Troubleshooting tips for overcoming “Sorry but we’re having trouble signing you in Outlook” error

When trying to log into Microsoft Outlook, the user may sometimes encounter issues. One issue of this sort, is receiving a message upon attempting to sign in that reads, ‘sorry, but we’re having trouble signing you into Outlook’. If this is a message you are consistently seeing, then chances are that is why you are here today, reading this article.

Thankfully, there are means by which you can attempt to resolve this issue, which is what this piece will discuss. In order to solve the, “sorry, but we’re having trouble signing you into Outlook” error, it will mainly come down to clearing your browser cache in order to, hopefully, prompt Outlook to stop displaying an error to you.

First, we will explain it in a step-by-step guide, before breaking off into a more detailed analysis of the process and the steps encompassed by it. As such, do not worry if the mere bullet points are not enough for you to work with.

As something of a quick disclaimer, this blog will use Microsoft Edge as the browser in question. Of course, you may use another browser, but the steps should not prove overly dissimilar regardless of the browser you use.

Step by step: How to fix “Sorry but we’re having trouble signing you in Outlook” error

  • First, close all Microsoft applications that you currently have open.
  • Now, close any browsers you have open.
  • Follow the instructions your browser offers to clear your cache. Again, in this case, it will be Microsoft Edge.

So, to clear the cache of Microsoft Edge, you need to do the following:

  • Open Microsoft Edge.
  • Click on ‘Menu’, the three dots located in the top right of your screen.
  • Now, click ‘Settings’.
  • Here, go to the subsection titled ‘Privacy, search and services’.
  • There will be an option, ‘Clear browsing data’.
  • Under this, choose the option named ‘Choose what to clear’.
  • Select ‘Cached images and files’, as well as ‘Cookies and other site data’, and then clear them.

So, your first step in the process is, as mentioned above, to close not only any Microsoft application you have open, but to also close any browsers you have open. To carry on with the process, it is best to start from the desktop.

After doing this, open your browser to your home page. From here, you will want to click ‘Menu’, the three dots towards the top of your screen. In case you are in need of any further clarity, then look towards the screenshot below, where the ‘Menu’ button has been highlighted by a red rectangle.

Clicking the ‘Menu’ icon will open a dropdown list of options to you. Of everything offered to you, you should look to click the option titled ‘Settings’, which has yet again been highlighted in the below image.

Opting to click settings should open a new tab, the settings menu. On this menu will be a listing menu to your left, detailing each subsection of browser options that you are free to roam. For this process, though, you will want to click on the second option listed, which is titled ‘Privacy, search and services’.

Clicking this will show you the submenu of privacy, search and service settings (unsurprisingly). From here, scroll down slightly and you should see a heading titled ‘Clear Browsing Data’. Look under this title, and you should find a blue box, in which the words ‘Choose what to clear’ should read. Click that.

After clicking this box, another menu will pop up and it is this you will need to edit. There will be four options offered to you, and by default, all will be ticked. Now, you will want to un-select the top two boxes, meaning the only two left ticked should be titled ‘Cookies and other site data’, as well as ‘Cached images and files’.

Once this is the case, you should want to click ‘Clear Now’, the blue box at the bottom of your menu. It has been highlighted in the screenshot below. Also in the below image, the two boxes we told you to deselect have been deselected themselves. So, should you need some more assistance with that, it will be evident in the picture.

Doing this will clear your recent cache, and should be in itself enough to solve your Outlook signing in error. If it is not though, do not worry. You may need to quit OneDrive if your computer is running it, which may well be the case if you are currently operating on a computer with Windows 10 installed.

In order to quit OneDrive, the steps are very simple. First, look towards the bottom of your screen, on the navigation bar of your computer. Towards the right hand side should be a cloud, which represents your Microsoft OneDrive.

When hovering over this cloud, click it to open a small menu. From here, look at the bottom of the menu, where there will be three boxes. The one farthest right will be titled ‘Help & Settings’. Click that.

Clicking this will open a small, new menu. Of all the new options offered, you will want to look to the very bottom of the list where there will be an option titled ‘Close OneDrive’.

Doing this will ensure that you have completely quit the application. Now you should be able to re-enter your Outlook, and indeed your OneDrive, and you should find that the error message has been resolved!

Thank you for taking the time to read this blog, I hope you found it as helpful as you wanted it to be! As is the case with every article we publish on the site, if at any point you run into any issues whilst following this walkthrough, or simply wish to share some of your thoughts, then please do not hesitate to get in touch with a member of our team.

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Michael Fontana

Michael Fontana has been the managing director of telecoms and MSP Optionbox for over a decade and has worked in various telecommunication roles over the last 20 years. Michael has been involved in many exciting projects, such as co-founding telecoms and IT businesses and has now built up a team of more than 15 staff, serving over 300 clients nationwide. With a wealth of experience in IT and a passion for technology, Michael is now helping BTP to produce the highest quality guides on the internet. You can connect with Michael on LinkedIn.

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