Microsoft 365 troubleshooting: Diagnostic tools at your fingertips

As companies made the migration to Microsoft 365 this year, many Exchange admins found that their collection of troubleshooting tools for on-premises Exchange Server don’t always work well — or even at all — with Outlook in Office 365. Fortunately, our Exchange expert Edward van Biljon lets you know about several new diagnostic tools that are made for Microsoft 365. This article, first published in November, was a lifesaver for many IT pros, and that is why it is one of TechGenix’s 20 Best for 2020.

As Exchange admins, we have dealt with our fair share of Outlook problems that occur on users’ machines. For those who have migrated to Microsoft 365, it’s good to know that troubleshooting can still be done because of the number of diagnostic tools available. And that’s a good thing — there are a number of things that can go wrong. Here are some of them:

  • Outlook won’t start
  • OST file corrupt
  • PST file won’t open
  • Outlook starts and then quits
  • Plugins that cause Outlook to stop responding
  • Many other errors

Common Microsoft 365 troubleshooting issues

When it comes to Office 365 (or, as it’s now called, Microsoft 365), the Outlook issues are still there, albeit maybe on a lesser scale. But there are a few Microsoft 365 errors that are pretty common and need troubleshooting. These include:

  • Outlook not starting
  • Cannot send or receive email in Outlook
  • Outlook profile won’t connect on your machine
  • Other errors

When you run into issues with Exchange on-premises, sometimes there is something on the server itself that needs to be fixed. If clients cannot connect to Outlook, you need to check if the Microsoft Information Store Service is started or running, does the server have enough resources or has it hit backpressure and caused email to stop flowing, or is that file server with the PST files on not accessible and causing issues with users’ Outlook? As you can see, troubleshooting and resolving on-premises Exchange might be easier than Microsoft 365.

Microsoft Support and Recovery Assistant

If your mailboxes are in the cloud, what do you do if Outlook won’t connect? You obviously cannot log in to the server and check the Microsoft Information Store as you don’t have access to the Exchange environment. You would need to log a call with Microsoft to check and get advice. Microsoft has actually made it easier for you to troubleshoot with a tool available called Microsoft Support and Recovery Assistant. What can this tool do for you? Here are three main Microsoft 365 troubleshooting features it can assist you with:

  • Outlook not starting
  • Can’t send or receive email
  • Outlook won’t connect from your desktop/laptop

I have used this tool a number of times, and it has fixed the issue with Outlook 99.9 percent of the time. Yes, there will be that 0.1 percent where you do need to log a call with Microsoft. When you download the application, it will ask you to download a 25MB+ file and install it. You may think you have a bad installer as nothing happens for about one minute before you are presented with the screen below:

Once you have read the services agreement (some people do read it!), you can click on “I agree” to proceed or “Cancel” to quit the application. Once you click “I Agree,” a new window will open as shown below:

On this page, you have the option to either leave the default on “No” and click “Cancel,” if you click “Yes,” you will notice the Next button will become available:

Click “Next” to continue. What the tool will do is check if Outlook is running. If it isn’t, you will receive a warning and you can continue. Once you continue, the tool will actually check the profile and then give you a report at the end and the next steps. If you quit the tool halfway and open it again, you will now notice that you have a whole lot more options available to you as shown below:

This is pretty cool as you can select an option that you are having an issue with. If you notice I selected Outlook and below that, it says “Resolve over 10 different problems.” If you click “Next,” you will be shown a list and you can now select the problem you are having. Below is an example of this:

Common issues

One of the common issues is that Outlook stops responding or freezes and this can be due to antivirus or a plugin that might not be compatible with Outlook. When new items are added to the tool, it will show “New” next to that item. Microsoft Teams meeting option is new. If you click an item, you can then click “Next” and you will be taken back to the beginning again where it will ask you if this is the affected machine. Once you select “Yes” and then click “Next,” the tool will start troubleshooting the issue. Here is a window you will see:

You will notice in the window above when running it live that it will start showing what it has found. If you are not running an Office version that is supported, you will be presented with this window:

This troubleshooting tool is obviously looking for a Microsoft 365 version of Office. In this case, I was running Office 2019 retail version, but you get the gist of it. To wrap up, you can see that Microsoft has made this tool to make it easier for admins in their Microsoft 365 troubleshooting. The tool is obviously limited in what it can try to fix. If you run into an issue that does require support from the Microsoft team itself, the tool will be a great help in gathering the logs you can use during the call.

Microsoft 365 troubleshooting: Every situation is different

The tool will advise you to update your version of Office to the latest version and then try again. Sometimes an update does assist in fixing an issue and other times not. Every machine is different as people run different flavors of antivirus or have Group Policy that locks the machine down.

Featured image: Shutterstock

Edward van Biljon

Edward van Biljon is an experienced messaging specialist working in the IT and services industry. He is skilled in WSUS, domain name system, datacenters, printer support, and System Center Configuration Manager (SCCM). He has a background as a strong IT professional and has an international diploma in programming focused on computer programming.

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