality in the chosen option. For example, Exchange Online offers Administration, Deployment and migration, Domain management, Mobile devices, Outlook and other clients, Sending and receiving email, and setting up and configuring email. So good so far. I was on familiar ground here and the options offered seemed reasonable.

Panel 3 gets closer to the meat of the matter. I chose to DIY troubleshoot a connection problem with Outlook 2011 for Mac. The option “Connecting to Exchange Online” seemed close to what I wanted to do, so I chose that and the troubleshooter promptly displayed the screen shown below.


OK. It thinks that there’s four issues that could be causing my problem. I looked at all of the solutions and the last of the five famous panels promptly popped up with a selected Microsoft Knowledge Base article! For example, the solution presented for figuring out why Outlook might experience a slow connection is KB2441551.


I certainly don’t mind Microsoft directing my attention to KB2441551 but Google or Bing are equally happy to find the same solution. I typed in “Slow Outlook Performance Office 365” into both and the article popped up in position 5 in Google’s results and position 3 for Bing.

The Troubleshooter does provide value in acting as a filter for many of the potential issues that could cause a problem to occur. However, the results provided by the search engines turned up links to videos and blogs that could also help, including the Exchange group’s own blog.

What was of more concern was the somewhat scattergun approach applied to solving the problem as described in KB2441551. Twelve separate issues were described so the information is certainly comprehensive. I was told to:

  1. Enable cached Exchange mode
  2. Determine Global Catalog usage
  3. Download the Offline Address Book
  4. Check the OST file size
  5. Reduce the number of items in critical folders
  6. Disable add-ins
  7. Start in safe mode
  8. Disable Lync Online integration
  9. Disable email scanners
  10. Verify Group Policy settings
  11. Repair Outlook
  12. Cache additional mailboxes

Wow! I can imagine the eyes of an inexperienced administrator watering as they go down through the list. It’s quite a response to a simple question, which then leads to the feeling that perhaps Microsoft has some more work to do on the DIY Troubleshooter before it can really deliver helpful results at the granular level that will make the tool extremely effective.

Don’t get me wrong. It is extraordinarily difficult to apply something like artificial intelligence techniques to interrogate a user or administrator and gather details of their problem in a way that makes it possible to assess a body of knowledge and determine the right answer. Technologists have been grappling with similar problems for years and indeed, some recent attempts were made by companies to analyze problems against knowledge bases for products like Exchange. Zenprise is one such example who tried to problem solve by reference to Microsoft’s knowledge base and other sources and they gave up and went and built mobile device management software instead (and do a good job of that).

I therefore applaud Microsoft for starting off to provide DIY tools to figure out what might be going wrong with Office 365. However, this Troubleshooter is very much a V1.0 solution that will only deliver value to inexperienced users. This might indeed be the target audience and perhaps future versions will cater for the needs of more experienced users who might actually know how to use a search engine intelligently. We’ll just have to wait and see.

Discuss this Blog Entry 5

on Nov 16, 2011
@Kim121, I agree with you that this tool could lead inexperienced users into some confusion. However, on the upside it's good to see Microsoft investing in tools that help to troubleshoot problems and we can expect that future versions will be both more intelligent and comprehensive. At least, that's what I hope. TR
on Nov 17, 2011
Microsoft is definitely heading in the right direction with the Office 365 troubleshooter tool, however Kim makes a good point in that this will lead to confusion for the inexperienced user and should only be used by IT support staff. If you engage a microsoft online partner and have the migration completed by professionals, you should not experience that many issues as office 365 is pretty streamlines. CTX Solutions are offering free Office 365 migration/implementation services, so you have no excuse
on Nov 11, 2011
Every new platform discovers new ways of consuming IT resources...
on Nov 11, 2011
I thought cloud solutions were supposed to free up IT resources.
on Nov 15, 2011
I think this will lead to more confusions and error to unexperienced users. They should stick to search engine capabilites for easier results.

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Tony Redmond is a senior contributing editor for Windows IT Pro. His latest books are Office 365 for Exchange Professionals (eBook, May 2015) and Microsoft Exchange Server 2013 Inside Out: Mailbox...
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